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The present paper reports the crystal structures of two short phosphono­tripeptides (one in two crystal forms) containing one [Delta]Phe (dehydro­phenyl­alanine) residue, namely dimethyl (3-{[tert-but­oxy­carbonyl­glycyl-[alpha],[beta]-(Z)-dehydro­phenyl­alanyl]­amino}­propyl)­phosphon­ate, Boc0-Gly1-[Delta](Z)Phe2-[alpha]-Abu3PO3Me2, C21H32N3O7P, (I), and diethyl (4-{[tert-but­oxy­carbonyl­glycyl-[alpha],[beta]-(Z)-dehydrophenyl­alanyl]­amino}­butyl)­phos­phon­ate, Boc0-Gly1-[Delta](Z)Phe2-[alpha]-Nva3PO3Et2, as the propan-2-ol monosolvate 0.122-hydrate, C24H38N3O7P·C3H8O·0.122H2O, (II), and the ethanol monosolvate 0.076-hydrate, C24H38N3O7P·C2H6O·0.076H2O, (III). The crystals of (II) and (III) are isomorphous but differ in the type of solvent. The phosphono group is linked directly to the last C[alpha] atom in the main chain for all three peptides. All the amino acids are trans linked in the main chains. The crystal structures exhibit no intra­molecular hydrogen bonds and are stabilized by inter­molecular hydrogen bonds only.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113002539/sk3464sup1.cif
Contains datablocks I, II, III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113002539/sk3464Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113002539/sk3464IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113002539/sk3464IIIsup4.hkl
Contains datablock III

CCDC references: 934572; 934573; 934574

Comment top

In previous reports we have described the crystal structures of dehydropeptides containing two α,β-dehydroamino acid residues (with a double bond between the Cα and Cβ atoms) (Makowski et al., 2005, 2006, 2010; Lisowski et al., 2007). In short peptides, the presence of one or more ΔPhe residues causes an α,β-turn conformation (Główka et al., 1987; Główka, 1988) and a 310 helical conformation in longer peptides (Rajashankar et al., 1992; Padmanabhan & Singh, 1993; Rajashankar, Ramakumar, Jain & Chauhan, 1995; Rajashankar, Ramakumar, Mal et al., 1995). In this paper, we describe peptides with only one ΔPhe residue and, additionally, a phosphono group linked to the last Cα atom in the main chain. These phosphonodehydropeptides are a new class of peptide derivatives and their activity against cathepsin C was examined (Latajka et al., 2013).

Tripeptide (I), Boc0-Gly1-Δ(Z)Phe2-α-Abu3PO3Me2, contains one dehydrophenylalanyl residue with a Z configuration (the aromatic ring is located cis to the N atom). There is one molecule in the asymmetric unit (Fig. 1). Important bond lengths, bond angles and torsion angles are presented in Table 1. The CαCβ (C8C9) distance for the ΔPhe residue of (I) is 1.329 (5) Å, which agrees with other structures containing ΔPhe (Główka et al., 1987; Makowski et al., 2005, 2010) and also with the classical value of a double C C bond (Allen et al., 1987). Because of the unsaturated character of the bond between Cα and Cβ, the side-chain atoms of the ΔPhe residue are closer to the main chain than in the saturated form. This causes a shortening of the N—Cα (N2—C8), Cβ—Cγ (C9—C10) and Cα—C (C8—C16) bonds, which is similar to the previous data. The values of the angles also deviate from standard data, e.g. the N—Cα—C angle is smaller [115.5 (3)°] than the value of 120° for a standard trigonal bond angle, while the angles for N—CαCβ and CαCβ—Cγ are larger [126.8 (3) and 130.4 (4)°, respectively]. The values of the torsion angles of ΔPhe [χ2 = 3.1 (7)°, χ2,1 = 154.2 (4)° and χ2,2 = -24.2 (7)°] indicate that the side chain is almost planar. All amino acids in (I) are located trans to each other in the main chain. The value of the torsion angle between Gly–ΔPhe is ω1 = -168.4 (3)° and that between ΔPhe–AbuP is ω2 = 179.2 (3)°; the deviations from the ideal value of ±180° are 11.6 and 0.8°, respectively. The Boc group is located trans to the main chain. The phosphono group is linked directly to chiral atom C17. The bond length between Cα17 and atom P1 is 1.811 (4) Å, which is similar to the standard organic phosphonic bond length of 1.800 Å (Allen et al., 1987) and previous results obtained for organic compounds containing a C—P bond (Hong et al., 2009; Cheng et al., 2011). The O5—P1—O6 [113.8 (2)°] and O5—P1—O7 [116.35 (17)°] angles are larger than the O6—P1—O7 angle [102.7 (2)°], suggesting that the phosphono group has a distorted tetrahedral shape. Atoms C16, N31, C17, P1, O5, O7, C18, C19, C20 and C21 in (I) are slightly disordered, with an occupancy of 0.943 (3). The crystal structure of (I) is stabilized by nine intermolecular hydrogen bonds (Table 2). There are no intramolecular stabilizing hydrogen bonds, which corresponds to the spectroscopic studies of this peptide (Latajka et al., 2013). Thus, tripeptide (I) cannot adopt the ordered structure containing turns.

