The title compound, C27H39N3O9, is a key intermediate in the synthesis of novel β-turn mimetics based on electrophilic amination of enantiomerically pure (S)-pyroglutamic acid. The molecule adopts an extended conformation which is not stabilized by either intra- or intermolecular hydrogen bonding. The pyrrolidine five-membered ring adopts an envelope conformation, with the unsubstituted C atom situated at the flap and the other four atoms almost coplanar.
Supporting information
CCDC reference: 269369
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.012 Å
- R factor = 0.052
- wR factor = 0.158
- Data-to-parameter ratio = 7.8
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.92
| Author Response:
During the work, we had approached serious problems with
growing good quality crystals. Several early attempts had
failed before the succesful crystalization conditions were found.
Despite our efforts, the quality of crystals was not particularly high
and this is reflected by reduced completeness of the x-ray data.
We worked hard to improve that and the data set reported in the paper
is the best of six which were collected. Nevertheless, its completeness
is reduced to 0.92. After determining the structure
we have discovered that
crystal structure is not stabilized by intramolecular
hydrogen bonding and packing is quite loose. Presumably, that caused
our crystallization problems.
Results of the x-ray analysis will be used for comparison
with the solid state NMR spectra. That was the reason
why we decided not to constrain the N3-H3 bond and
allowed the H3 atom to refine freely. Our experience indicates
that unconstrained N-H distances better correlate with
the solid state NMR data.
|
PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.55 Ratio
| Author Response: ...
Allert refers to the terminal tert-butyl group
with the pivotal C24 atom.
The C25 atom is partially disordered. It can be
refined in two positions with SOF's 0.6 and 0.4, respectively.
However, remaining two methyl C26 and C27 atoms do not show signs of disorder.
Therefore, according to the Referee suggestion all tert-butyl atoms
i.e. C24, C25, C26 and C27 were refined in single sites with their
the SOF's equal 1.
|
PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 6.13 Ratio
| Author Response: ...
Displacement parameters of H atoms
were taken as 1.2 equivalent parameters of their parent carbon
atoms. Alert refers to H atoms bonded to C25 atom of the
terminal tert-butyl group. Ueq of the C25 is high due to
reasons explained in vrf_PLAT220_kkI.
|
PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C24
| Author Response: ...
C24 is the pivotal atom of the terminal tert-butyl group,
it is bonded to the C25 atom described in vrf_PLAT220_kkI.
|
Alert level B
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C19
| Author Response: ...
C24 is the pivotal atom of the terminal tert-butyl group,
it is bonded to the C25 atom described in vrf_PLAT220_kkI.
|
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 12
PLAT353_ALERT_3_B Long N-H Bond (0.87A) N3 - H3 ... 1.13 Ang.
Alert level C
REFLT03_ALERT_1_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 69.96
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 2805
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 3051
Completeness (_total/calc) 91.94%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.84
PLAT213_ALERT_2_C Atom C25 has ADP max/min Ratio ............. 3.90 prolat
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
| Author Response: ...
C24 is the pivotal atom of the terminal tert-butyl group,
it is bonded to the C25 atom described in vrf_PLAT220_kkI.
|
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
| Author Response: ...
C24 is the pivotal atom of the terminal tert-butyl group,
it is bonded to the C25 atom described in vrf_PLAT220_kkI.
|
PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3 ... ?
