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The structure of the synthetic protected dipeptide (Z)-Pro-Leuol [systematic name: benzyl 2-(1-hydroxy­methyl-3-methyl­butyl­amino­carbonyl)­pyrrolidine-1-carboxyl­ate], C19H28N2O4, was determined by X-ray crystallography. The peptide adopts a novel backbone conformation compared with other longer oligopeptides containing Pro-Leuol.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010001502X/qa0435sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010001502X/qa0435Isup2.hkl
Contains datablock I

CCDC reference: 156209

Comment top

The sequence Pro-Leucinol is the C-terminal dipeptide of several naturally occurring peptaibols, i.e. peptides containing α-aminoisobutyric acid (Aib) and an alcoholic C-terminus (Brückner & Graf, 1983; Benedetti et al., 1982), among them harzianin (Rebuffat et al., 1994, 1995), hypomuricin (Becker, 1996; Becker et al., 1997) and trichovirin (Kieß and Brückner, 1990; Brückner et al., 1991). The crystal structures of the four, eight and twelve C-terminal residues comprising peptides of trichovirin were solved by our group (Geßmann et al., 1994, 1999). Interestingely, while proline in the longer peptides adopts main-chain torsion angles ϕ and ψ which lie in the 310-helical region, proline in the dipeptide adopts a semi-extended conformation with ϕ and ψ values of −71.3 and 146.1°, respectively. The ϕ values of Leu in the longer peptides have been observed as unusually small for the helical region, while the ϕ value (−77.8°) of Leu in the title compound, (I), lies inside the helical region. The pyrrolidine ring of Pro adopts the Cγ-exo (Ashida & Kakudo, 1974) conformation, with puckering parameters (Cremer & Pople, 1975) Q = 0.284 Å and Φ = 292.98°. In the crystal, the peptides are hydrogen bonded along the [100] direction via two hydrogen bonds (see Table 2). In the other directions, these columns of molecules are packed via apolar crystal contacts. \scheme

Experimental top

Z-Pro-Leuol was synthezized from commercially available Z—L-Pro-OH (from Bachem, Bubendorf, Switzerland) and H—L-Leuol (from Fluka, Buchs, Switzerland) by using WSC (water-soluble carbodiimide) and HOBt (1-hydroxybezotrialole) as coupling reagents. This approach is known to prevent racemization. Further, it is known that C-terminal Pro in peptide coupling does not racemize as no azlactone can be formed on activation. Chiral purity was also confirmed by enantioselective gas chromatography of a total hydrolysate of the dipeptide on a Chirasil-L-Val capillary column according to procedures described previously (Brückner & Jung, 1982). For this reason, the Flack parameter was not refined. The protected dipeptide was crystallized from a hot ethanol–water mixture (60:40). Very few plate-like crystals were obtained and all reached a length of 1 mm. The crystals were fragile and easily damaged by attempts to cut smaller pieces with more appopriate dimensions for data collection. An intact crystal was sealed in a glass capillary for data collection. The collimator used has a diameter of 1 mm.

Refinement top

Data were collected from θ = 1–70°. Subsequently, 1978 Friedel pairs were measured, from θ = 1–49°. All equivalent data were averaged, including the Friedel pairs. H atoms were calculated and a riding model was used during the refinement. The C-terminal H atom was located by difference Fourier syntheses and its displacement parameter was fixed during refinement.

Computing details top

Data collection: CAD-4 Software (Enraf Nonius, 1989); cell refinement: CAD-4 Software; data reduction: Xtal3.7 DIFDAT ABSORB ADDREF (Hall et al., 2000); program(s) used to solve structure: Xtal3.7 CRISP; program(s) used to refine structure: Xtal3.7 CRILSQ; software used to prepare material for publication: Xtal3.7 BONDLA CIFIO.