The structure of tripeptide (II), Boc0-Gly1-Δ(Z)Phe2-α-Nva3PO3Et2, contains three different species in the asymmetric unit, namely (II), propan-2-ol and water. The atom-numbering scheme is shown in Fig. 2 and selected bond lengths and angles are given in Table 3. Compound (II) also contains one dehydrophenylalanyl residue and has the same configuration as (I), i.e. Z. The C8C9 bond is 1.3360 (18) Å and this raises the possibility of steric contacts between the side and main chains. Because of this there is also a shortening of the nearest bonds, viz. N—Cα (N2—C8), Cβ–Cγ (C9—C10) and Cα–C (C8—C16). The torsion angles of the ΔPhe residue [χ2 = 4.5 (2)°, χ2,1 = -165.79 (13)° and χ2,2 = 14.8 (2)°] indicate the almost planar conformation of its side chain. All amino acids in (II) are located trans to each other, with torsion angles Gly–ΔPhe ω1 = -172.05 (10)° and ΔPhe–NvaP ω2 = -176.69 (11)°; the deviations from the ideal values are 7.95 and 3.31°, respectively. The torsion angles of the Boc group correspond to a transtrans conformation. The phosphono group is linked to chiral atom C17. The C17—P1 bond is 1.8066 (16) Å, similar to the value in (I). Like in peptide (I), the phosphono group displays a distorted tetrahedral shape, with O5—P1—O6 = 114.89 (6)°, O5—P1—O7 = 113.76 (6)° and O6—P1—O7 105.36 (7)°. This shows that the type of group [methoxy in (I) or ethoxy in (II)] linked directly to the P atom has almost no effect on the angles of the phosphono group. In (II), there are some disordered atoms, two ethoxy groups and the side chain of the (1-aminobutyl)phosphonate. In the side chain of Nva, atoms C19 and C20 are in two positions. Both ethoxy groups connected to the P atom are also disordered. The crystal structure of (II) is stabilized by ten intermolecular hydrogen bonds of different types, namely N—H···O, O—H···O, C—H···O and C—H···N (Table 4). The O atom of the propan-2-ol molecule takes part in two different hydrogen bonds, once as a proton-acceptor atom [N2—H2···O31i; symmetry code: (i) -x + 1, -y + 1, -z + 1] and once as a proton-donor atom (O31—H31···O4 [Symmetry code?]). This propan-2-ol molecule links two molecules of the tripeptide. A water molecule also plays the same linking role between neighbouring peptides, taking part in two hydrogen bonds [O1W—H2W···O3 and O1W—H1W···O5ii; symmetry code: (ii) -x + 1, -y + 1, -z]. Because of the presence of water and propan-2-ol molecules, there is no possibility of the formation of an intramolecular hydrogen-bond network which could stabilize the conformation of (II).

Tripeptide (III) is a second form of (II). The dehydrophenylalanyl residue has the Z configuration. There are three types of species in the asymmetric unit, namely the tripeptide, ethanol and water. The atom-numbering scheme is shown in Fig. 3 and selected bond lengths and angles are given in Table 5. The C8C9 double bond in the ΔPhe residue is 1.3405 (15) Å, which is the longest in the structures presented in this paper. Compared with (I) and (II), the double-bond elongations are 0.0115 and 0.0045 Å, respectively. Because of the presence of a double bond, there is a shortening of the C8—N2 and C9—C10 bonds, which causes a closer positioning of the side chain of ΔPhe. The ΔPhe torsion angles are χ2 = 4.74 (18)°, χ2,1 = -165.79 (12)° and χ2,2 = 14.66 (19)°, and they indicate near-planarity, like in (I) and (II). The amino acids in the main chain are located trans to each other, with Gly–ΔPhe and ΔPhe–NvaP torsion angles of -170.05 (9) and 176.06 (9)°, respectively. The Boc group is also trans to the main chain. Atom C17 is chiral and connected directly to atom P1. The C17—P1 bond length is 1.8091 (13) Å. The phosphono group adopts the same shape as in (I) and (II), with O5—P1—O6 = 114.54 (6)°, O5—P1—O7 = 113.72 (6)° and O6—P1—O7 = 106.43 (6)°. Two disordered ethoxy groups are linked to atom P1. In (II), where the solvent is propan-2-ol, the disorder occurs in the (1-aminobutyl)phosphonate residue. Compared with (II), the side chain of this residue in (III) is ordered, while the ethanol solvent molecule is disordered. The crystal structure of (III) is stabilized by 13 intermolecular hydrogen bonds, namely N—H···O, C—H···N, O—H···O and C—H···O (Table 6). The ethanol and water molecules link two neighbouring phosphonopeptide molecules via hydrogen bonds. There is no turn in the secondary structure of (III); it cannot be stabilized because of the lack of intramolecular hydrogen bonds.

Related literature top

For related literature, see: Allen et al. (1987); Cheng et al. (2011); Główka (1988); Główka et al. (1987); Hong et al. (2009); Latajka et al. (2013); Lisowski et al. (2007); Makowski et al. (2005, 2006, 2010); Padmanabhan & Singh (1993); Rajashankar et al. (1992); Rajashankar, Ramakumar, Jain & Chauhan (1995); Rajashankar, Ramakumar, Mal, Jain & Chauhan (1995); Sheldrick (2008).