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 69.96
From the CIF: _reflns_number_total 2805
Count of symmetry unique reflns 3051
Completeness (_total/calc) 91.94%
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
4 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
7 ALERT type 2 Indicator that the structure model may be wrong or deficient
6 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: KM-4 Software (Kuma, 1991); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 1995); program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
(3
R,5S)-1-Benzyl 2-
tert-butyl
4-[
N,
N'-bis(
tert-butyloxycarbonyl)hydrazino]-5-oxopyrrolidine-1,5-dicarboxylate
top
Crystal data top
C27H39N3O9 | Dx = 1.200 Mg m−3 Dm = 1.17 Mg m−3 Dm measured by not measured |
Mr = 549.61 | Melting point: 372 K |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
a = 9.883 (2) Å | Cell parameters from 90 reflections |
b = 10.103 (2) Å | θ = 5–12° |
c = 15.892 (2) Å | µ = 0.75 mm−1 |
β = 106.59 (1)° | T = 293 K |
V = 1520.7 (5) Å3 | Prism, colourless |
Z = 2 | 0.5 × 0.2 × 0.1 mm |
F(000) = 588 | |
Data collection top
Kuma KM-4 diffractometer | 1442 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.058 |
Graphite monochromator | θmax = 70.0°, θmin = 2.9° |
ω–2θ scans | h = −12→11 |
Absorption correction: ψ scan (XPREP; Bruker, 2003) | k = −12→1 |
Tmin = 0.835, Tmax = 0.928 | l = −1→19 |
3512 measured reflections | 3 standard reflections every 100 reflections |
2805 independent reflections | intensity decay: 3% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.158 | w = 1/[σ2(Fo2) + (0.0812P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
2805 reflections | Δρmax = 0.24 e Å−3 |
358 parameters | Δρmin = −0.27 e Å−3 |
1 restraint | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0125 (14) |
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 goodness 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 | |
O1 | 0.3807 (5) | 0.8827 (5) | 1.1012 (3) | 0.0651 (12) | |
O2 | 0.3544 (5) | 0.6673 (5) | 1.0645 (3) | 0.0680 (12) | |
O3 | 0.3454 (5) | 0.6266 (5) | 0.8889 (3) | 0.0746 (14) | |
O4 | 0.5868 (4) | 0.8764 (5) | 0.6841 (3) | 0.0696 (13) | |
O5 | 0.7152 (4) | 0.6935 (5) | 0.7392 (3) | 0.0607 (12) | |
O6 | 0.1695 (4) | 0.8026 (6) | 0.6400 (3) | 0.0784 (16) | |
O7 | 0.3456 (4) | 0.6789 (6) | 0.6161 (3) | 0.0690 (13) | |
O8 | 0.1348 (4) | 0.9693 (5) | 0.9289 (3) | 0.0734 (15) | |
