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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003880/bt6586sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003880/bt6586Isup2.hkl
Contains datablock I

CCDC reference: 269369

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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.

(3R,5S)-1-Benzyl 2-tert-butyl 4-[N,N'-bis(tert-butyloxycarbonyl)hydrazino]-5-oxopyrrolidine-1,5-dicarboxylate top
Crystal data top
C27H39N3O9Dx = 1.200 Mg m3
Dm = 1.17 Mg m3
Dm measured by not measured
Mr = 549.61Melting point: 372 K
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
a = 9.883 (2) ÅCell parameters from 90 reflections
b = 10.103 (2) Åθ = 5–12°
c = 15.892 (2) ŵ = 0.75 mm1
β = 106.59 (1)°T = 293 K
V = 1520.7 (5) Å3Prism, colourless
Z = 20.5 × 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 tubeRint = 0.058
Graphite monochromatorθmax = 70.0°, θmin = 2.9°
ω–2θ scansh = 1211
Absorption correction: ψ scan
(XPREP; Bruker, 2003)
k = 121
Tmin = 0.835, Tmax = 0.928l = 119
3512 measured reflections3 standard reflections every 100 reflections
2805 independent reflections intensity decay: 3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H 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 reflectionsΔρmax = 0.24 e Å3
358 parametersΔρmin = 0.27 e Å3
1 restraintExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
O10.3807 (5)0.8827 (5)1.1012 (3)0.0651 (12)
O20.3544 (5)0.6673 (5)1.0645 (3)0.0680 (12)
O30.3454 (5)0.6266 (5)0.8889 (3)0.0746 (14)
O40.5868 (4)0.8764 (5)0.6841 (3)0.0696 (13)
O50.7152 (4)0.6935 (5)0.7392 (3)0.0607 (12)
O60.1695 (4)0.8026 (6)0.6400 (3)0.0784 (16)
O70.3456 (4)0.6789 (6)0.6161 (3)0.0690 (13)
O80.1348 (4)0.9693 (5)0.9289 (3)0.0734 (15)
O90.2594 (4)1.1571 (4)0.9575 (3)0.0569 (11)
N10.3782 (5)0.8245 (5)0.9654 (3)0.0454 (12)
N20.3762 (4)0.7782 (6)0.7440 (3)0.0553 (14)
N30.5138 (4)0.7265 (6)0.7682 (3)0.0531 (13)
H30.514 (7)0.616 (8)0.779 (5)0.08 (2)*
C10.5092 (7)0.8001 (7)1.2473 (4)0.0581 (17)
C20.6362 (9)0.8628 (10)1.2495 (5)0.086 (2)
H210.63730.93531.21360.103*
C30.7604 (10)0.8148 (13)1.3061 (7)0.109 (3)
H310.84530.85711.30930.131*
C40.7597 (11)0.7081 (15)1.3563 (6)0.114 (4)
H410.84450.67611.39280.137*
C50.6352 (11)0.6453 (11)1.3547 (5)0.097 (3)
H510.63530.57351.39130.117*
C60.5121 (8)0.6896 (8)1.2989 (4)0.0698 (19)
H610.42850.64471.29550.084*
C70.3723 (7)0.8497 (9)1.1883 (4)0.0680 (19)
H710.30040.78241.18350.082*
H720.34360.92771.21450.082*
C80.3718 (6)0.7804 (7)1.0480 (4)0.0536 (15)
C90.3498 (6)0.7478 (7)0.8913 (4)0.0504 (15)
C100.3308 (6)0.8376 (7)0.8135 (4)0.0478 (15)
H1010.22960.85640.79030.057*
C110.4029 (6)0.9649 (7)0.8534 (4)0.0504 (15)