Experimental top

The syntheses of the title compounds were described by Latajka et al. (2013). Crystals of (I) were recrystallized from ethanol at 293 K, those of (II) from propan-2-ol at 278 K and those of (III) from ethanol at 293 K.

Refinement top

All C-bound H atoms were introduced in positions calculated from geometry, with C—H = 0.95–1.0 Å. The N- and O-bound H atoms were found from difference Fourier maps; the O—H bonds were restrained with a distance of 0.84 Å; in the final refinement step, AFIX3 was used (SHELXL97; Sheldrick, 2008). For C- and N-bound H atoms, except for the methyl groups, Uiso(H) = 1.2Ueq(C,N); for the methyl groups, Uiso(H) = 1.5Ueq(C).

In the case of (I), it was found during refinement that the position of the phosphonate group is slightly disordered. The disorder groups were modelled using SAME restraints (SHELXL97). Additionally, the N3—C16 and N31—C16 bonds were modelled using the SADI command (SHELXL97). Atoms C16 and C161 were in the same position and therefore were modelled with constraints EADP and EXYZ (SHELXL97). In the absence of significant anomalous dispersion effects, Friedel pairs were merged and the absolute structure was not determined.

In (II), disorder is present in the side-chain of the (1-aminobutyl)phosphonate (C19 and C20) and two ethoxy groups (C21, C22, C23 and C24). In the side-chain of (1-aminobutyl)phosphonate, the disorder was modelled for atoms C19 and C20 with the same occupancy of 0.876 (3). In one of the ethoxy groups, disordered atom C21 was modelled over two positions. Atoms C22 and C22A were in the same position, therefore EADP and EXYZ instructions were used. For the second ethoxy group, disordered atoms C23 and C24 were each modelled over two positions.

In (III), two ethoxy groups (C21, C22, C23 and C24) and the ethanol molecule (C31, C32 and O31) are disordered. For atoms C21, C23, C24 and O31, disorder was modelled for each over two positions. Atoms C22, C31 and C32 were in the same position and were therefore modelled using EADP and EXYZ instructions.

After refinement of (II) and (III), additional peaks were found in the difference Fourier maps, one peak in each case. In (II), the highest residual electron density was 0.83 e Å-3 and this was modelled as a water O atom. In the adopted model, the R factor decreases from 0.049 to 0.045. In (III), the highest peak was 0.48 e Å-3 and this was modelled as in (II). The R factor decreases from 0.045 to 0.044. In both (II) and (III), the water molecules labelled O1W are cooperatively disordered with the ethoxy groups (C21 and C22 atoms in both structures) and have partial occupancies of 0.122 (3) and 0.076 (4), respectively. The water molecules occupy a similar position as the disordered ethoxy groups. [Rather than use software-specific terms such as AFIX3, please paraphrase their effect or action.]