O9 | 0.2594 (4) | 1.1571 (4) | 0.9575 (3) | 0.0569 (11) | |
N1 | 0.3782 (5) | 0.8245 (5) | 0.9654 (3) | 0.0454 (12) | |
N2 | 0.3762 (4) | 0.7782 (6) | 0.7440 (3) | 0.0553 (14) | |
N3 | 0.5138 (4) | 0.7265 (6) | 0.7682 (3) | 0.0531 (13) | |
H3 | 0.514 (7) | 0.616 (8) | 0.779 (5) | 0.08 (2)* | |
C1 | 0.5092 (7) | 0.8001 (7) | 1.2473 (4) | 0.0581 (17) | |
C2 | 0.6362 (9) | 0.8628 (10) | 1.2495 (5) | 0.086 (2) | |
H21 | 0.6373 | 0.9353 | 1.2136 | 0.103* | |
C3 | 0.7604 (10) | 0.8148 (13) | 1.3061 (7) | 0.109 (3) | |
H31 | 0.8453 | 0.8571 | 1.3093 | 0.131* | |
C4 | 0.7597 (11) | 0.7081 (15) | 1.3563 (6) | 0.114 (4) | |
H41 | 0.8445 | 0.6761 | 1.3928 | 0.137* | |
C5 | 0.6352 (11) | 0.6453 (11) | 1.3547 (5) | 0.097 (3) | |
H51 | 0.6353 | 0.5735 | 1.3913 | 0.117* | |
C6 | 0.5121 (8) | 0.6896 (8) | 1.2989 (4) | 0.0698 (19) | |
H61 | 0.4285 | 0.6447 | 1.2955 | 0.084* | |
C7 | 0.3723 (7) | 0.8497 (9) | 1.1883 (4) | 0.0680 (19) | |
H71 | 0.3004 | 0.7824 | 1.1835 | 0.082* | |
H72 | 0.3436 | 0.9277 | 1.2145 | 0.082* | |
C8 | 0.3718 (6) | 0.7804 (7) | 1.0480 (4) | 0.0536 (15) | |
C9 | 0.3498 (6) | 0.7478 (7) | 0.8913 (4) | 0.0504 (15) | |
C10 | 0.3308 (6) | 0.8376 (7) | 0.8135 (4) | 0.0478 (15) | |
H101 | 0.2296 | 0.8564 | 0.7903 | 0.057* | |
C11 | 0.4029 (6) | 0.9649 (7) | 0.8534 (4) | 0.0504 (15) | |
H111 | 0.5023 | 0.9638 | 0.8563 | 0.060* | |
H112 | 0.3586 | 1.0413 | 0.8197 | 0.060* | |
C12 | 0.3834 (6) | 0.9666 (6) | 0.9449 (4) | 0.0431 (14) | |
H121 | 0.4630 | 1.0103 | 0.9870 | 0.038 (14)* | |
C13 | 0.6045 (6) | 0.7779 (7) | 0.7242 (4) | 0.0504 (15) | |
C14 | 0.8345 (6) | 0.7251 (8) | 0.7018 (4) | 0.0626 (19) | |
C15 | 0.8964 (7) | 0.8592 (10) | 0.7331 (6) | 0.084 (3) | |
H151 | 0.8250 | 0.9259 | 0.7140 | 0.101* | |
H152 | 0.9734 | 0.8774 | 0.7092 | 0.101* | |
H153 | 0.9301 | 0.8594 | 0.7961 | 0.101* | |
C16 | 0.7818 (7) | 0.7146 (10) | 0.6046 (4) | 0.087 (3) | |
H161 | 0.7158 | 0.7846 | 0.5821 | 0.105* | |
H162 | 0.7360 | 0.6307 | 0.5889 | 0.105* | |
H163 | 0.8598 | 0.7216 | 0.5801 | 0.105* | |
C17 | 0.9347 (8) | 0.6134 (10) | 0.7385 (6) | 0.097 (3) | |
H171 | 0.9682 | 0.6213 | 0.8012 | 0.117* | |
H172 | 1.0133 | 0.6172 | 0.7144 | 0.117* | |
H173 | 0.8866 | 0.5304 | 0.7233 | 0.117* | |
C18 | 0.2865 (6) | 0.7554 (7) | 0.6633 (4) | 0.0578 (17) | |
C19 | 0.2778 (7) | 0.6536 (10) | 0.5217 (5) | 0.077 (2) | |
C20 | 0.2656 (15) | 0.7807 (14) | 0.4744 (7) | 0.146 (5) | |
H201 | 0.3534 | 0.8277 | 0.4937 | 0.176* | |