(I) top
Crystal data top
C19H28N2O4F(000) = 752
Mr = 348.44Dx = 1.200 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 6.371 (4) Åθ = 10.0–21.4°
b = 8.824 (8) ŵ = 0.68 mm1
c = 34.303 (10) ÅT = 293 K
V = 1928 (2) Å3Rod, colourless
Z = 41.0 × 0.4 × 0.2 mm
Data collection top
CAD-4
diffractometer
Rint = 0.069
ω–4/3θ scansθmax = 70.0°, θmin = 2.6°
Absorption correction: analytical
(Xtal3.7 ABSORB; Hall et al., 2000)
h = 67
Tmin = 0.736, Tmax = 0.875k = 810
4821 measured reflectionsl = 3341
2111 independent reflections5 standard reflections every 3600 min
1398 reflections with I > 2.5σ(I) intensity decay: 11.2%
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: fullWeighting scheme based on measured s.u.'s w = 1/σ2(F)
R[F2 > 2σ(F2)] = 0.067(Δ/σ)max < 0.001
wR(F2) = 0.093Δρmax = 0.39 e Å3
S = 2.00Δρmin = 0.49 e Å3
2049 reflectionsExtinction correction: Zachariasen (1967)
227 parametersExtinction coefficient: 4647.9 (18)
0 restraintsAbsolute structure: assumed from synthesis, see text
4 constraints
Crystal data top
C19H28N2O4V = 1928 (2) Å3
Mr = 348.44Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 6.371 (4) ŵ = 0.68 mm1
b = 8.824 (8) ÅT = 293 K
c = 34.303 (10) Å1.0 × 0.4 × 0.2 mm
Data collection top
CAD-4
diffractometer
1398 reflections with I > 2.5σ(I)
Absorption correction: analytical
(Xtal3.7 ABSORB; Hall et al., 2000)
Rint = 0.069
Tmin = 0.736, Tmax = 0.8755 standard reflections every 3600 min
4821 measured reflections intensity decay: 11.2%
2111 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.093H-atom parameters constrained
S = 2.00Δρmax = 0.39 e Å3
2049 reflectionsΔρmin = 0.49 e Å3
227 parametersAbsolute structure: assumed from synthesis, see text
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C061.0761 (10)0.2037 (6)0.60525 (14)0.063 (4)
C010.8772 (10)0.2614 (9)0.60357 (19)0.095 (5)
C020.7568 (14)0.2391 (10)0.5708 (2)0.120 (6)
C030.8200 (17)0.1584 (10)0.5413 (2)0.122 (7)
C041.025 (2)0.0998 (11)0.5420 (2)0.143 (8)
C051.1444 (12)0.1223 (8)0.5732 (2)0.100 (5)
C071.2225 (10)0.2249 (6)0.63978 (15)0.074 (4)
O011.1434 (5)0.3468 (4)0.66349 (8)0.056 (2)
C081.2873 (8)0.4045 (6)0.68994 (15)0.054 (3)
O081.4696 (5)0.3631 (4)0.68987 (10)0.065 (2)
N11.1986 (6)0.5048 (4)0.71294 (11)0.050 (2)
C1A0.9774 (7)0.5514 (6)0.71189 (12)0.048 (3)
C1B0.9482 (10)0.6420 (7)0.74971 (13)0.075 (4)
C1G1.1330 (11)0.6045 (9)0.77379 (17)0.099 (5)
C1D1.3109 (8)0.5663 (6)0.74663 (15)0.063 (3)
C10.9286 (7)0.6456 (6)0.67665 (12)0.048 (3)
O11.0475 (5)0.7454 (4)0.66423 (10)0.069 (2)
N20.7349 (6)0.6280 (5)0.66153 (11)0.053 (2)
C2A0.6460 (8)0.7218 (6)0.63108 (13)0.052 (3)
C2B0.4690 (8)0.6316 (6)0.61111 (12)0.056 (3)
C2G0.3603 (10)0.7060 (7)0.57690 (14)0.071 (4)
C2D10.1933 (11)0.6045 (8)0.56176 (19)0.102 (5)
C2D20.5115 (15)0.7432 (12)0.54529 (18)0.135 (7)
C20.5742 (7)0.8717 (6)0.64861 (14)0.059 (3)
O20.4373 (6)0.8583 (4)0.68042 (10)0.075 (2)
H010.822200.316780.625000.11800*
H020.621720.284510.569650.15000*
H030.729610.139510.519790.15300*
H041.077940.044630.520310.17900*
H051.282020.080900.573580.12500*
H07a1.227720.134250.654690.09300*
H07b1.359430.249150.630760.09300*
H1A0.889630.464350.712280.06000*
H1Ba0.943770.747590.744370.09400*
H1Bb0.822560.612500.762560.09400*
H1Ga1.170060.689010.789520.12300*
H1Gb1.102540.520110.790020.12300*
H1Da1.402120.492980.757770.07800*
H1Db1.389070.654040.739810.07800*
H2A0.752180.742020.612340.06400*
H2Ba0.527570.538950.602110.07000*
H2Bb0.365170.610920.630270.07000*
H2G0.296980.797290.585650.08800*
H2D1a0.125500.651660.540290.15300*
H2D1b0.093630.585470.581770.15300*
H2D1c0.253980.511500.553550.15300*
H2D2a0.438880.789700.524270.20200*
H2D2b0.577220.652950.536420.20200*
H2D2c0.615100.810880.555000.20200*
H2c0.695120.925560.657000.07400*
H2b0.504770.927830.628800.07400*
H20.653140.550890.671280.06600*
H0.3073 (6)0.8793 (4)0.67241 (10)0.20000*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C060.068 (4)0.051 (3)0.070 (3)0.008 (3)0.005 (3)0.002 (3)
C010.061 (4)0.119 (6)0.105 (5)0.017 (4)0.002 (4)0.035 (4)
C020.116 (7)0.136 (7)0.109 (5)0.022 (5)0.031 (6)0.048 (6)
C030.148 (8)0.107 (7)0.112 (6)0.036 (6)0.043 (6)0.028 (5)
C040.203 (11)0.128 (8)0.098 (5)0.047 (8)0.036 (7)0.059 (5)