Computing details top

For all compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-labelling scheme for the major component only. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The molecular structure of (II), showing the atom-labelling scheme. Bonds between disordered atoms with a lower occupancy are shown as dashed lines. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 3] Fig. 3. The molecular structure of (III), showing the atom-labelling scheme. Bonds between disordered atoms with a lower occupancy are shown as dashed lines. Displacement ellipsoids are drawn at the 50% probability level.
(I) Dimethyl (3-{[tert-butoxycarbonylglycyl-α,β-(Z)-dehydrophenylalanyl]amino}propyl)phosphonate top
Crystal data top
C21H32N3O7PF(000) = 1000
Mr = 469.47Dx = 1.270 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 17556 reflections
a = 8.597 (3) Åθ = 3–29°
b = 18.023 (4) ŵ = 0.16 mm1
c = 15.852 (4) ÅT = 100 K
V = 2456.2 (12) Å3Needle, colourless
Z = 40.30 × 0.15 × 0.08 mm
Data collection top
Oxford Xcalibur PX κ-geometry
diffractometer with CCD area detector
3134 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.098
Graphite monochromatorθmax = 29.0°, θmin = 3.3°
ω and ϕ scansh = 1111
30498 measured reflectionsk = 2423
3370 independent reflectionsl = 2119
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.23 w = 1/[σ2(Fo2) + (0.045P)2 + 1.3496P]
where P = (Fo2 + 2Fc2)/3
3370 reflections(Δ/σ)max < 0.001
334 parametersΔρmax = 0.29 e Å3
23 restraintsΔρmin = 0.25 e Å3
Crystal data top
C21H32N3O7PV = 2456.2 (12) Å3
Mr = 469.47Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 8.597 (3) ŵ = 0.16 mm1
b = 18.023 (4) ÅT = 100 K
c = 15.852 (4) Å0.30 × 0.15 × 0.08 mm
Data collection top
Oxford Xcalibur PX κ-geometry
diffractometer with CCD area detector
3134 reflections with I > 2σ(I)
30498 measured reflectionsRint = 0.098
3370 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06723 restraints
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.23Δρmax = 0.29 e Å3
3370 reflectionsΔρmin = 0.25 e Å3
334 parameters
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*/UeqOcc. (<1)
C10.3576 (5)0.8746 (2)0.4021 (3)0.0215 (8)
C20.2514 (6)0.9355 (3)0.3688 (3)0.0378 (12)
H2A0.30610.98320.37090.057*
H2B0.15750.93820.40370.057*
H2C0.22230.92450.31040.057*
C30.5102 (5)0.8735 (3)0.3547 (3)0.0355 (11)
H3A0.56060.92210.35950.053*
H3B0.49070.86250.29510.053*
H3C0.57820.83540.37870.053*
C40.2758 (6)0.8000 (3)0.3997 (3)0.0396 (12)
H4A0.34440.76190.42320.059*
H4B0.25010.78740.34120.059*
H4C0.18010.80260.43320.059*
O10.3819 (3)0.89845 (15)0.48950 (18)0.0228 (6)
O20.5417 (3)0.80166 (17)0.52359 (19)0.0291 (7)
C50.4731 (4)0.8583 (2)0.5414 (3)0.0202 (8)
N10.4819 (4)0.8931 (2)0.6177 (2)0.0213 (7)
H10.415 (6)0.926 (3)0.634 (3)0.026*
C60.5601 (5)0.8588 (2)0.6866 (3)0.0223 (8)
H6A0.60620.89800.72260.027*
H6B0.64640.82820.66430.027*
C70.4562 (4)0.81006 (19)0.7409 (2)0.0172 (7)
O30.3254 (3)0.78945 (14)0.72015 (17)0.0198 (6)
N20.5227 (4)0.78868 (17)0.8150 (2)0.0162 (6)
H20.600 (5)0.805 (2)0.839 (3)0.019*
C80.4512 (4)0.73264 (19)0.8638 (2)0.0152 (7)
C90.4083 (4)0.7375 (2)0.9442 (2)0.0187 (8)
H90.36680.69320.96740.022*
C100.4148 (4)0.8005 (2)1.0029 (2)0.0192 (8)
C110.3090 (5)0.8015 (3)1.0697 (3)0.0284 (9)
H110.23860.76131.07640.034*
C120.3044 (6)0.8596 (3)1.1262 (3)0.0380 (12)
H120.22940.85951.17020.046*
C130.4078 (6)0.9181 (3)1.1194 (3)0.0336 (11)
H130.40600.95771.15900.040*
C140.5141 (5)0.9178 (2)1.0535 (3)0.0287 (9)