H202 | 0.1919 | 0.8328 | 0.4862 | 0.176* | |
H203 | 0.2435 | 0.7641 | 0.4125 | 0.176* | |
C21 | 0.1423 (8) | 0.5786 (12) | 0.5106 (6) | 0.108 (3) | |
H211 | 0.1586 | 0.5058 | 0.5511 | 0.130* | |
H212 | 0.1092 | 0.5455 | 0.4516 | 0.130* | |
H213 | 0.0725 | 0.6365 | 0.5219 | 0.130* | |
C22 | 0.3845 (9) | 0.5645 (13) | 0.4984 (6) | 0.116 (4) | |
H221 | 0.3891 | 0.4816 | 0.5286 | 0.139* | |
H222 | 0.4757 | 0.6061 | 0.5156 | 0.139* | |
H223 | 0.3566 | 0.5492 | 0.4362 | 0.139* | |
C23 | 0.2439 (6) | 1.0313 (6) | 0.9442 (4) | 0.0459 (14) | |
C24 | 0.1384 (6) | 1.2457 (6) | 0.9578 (6) | 0.067 (2) | |
C25 | 0.2072 (10) | 1.3770 (9) | 0.9806 (12) | 0.194 (8) | |
H251 | 0.1418 | 1.4376 | 0.9942 | 0.233* | |
H252 | 0.2356 | 1.4101 | 0.9316 | 0.233* | |
H253 | 0.2887 | 1.3680 | 1.0305 | 0.233* | |
C26 | 0.0369 (10) | 1.2441 (12) | 0.8676 (6) | 0.127 (4) | |
H261 | −0.0164 | 1.1633 | 0.8593 | 0.153* | |
H262 | 0.0882 | 1.2499 | 0.8248 | 0.153* | |
H263 | −0.0262 | 1.3181 | 0.8610 | 0.153* | |
C27 | 0.0708 (8) | 1.1984 (11) | 1.0257 (6) | 0.102 (3) | |
H271 | 0.0113 | 1.1238 | 1.0032 | 0.123* | |
H272 | 0.0152 | 1.2684 | 1.0396 | 0.123* | |
H273 | 0.1428 | 1.1726 | 1.0777 | 0.123* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.087 (3) | 0.055 (3) | 0.058 (3) | 0.008 (3) | 0.028 (2) | −0.001 (3) |
O2 | 0.082 (3) | 0.047 (3) | 0.081 (3) | 0.003 (2) | 0.033 (3) | 0.007 (3) |
O3 | 0.093 (4) | 0.050 (3) | 0.089 (4) | −0.006 (3) | 0.040 (3) | −0.015 (3) |
O4 | 0.052 (2) | 0.070 (3) | 0.094 (4) | 0.007 (2) | 0.032 (2) | 0.012 (3) |
O5 | 0.0431 (19) | 0.074 (3) | 0.076 (3) | 0.015 (2) | 0.0352 (19) | 0.010 (3) |
O6 | 0.051 (2) | 0.120 (4) | 0.063 (3) | 0.015 (3) | 0.015 (2) | −0.019 (3) |
O7 | 0.052 (2) | 0.097 (4) | 0.063 (3) | −0.005 (3) | 0.025 (2) | −0.021 (3) |
O8 | 0.044 (2) | 0.062 (3) | 0.119 (4) | −0.010 (2) | 0.030 (3) | −0.020 (3) |
O9 | 0.048 (2) | 0.039 (2) | 0.091 (3) | 0.0065 (19) | 0.032 (2) | 0.002 (2) |
N1 | 0.049 (2) | 0.047 (3) | 0.043 (3) | 0.001 (2) | 0.017 (2) | −0.004 (2) |
N2 | 0.035 (2) | 0.083 (4) | 0.051 (3) | 0.008 (3) | 0.016 (2) | −0.010 (3) |
N3 | 0.036 (2) | 0.069 (4) | 0.062 (3) | 0.005 (3) | 0.027 (2) | −0.004 (3) |
C1 | 0.074 (4) | 0.061 (4) | 0.049 (4) | −0.007 (4) | 0.032 (3) | −0.005 (3) |
C2 | 0.087 (5) | 0.099 (7) | 0.077 (5) | −0.016 (5) | 0.033 (5) | 0.004 (5) |
C3 | 0.079 (6) | 0.152 (10) | 0.095 (6) | −0.015 (7) | 0.021 (5) | −0.007 (8) |
C4 | 0.096 (7) | 0.175 (12) | 0.062 (5) | 0.035 (8) | 0.007 (5) | 0.005 (7) |