H1110.50230.96380.85630.060*
H1120.35861.04130.81970.060*
C120.3834 (6)0.9666 (6)0.9449 (4)0.0431 (14)
H1210.46301.01030.98700.038 (14)*
C130.6045 (6)0.7779 (7)0.7242 (4)0.0504 (15)
C140.8345 (6)0.7251 (8)0.7018 (4)0.0626 (19)
C150.8964 (7)0.8592 (10)0.7331 (6)0.084 (3)
H1510.82500.92590.71400.101*
H1520.97340.87740.70920.101*
H1530.93010.85940.79610.101*
C160.7818 (7)0.7146 (10)0.6046 (4)0.087 (3)
H1610.71580.78460.58210.105*
H1620.73600.63070.58890.105*
H1630.85980.72160.58010.105*
C170.9347 (8)0.6134 (10)0.7385 (6)0.097 (3)
H1710.96820.62130.80120.117*
H1721.01330.61720.71440.117*
H1730.88660.53040.72330.117*
C180.2865 (6)0.7554 (7)0.6633 (4)0.0578 (17)
C190.2778 (7)0.6536 (10)0.5217 (5)0.077 (2)
C200.2656 (15)0.7807 (14)0.4744 (7)0.146 (5)
H2010.35340.82770.49370.176*
H2020.19190.83280.48620.176*
H2030.24350.76410.41250.176*
C210.1423 (8)0.5786 (12)0.5106 (6)0.108 (3)
H2110.15860.50580.55110.130*
H2120.10920.54550.45160.130*
H2130.07250.63650.52190.130*
C220.3845 (9)0.5645 (13)0.4984 (6)0.116 (4)
H2210.38910.48160.52860.139*
H2220.47570.60610.51560.139*
H2230.35660.54920.43620.139*
C230.2439 (6)1.0313 (6)0.9442 (4)0.0459 (14)
C240.1384 (6)1.2457 (6)0.9578 (6)0.067 (2)
C250.2072 (10)1.3770 (9)0.9806 (12)0.194 (8)
H2510.14181.43760.99420.233*
H2520.23561.41010.93160.233*
H2530.28871.36801.03050.233*
C260.0369 (10)1.2441 (12)0.8676 (6)0.127 (4)
H2610.01641.16330.85930.153*
H2620.08821.24990.82480.153*
H2630.02621.31810.86100.153*
C270.0708 (8)1.1984 (11)1.0257 (6)0.102 (3)
H2710.01131.12381.00320.123*
H2720.01521.26841.03960.123*
H2730.14281.17261.07770.123*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.087 (3)0.055 (3)0.058 (3)0.008 (3)0.028 (2)0.001 (3)
O20.082 (3)0.047 (3)0.081 (3)0.003 (2)0.033 (3)0.007 (3)
O30.093 (4)0.050 (3)0.089 (4)0.006 (3)0.040 (3)0.015 (3)
O40.052 (2)0.070 (3)0.094 (4)0.007 (2)0.032 (2)0.012 (3)
O50.0431 (19)0.074 (3)0.076 (3)0.015 (2)0.0352 (19)0.010 (3)
O60.051 (2)0.120 (4)0.063 (3)0.015 (3)0.015 (2)0.019 (3)
O70.052 (2)0.097 (4)0.063 (3)0.005 (3)0.025 (2)0.021 (3)
O80.044 (2)0.062 (3)0.119 (4)0.010 (2)0.030 (3)0.020 (3)
O90.048 (2)0.039 (2)0.091 (3)0.0065 (19)0.032 (2)0.002 (2)
N10.049 (2)0.047 (3)0.043 (3)0.001 (2)0.017 (2)0.004 (2)
N20.035 (2)0.083 (4)0.051 (3)0.008 (3)0.016 (2)0.010 (3)
N30.036 (2)0.069 (4)0.062 (3)0.005 (3)0.027 (2)0.004 (3)
C10.074 (4)0.061 (4)0.049 (4)0.007 (4)0.032 (3)0.005 (3)
C20.087 (5)0.099 (7)0.077 (5)0.016 (5)0.033 (5)0.004 (5)
C30.079 (6)0.152 (10)0.095 (6)0.015 (7)0.021 (5)0.007 (8)
C40.096 (7)0.175 (12)0.062 (5)0.035 (8)0.007 (5)0.005 (7)
C50.117 (7)0.119 (8)0.053 (4)0.013 (7)0.018 (5)0.012 (5)
C60.089 (5)0.068 (5)0.055 (4)0.010 (4)0.025 (4)0.005 (4)