H140.58600.95761.04830.034*
C150.5175 (5)0.8606 (2)0.9954 (3)0.0216 (8)
H150.58980.86200.95010.026*
O40.3059 (3)0.62187 (14)0.83751 (18)0.0196 (6)
C160.4192 (4)0.6604 (2)0.8181 (2)0.0169 (7)0.943 (3)
N30.5213 (4)0.64126 (18)0.7571 (2)0.0170 (7)0.943 (3)
H30.595 (5)0.662 (3)0.754 (3)0.020*0.943 (3)
C170.5075 (4)0.5730 (2)0.7082 (2)0.0159 (8)0.943 (3)
H170.39900.55380.71480.019*0.943 (3)
C180.5383 (5)0.5856 (3)0.6131 (3)0.0234 (9)0.943 (3)
H18A0.63620.61390.60660.028*0.943 (3)
H18B0.55280.53680.58540.028*0.943 (3)
C190.4095 (5)0.6267 (3)0.5689 (3)0.0290 (10)0.943 (3)
H19A0.43720.63380.50950.043*0.943 (3)
H19B0.39440.67510.59580.043*0.943 (3)
H19C0.31310.59790.57270.043*0.943 (3)
P10.64018 (11)0.50407 (5)0.74984 (7)0.0169 (2)0.943 (3)
O50.8040 (3)0.51538 (16)0.7261 (2)0.0239 (7)0.943 (3)
O60.6126 (4)0.4998 (2)0.8477 (2)0.0244 (9)0.943 (3)
C200.7098 (7)0.5403 (3)0.9062 (3)0.0386 (12)0.943 (3)
H20A0.73880.50780.95320.058*0.943 (3)
H20B0.65260.58320.92790.058*0.943 (3)
H20C0.80400.55720.87710.058*0.943 (3)
O70.5615 (4)0.43075 (15)0.7172 (2)0.0247 (7)0.943 (3)
C210.6347 (6)0.3600 (2)0.7311 (4)0.0462 (16)0.943 (3)
H21A0.57840.32150.70000.069*0.943 (3)
H21B0.63300.34840.79150.069*0.943 (3)
H21C0.74270.36200.71140.069*0.943 (3)
C1610.4192 (4)0.6604 (2)0.8181 (2)0.0169 (7)0.057 (3)
N310.550 (4)0.628 (3)0.791 (4)0.050*0.057 (3)
H310.63740.65180.78060.060*0.057 (3)
C1710.530 (7)0.548 (3)0.7828 (19)0.050*0.057 (3)
H1710.41970.53610.79780.060*0.057 (3)
C1810.637 (17)0.505 (5)0.844 (4)0.050*0.057 (3)
H18C0.60430.45290.84650.060*0.057 (3)
H18D0.74520.50700.82260.060*0.057 (3)
C1910.633 (14)0.538 (6)0.932 (3)0.050*0.057 (3)
H19D0.70770.51140.96820.075*0.057 (3)
H19E0.52840.53280.95580.075*0.057 (3)
H19F0.66150.59060.93000.075*0.057 (3)
P110.560 (3)0.5220 (13)0.6736 (15)0.050*0.057 (3)
O510.721 (4)0.532 (3)0.643 (3)0.050*0.057 (3)
O610.434 (5)0.562 (3)0.619 (3)0.050*0.057 (3)
C2010.401 (11)0.537 (5)0.534 (3)0.050*0.057 (3)
H20D0.31930.56850.50930.075*0.057 (3)
H20E0.36660.48570.53490.075*0.057 (3)
H20F0.49570.54150.49940.075*0.057 (3)
O710.505 (6)0.4385 (17)0.678 (3)0.050*0.057 (3)
C2110.551 (12)0.391 (3)0.609 (5)0.050*0.057 (3)
H21D0.51190.34060.61880.075*0.057 (3)
H21E0.66510.38960.60500.075*0.057 (3)
H21F0.50820.41010.55590.075*0.057 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0227 (19)0.022 (2)0.0198 (18)0.0023 (16)0.0030 (16)0.0037 (16)
C20.046 (3)0.041 (3)0.026 (2)0.021 (2)0.010 (2)0.005 (2)
C30.025 (2)0.054 (3)0.027 (2)0.001 (2)0.0027 (18)0.011 (2)
C40.046 (3)0.037 (3)0.036 (3)0.017 (2)0.002 (2)0.002 (2)
O10.0244 (15)0.0210 (14)0.0229 (14)0.0072 (11)0.0005 (12)0.0010 (11)
O20.0272 (16)0.0299 (17)0.0301 (16)0.0098 (13)0.0020 (12)0.0023 (13)
C50.0152 (18)0.022 (2)0.023 (2)0.0005 (15)0.0039 (15)0.0048 (15)
N10.0218 (17)0.0253 (18)0.0168 (16)0.0045 (14)0.0010 (14)0.0063 (14)
C60.0170 (18)0.026 (2)0.024 (2)0.0017 (16)0.0003 (15)0.0072 (16)
C70.0161 (16)0.0170 (16)0.0186 (19)0.0051 (13)0.0044 (15)0.0003 (14)
O30.0155 (13)0.0201 (13)0.0237 (13)0.0002 (10)0.0016 (10)0.0006 (11)
N20.0125 (14)0.0162 (15)0.0199 (16)0.0028 (12)0.0015 (12)0.0004 (13)
C80.0134 (17)0.0128 (17)0.0193 (18)0.0016 (13)0.0025 (14)0.0022 (14)
C90.0157 (18)0.020 (2)0.0199 (18)0.0007 (15)0.0001 (14)0.0058 (15)
C100.0186 (17)0.020 (2)0.0186 (19)0.0001 (14)0.0037 (15)0.0063 (15)
C110.034 (2)0.029 (2)0.022 (2)0.0122 (19)0.0037 (18)0.0002 (17)
C120.039 (3)0.049 (3)0.026 (2)0.011 (2)0.014 (2)0.008 (2)