C5 | 0.117 (7) | 0.119 (8) | 0.053 (4) | 0.013 (7) | 0.018 (5) | 0.012 (5) |
C6 | 0.089 (5) | 0.068 (5) | 0.055 (4) | −0.010 (4) | 0.025 (4) | 0.005 (4) |
C7 | 0.076 (4) | 0.086 (5) | 0.051 (4) | 0.005 (4) | 0.034 (3) | 0.003 (4) |
C8 | 0.047 (3) | 0.053 (4) | 0.063 (4) | 0.007 (3) | 0.017 (3) | −0.002 (4) |
C9 | 0.046 (3) | 0.055 (5) | 0.058 (4) | −0.002 (3) | 0.027 (3) | −0.005 (3) |
C10 | 0.039 (3) | 0.063 (4) | 0.048 (3) | 0.002 (3) | 0.022 (3) | −0.005 (3) |
C11 | 0.042 (3) | 0.054 (4) | 0.063 (4) | 0.000 (3) | 0.028 (3) | −0.002 (3) |
C12 | 0.040 (3) | 0.043 (3) | 0.050 (3) | 0.003 (3) | 0.019 (3) | 0.004 (3) |
C13 | 0.044 (3) | 0.054 (4) | 0.052 (4) | 0.009 (3) | 0.013 (3) | −0.003 (3) |
C14 | 0.041 (3) | 0.086 (5) | 0.073 (4) | 0.016 (4) | 0.035 (3) | 0.012 (4) |
C15 | 0.048 (4) | 0.115 (7) | 0.097 (6) | −0.001 (4) | 0.032 (4) | −0.005 (5) |
C16 | 0.066 (4) | 0.132 (8) | 0.075 (5) | 0.003 (5) | 0.037 (4) | −0.004 (5) |
C17 | 0.070 (4) | 0.130 (8) | 0.111 (6) | 0.043 (5) | 0.056 (5) | 0.031 (6) |
C18 | 0.049 (3) | 0.072 (5) | 0.060 (4) | 0.001 (4) | 0.028 (3) | −0.013 (4) |
C19 | 0.072 (4) | 0.109 (7) | 0.055 (4) | −0.019 (5) | 0.024 (3) | −0.022 (5) |
C20 | 0.230 (13) | 0.145 (11) | 0.082 (7) | 0.007 (10) | 0.074 (8) | 0.013 (7) |
C21 | 0.073 (5) | 0.160 (9) | 0.089 (6) | −0.034 (6) | 0.018 (4) | −0.039 (6) |
C22 | 0.094 (6) | 0.162 (10) | 0.108 (7) | −0.022 (6) | 0.055 (6) | −0.074 (7) |
C23 | 0.042 (3) | 0.051 (4) | 0.048 (3) | −0.002 (3) | 0.017 (3) | 0.003 (3) |
C24 | 0.047 (3) | 0.037 (3) | 0.123 (6) | 0.011 (3) | 0.033 (4) | 0.001 (4) |
C25 | 0.095 (7) | 0.037 (5) | 0.47 (3) | −0.001 (5) | 0.105 (11) | −0.040 (10) |
C26 | 0.094 (6) | 0.155 (10) | 0.129 (8) | 0.064 (7) | 0.025 (6) | 0.057 (8) |
C27 | 0.094 (5) | 0.127 (8) | 0.107 (6) | 0.018 (6) | 0.061 (5) | −0.018 (6) |
Geometric parameters (Å, º) top
O1—C8 | 1.322 (8) | N3—H3 | 1.13 (8) |
O2—C8 | 1.196 (8) | C2—H21 | 0.93 |
O3—C9 | 1.225 (8) | C3—H31 | 0.93 |
O4—C13 | 1.167 (8) | C4—H41 | 0.93 |
O5—C13 | 1.354 (7) | C5—H51 | 0.93 |
O6—C18 | 1.206 (7) | C6—H61 | 0.93 |
O7—C18 | 1.323 (7) | C7—H71 | 0.97 |
O8—C23 | 1.207 (7) | C7—H72 | 0.97 |
O9—C23 | 1.290 (7) | C10—H101 | 0.98 |
N1—C9 | 1.370 (8) | C11—H111 | 0.97 |
N1—C8 | 1.404 (8) | C11—H112 | 0.97 |
N1—C12 | 1.476 (8) | C12—H121 | 0.98 |
N2—C18 | 1.355 (7) | C15—H151 | 0.96 |
N2—N3 | 1.404 (6) | C15—H152 | 0.96 |
N2—C10 | 1.436 (7) | C15—H153 | 0.96 |
