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The title pentapeptide, Boc0—Gly1–ΔZPhe2—Gly3–ΔEPhe4—Gly5—OMe, C30H35N5O8·2H2O, adopts the type I β-turn conformation for the ΔZPhe2—Gly3 residues. It is stabilized by a 4\rightarrow1 intramolecular hydrogen bond between the ΔEPhe4 NH and Gly1 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806002273/sg6057sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806002273/sg6057Isup2.hkl
Contains datablock I

CCDC reference: 298540

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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

Computing details top

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
C30H35N5O8·2H2OF(000) = 1336
Mr = 629.66Dx = 1.274 Mg m3
Orthorhombic, P 21 21 2Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2 2abCell parameters from 5475 reflections
a = 15.371 (4) Åθ = 3–73°
b = 23.889 (6) ŵ = 0.81 mm1
c = 8.940 (3) ÅT = 100 K
V = 3282.7 (16) Å3Needle, colourless
Z = 40.04 × 0.03 × 0.01 mm
Data collection top
Xcalibur PX κ-geometry
diffractometer CCD detector
3775 independent reflections
Radiation source: fine-focus sealed tube1835 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.146
ω and φ scansθmax = 76.7°, θmin = 3.4°
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2003)
h = 1915
Tmin = 0.910, Tmax = 0.983k = 3022
22419 measured reflectionsl = 910
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H 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 parametersΔρmax = 0.40 e Å3
4 restraintsΔρmin = 0.32 e Å3
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
xyzUiso*/UeqOcc. (<1)
C10.7579 (6)0.5031 (3)0.1559 (13)0.048 (3)
C20.8257 (5)0.5432 (3)0.2195 (12)0.058 (3)
H2A0.82230.54300.32900.086*
H2B0.88390.53130.18800.086*
H2C0.81430.58110.18240.086*
C30.7576 (8)0.5008 (4)0.0126 (10)0.069 (4)
H3A0.71250.47470.04630.103*
H3B0.74560.53810.05270.103*
H3C0.81460.48800.04820.103*
C4A0.6559 (11)0.5097 (7)0.1864 (19)0.029 (4)*0.50
H4A10.59690.49530.20230.043*0.50
H4A20.65340.54300.12230.043*0.50
H4A30.69140.48090.13800.043*0.50
C4B0.6757 (11)0.5174 (7)0.260 (2)0.039 (5)*0.50
H4B10.66350.48780.33350.058*0.50
H4B20.73880.52160.24890.058*0.50
H4B30.65080.55280.29560.058*0.50
O10.7760 (4)0.4441 (2)0.2208 (7)0.0435 (19)