C050.100 (5)0.096 (5)0.103 (5)0.016 (5)0.004 (5)0.036 (4)
C070.076 (4)0.064 (4)0.083 (4)0.005 (3)0.001 (3)0.015 (3)
O010.0399 (18)0.057 (2)0.070 (2)0.0076 (17)0.0028 (16)0.0090 (17)
C080.049 (3)0.042 (3)0.070 (3)0.003 (3)0.001 (3)0.014 (3)
O080.0301 (18)0.058 (2)0.107 (3)0.0137 (16)0.0007 (17)0.008 (2)
N10.037 (2)0.050 (2)0.065 (3)0.0124 (19)0.014 (2)0.002 (2)
C1A0.030 (2)0.054 (3)0.060 (3)0.007 (2)0.002 (2)0.001 (3)
C1B0.074 (4)0.098 (4)0.052 (3)0.003 (4)0.012 (3)0.004 (3)
C1G0.076 (4)0.126 (6)0.095 (4)0.033 (4)0.025 (4)0.044 (4)
C1D0.046 (3)0.062 (3)0.081 (3)0.003 (3)0.021 (3)0.004 (3)
C10.032 (2)0.056 (3)0.055 (3)0.008 (2)0.007 (2)0.007 (2)
O10.0361 (19)0.070 (3)0.101 (3)0.0110 (18)0.002 (2)0.020 (2)
N20.038 (2)0.056 (3)0.065 (2)0.0001 (19)0.0093 (18)0.008 (2)
C2A0.040 (3)0.056 (3)0.059 (3)0.002 (2)0.007 (2)0.009 (3)
C2B0.050 (3)0.056 (3)0.062 (3)0.006 (3)0.010 (3)0.006 (3)
C2G0.073 (4)0.078 (4)0.061 (3)0.001 (3)0.015 (3)0.002 (3)
C2D10.094 (5)0.116 (6)0.095 (4)0.003 (5)0.039 (4)0.004 (4)
C2D20.135 (8)0.205 (9)0.064 (3)0.031 (6)0.014 (5)0.037 (4)
C20.033 (3)0.060 (3)0.085 (3)0.004 (3)0.009 (3)0.004 (3)
O20.058 (2)0.080 (3)0.086 (2)0.001 (2)0.002 (2)0.021 (2)
Geometric parameters (Å, º) top
C06—C011.367 (9)C1G—H1Ga0.950 (7)
C06—C051.382 (9)C1G—H1Gb0.950 (7)
C06—C071.519 (8)C1D—H1Da0.950 (5)
C01—C021.375 (10)C1D—H1Db0.950 (5)
C01—H010.950 (7)C1—O11.237 (6)
C02—C031.302 (12)C1—N21.347 (6)
C02—H020.950 (9)N2—C2A1.448 (6)
C03—C041.405 (16)N2—H20.920 (4)
C03—H030.950 (9)C2A—C2B1.541 (7)
C04—C051.329 (12)C2A—C21.523 (7)
C04—H040.950 (9)C2A—H2A0.950 (5)
C05—H050.950 (8)C2B—C2G1.512 (7)
C07—O011.440 (6)C2B—H2Ba0.950 (5)
C07—H07a0.950 (5)C2B—H2Bb0.950 (5)
C07—H07b0.950 (6)C2G—C2D11.484 (9)
O01—C081.386 (6)C2G—C2D21.487 (10)
C08—O081.218 (6)C2G—H2G0.950 (6)
C08—N11.313 (6)C2D1—H2D1a0.950 (7)
N1—C1A1.469 (6)C2D1—H2D1b0.950 (7)
N1—C1D1.464 (6)C2D1—H2D1c0.950 (7)
C1A—C1B1.535 (7)C2D2—H2D2a0.950 (8)
C1A—C11.499 (6)C2D2—H2D2b0.950 (10)
C1A—H1A0.950 (5)C2D2—H2D2c0.950 (9)
C1B—C1G1.476 (9)C2—O21.402 (6)
C1B—H1Ba0.950 (6)C2—H2c0.950 (5)
C1B—H1Bb0.950 (6)C2—H2b0.950 (5)
C1G—C1D1.505 (8)O2—H0.892 (5)
C06···C022.373 (10)C1D···H2Bb4.026 (5)
C06···C032.763 (11)C1D···H2c3.532 (5)
C06···C042.379 (9)C1D···H23.384 (5)
C06···O012.402 (6)C1D···H3.757 (7)
C06···C083.659 (7)C1···C2A2.477 (7)
C06···O084.085 (6)C1···C2B3.694 (7)
C06···C2D13.911 (9)C1···C2B4.114 (7)
C06···H012.018 (6)C1···C2G4.423 (7)
C06···H023.222 (6)C1···C2D14.302 (8)
C06···H023.753 (6)C1···C23.163 (7)
C06···H033.713 (5)C1···O23.652 (6)
C06···H043.234 (5)C1···O23.748 (6)
C06···H052.019 (6)C1···H013.466 (5)
C06···H07a2.046 (5)C1···H1A2.028 (5)
C06···H07b2.046 (6)C1···H1Ba2.493 (4)
C06···H1Ga3.938 (5)C1···H1Bb3.037 (4)
C06···H2G3.910 (6)C1···H1Gb3.503 (6)
C06···H2D1b3.466 (6)C1···H1Db3.648 (5)
C06···H2D1c3.436 (6)C1···H2A2.618 (4)
C06···H2c3.881 (6)C1···H2Ba3.735 (5)
C06···H2b3.746 (6)C1···H2Bb3.938 (5)
C06···H3.958 (7)C1···H2Bb3.219 (5)
C01···C032.350 (11)C1···H2D1b3.461 (4)
C01···C042.718 (11)C1···H2c2.962 (5)
C01···C052.342 (10)C1···H2b4.023 (5)
C01···C074.363 (9)C1···H21.952 (5)
C01···C072.547 (9)C1···H3.178 (6)
C01···O012.769 (7)O1···N22.246 (5)
C01···C084.147 (8)O1···C2A2.807 (6)
C01···O084.039 (7)O1···C2A3.985 (6)
C01···C1G4.429 (9)O1···C2B4.232 (6)
C01···C14.229 (9)O1···C2B3.397 (6)
C01···N23.904 (9)O1···C2G3.615 (6)
C01···C2A4.423 (10)O1···C2D13.842 (8)
C01···C2B4.183 (9)O1···C23.576 (6)
C01···C2D13.909 (10)O1···C23.259 (6)
C01···C24.235 (9)O1···O24.051 (6)
C01···H022.011 (6)O1···H2.053 (5)
C01···H033.209 (7)O1···O22.733 (5)
C01···H043.668 (7)O1···H07a3.633 (5)
C01···H053.201 (7)O1···H1A3.143 (4)
C01···H07a3.053 (7)O1···H1Ba2.827 (4)
C01···H07b3.213 (7)O1···H1Bb3.848 (4)
C01···H07b3.429 (7)O1···H1Gb3.042 (4)
C01···H1Ga3.735 (7)O1···H1Db3.479 (4)
C01···H2Ba3.311 (7)O1···H2A2.590 (4)
C01···H2D1b3.262 (8)O1···H2Bb2.619 (4)
C01···H2D1c3.685 (7)O1···H2G3.163 (4)
C01···H2c3.672 (8)O1···H2D1b3.175 (4)
C01···H2b3.878 (7)O1···H2c2.762 (4)
C01···H23.736 (7)O1···H2b3.544 (4)
C02···C042.326 (14)O1···H2b4.003 (4)
C02···C044.378 (12)O1···H23.052 (4)
C02···C052.677 (12)O1···H2.053 (5)
C02···C054.036 (12)N2···C2B2.421 (6)