C130.046 (3)0.030 (2)0.025 (2)0.010 (2)0.002 (2)0.006 (2)
C140.032 (2)0.026 (2)0.028 (2)0.0089 (18)0.0033 (19)0.0006 (19)
C150.024 (2)0.0209 (19)0.0203 (19)0.0033 (16)0.0013 (16)0.0011 (16)
O40.0139 (12)0.0174 (13)0.0275 (14)0.0030 (10)0.0016 (11)0.0009 (11)
C160.0144 (16)0.0143 (17)0.0219 (19)0.0035 (13)0.0022 (14)0.0028 (14)
N30.0110 (14)0.0151 (15)0.0248 (18)0.0024 (11)0.0031 (15)0.0016 (15)
C170.0141 (17)0.0156 (18)0.0181 (19)0.0000 (15)0.0027 (15)0.0009 (15)
C180.023 (2)0.029 (2)0.019 (2)0.0019 (17)0.0003 (17)0.0048 (18)
C190.028 (2)0.039 (3)0.020 (2)0.009 (2)0.0017 (18)0.0046 (19)
P10.0157 (4)0.0155 (4)0.0194 (4)0.0003 (4)0.0014 (5)0.0002 (4)
O50.0169 (14)0.0237 (14)0.0311 (17)0.0030 (11)0.0026 (12)0.0060 (12)
O60.024 (2)0.0282 (17)0.0211 (15)0.0019 (14)0.0013 (13)0.0021 (13)
C200.050 (3)0.040 (3)0.027 (2)0.005 (3)0.010 (2)0.010 (2)
O70.0268 (16)0.0139 (14)0.0335 (17)0.0002 (12)0.0072 (14)0.0032 (13)
C210.042 (3)0.015 (2)0.081 (5)0.003 (2)0.017 (3)0.011 (3)
C1610.0144 (16)0.0143 (17)0.0219 (19)0.0035 (13)0.0022 (14)0.0028 (14)
Geometric parameters (Å, º) top
C1—O11.466 (5)N3—H30.74 (5)
C1—C31.512 (6)C17—C181.548 (6)
C1—C41.517 (6)C17—P11.811 (4)
C1—C21.523 (6)C17—H171.0000
C2—H2A0.9800C18—C191.505 (6)
C2—H2B0.9800C18—H18A0.9900
C2—H2C0.9800C18—H18B0.9900
C3—H3A0.9800C19—H19A0.9800
C3—H3B0.9800C19—H19B0.9800
C3—H3C0.9800C19—H19C0.9800
C4—H4A0.9800P1—O51.472 (3)
C4—H4B0.9800P1—O61.571 (3)
C4—H4C0.9800P1—O71.572 (3)
O1—C51.347 (5)O6—C201.446 (6)
O2—C51.212 (5)C20—H20A0.9800
C5—N11.366 (5)C20—H20B0.9800
N1—C61.424 (5)C20—H20C0.9800
N1—H10.87 (5)O7—C211.439 (5)
C6—C71.519 (5)C21—H21A0.9800
C6—H6A0.9900C21—H21B0.9800
C6—H6B0.9900C21—H21C0.9800
C7—O31.229 (4)N31—C1711.46 (2)
C7—N21.362 (5)N31—H310.8800
N2—C81.413 (5)C171—C1811.55 (2)
N2—H20.81 (5)C171—P111.813 (19)
C8—C91.329 (5)C171—H1711.0000
C8—C161.515 (5)C181—C1911.51 (2)
C9—C101.468 (6)C181—H18C0.9900
C9—H90.9500C181—H18D0.9900
C10—C111.397 (6)C191—H19D0.9800
C10—C151.403 (5)C191—H19E0.9800
C11—C121.378 (7)C191—H19F0.9800
C11—H110.9500P11—O511.475 (19)
C12—C131.384 (7)P11—O611.566 (19)
C12—H120.9500P11—O711.578 (19)
C13—C141.388 (7)O61—C2011.45 (2)
C13—H130.9500C201—H20D0.9800
C14—C151.383 (6)C201—H20E0.9800
C14—H140.9500C201—H20F0.9800
C15—H150.9500O71—C2111.44 (2)
O4—C161.235 (4)C211—H21D0.9800
C16—N31.352 (5)C211—H21E0.9800
N3—C171.459 (5)C211—H21F0.9800
O1—C1—C3110.5 (3)P1—C17—H17108.2
O1—C1—C4110.4 (4)C19—C18—C17113.6 (4)
C3—C1—C4112.3 (4)C19—C18—H18A108.9
O1—C1—C2101.6 (3)C17—C18—H18A108.9
C3—C1—C2110.9 (4)C19—C18—H18B108.9
C4—C1—C2110.6 (4)C17—C18—H18B108.9
C5—O1—C1120.1 (3)H18A—C18—H18B107.7
O2—C5—O1126.4 (4)C18—C19—H19A109.5
O2—C5—N1124.5 (4)C18—C19—H19B109.5
O1—C5—N1109.0 (3)H19A—C19—H19B109.5
C5—N1—C6120.4 (4)C18—C19—H19C109.5
C5—N1—H1123 (3)H19A—C19—H19C109.5
C6—N1—H1112 (3)H19B—C19—H19C109.5
N1—C6—C7114.1 (3)O5—P1—O6113.8 (2)
N1—C6—H6A108.7O5—P1—O7116.35 (17)
C7—C6—H6A108.7O6—P1—O7102.7 (2)
N1—C6—H6B108.7O5—P1—C17114.50 (17)
C7—C6—H6B108.7O6—P1—C17107.35 (18)
H6A—C6—H6B107.6O7—P1—C17100.68 (18)
O3—C7—N2122.0 (3)C20—O6—P1121.4 (4)
O3—C7—C6124.1 (3)C21—O7—P1120.4 (3)
N2—C7—C6113.9 (3)C171—N31—H31124.5
C7—N2—C8119.5 (3)N31—C171—C181111 (3)
C7—N2—H2130 (3)N31—C171—P11109 (2)
C8—N2—H2110 (3)C181—C171—P11113 (3)
C9—C8—N2126.8 (3)N31—C171—H171107.9
C9—C8—C16117.7 (3)C181—C171—H171107.9
N2—C8—C16115.5 (3)P11—C171—H171107.9
C8—C9—C10130.4 (4)C191—C181—C171112 (3)
C8—C9—H9114.8C191—C181—H18C109.2
C10—C9—H9114.8C171—C181—H18C109.2
C11—C10—C15117.6 (4)C191—C181—H18D109.2