O20.9111 (4)0.4382 (2)0.1193 (9)0.061 (2)
C50.8520 (6)0.4201 (3)0.1951 (12)0.033 (2)
O30.8417 (3)0.2565 (2)0.2510 (7)0.0256 (14)
N10.8562 (4)0.3704 (2)0.2660 (9)0.034 (2)
H10.81040.35790.31500.041*
C60.9355 (5)0.3370 (3)0.2624 (10)0.029 (2)
H6A0.97470.35140.18340.035*
H6B0.96600.34020.35960.035*
C70.9140 (5)0.2758 (3)0.2316 (10)0.027 (2)
N20.9834 (4)0.2460 (2)0.1819 (7)0.0236 (16)
H21.03400.26310.17520.028*
C80.9786 (5)0.1881 (3)0.1395 (9)0.0219 (18)
C160.8990 (5)0.1711 (3)0.0568 (10)0.026 (2)
O40.8645 (3)0.1247 (2)0.0785 (7)0.0321 (15)
C91.0444 (5)0.1527 (3)0.1501 (9)0.0213 (19)
H91.03440.11610.11220.026*
C101.1311 (5)0.1631 (3)0.2132 (10)0.028 (2)
C111.1445 (5)0.1909 (3)0.3478 (9)0.026 (2)
H11A1.09560.20640.39780.032*
C121.2269 (5)0.1972 (3)0.4136 (10)0.031 (2)
H12A1.23400.21470.50840.037*
C131.2970 (5)0.1770 (3)0.3343 (11)0.036 (2)
H13A1.35350.18120.37580.043*
C141.2889 (5)0.1512 (3)0.1985 (10)0.030 (2)
H14A1.33880.13930.14430.036*
C151.2039 (5)0.1424 (3)0.1406 (10)0.033 (2)
H15A1.19690.12200.05020.040*
N30.8699 (4)0.2065 (2)0.0507 (7)0.0213 (16)
H30.89580.23900.06280.026*
O50.6422 (3)0.1902 (2)0.1579 (6)0.0230 (13)
C170.7966 (4)0.1918 (3)0.1470 (9)0.0228 (19)
H17A0.80040.21450.23930.027*
H17B0.80270.15200.17640.027*
C180.7077 (5)0.1997 (3)0.0806 (9)0.0187 (18)
O60.4788 (3)0.1952 (2)0.1176 (6)0.0273 (14)
N40.7044 (4)0.2190 (3)0.0583 (8)0.0244 (17)
H40.75360.22410.10660.029*
C190.6249 (5)0.2322 (3)0.1338 (10)0.0220 (19)
C270.5574 (5)0.1871 (4)0.1370 (10)0.031 (2)
C200.6194 (5)0.2833 (3)0.1921 (9)0.025 (2)
H200.66600.30730.16430.030*
C210.5544 (5)0.3102 (4)0.2921 (10)0.029 (2)
C220.5621 (5)0.3682 (3)0.3053 (11)0.034 (2)
H22A0.60660.38700.25140.041*
C230.5048 (6)0.4000 (4)0.3978 (12)0.056 (3)
H23A0.51170.43930.40800.067*
C240.4382 (6)0.3717 (4)0.4732 (11)0.042 (3)
H24A0.39980.39180.53670.051*
C250.4282 (5)0.3146 (4)0.4556 (9)0.029 (2)
H25A0.38110.29580.50300.035*
C260.4868 (5)0.2846 (3)0.3686 (10)0.028 (2)
H26A0.48030.24520.36130.033*
O70.4980 (4)0.1059 (2)0.4190 (7)0.0357 (16)
C290.4849 (5)0.0808 (4)0.3049 (11)0.030 (2)
C280.5317 (5)0.0863 (3)0.1573 (10)0.033 (2)
H28A0.48860.09050.07560.040*
H28B0.56600.05200.13790.040*
N50.5894 (4)0.1349 (2)0.1591 (8)0.0248 (17)
H50.64540.13020.17470.030*