C02···C074.147 (10)N2···C2G3.820 (7)
C02···C073.797 (10)N2···C2D24.354 (8)
C02···O014.133 (9)N2···C22.422 (6)
C02···C2B4.156 (10)N2···O22.854 (6)
C02···C2D14.270 (12)N2···H013.070 (5)
C02···C24.358 (10)N2···H1A2.468 (4)
C02···H012.025 (8)N2···H1Ba3.310 (4)
C02···H031.966 (8)N2···H1Bb3.513 (4)
C02···H043.183 (9)N2···H1Gb3.975 (5)
C02···H043.835 (8)N2···H1Db3.481 (4)
C02···H053.332 (9)N2···H2A1.967 (4)
C02···H053.627 (9)N2···H2Ba2.553 (4)
C02···H07b3.263 (8)N2···H2Bb2.592 (4)
C02···H2Ba3.207 (9)N2···H2D1b3.585 (4)
C02···H2D1b3.754 (9)N2···H2c2.642 (5)
C02···H2D1c4.020 (9)N2···H2b3.226 (4)
C02···H2D2b4.005 (9)N2···H3.532 (6)
C02···H2D2c3.922 (10)C2A···C2G2.605 (7)
C02···H2b3.752 (9)C2A···C2D14.345 (9)
C03···C044.030 (13)C2A···C2D13.878 (9)
C03···C052.361 (13)C2A···C2D23.071 (8)
C03···C074.282 (11)C2A···O22.467 (6)
C03···C2D14.304 (11)C2A···H013.752 (6)
C03···C2D24.159 (14)C2A···H1A3.915 (5)
C03···H013.194 (8)C2A···H2Ba2.039 (5)
C03···H021.944 (10)C2A···H2Bb2.039 (5)
C03···H033.792 (10)C2A···H2G2.796 (5)
C03···H042.056 (10)C2A···H2D1b3.527 (5)
C03···H043.703 (9)C2A···H2D2a3.940 (5)
C03···H053.219 (10)C2A···H2D2b3.332 (5)
C03···H053.666 (10)C2A···H2D2c2.733 (5)
C03···H2D1c3.607 (9)C2A···H2c2.030 (5)
C03···H2D2c3.366 (10)C2A···H2b2.030 (5)
C04···C073.749 (10)C2A···H22.044 (5)
C04···C2G4.251 (12)C2A···H2.933 (6)
C04···C2D24.258 (12)C2B···C2D12.451 (8)
C04···C2D24.418 (15)C2B···C2D22.478 (8)
C04···H013.667 (9)C2B···C22.568 (7)
C04···H023.188 (12)C2B···O23.114 (6)
C04···H024.010 (8)C2B···H013.607 (5)
C04···H033.388 (10)C2B···H023.514 (5)
C04···H032.060 (12)C2B···H07b3.511 (6)
C04···H051.971 (12)C2B···H2A2.051 (5)
C04···H07b3.943 (10)C2B···H2G2.025 (5)
C04···H2G3.517 (10)C2B···H2D1a3.274 (5)
C04···H2D1a4.006 (10)C2B···H2D1b2.626 (5)
C04···H2D1c3.832 (9)C2B···H2D1c2.626 (5)
C04···H2D1c3.935 (11)C2B···H2D2a3.295 (4)
C04···H2D2a3.848 (11)C2B···H2D2b2.660 (4)
C04···H2D2b3.509 (9)C2B···H2D2c2.660 (5)
C04···H2D2c3.677 (12)C2B···H2c3.359 (5)
C05···C072.506 (9)C2B···H2b2.693 (5)
C05···O013.676 (8)C2B···H22.479 (4)
C05···C2G3.925 (10)C2B···H3.204 (6)
C05···C2D14.284 (11)C2G···C23.170 (7)
C05···C2D24.193 (12)C2G···O23.829 (6)
C05···C24.368 (9)C2G···H043.992 (6)
C05···H013.211 (7)C2G···H053.348 (7)
C05···H023.626 (8)C2G···H2A2.795 (6)
C05···H023.363 (8)C2G···H2Ba2.014 (6)
C05···H033.220 (7)C2G···H2Bb2.014 (5)
C05···H033.859 (7)C2G···H2D1a2.011 (6)
C05···H041.986 (7)C2G···H2D1b2.011 (6)
C05···H07a2.846 (7)C2G···H2D1c2.011 (6)
C05···H07b2.650 (7)C2G···H2D2a2.014 (5)
C05···H2G3.058 (7)C2G···H2D2b2.014 (6)
C05···H2D1c3.569 (8)C2G···H2D2c2.014 (6)
C05···H2D2a3.867 (7)C2G···H2c3.982 (6)
C05···H2b3.442 (7)C2G···H2b2.802 (6)
C07···C082.375 (7)C2G···H23.979 (5)
C07···O082.630 (7)C2G···H3.632 (6)
C07···N13.524 (7)C2D1···C2D22.435 (12)
C07···C1A4.106 (7)C2D1···C2D24.078 (10)
C07···C1B4.011 (7)C2D1···H023.936 (8)
C07···C1G3.879 (9)C2D1···H033.538 (7)
C07···C14.346 (8)C2D1···H043.957 (7)
C07···C2B4.039 (8)C2D1···H2A3.519 (7)
C07···C2D14.292 (9)C2D1···H2Ba2.605 (7)
C07···C23.851 (8)C2D1···H2Bb2.593 (7)
C07···O23.779 (7)C2D1···H2G2.000 (7)
C07···H013.938 (7)C2D1···H2D2a2.602 (7)
C07···H012.724 (6)C2D1···H2D2a3.494 (7)
C07···H023.540 (6)C2D1···H2D2b2.630 (7)
C07···H052.630 (5)C2D1···H2D2c3.254 (8)
C07···H1A3.892 (6)C2D2···C23.742 (8)
C07···H1Bb3.506 (5)C2D2···H033.863 (10)
C07···H1Ga3.498 (6)C2D2···H043.420 (9)
C07···H1Gb3.654 (6)C2D2···H043.929 (10)
C07···H2Ba3.623 (6)C2D2···H053.458 (10)
C07···H2Bb3.541 (6)C2D2···H2A2.764 (7)
C07···H2D1b3.842 (6)C2D2···H2Ba2.657 (8)
C07···H2D1c3.897 (6)C2D2···H2Bb3.276 (7)
C07···H2b3.201 (6)C2D2···H2G2.003 (8)
C07···H3.293 (7)C2D2···H2D1a3.163 (7)
O01···O082.271 (5)C2D2···H2D1a2.594 (10)
O01···N12.223 (5)C2D2···H2D1a3.998 (10)
O01···C1A2.671 (6)C2D2···H2D1b3.255 (9)
O01···C1B3.532 (6)C2D2···H2D1c2.637 (10)
O01···C1B4.133 (6)C2D2···H2D2a3.632 (8)
O01···C1G3.507 (8)C2D2···H2b3.296 (7)
O01···C1D3.609 (6)C2···H053.674 (5)
O01···C13.004 (6)C2···H07a3.207 (5)
O01···O13.570 (6)C2···H07b3.653 (6)
O01···N23.597 (5)C2···H1Ga3.873 (5)
O01···C2B3.721 (6)C2···H1Gb3.223 (5)
O01···C2D14.177 (8)C2···H1Da3.388 (5)
O01···H012.450 (3)C2···H1Db3.856 (5)
O01···H053.975 (3)C2···H2A2.035 (5)
O01···H07a1.974 (4)C2···H2Ba3.355 (5)