C70.076 (4)0.086 (5)0.051 (4)0.005 (4)0.034 (3)0.003 (4)
C80.047 (3)0.053 (4)0.063 (4)0.007 (3)0.017 (3)0.002 (4)
C90.046 (3)0.055 (5)0.058 (4)0.002 (3)0.027 (3)0.005 (3)
C100.039 (3)0.063 (4)0.048 (3)0.002 (3)0.022 (3)0.005 (3)
C110.042 (3)0.054 (4)0.063 (4)0.000 (3)0.028 (3)0.002 (3)
C120.040 (3)0.043 (3)0.050 (3)0.003 (3)0.019 (3)0.004 (3)
C130.044 (3)0.054 (4)0.052 (4)0.009 (3)0.013 (3)0.003 (3)
C140.041 (3)0.086 (5)0.073 (4)0.016 (4)0.035 (3)0.012 (4)
C150.048 (4)0.115 (7)0.097 (6)0.001 (4)0.032 (4)0.005 (5)
C160.066 (4)0.132 (8)0.075 (5)0.003 (5)0.037 (4)0.004 (5)
C170.070 (4)0.130 (8)0.111 (6)0.043 (5)0.056 (5)0.031 (6)
C180.049 (3)0.072 (5)0.060 (4)0.001 (4)0.028 (3)0.013 (4)
C190.072 (4)0.109 (7)0.055 (4)0.019 (5)0.024 (3)0.022 (5)
C200.230 (13)0.145 (11)0.082 (7)0.007 (10)0.074 (8)0.013 (7)
C210.073 (5)0.160 (9)0.089 (6)0.034 (6)0.018 (4)0.039 (6)
C220.094 (6)0.162 (10)0.108 (7)0.022 (6)0.055 (6)0.074 (7)
C230.042 (3)0.051 (4)0.048 (3)0.002 (3)0.017 (3)0.003 (3)
C240.047 (3)0.037 (3)0.123 (6)0.011 (3)0.033 (4)0.001 (4)
C250.095 (7)0.037 (5)0.47 (3)0.001 (5)0.105 (11)0.040 (10)
C260.094 (6)0.155 (10)0.129 (8)0.064 (7)0.025 (6)0.057 (8)
C270.094 (5)0.127 (8)0.107 (6)0.018 (6)0.061 (5)0.018 (6)
Geometric parameters (Å, º) top
O1—C81.322 (8)N3—H31.13 (8)
O2—C81.196 (8)C2—H210.93
O3—C91.225 (8)C3—H310.93
O4—C131.167 (8)C4—H410.93
O5—C131.354 (7)C5—H510.93
O6—C181.206 (7)C6—H610.93
O7—C181.323 (7)C7—H710.97
O8—C231.207 (7)C7—H720.97
O9—C231.290 (7)C10—H1010.98
N1—C91.370 (8)C11—H1110.97
N1—C81.404 (8)C11—H1120.97
N1—C121.476 (8)C12—H1210.98
N2—C181.355 (7)C15—H1510.96
N2—N31.404 (6)C15—H1520.96
N2—C101.436 (7)C15—H1530.96
N3—C131.386 (8)C16—H1610.96
C9—C101.502 (9)C16—H1620.96
C10—C111.518 (9)C16—H1630.96
C11—C121.521 (8)C17—H1710.96
C12—C231.523 (8)C17—H1720.96
O1—C71.450 (7)C17—H1730.96
O5—C141.498 (6)C20—H2010.96
O7—C191.480 (8)C20—H2020.96
O9—C241.495 (7)C20—H2030.96
C1—C61.385 (10)C21—H2110.96
C1—C21.397 (10)C21—H2120.96
C1—C71.495 (9)C21—H2130.96
C2—C31.386 (13)C22—H2210.96
C3—C41.343 (16)C22—H2220.96
C4—C51.378 (14)C22—H2230.96
C5—C61.360 (11)C25—H2510.96
C14—C161.486 (9)C25—H2520.96
C14—C151.511 (12)C25—H2530.96
C14—C171.505 (10)C26—H2610.96
C19—C201.475 (15)C26—H2620.96
C19—C211.505 (11)C26—H2630.96
C19—C221.512 (12)C27—H2710.96
C24—C251.487 (11)C27—H2720.96
C24—C261.497 (12)C27—H2730.96
C24—C271.500 (11)
C8—O1—C7114.8 (6)C14—C15—H152109.5
C13—O5—C14118.9 (5)H151—C15—H152109.5
C18—O7—C19121.9 (5)C14—C15—H153109.5
C23—O9—C24122.2 (5)H151—C15—H153109.5
C9—N1—C8124.8 (6)H152—C15—H153109.5
C9—N1—C12111.9 (5)C14—C16—H161109.5
C8—N1—C12121.9 (5)C14—C16—H162109.5
C18—N2—N3121.1 (5)H161—C16—H162109.5
C18—N2—C10122.4 (4)C14—C16—H163109.5
N3—N2—C10115.8 (4)H161—C16—H163109.5