O80.4222 (3)0.0411 (2)0.2882 (7)0.0339 (16)
C300.3726 (5)0.0289 (3)0.4235 (10)0.041 (3)
H30A0.32930.00010.40200.061*
H30B0.41220.01560.50180.061*
H30C0.34320.06300.45770.061*
O90.7442 (4)0.1008 (3)0.3096 (8)0.0365 (17)
H9A0.787 (3)0.119 (3)0.270 (9)0.044*
H9B0.738 (5)0.115 (3)0.398 (4)0.044*
O100.6561 (4)0.1664 (3)0.4805 (8)0.0417 (18)
H10A0.609 (3)0.147 (3)0.481 (10)0.050*
H10B0.650 (6)0.173 (3)0.386 (2)0.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.048 (7)0.011 (4)0.084 (9)0.003 (4)0.014 (7)0.014 (6)
C20.077 (8)0.020 (5)0.075 (9)0.001 (5)0.022 (7)0.003 (6)
C30.115 (12)0.029 (6)0.063 (9)0.010 (7)0.010 (8)0.007 (7)
O10.027 (4)0.029 (3)0.074 (6)0.013 (3)0.021 (4)0.015 (4)
O20.055 (5)0.041 (4)0.088 (7)0.019 (4)0.042 (5)0.026 (4)
C50.030 (5)0.019 (4)0.051 (7)0.005 (4)0.006 (5)0.007 (4)
O30.015 (3)0.029 (3)0.032 (4)0.001 (3)0.002 (3)0.006 (3)
N10.020 (4)0.026 (4)0.055 (6)0.011 (3)0.019 (4)0.010 (4)
C60.023 (4)0.020 (4)0.045 (6)0.006 (4)0.006 (4)0.006 (4)
C70.026 (5)0.028 (4)0.026 (6)0.007 (4)0.007 (4)0.007 (4)
N20.009 (3)0.027 (4)0.034 (5)0.002 (3)0.006 (3)0.004 (3)
C80.022 (4)0.023 (4)0.020 (5)0.000 (4)0.003 (4)0.003 (4)
C160.023 (4)0.029 (5)0.025 (6)0.004 (4)0.008 (4)0.001 (4)
O40.021 (3)0.030 (3)0.045 (4)0.006 (3)0.001 (3)0.003 (3)
C90.019 (4)0.015 (4)0.030 (5)0.003 (3)0.003 (4)0.004 (4)
C100.015 (4)0.033 (5)0.035 (6)0.007 (4)0.000 (4)0.005 (4)
C110.029 (5)0.033 (5)0.017 (5)0.001 (4)0.006 (4)0.010 (4)
C120.028 (5)0.039 (5)0.026 (6)0.005 (4)0.003 (4)0.001 (4)
C130.023 (5)0.040 (5)0.046 (7)0.004 (4)0.008 (5)0.010 (5)
C140.020 (4)0.031 (5)0.039 (6)0.006 (4)0.003 (4)0.009 (5)
C150.026 (5)0.030 (5)0.042 (6)0.004 (4)0.000 (5)0.007 (5)
N30.014 (3)0.024 (4)0.025 (4)0.002 (3)0.001 (3)0.002 (3)
O50.012 (3)0.024 (3)0.033 (4)0.005 (2)0.003 (3)0.001 (3)
C170.014 (4)0.024 (4)0.031 (5)0.001 (4)0.002 (4)0.001 (4)
C180.023 (4)0.015 (4)0.018 (5)0.003 (4)0.007 (4)0.005 (3)
O60.011 (3)0.031 (3)0.040 (4)0.005 (3)0.004 (3)0.001 (3)
N40.008 (3)0.032 (4)0.034 (5)0.002 (3)0.000 (3)0.001 (4)
C190.010 (4)0.028 (4)0.028 (5)0.003 (3)0.004 (4)0.007 (4)
C270.016 (4)0.036 (5)0.040 (6)0.005 (4)0.001 (4)0.002 (5)
C200.021 (4)0.037 (5)0.018 (5)0.005 (4)0.003 (4)0.003 (4)
C210.018 (4)0.038 (5)0.030 (6)0.003 (4)0.000 (4)0.003 (5)