N3—C13 | 1.386 (8) | C16—H161 | 0.96 |
C9—C10 | 1.502 (9) | C16—H162 | 0.96 |
C10—C11 | 1.518 (9) | C16—H163 | 0.96 |
C11—C12 | 1.521 (8) | C17—H171 | 0.96 |
C12—C23 | 1.523 (8) | C17—H172 | 0.96 |
O1—C7 | 1.450 (7) | C17—H173 | 0.96 |
O5—C14 | 1.498 (6) | C20—H201 | 0.96 |
O7—C19 | 1.480 (8) | C20—H202 | 0.96 |
O9—C24 | 1.495 (7) | C20—H203 | 0.96 |
C1—C6 | 1.385 (10) | C21—H211 | 0.96 |
C1—C2 | 1.397 (10) | C21—H212 | 0.96 |
C1—C7 | 1.495 (9) | C21—H213 | 0.96 |
C2—C3 | 1.386 (13) | C22—H221 | 0.96 |
C3—C4 | 1.343 (16) | C22—H222 | 0.96 |
C4—C5 | 1.378 (14) | C22—H223 | 0.96 |
C5—C6 | 1.360 (11) | C25—H251 | 0.96 |
C14—C16 | 1.486 (9) | C25—H252 | 0.96 |
C14—C15 | 1.511 (12) | C25—H253 | 0.96 |
C14—C17 | 1.505 (10) | C26—H261 | 0.96 |
C19—C20 | 1.475 (15) | C26—H262 | 0.96 |
C19—C21 | 1.505 (11) | C26—H263 | 0.96 |
C19—C22 | 1.512 (12) | C27—H271 | 0.96 |
C24—C25 | 1.487 (11) | C27—H272 | 0.96 |
C24—C26 | 1.497 (12) | C27—H273 | 0.96 |
C24—C27 | 1.500 (11) | | |
| | | |
C8—O1—C7 | 114.8 (6) | C14—C15—H152 | 109.5 |
C13—O5—C14 | 118.9 (5) | H151—C15—H152 | 109.5 |
C18—O7—C19 | 121.9 (5) | C14—C15—H153 | 109.5 |
C23—O9—C24 | 122.2 (5) | H151—C15—H153 | 109.5 |
C9—N1—C8 | 124.8 (6) | H152—C15—H153 | 109.5 |
C9—N1—C12 | 111.9 (5) | C14—C16—H161 | 109.5 |
C8—N1—C12 | 121.9 (5) | C14—C16—H162 | 109.5 |
C18—N2—N3 | 121.1 (5) | H161—C16—H162 | 109.5 |
C18—N2—C10 | 122.4 (4) | C14—C16—H163 | 109.5 |
N3—N2—C10 | 115.8 (4) | H161—C16—H163 | 109.5 |
C13—N3—N2 | 116.0 (5) | H162—C16—H163 | 109.5 |
C13—N3—H3 | 118 (4) | C14—C17—H171 | 109.5 |
N2—N3—H3 | 112 (3) | C14—C17—H172 | 109.5 |
C6—C1—C2 | 119.0 (7) | H171—C17—H172 | 109.5 |
C6—C1—C7 | 120.3 (6) | C14—C17—H173 | 109.5 |
C2—C1—C7 | 120.7 (7) | H171—C17—H173 | 109.5 |
C3—C2—C1 | 118.8 (9) | H172—C17—H173 | 109.5 |
C3—C2—H21 | 120.6 | O6—C18—O7 | 126.7 (6) |
C1—C2—H21 | 120.6 | O6—C18—N2 | 122.2 (6) |
C4—C3—C2 | 120.9 (10) | O7—C18—N2 | 111.1 (5) |
C4—C3—H31 | 119.6 | C20—C19—O7 | 108.3 (7) |
C2—C3—H31 | 119.6 | C20—C19—C21 | 116.0 (9) |
C3—C4—C5 | 120.9 (10) | O7—C19—C21 | 109.7 (6) |
C3—C4—H41 | 119.5 | C20—C19—C22 | 110.7 (8) |
C5—C4—H41 | 119.5 | O7—C19—C22 | 101.9 (6) |
C6—C5—C4 | 119.3 (9) | C21—C19—C22 | 109.3 (9) |
C6—C5—H51 | 120.4 | C19—C20—H201 | 109.5 |
C4—C5—H51 | 120.4 | C19—C20—H202 | 109.5 |
C5—C6—C1 | 121.1 (8) | H201—C20—H202 | 109.5 |
C5—C6—H61 | 119.5 | C19—C20—H203 | 109.5 |
C1—C6—H61 | 119.5 | H201—C20—H203 | 109.5 |