C13—N3—N2116.0 (5)H162—C16—H163109.5
C13—N3—H3118 (4)C14—C17—H171109.5
N2—N3—H3112 (3)C14—C17—H172109.5
C6—C1—C2119.0 (7)H171—C17—H172109.5
C6—C1—C7120.3 (6)C14—C17—H173109.5
C2—C1—C7120.7 (7)H171—C17—H173109.5
C3—C2—C1118.8 (9)H172—C17—H173109.5
C3—C2—H21120.6O6—C18—O7126.7 (6)
C1—C2—H21120.6O6—C18—N2122.2 (6)
C4—C3—C2120.9 (10)O7—C18—N2111.1 (5)
C4—C3—H31119.6C20—C19—O7108.3 (7)
C2—C3—H31119.6C20—C19—C21116.0 (9)
C3—C4—C5120.9 (10)O7—C19—C21109.7 (6)
C3—C4—H41119.5C20—C19—C22110.7 (8)
C5—C4—H41119.5O7—C19—C22101.9 (6)
C6—C5—C4119.3 (9)C21—C19—C22109.3 (9)
C6—C5—H51120.4C19—C20—H201109.5
C4—C5—H51120.4C19—C20—H202109.5
C5—C6—C1121.1 (8)H201—C20—H202109.5
C5—C6—H61119.5C19—C20—H203109.5
C1—C6—H61119.5H201—C20—H203109.5
O1—C7—C1112.8 (5)H202—C20—H203109.5
O1—C7—H71109.0C19—C21—H211109.5
C1—C7—H71109.0C19—C21—H212109.5
O1—C7—H72109.0H211—C21—H212109.5
C1—C7—H72109.0C19—C21—H213109.5
H71—C7—H72107.8H211—C21—H213109.5
O2—C8—O1126.4 (6)H212—C21—H213109.5
O2—C8—N1123.7 (6)C19—C22—H221109.5
O1—C8—N1109.7 (6)C19—C22—H222109.5
O3—C9—N1126.1 (6)H221—C22—H222109.5
O3—C9—C10125.7 (6)C19—C22—H223109.5
N1—C9—C10108.2 (6)H221—C22—H223109.5
N2—C10—C9112.8 (5)H222—C22—H223109.5
N2—C10—C11117.6 (5)O8—C23—O9126.9 (6)
C9—C10—C11103.5 (5)O8—C23—C12122.1 (6)
N2—C10—H101107.5O9—C23—C12110.9 (5)
C9—C10—H101107.5C26—C24—O9107.9 (6)
C11—C10—H101107.5C26—C24—C27111.8 (7)
C12—C11—C10103.7 (5)O9—C24—C27109.4 (6)
C12—C11—H111111.0C26—C24—C25112.2 (10)
C10—C11—H111111.0O9—C24—C25103.0 (5)
C12—C11—H112111.0C27—C24—C25112.1 (9)
C10—C11—H112111.0C24—C25—H251109.5
H111—C11—H112109.0C24—C25—H252109.5
N1—C12—C11102.8 (5)H251—C25—H252109.5
N1—C12—C23109.3 (5)C24—C25—H253109.5
C11—C12—C23111.1 (5)H251—C25—H253109.5
N1—C12—H121111.1H252—C25—H253109.5
C11—C12—H121111.1C24—C26—H261109.5
C23—C12—H121111.1C24—C26—H262109.5
O4—C13—O5128.4 (6)H261—C26—H262109.5
O4—C13—N3125.2 (6)C26—C26—H263109.5
O5—C13—N3106.4 (6)H261—C26—H263109.5
C16—C14—O5108.4 (5)H262—C26—H263109.5
C16—C14—C17110.2 (7)C24—C27—H271109.5
O5—C14—C17101.0 (5)C24—C27—H272109.5
C16—C14—C15113.3 (7)H271—C27—H272109.5
O5—C14—C15110.5 (5)C24—C27—H273109.5
C17—C14—C15112.6 (6)H271—C27—H273109.5
C14—C15—H151109.5H272—C27—H273109.5
O1—C8—N1—C124.0 (7)C9—C10—N2—C18117.9 (6)
O1—C8—N1—C9169.1 (5)N2—N3—C13—O5164.3 (5)
C8—N1—C12—C11174.9 (5)N3—C13—O5—C14178.2 (5)
C8—N1—C12—C2367.0 (7)C10—N2—N3—C13122.1 (6)
C8—N1—C9—O317.0 (9)C1—C7—O1—C880.3 (7)
C8—N1—C9—C10165.3 (5)N1—C9—C10—C1120.0 (5)
N1—C12—C23—O9157.4 (5)C9—C10—C11—C1230.3 (5)
C12—C23—O9—C24178.4 (5)C10—C11—C12—N129.4 (5)
O7—C18—N2—C10168.5 (6)C11—C12—N1—C918.2 (6)
N2—C18—O7—C19171.6 (6)C12—N1—C9—C101.1 (6)
 

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