C220.033 (5)0.025 (5)0.044 (6)0.007 (4)0.016 (5)0.007 (5)
C230.047 (7)0.044 (6)0.076 (10)0.023 (5)0.027 (7)0.004 (6)
C240.026 (5)0.054 (7)0.047 (7)0.021 (5)0.001 (5)0.001 (6)
C250.017 (4)0.048 (6)0.021 (5)0.007 (4)0.000 (4)0.010 (5)
C260.009 (4)0.038 (5)0.037 (6)0.001 (4)0.006 (4)0.001 (4)
O70.031 (4)0.044 (4)0.033 (4)0.008 (3)0.001 (3)0.004 (3)
C290.014 (4)0.035 (5)0.040 (6)0.003 (4)0.004 (4)0.007 (5)
C280.028 (5)0.035 (5)0.037 (6)0.010 (4)0.010 (4)0.002 (5)
N50.019 (4)0.021 (3)0.035 (5)0.003 (3)0.003 (3)0.000 (3)
O80.024 (3)0.038 (4)0.040 (4)0.006 (3)0.010 (3)0.006 (3)
C300.047 (6)0.033 (5)0.042 (7)0.004 (5)0.016 (6)0.009 (5)
O90.023 (3)0.049 (4)0.038 (5)0.007 (3)0.005 (3)0.001 (4)
O100.033 (4)0.050 (4)0.042 (5)0.013 (3)0.004 (4)0.013 (4)
Geometric parameters (Å, º) top
C1—C31.507 (14)C14—H14A0.9500
C1—C21.526 (11)C15—H15A0.9500
C1—O11.549 (9)N3—C171.461 (8)
C1—C4A1.600 (18)N3—H30.88
C1—C4B1.61 (2)O5—C181.242 (9)
C2—H2A0.98C17—C181.501 (9)
C2—H2B0.98C17—H17A0.9900
C2—H2C0.98C17—H17B0.9900
C3—H3A0.98C18—N41.326 (10)
C3—H3B0.98O6—C271.236 (8)
C3—H3C0.98N4—C191.430 (9)
C4A—H4A10.98N4—H40.88
C4A—H4A20.98C19—C201.332 (10)
C4A—H4A30.98C19—C271.495 (10)
C4B—H4B10.98C27—N51.357 (9)
C4B—H4B20.98C20—C211.486 (10)
C4B—H4B30.98C20—H200.9500
O1—C51.321 (9)C21—C261.386 (10)
O2—C51.214 (10)C21—C221.396 (10)
C5—N11.347 (9)C22—C231.426 (11)
O3—C71.216 (8)C22—H22A0.9500
N1—C61.457 (8)C23—C241.399 (12)
N1—H10.88C23—H23A0.9500
C6—C71.525 (9)C24—C251.382 (11)
C6—H6A0.99C24—H24A0.9500
C6—H6B0.9900C25—C261.389 (10)
C7—N21.357 (9)C25—H25A0.9500
N2—C81.437 (8)C26—H26A0.9500
N2—H20.88O7—C291.199 (10)
C8—C91.321 (9)C29—O81.361 (9)
C8—C161.486 (10)C29—C281.509 (11)
C16—O41.243 (8)C28—N51.460 (8)
C16—N31.357 (10)C28—H28A0.9900
C9—C101.468 (9)C28—H28B0.9900
C9—H90.9500N5—H50.88
C10—C151.385 (10)O8—C301.459 (10)
C10—C111.391 (11)C30—H30A0.9800
C11—C121.405 (10)C30—H30B0.9800
C11—H11A0.9500C30—H30C0.9800
C12—C131.377 (10)O9—H9A0.86
C12—H12A0.9500O9—H9B0.86
C13—C141.367 (11)O10—H10A0.86
C13—H13A0.9500O10—H10B0.86
C14—C151.420 (10)
C3—C1—C2113.4 (9)C12—C13—H13A118.5
C3—C1—O1110.0 (8)C13—C14—C15118.2 (9)
C2—C1—O1108.0 (8)C13—C14—H14A120.9
C3—C1—C4A99.8 (11)C15—C14—H14A120.9
C2—C1—C4A122.9 (10)C10—C15—C14121.4 (9)
O1—C1—C4A101.7 (8)C10—C15—H15A119.3