C11—C10—C9117.8 (4)C171—C181—H18D109.2
C15—C10—C9124.5 (4)H18C—C181—H18D109.2
C12—C11—C10121.4 (4)C181—C191—H19D109.5
C12—C11—H11119.3C181—C191—H19E109.5
C10—C11—H11119.3H19D—C191—H19E109.5
C11—C12—C13120.7 (4)C181—C191—H19F109.5
C11—C12—H12119.7H19D—C191—H19F109.5
C13—C12—H12119.7H19E—C191—H19F109.5
C12—C13—C14118.6 (4)O51—P11—O61114 (2)
C12—C13—H13120.7O51—P11—O71114 (2)
C14—C13—H13120.7O61—P11—O71105 (2)
C15—C14—C13121.2 (4)O51—P11—C171115 (2)
C15—C14—H14119.4O61—P11—C171108 (2)
C13—C14—H14119.4O71—P11—C17199.5 (19)
C14—C15—C10120.4 (4)C201—O61—P11121 (3)
C14—C15—H15119.8O61—C201—H20D109.5
C10—C15—H15119.8O61—C201—H20E109.5
O4—C16—N3123.1 (3)H20D—C201—H20E109.5
O4—C16—C8120.5 (3)O61—C201—H20F109.5
N3—C16—C8116.4 (3)H20D—C201—H20F109.5
C16—N3—C17122.9 (3)H20E—C201—H20F109.5
C16—N3—H3118 (4)C211—O71—P11117 (3)
C17—N3—H3118 (4)O71—C211—H21D109.5
N3—C17—C18112.3 (3)O71—C211—H21E109.5
N3—C17—P1109.5 (3)H21D—C211—H21E109.5
C18—C17—P1110.4 (3)O71—C211—H21F109.5
N3—C17—H17108.2H21D—C211—H21F109.5
C18—C17—H17108.2H21E—C211—H21F109.5
C3—C1—O1—C561.7 (5)C8—C16—N3—C17179.2 (3)
C4—C1—O1—C563.1 (5)C16—N3—C17—C18136.7 (4)
C2—C1—O1—C5179.5 (4)C16—N3—C17—P1100.4 (4)
C1—O1—C5—O20.1 (6)N3—C17—C18—C1972.2 (5)
C1—O1—C5—N1177.8 (3)P1—C17—C18—C19165.3 (3)
O2—C5—N1—C67.9 (6)N3—C17—P1—O576.7 (3)
O1—C5—N1—C6174.3 (3)C18—C17—P1—O547.4 (3)
C5—N1—C6—C789.8 (4)N3—C17—P1—O650.7 (3)
N1—C6—C7—O313.6 (6)C18—C17—P1—O6174.8 (3)
N1—C6—C7—N2168.3 (3)N3—C17—P1—O7157.7 (3)
O3—C7—N2—C89.8 (5)C18—C17—P1—O778.2 (3)
C6—C7—N2—C8168.4 (3)O5—P1—O6—C2031.0 (4)
C7—N2—C8—C9124.7 (4)O7—P1—O6—C20157.6 (4)
C7—N2—C8—C1654.3 (4)C17—P1—O6—C2096.8 (4)
N2—C8—C9—C103.1 (7)O5—P1—O7—C2151.5 (5)
C16—C8—C9—C10175.9 (4)O6—P1—O7—C2173.4 (4)
C8—C9—C10—C11154.2 (4)C17—P1—O7—C21175.9 (4)
C8—C9—C10—C1524.2 (7)N31—C171—C181—C19146 (12)
C15—C10—C11—C120.4 (7)P11—C171—C181—C191169 (9)
C9—C10—C11—C12178.1 (4)N31—C171—P11—O5167 (4)
C10—C11—C12—C131.6 (8)C181—C171—P11—O5157 (6)
C11—C12—C13—C141.3 (8)N31—C171—P11—O6162 (4)
C12—C13—C14—C150.2 (7)C181—C171—P11—O61174 (6)
C13—C14—C15—C101.4 (7)N31—C171—P11—O71171 (4)
C11—C10—C15—C141.1 (6)C181—C171—P11—O7165 (6)
C9—C10—C15—C14179.4 (4)O51—P11—O61—C20168 (7)
C9—C8—C16—O430.7 (5)O71—P11—O61—C20158 (7)
N2—C8—C16—O4148.4 (3)C171—P11—O61—C201163 (6)
C9—C8—C16—N3148.6 (4)O51—P11—O71—C21141 (7)
N2—C8—C16—N332.3 (5)O61—P11—O71—C21185 (6)
O4—C16—N3—C170.0 (6)C171—P11—O71—C211163 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O5i0.87 (5)2.04 (5)2.830 (5)152 (4)
N2—H2···O4ii0.81 (5)2.21 (5)2.942 (4)149 (4)
N3—H3···O3ii0.74 (5)2.23 (5)2.955 (4)168 (5)
C3—H3C···O20.982.402.987 (6)118
C6—H6A···O4ii0.992.533.210 (5)126
C9—H9···O40.952.482.825 (5)101
C15—H15···O4ii0.952.593.537 (5)173
C17—H17···O41.002.442.825 (5)103
C20—H20C···O50.982.513.001 (7)111
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x+1/2, y+3/2, z.
(II) Diethyl (4-{[tert-butoxycarbonylglycyl-α,β-(Z)-dehydrophenylalanyl]amino}butyl)phosphonate propan-2-ol monosolvate 0.122-hydrate top
Crystal data top
C24H38N3O7P·C3H8O·0.122H2OZ = 2
Mr = 573.80F(000) = 618.4
Triclinic, P1Dx = 1.209 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.131 (4) ÅCell parameters from 12025 reflections
b = 12.866 (5) Åθ = 2–32°
c = 13.368 (5) ŵ = 0.14 mm1
α = 68.90 (4)°T = 110 K
β = 75.94 (4)°Needle, colourless
γ = 84.11 (4)°0.44 × 0.08 × 0.07 mm
V = 1576.7 (11) Å3
Data collection top
Oxford Xcalibur PX κ-geometry
diffractometer with CCD area detector