O1—C7—C1 | 112.8 (5) | H202—C20—H203 | 109.5 |
O1—C7—H71 | 109.0 | C19—C21—H211 | 109.5 |
C1—C7—H71 | 109.0 | C19—C21—H212 | 109.5 |
O1—C7—H72 | 109.0 | H211—C21—H212 | 109.5 |
C1—C7—H72 | 109.0 | C19—C21—H213 | 109.5 |
H71—C7—H72 | 107.8 | H211—C21—H213 | 109.5 |
O2—C8—O1 | 126.4 (6) | H212—C21—H213 | 109.5 |
O2—C8—N1 | 123.7 (6) | C19—C22—H221 | 109.5 |
O1—C8—N1 | 109.7 (6) | C19—C22—H222 | 109.5 |
O3—C9—N1 | 126.1 (6) | H221—C22—H222 | 109.5 |
O3—C9—C10 | 125.7 (6) | C19—C22—H223 | 109.5 |
N1—C9—C10 | 108.2 (6) | H221—C22—H223 | 109.5 |
N2—C10—C9 | 112.8 (5) | H222—C22—H223 | 109.5 |
N2—C10—C11 | 117.6 (5) | O8—C23—O9 | 126.9 (6) |
C9—C10—C11 | 103.5 (5) | O8—C23—C12 | 122.1 (6) |
N2—C10—H101 | 107.5 | O9—C23—C12 | 110.9 (5) |
C9—C10—H101 | 107.5 | C26—C24—O9 | 107.9 (6) |
C11—C10—H101 | 107.5 | C26—C24—C27 | 111.8 (7) |
C12—C11—C10 | 103.7 (5) | O9—C24—C27 | 109.4 (6) |
C12—C11—H111 | 111.0 | C26—C24—C25 | 112.2 (10) |
C10—C11—H111 | 111.0 | O9—C24—C25 | 103.0 (5) |
C12—C11—H112 | 111.0 | C27—C24—C25 | 112.1 (9) |
C10—C11—H112 | 111.0 | C24—C25—H251 | 109.5 |
H111—C11—H112 | 109.0 | C24—C25—H252 | 109.5 |
N1—C12—C11 | 102.8 (5) | H251—C25—H252 | 109.5 |
N1—C12—C23 | 109.3 (5) | C24—C25—H253 | 109.5 |
C11—C12—C23 | 111.1 (5) | H251—C25—H253 | 109.5 |
N1—C12—H121 | 111.1 | H252—C25—H253 | 109.5 |
C11—C12—H121 | 111.1 | C24—C26—H261 | 109.5 |
C23—C12—H121 | 111.1 | C24—C26—H262 | 109.5 |
O4—C13—O5 | 128.4 (6) | H261—C26—H262 | 109.5 |
O4—C13—N3 | 125.2 (6) | C26—C26—H263 | 109.5 |
O5—C13—N3 | 106.4 (6) | H261—C26—H263 | 109.5 |
C16—C14—O5 | 108.4 (5) | H262—C26—H263 | 109.5 |
C16—C14—C17 | 110.2 (7) | C24—C27—H271 | 109.5 |
O5—C14—C17 | 101.0 (5) | C24—C27—H272 | 109.5 |
C16—C14—C15 | 113.3 (7) | H271—C27—H272 | 109.5 |
O5—C14—C15 | 110.5 (5) | C24—C27—H273 | 109.5 |
C17—C14—C15 | 112.6 (6) | H271—C27—H273 | 109.5 |
C14—C15—H151 | 109.5 | H272—C27—H273 | 109.5 |
| | | |
O1—C8—N1—C12 | −4.0 (7) | C9—C10—N2—C18 | 117.9 (6) |
O1—C8—N1—C9 | −169.1 (5) | N2—N3—C13—O5 | −164.3 (5) |
C8—N1—C12—C11 | 174.9 (5) | N3—C13—O5—C14 | −178.2 (5) |
C8—N1—C12—C23 | −67.0 (7) | C10—N2—N3—C13 | −122.1 (6) |
C8—N1—C9—O3 | −17.0 (9) | C1—C7—O1—C8 | 80.3 (7) |
C8—N1—C9—C10 | 165.3 (5) | N1—C9—C10—C11 | 20.0 (5) |
N1—C12—C23—O9 | 157.4 (5) | C9—C10—C11—C12 | −30.3 (5) |
C12—C23—O9—C24 | 178.4 (5) | C10—C11—C12—N1 | 29.4 (5) |
O7—C18—N2—C10 | −168.5 (6) | C11—C12—N1—C9 | −18.2 (6) |
N2—C18—O7—C19 | −171.6 (6) | C12—N1—C9—C10 | −1.1 (6) |