C3—C1—C4B125.9 (12)C14—C15—H15A119.3
C2—C1—C4B100.7 (10)C16—N3—C17121.4 (7)
O1—C1—C4B96.7 (9)C16—N3—H3119.3
C1—C2—H2A109.5C17—N3—H3119.3
C1—C2—H2B109.5N3—C17—C18116.0 (7)
H2A—C2—H2B109.5N3—C17—H17A108.3
C1—C2—H2C109.5C18—C17—H17A108.3
H2A—C2—H2C109.5N3—C17—H17B108.3
H2B—C2—H2C109.5C18—C17—H17B108.3
C1—C3—H3A109.5H17A—C17—H17B107.4
C1—C3—H3B109.5O5—C18—N4123.6 (7)
H3A—C3—H3B109.5O5—C18—C17119.7 (7)
C1—C3—H3C109.5N4—C18—C17116.7 (7)
H3A—C3—H3C109.5C18—N4—C19123.5 (7)
H3B—C3—H3C109.5C18—N4—H4118.3
C1—C4A—H4A1153.7C19—N4—H4118.3
C1—C4A—H4A291.1C20—C19—N4116.1 (7)
H4A1—C4A—H4A2109.5C20—C19—C27127.5 (8)
C1—C4A—H4A346.2N4—C19—C27116.4 (7)
H4A1—C4A—H4A3109.5O6—C27—N5121.2 (8)
H4A2—C4A—H4A3109.5O6—C27—C19124.3 (8)
C1—C4B—H4B1112.6N5—C27—C19114.4 (7)
H4B1—C4B—H4B2109.5C19—C20—C21132.4 (8)
C1—C4B—H4B3132.6C19—C20—H20113.8
H4B1—C4B—H4B3109.5C21—C20—H20113.8
H4B2—C4B—H4B3109.5C26—C21—C22117.3 (8)
C5—O1—C1119.3 (7)C26—C21—C20127.6 (8)
O2—C5—O1127.1 (8)C22—C21—C20115.0 (8)
O2—C5—N1122.8 (8)C21—C22—C23121.7 (8)
O1—C5—N1110.1 (8)C21—C22—H22A119.2
C5—N1—C6120.8 (7)C23—C22—H22A119.2
C5—N1—H1119.6C24—C23—C22118.3 (9)
C6—N1—H1119.6C24—C23—H23A120.9
N1—C6—C7110.3 (6)C22—C23—H23A120.9
N1—C6—H6A109.6C25—C24—C23120.3 (9)
C7—C6—H6A109.6C25—C24—H24A119.9
N1—C6—H6B109.6C23—C24—H24A119.9
C7—C6—H6B109.6C24—C25—C26120.0 (8)
H6A—C6—H6B108.1C24—C25—H25A120.0
O3—C7—N2124.6 (8)C26—C25—H25A120.0
O3—C7—C6122.4 (7)C21—C26—C25122.4 (8)
N2—C7—C6113.1 (7)C21—C26—H26A118.8
C7—N2—C8123.4 (7)C25—C26—H26A118.8
C7—N2—H2118.3O7—C29—O8124.1 (8)
C8—N2—H2118.3O7—C29—C28128.4 (8)
C9—C8—N2123.8 (7)O8—C29—C28107.6 (8)
C9—C8—C16119.4 (7)N5—C28—C29110.4 (7)
N2—C8—C16115.9 (7)N5—C28—H28A109.6
O4—C16—N3121.7 (8)C29—C28—H28A109.6
O4—C16—C8121.1 (8)N5—C28—H28B109.6
N3—C16—C8117.0 (7)C29—C28—H28B109.6
C8—C9—C10128.0 (7)H28A—C28—H28B108.1
C8—C9—H9116.0C27—N5—C28120.6 (7)
C10—C9—H9116.0C27—N5—H5119.7
C15—C10—C11117.1 (8)C28—N5—H5119.7
C15—C10—C9119.6 (8)C29—O8—C30114.7 (7)
C11—C10—C9123.2 (7)O8—C30—H30A109.5
C10—C11—C12123.2 (8)O8—C30—H30B109.5
C10—C11—H11A118.4H30A—C30—H30B109.5
C12—C11—H11A118.4O8—C30—H30C109.5
C13—C12—C11116.8 (8)H30A—C30—H30C109.5
C13—C12—H12A121.6H30B—C30—H30C109.5
C11—C12—H12A121.6H9A—O9—H9B105
C14—C13—C12123.0 (9)H10A—O10—H10B91