O01···H07b1.974 (3)C2···H2Bb2.732 (5)
O01···H1A2.548 (3)C2···H2G2.866 (5)
O01···H1Ba3.326 (3)C2···H2D2c3.266 (5)
O01···H1Bb3.280 (3)C2···H22.978 (5)
O01···H1Ga2.920 (3)C2···H1.887 (6)
O01···H1Gb3.648 (4)O2···H07a2.914 (4)
O01···H1Da3.852 (3)O2···H07b3.878 (5)
O01···H2Ba3.647 (3)O2···H1Ba3.956 (4)
O01···H2Bb2.954 (4)O2···H1Bb3.405 (4)
O01···H2D1b3.520 (3)O2···H1Ga3.979 (4)
O01···H23.615 (4)O2···H1Gb3.415 (4)
O01···H23.723 (4)O2···H1Gb3.859 (4)
C08···C1A2.479 (7)O2···H1Da2.637 (4)
C08···C1B3.449 (8)O2···H1Db2.738 (4)
C08···C1B3.642 (8)O2···H1Db3.940 (4)
C08···C1G3.965 (9)O2···H2A3.245 (4)
C08···C1G3.515 (8)O2···H2Ba3.936 (4)
C08···C1D2.417 (7)O2···H2Bb2.817 (4)
C08···C13.155 (7)O2···H2G3.414 (4)
C08···O13.487 (6)O2···H2c1.922 (4)
C08···N23.602 (6)O2···H2b1.923 (4)
C08···N24.150 (7)O2···H23.058 (4)
C08···C2A4.140 (7)H01···H022.3059 (7)
C08···C2B3.559 (7)H01···H07a3.2104 (15)
C08···O24.131 (7)H01···H07b3.480 (2)
C08···H013.787 (5)H01···H07b3.0145 (19)
C08···H07a2.700 (5)H01···H1A3.2930 (9)
C08···H07b2.492 (5)H01···H1Ga3.1419 (9)
C08···H1A3.949 (6)H01···H2Ba2.8254 (15)
C08···H1A2.699 (5)H01···H2D1b3.2880 (17)
C08···H1Ba3.027 (5)H01···H22.8192 (15)
C08···H1Bb3.128 (5)H02···H032.2438 (8)
C08···H1Ga4.008 (5)H02···H043.4457 (10)
C08···H1Ga3.550 (5)H02···H052.8160 (15)
C08···H1Gb3.770 (5)H02···H07b2.6989 (8)
C08···H1Da2.561 (5)H02···H2Ba2.5770 (18)
C08···H1Db3.865 (5)H02···H2D1c3.1314 (17)
C08···H1Db2.863 (5)H02···H2D2b3.457 (3)
C08···H2Ba3.582 (5)H03···H042.3719 (14)
C08···H2Bb2.785 (5)H03···H043.255 (2)
C08···H22.741 (5)H03···H053.4355 (16)
O08···N12.274 (5)H03···H2D1a3.3599 (19)
O08···C1A3.714 (6)H03···H2D1c2.8511 (9)
O08···C1A3.629 (6)H03···H2D2a3.603 (3)
O08···C1B3.897 (7)H03···H2D2c3.225 (2)
O08···C1G4.174 (8)H04···H052.2653 (7)
O08···C1G3.629 (8)H04···H2G3.4256 (14)
O08···C1D3.682 (6)H04···H2D1a3.548 (3)
O08···C1D2.833 (6)H04···H2D1c3.3052 (10)
O08···C13.869 (6)H04···H2D2a3.439 (2)
O08···C14.278 (6)H04···H2D2a3.2197 (18)
O08···N23.044 (5)H04···H2D2b2.6128 (12)
O08···C2A3.918 (6)H05···H07a2.8431 (8)
O08···C2B3.594 (6)H05···H07b2.5090 (9)
O08···H013.188 (3)H05···H2G2.538 (2)
O08···H07a2.812 (4)H05···H2D2a3.235 (2)
O08···H07b2.370 (3)H05···H2D2c3.2536 (19)
O08···H1A3.878 (4)H05···H2b2.7251 (9)
O08···H1A2.924 (3)H07a···H07b1.5512 (7)
O08···H1Ba3.614 (3)H07a···H1Bb2.8629 (8)
O08···H1Bb3.319 (4)H07a···H1Ga3.2121 (13)
O08···H1Ga2.851 (3)H07a···H1Gb3.0062 (11)
O08···H1Da2.631 (3)H07a···H2c3.5020 (19)
O08···H1Da3.816 (4)H07a···H2b2.6874 (14)
O08···H1Db3.129 (4)H07a···H2.385 (4)
O08···H1Db3.167 (4)H07b···H2Ba2.942 (2)
O08···H2Ba3.407 (4)H07b···H2Bb3.193 (3)
O08···H2Bb3.067 (4)H07b···H2D1c3.5812 (15)
O08···N23.044 (5)H07b···H2b2.984 (3)
O08···H22.126 (3)H07b···H23.539 (2)
N1···C1B3.572 (8)H07b···H3.578 (4)
N1···C1B2.367 (7)H1A···H1Ba2.753 (2)
N1···C1G4.140 (9)H1A···H1Ba2.6450 (14)
N1···C1G2.304 (7)H1A···H1Bb2.2059 (8)
N1···C12.460 (6)H1A···H1Ga2.460 (2)
N1···O12.868 (5)H1A···H1Gb3.0321 (8)
N1···N23.996 (6)H1A···H1Da3.627 (2)
N1···N23.608 (6)H1A···H1Da3.4849 (18)
N1···C2B4.052 (6)H1A···H22.1980 (8)
N1···O23.646 (6)H1Ba···H1Bb3.555 (3)
N1···H07a3.836 (5)H1Ba···H1Bb1.5513 (9)
N1···H07b3.753 (4)H1Ba···H1Ga2.1781 (7)
N1···H1A2.000 (4)H1Ba···H1Gb2.7395 (14)
N1···H1Ba2.849 (4)H1Ba···H1Gb2.695 (2)
N1···H1Ba2.896 (4)H1Ba···H1Da3.0903 (17)
N1···H1Bb3.565 (5)H1Ba···H1Db2.9587 (18)
N1···H1Bb3.089 (4)H1Ba···H1Db3.632 (2)
N1···H1Ga3.095 (4)H1Ba···H23.5675 (11)
N1···H1Ga3.645 (4)H1Ba···H3.579 (4)
N1···H1Gb2.718 (4)H1Bb···H1Ga2.4924 (13)
N1···H1Da2.014 (4)H1Bb···H1Gb2.1757 (10)
N1···H1Db2.014 (4)H1Bb···H1Da2.8834 (16)
N1···H2Bb3.169 (4)H1Bb···H1Db2.8932 (17)
N1···H23.255 (4)H1Bb···H23.3562 (9)
N1···H23.779 (4)H1Bb···H3.146 (4)
N1···H3.652 (6)H1Ga···H1Gb1.5513 (13)
C1A···C1B3.874 (8)H1Ga···H1Da2.5228 (13)
C1A···C1G2.390 (7)H1Ga···H1Db2.2249 (7)
C1A···C1G4.035 (10)H1Ga···H2c3.0835 (17)
C1A···C1D4.412 (7)H1Gb···H1Da2.2191 (11)
C1A···C1D2.440 (7)H1Gb···H1Db2.7742 (10)
C1A···O12.409 (6)H1Gb···H2c2.3792 (7)
C1A···N22.414 (6)H1Gb···H3.166 (4)
C1A···C2A3.795 (6)H1Da···H1Db3.274 (3)
C1A···C24.393 (7)H1Da···H1Db1.5512 (12)
C1A···O24.134 (6)H1Da···H2c3.0474 (8)
C1A···H013.761 (5)H1Da···H23.4088 (9)