C14—C13—H13A118.5
C3—C1—O1—C564.4 (12)C8—C16—N3—C17174.9 (7)
C2—C1—O1—C559.9 (12)C16—N3—C17—C1880.2 (9)
C4A—C1—O1—C5169.5 (10)N3—C17—C18—O5177.2 (7)
C4B—C1—O1—C5163.5 (10)N3—C17—C18—N40.2 (10)
C1—O1—C5—O22.8 (16)O5—C18—N4—C191.3 (12)
C1—O1—C5—N1177.4 (8)C17—C18—N4—C19176.0 (6)
O2—C5—N1—C63.9 (15)C18—N4—C19—C20126.5 (9)
O1—C5—N1—C6176.3 (8)C18—N4—C19—C2752.9 (11)
C5—N1—C6—C7135.2 (9)C20—C19—C27—O641.1 (15)
N1—C6—C7—O319.3 (13)N4—C19—C27—O6138.3 (9)
N1—C6—C7—N2161.0 (7)C20—C19—C27—N5140.8 (9)
O3—C7—N2—C82.9 (14)N4—C19—C27—N539.9 (11)
C6—C7—N2—C8177.4 (7)N4—C19—C20—C21171.5 (8)
C7—N2—C8—C9151.1 (9)C27—C19—C20—C219.2 (16)
C7—N2—C8—C1639.2 (11)C19—C20—C21—C2610.1 (16)
C9—C8—C16—O447.0 (12)C19—C20—C21—C22167.9 (9)
N2—C8—C16—O4142.8 (8)C26—C21—C22—C232.1 (14)
C9—C8—C16—N3128.1 (8)C20—C21—C22—C23179.7 (8)
N2—C8—C16—N342.1 (10)C21—C22—C23—C241.7 (15)
N2—C8—C9—C104.2 (14)C22—C23—C24—C251.0 (15)
C16—C8—C9—C10173.5 (8)C23—C24—C25—C263.1 (15)
C8—C9—C10—C15138.0 (9)C22—C21—C26—C250.0 (14)
C8—C9—C10—C1144.9 (13)C20—C21—C26—C25177.9 (8)
C15—C10—C11—C121.9 (12)C24—C25—C26—C212.7 (14)
C9—C10—C11—C12175.2 (7)O7—C29—C28—N59.9 (14)
C10—C11—C12—C133.5 (12)O8—C29—C28—N5170.1 (6)
C11—C12—C13—C140.8 (13)O6—C27—N5—C281.4 (14)
C12—C13—C14—C153.2 (13)C19—C27—N5—C28176.8 (7)
C11—C10—C15—C142.3 (12)C29—C28—N5—C2779.8 (10)
C9—C10—C15—C14179.5 (7)O7—C29—O8—C302.4 (12)
C13—C14—C15—C104.8 (12)C28—C29—O8—C30177.7 (7)
O4—C16—N3—C170.2 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O30.882.032.869 (8)160
N3—H3···O6i0.882.082.944 (8)166
N2—H2···O5i0.882.012.885 (7)174
N5—H5···O90.882.062.853 (9)149
O9—H9A···O40.862.092.831 (9)143
O9—H9B···O10ii0.862.072.794 (9)141
O10—H10A···O7iii0.862.162.967 (9)156
O10—H10B···O50.862.092.947 (9)177
C2—H2B···O20.982.352.970 (10)121
C3—H3C···O20.982.423.031 (12)120
C6—H6A···O20.992.362.761 (9)103
N4—H4···N30.882.312.741 (8)110
N5—H5···N40.882.532.825 (8)100
C26—H26A···O60.952.483.101 (10)122
C28—H28A···O2iv0.992.223.145 (11)155
C28—H28B···O8v0.992.603.337 (10)131
C28—H28A···O2iv0.992.223.145 (11)155
C26—H26A···O60.952.483.101 (10)122
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x, y, z1; (iii) x, y, z+1; (iv) x1/2, y+1/2, z; (v) x+1, y, z.
 

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