C1A···H1Ba3.113 (5)H1Da···H3.189 (4)
C1A···H1Ba2.070 (5)H1Db···H23.0306 (8)
C1A···H1Bb2.070 (4)H1Db···H3.093 (4)
C1A···H1Ga3.333 (6)H2A···H2Ba2.3199 (14)
C1A···H1Ga3.174 (4)H2A···H2Bb2.7920 (15)
C1A···H1Gb2.810 (4)H2A···H2G3.623 (2)
C1A···H1Da4.021 (5)H2A···H2G3.0800 (18)
C1A···H1Da3.173 (4)H2A···H2D1a3.5215 (12)
C1A···H1Db3.973 (5)H2A···H2D1b2.7821 (13)
C1A···H1Db2.936 (5)H2A···H2D2b2.9398 (8)
C1A···H2Bb3.771 (4)H2A···H2D2c2.2363 (6)
C1A···H22.491 (4)H2A···H2c2.2587 (11)
C1A···H3.824 (6)H2A···H2b2.3434 (13)
C1B···C1G4.192 (11)H2A···H22.7074 (11)
C1B···C1D4.093 (9)H2Ba···H2Bb1.5514 (5)
C1B···C1D4.116 (9)H2Ba···H2G2.7702 (18)
C1B···C1D2.408 (8)H2Ba···H2D1a3.4710 (13)
C1B···C12.509 (6)H2Ba···H2D1b2.8807 (17)
C1B···O13.135 (6)H2Ba···H2D1c2.4231 (9)
C1B···N23.318 (6)H2Ba···H2D2a3.5136 (14)
C1B···O24.359 (7)H2Ba···H2D2b2.4878 (7)
C1B···O24.248 (7)H2Ba···H2D2c2.9463 (19)
C1B···H07a3.466 (5)H2Ba···H2b3.555 (3)
C1B···H1A2.060 (6)H2Ba···H22.5061 (7)
C1B···H1A3.295 (6)H2Bb···H2G2.2883 (12)
C1B···H1Ba3.554 (7)H2Bb···H2D1a3.4623 (9)
C1B···H1Ga2.009 (6)H2Bb···H2D1b2.4106 (9)
C1B···H1Gb3.619 (7)H2Bb···H2D1c2.8631 (8)
C1B···H1Gb2.009 (6)H2Bb···H2D2b3.5109 (9)
C1B···H1Da3.826 (7)H2Bb···H2D2c3.5093 (11)
C1B···H1Da3.729 (7)H2Bb···H2c3.601 (2)
C1B···H1Da3.189 (6)H2Bb···H2b2.935 (3)
C1B···H1Db2.831 (6)H2Bb···H22.3717 (10)
C1B···H1Db3.580 (7)H2Bb···H2.799 (4)
C1B···H23.379 (5)H2G···H2D1a2.2947 (8)
C1B···H3.893 (7)H2G···H2D1b2.2781 (15)
C1G···C14.410 (10)H2G···H2D1c2.765 (2)
C1G···C13.596 (7)H2G···H2D2a2.2923 (6)
C1G···O13.996 (7)H2G···H2D2b2.7678 (10)
C1G···O13.986 (8)H2G···H2D2c2.2862 (12)
C1G···C23.845 (8)H2G···H2b2.2958 (8)
C1G···O24.362 (8)H2G···H3.064 (4)
C1G···O23.832 (8)H2D1a···H2D1b1.5515 (4)
C1G···H013.955 (6)H2D1a···H2D1c1.5513 (10)
C1G···H07a3.372 (7)H2D1a···H2D2a2.4025 (12)
C1G···H1A2.896 (7)H2D1a···H2D2a2.5662 (7)
C1G···H1A3.214 (8)H2D1a···H2D2b3.496 (2)
C1G···H1Ba2.016 (7)H2D1a···H2D2b2.8809 (19)
C1G···H1Ba3.248 (8)H2D1a···H2D2b3.1610 (11)
C1G···H1Bb2.016 (7)H2D1a···H2D2c3.2861 (10)
C1G···H1Da2.052 (7)H2D1a···H2D2c3.4580 (19)
C1G···H1Db2.052 (7)H2D1a···H2D2c3.578 (2)
C1G···H2c3.055 (7)H2D1b···H2D1c1.5514 (5)
C1G···H3.902 (8)H2D1b···H2D2a3.4607 (13)
C1D···C13.491 (7)H2D1b···H2D2b3.5023 (18)
C1D···O13.647 (6)H2D1c···H2D2a2.902 (2)
C1D···N24.014 (7)H2D1c···H2D2b2.4786 (13)
C1D···C24.049 (7)H2D1c···H2D2c3.503 (2)
C1D···O23.528 (7)H2D2a···H2D2b3.1463 (12)
C1D···O23.493 (6)H2D2a···H2D2b1.5514 (9)
C1D···H1A3.974 (6)H2D2a···H2D2c1.5513 (6)
C1D···H1A3.066 (5)H2D2a···H2D2c3.5266 (10)
C1D···H1A3.995 (6)H2D2b···H2D2c1.5513 (12)
C1D···H1Ba3.261 (6)H2D2c···H2b2.8227 (8)
C1D···H1Ba2.835 (5)H2c···H2b1.5513 (6)
C1D···H1Bb3.185 (6)H2c···H23.353 (3)
C1D···H1Bb3.330 (6)H2c···H2.559 (4)
C1D···H1Ga2.035 (5)H2b···H2.001 (4)
C1D···H1Gb2.036 (5)
C01—C06—C05116.9 (6)N1—C1D—C1G101.8 (4)
C01—C06—C07123.8 (5)N1—C1D—H1Da111.4 (5)
C05—C06—C07119.4 (6)N1—C1D—H1Db111.4 (5)
C06—C01—C02119.9 (6)C1G—C1D—H1Da111.4 (5)
C06—C01—H01120.1 (6)C1G—C1D—H1Db111.4 (5)
C02—C01—H01120.0 (7)H1Da—C1D—H1Db109.5 (5)
C01—C02—C03122.8 (8)C1A—C1—O1123.0 (4)
C01—C02—H02118.6 (8)C1A—C1—N2115.9 (4)
C03—C02—H02118.6 (9)O1—C1—N2120.6 (4)
C02—C03—C04118.4 (8)C1—N2—C2A124.8 (4)
C02—C03—H03120.8 (10)C1—N2—H2117.6 (4)
C04—C03—H03120.8 (9)C2A—N2—H2117.6 (4)
C03—C04—C05119.3 (8)N2—C2A—C2B108.2 (4)
C03—C04—H04120.3 (10)N2—C2A—C2109.2 (4)
C05—C04—H04120.3 (12)N2—C2A—H2A108.5 (4)
C06—C05—C04122.6 (8)C2B—C2A—C2113.8 (4)
C06—C05—H05118.7 (7)C2B—C2A—H2A108.5 (4)
C04—C05—H05118.7 (8)C2—C2A—H2A108.5 (4)
C06—C07—O01108.5 (4)C2A—C2B—C2G117.1 (4)
C06—C07—H07a109.7 (5)C2A—C2B—H2Ba107.5 (4)
C06—C07—H07b109.7 (5)C2A—C2B—H2Bb107.5 (4)
O01—C07—H07a109.7 (4)C2G—C2B—H2Ba107.5 (4)
O01—C07—H07b109.7 (5)C2G—C2B—H2Bb107.5 (5)
H07a—C07—H07b109.5 (6)H2Ba—C2B—H2Bb109.5 (5)
C07—O01—C08114.3 (4)C2B—C2G—C2D1109.8 (5)
O01—C08—O08121.3 (4)C2B—C2G—C2D2111.4 (6)
O01—C08—N1110.8 (4)C2B—C2G—H2G108.5 (4)
O08—C08—N1127.9 (5)C2D1—C2G—C2D2110.0 (5)
C08—N1—C1A125.9 (4)C2D1—C2G—H2G108.5 (6)
C08—N1—C1D120.9 (4)C2D2—C2G—H2G108.5 (6)
C1A—N1—C1D112.6 (4)C2G—C2D1—H2D1a109.5 (6)
N1—C1A—C1B104.0 (4)C2G—C2D1—H2D1b109.5 (6)
N1—C1A—C1112.0 (4)C2G—C2D1—H2D1c109.5 (6)
N1—C1A—H1A109.7 (4)H2D1a—C2D1—H2D1b109.5 (7)
C1B—C1A—C1111.6 (4)H2D1a—C2D1—H2D1c109.5 (7)
C1B—C1A—H1A109.8 (4)H2D1b—C2D1—H2D1c109.5 (7)
C1—C1A—H1A109.7 (4)C2G—C2D2—H2D2a109.5 (8)
C1A—C1B—C1G105.0 (5)C2G—C2D2—H2D2b109.5 (8)
C1A—C1B—H1Ba110.6 (4)C2G—C2D2—H2D2c109.5 (6)
C1A—C1B—H1Bb110.6 (5)H2D2a—C2D2—H2D2b109.5 (7)
C1G—C1B—H1Ba110.6 (6)H2D2a—C2D2—H2D2c109.5 (10)
C1G—C1B—H1Bb110.6 (5)H2D2b—C2D2—H2D2c109.5 (9)
H1Ba—C1B—H1Bb109.5 (6)C2A—C2—O2114.9 (4)
C1B—C1G—C1D107.7 (5)C2A—C2—H2c108.1 (4)
C1B—C1G—H1Ga109.9 (7)C2A—C2—H2b108.1 (4)
C1B—C1G—H1Gb109.9 (6)O2—C2—H2c108.1 (4)
C1D—C1G—H1Ga109.9 (6)O2—C2—H2b108.1 (4)
C1D—C1G—H1Gb109.9 (6)H2c—C2—H2b109.5 (5)
H1Ga—C1G—H1Gb109.5 (6)C2—O2—H108.7 (4)
C05—C06—C01—C021.0 (10)C1A—C1B—C1G—H1Ga148.0 (5)
C05—C06—C01—H01179.0 (7)C1A—C1B—C1G—H1Gb91.5 (6)
C07—C06—C01—C02178.7 (6)H1Ba—C1B—C1G—C1D91.0 (6)
C07—C06—C01—H011.3 (11)H1Ba—C1B—C1G—H1Ga28.7 (8)
C01—C06—C05—C040.0 (10)H1Ba—C1B—C1G—H1Gb149.2 (6)
C01—C06—C05—H05180.0 (6)H1Bb—C1B—C1G—C1D147.6 (6)
C07—C06—C05—C04179.7 (7)H1Bb—C1B—C1G—H1Ga92.7 (7)
C07—C06—C05—H050.3 (10)H1Bb—C1B—C1G—H1Gb27.8 (8)
C01—C06—C07—O0116.5 (7)C1B—C1G—C1D—H1Da148.3 (5)
C01—C06—C07—H07a103.4 (7)C1B—C1G—C1D—H1Db89.2 (6)
C01—C06—C07—H07b136.3 (6)H1Ga—C1G—C1D—N1149.3 (5)
C05—C06—C07—O01163.2 (5)H1Ga—C1G—C1D—H1Da91.9 (7)
C05—C06—C07—H07a76.9 (7)H1Ga—C1G—C1D—H1Db30.6 (8)
C05—C06—C07—H07b43.4 (7)H1Gb—C1G—C1D—N190.2 (6)
C06—C01—C02—C033.2 (13)H1Gb—C1G—C1D—H1Da28.6 (8)
C06—C01—C02—H02176.8 (7)H1Gb—C1G—C1D—H1Db151.1 (6)
H01—C01—C02—C03176.8 (8)C1A—C1—N2—H28.7 (6)
H01—C01—C02—H023.2 (13)O1—C1—N2—C2A1.4 (7)
C01—C02—C03—C044.2 (14)O1—C1—N2—H2178.6 (4)
C01—C02—C03—H03175.8 (9)C1—N2—C2A—C2B157.8 (4)
H02—C02—C03—C04175.8 (9)C1—N2—C2A—H2A40.3 (6)
H02—C02—C03—H034.2 (15)H2—N2—C2A—C2B22.2 (5)
C02—C03—C04—C053.1 (14)H2—N2—C2A—C2102.2 (5)
C02—C03—C04—H04176.9 (9)H2—N2—C2A—H2A139.7 (4)
H03—C03—C04—C05177.0 (9)N2—C2A—C2B—C2G177.2 (4)
H03—C03—C04—H043.0 (16)N2—C2A—C2B—H2Ba56.1 (5)
C03—C04—C05—C061.0 (13)N2—C2A—C2B—H2Bb61.6 (5)
C03—C04—C05—H05179.0 (8)C2—C2A—C2B—C2G61.2 (5)
H04—C04—C05—C06179.0 (8)C2—C2A—C2B—H2Ba177.7 (4)
H04—C04—C05—H051.0 (14)C2—C2A—C2B—H2Bb59.9 (5)
C06—C07—O01—C08164.0 (4)H2A—C2A—C2B—C2G59.7 (6)
H07a—C07—O01—C0876.1 (6)H2A—C2A—C2B—H2Ba61.4 (5)
H07b—C07—O01—C0844.1 (6)H2A—C2A—C2B—H2Bb179.2 (4)
C07—O01—C08—O086.6 (6)N2—C2A—C2—H2c66.9 (5)
C07—O01—C08—N1174.0 (4)N2—C2A—C2—H2b174.7 (4)
O01—C08—N1—C1A0.5 (6)C2B—C2A—C2—O267.1 (5)
O01—C08—N1—C1D171.6 (4)C2B—C2A—C2—H2c172.1 (4)
O08—C08—N1—C1A179.9 (5)C2B—C2A—C2—H2b53.7 (5)
O08—C08—N1—C1D9.0 (8)H2A—C2A—C2—O2172.0 (4)
C08—N1—C1A—C1B168.1 (5)H2A—C2A—C2—H2c51.2 (6)
C08—N1—C1A—C171.3 (6)H2A—C2A—C2—H2b67.2 (5)
C08—N1—C1A—H1A50.8 (6)C2A—C2B—C2G—C2D1179.2 (5)
C1D—N1—C1A—C1117.0 (4)C2A—C2B—C2G—C2D258.7 (7)
C1D—N1—C1A—H1A120.9 (4)C2A—C2B—C2G—H2G60.7 (7)
C08—N1—C1D—C1G152.1 (5)H2Ba—C2B—C2G—C2D159.7 (6)
C08—N1—C1D—H1Da33.3 (7)H2Ba—C2B—C2G—C2D262.4 (7)
C08—N1—C1D—H1Db89.2 (6)H2Ba—C2B—C2G—H2G178.1 (5)
C1A—N1—C1D—H1Da138.9 (4)H2Bb—C2B—C2G—C2D158.1 (6)
C1A—N1—C1D—H1Db98.6 (5)H2Bb—C2B—C2G—C2D2179.8 (6)
N1—C1A—C1B—H1Ba104.2 (5)H2Bb—C2B—C2G—H2G60.4 (6)
N1—C1A—C1B—H1Bb134.4 (5)C2B—C2G—C2D1—H2D1a180.0 (5)
C1—C1A—C1B—C1G135.9 (5)C2B—C2G—C2D1—H2D1b60.0 (7)
C1—C1A—C1B—H1Ba16.6 (7)C2B—C2G—C2D1—H2D1c60.0 (7)
C1—C1A—C1B—H1Bb104.8 (5)C2D2—C2G—C2D1—H2D1a57.1 (8)
H1A—C1A—C1B—C1G102.2 (5)C2D2—C2G—C2D1—H2D1b177.1 (7)
H1A—C1A—C1B—H1Ba138.5 (5)C2D2—C2G—C2D1—H2D1c63.0 (8)
H1A—C1A—C1B—H1Bb17.1 (7)H2G—C2G—C2D1—H2D1a61.6 (7)
N1—C1A—C1—O141.4 (6)H2G—C2G—C2D1—H2D1b58.4 (7)
N1—C1A—C1—N2146.1 (4)H2G—C2G—C2D1—H2D1c178.4 (5)
C1A—C1—N2—C2A171.2 (4)C2B—C2G—C2D2—H2D2a180.0 (7)
C1—N2—C2A—C277.8 (5)C2B—C2G—C2D2—H2D2b60.0 (8)
N2—C2A—C2—O253.9 (5)C2B—C2G—C2D2—H2D2c60.0 (10)
C1B—C1A—C1—O174.7 (6)C2D1—C2G—C2D2—H2D2a58.0 (10)
C1B—C1A—C1—N297.8 (5)C2D1—C2G—C2D2—H2D2b62.0 (8)
H1A—C1A—C1—O1163.5 (4)C2D1—C2G—C2D2—H2D2c178.0 (7)
H1A—C1A—C1—N224.0 (6)H2G—C2G—C2D2—H2D2a60.6 (9)
C1A—C1B—C1G—C1D28.3 (7)H2G—C2G—C2D2—H2D2b179.4 (6)
C1B—C1G—C1D—N129.6 (6)H2G—C2G—C2D2—H2D2c59.4 (9)
C1A—N1—C1D—C1G20.1 (5)C2A—C2—O2—H103.6 (5)
C1D—N1—C1A—C1B3.6 (5)H2c—C2—O2—H135.5 (5)
N1—C1A—C1B—C1G15.1 (6)H2b—C2—O2—H17.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O20.922.13 (1)3.044 (5)176
O2—H···O10.892.05 (1)2.733 (5)132

Experimental details

Crystal data
Chemical formulaC19H28N2O4
Mr348.44
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)6.371 (4), 8.824 (8), 34.303 (10)
V3)1928 (2)
Z4
Radiation typeCu Kα
µ (mm1)0.68
Crystal size (mm)1.0 × 0.4 × 0.2
Data collection
DiffractometerCAD-4
diffractometer
Absorption correctionAnalytical
(Xtal3.7 ABSORB; Hall et al., 2000)
Tmin, Tmax0.736, 0.875
No. of measured, independent and
observed [I > 2.5σ(I)] reflections
4821, 2111, 1398
Rint0.069
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.093, 2.00
No. of reflections2049
No. of parameters227
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.39, 0.49
Absolute structureAssumed from synthesis, see text

Computer programs: CAD-4 Software (Enraf Nonius, 1989), CAD-4 Software, Xtal3.7 DIFDAT ABSORB ADDREF (Hall et al., 2000), Xtal3.7 CRISP, Xtal3.7 CRILSQ, Xtal3.7 BONDLA CIFIO.

Selected torsion angles (º) top
C06—C07—O01—C08164.0 (4)C1A—C1B—C1G—C1D28.3 (7)
C07—O01—C08—N1174.0 (4)C1B—C1G—C1D—N129.6 (6)
O01—C08—N1—C1A0.5 (6)C1A—N1—C1D—C1G20.1 (5)
C08—N1—C1A—C171.3 (6)C1D—N1—C1A—C1B3.6 (5)
N1—C1A—C1—N2146.1 (4)N1—C1A—C1B—C1G15.1 (6)
C1A—C1—N2—C2A171.2 (4)N2—C2A—C2B—C2G177.2 (4)
C1—N2—C2A—C277.8 (5)C2A—C2B—C2G—C2D1179.2 (5)
N2—C2A—C2—O253.9 (5)C2A—C2B—C2G—C2D258.7 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O20.922.126 (3)3.044 (5)175.61
O2—H···O10.8922.053 (5)2.733 (5)132.14
 

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