5951 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 32.6°, θmin = 2.5°
ω and ϕ scansh = 1514
23109 measured reflectionsk = 1519
10752 independent reflectionsl = 1820
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.031P)2]
where P = (Fo2 + 2Fc2)/3
10752 reflections(Δ/σ)max < 0.001
406 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.45 e Å3
Crystal data top
C24H38N3O7P·C3H8O·0.122H2Oγ = 84.11 (4)°
Mr = 573.80V = 1576.7 (11) Å3
Triclinic, P1Z = 2
a = 10.131 (4) ÅMo Kα radiation
b = 12.866 (5) ŵ = 0.14 mm1
c = 13.368 (5) ÅT = 110 K
α = 68.90 (4)°0.44 × 0.08 × 0.07 mm
β = 75.94 (4)°
Data collection top
Oxford Xcalibur PX κ-geometry
diffractometer with CCD area detector
5951 reflections with I > 2σ(I)
23109 measured reflectionsRint = 0.034
10752 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.35 e Å3
10752 reflectionsΔρmin = 0.45 e Å3
406 parameters
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*/UeqOcc. (<1)
C10.88289 (12)0.83953 (9)0.49438 (10)0.0223 (3)
C20.78410 (14)0.89598 (10)0.56612 (11)0.0315 (3)
H2A0.76320.84440.64230.047*
H2B0.70000.91680.53920.047*
H2C0.82580.96290.56290.047*
C31.00949 (13)0.79835 (10)0.53939 (11)0.0284 (3)
H3A1.07300.76490.49090.043*
H3B0.98440.74240.61320.043*
H3C1.05290.86110.54320.043*
C40.91378 (15)0.91661 (10)0.37548 (11)0.0321 (3)
H4A0.97740.87930.33060.048*
H4B0.95470.98480.36990.048*
H4C0.82920.93550.34900.048*
O10.80483 (8)0.74312 (6)0.50807 (7)0.02299 (19)
O20.96637 (9)0.68231 (7)0.38784 (7)0.0276 (2)
C50.86125 (12)0.66988 (9)0.45724 (10)0.0204 (3)
N10.78111 (11)0.58026 (8)0.49455 (9)0.0231 (2)
H10.7129 (14)0.5793 (11)0.5424 (11)0.028*
C60.82078 (14)0.48688 (10)0.45732 (10)0.0269 (3)
H6A0.78800.41790.51920.032*
H6B0.92140.48210.43910.032*
C70.77005 (13)0.48942 (10)0.35906 (10)0.0226 (3)
O30.80630 (9)0.41841 (7)0.31670 (7)0.0312 (2)
N20.68531 (11)0.57523 (8)0.31986 (8)0.0204 (2)
H20.6524 (13)0.6169 (10)0.3554 (10)0.024*
C80.61936 (12)0.57743 (9)0.23755 (9)0.0193 (2)
C90.61443 (12)0.66722 (10)0.14831 (9)0.0221 (3)
H90.56120.65950.10190.027*
C100.67873 (13)0.77603 (10)0.11089 (10)0.0241 (3)
C110.63240 (14)0.86320 (10)0.02841 (11)0.0317 (3)
H110.56120.85010.00030.038*
C120.68754 (16)0.96818 (11)0.01250 (12)0.0408 (4)
H120.65441.02600.06890.049*
C130.79096 (16)0.98913 (12)0.02853 (12)0.0425 (4)
H130.82841.06140.00120.051*
C140.83930 (15)0.90385 (12)0.10965 (12)0.0399 (4)
H140.91120.91760.13730.048*
C150.78402 (14)0.79865 (11)0.15108 (11)0.0310 (3)
H150.81780.74120.20730.037*
C160.53710 (12)0.47600 (9)0.26615 (10)0.0210 (3)
O40.48435 (9)0.42379 (7)0.36352 (6)0.0252 (2)
N30.52032 (11)0.44868 (8)0.18258 (8)0.0251 (2)
H30.5651 (14)0.4803 (11)0.1194 (11)0.030*
C170.43626 (13)0.35517 (10)0.19976 (10)0.0265 (3)
H170.40600.31480.28060.032*
C180.51460 (14)0.27329 (11)0.14702 (12)0.0338 (3)
H18A0.52960.30880.06610.041*
H18B0.45780.20710.16930.041*
C190.65442 (19)0.23403 (14)0.17748 (16)0.0320 (4)0.876 (3)
H19A0.69670.18020.14110.038*0.876 (3)
H19B0.71480.29900.14850.038*0.876 (3)
C200.64482 (18)0.18009 (13)0.29977 (14)0.0402 (5)0.876 (3)
H20A0.73570.15560.31330.060*0.876 (3)
H20B0.58510.11570.32920.060*0.876 (3)
H20C0.60740.23410.33610.060*0.876 (3)
C19A0.5932 (18)0.2156 (12)0.2239 (13)0.046 (4)*0.124 (3)
H19C0.53580.17410.29640.055*0.124 (3)
H19D0.65340.26600.23280.055*0.124 (3)
C20A0.6698 (13)0.1412 (11)0.1703 (10)0.045 (4)*0.124 (3)
H20D0.75220.11490.19880.068*0.124 (3)
H20E0.69530.18120.09080.068*0.124 (3)
H20F0.61380.07740.18510.068*0.124 (3)
P10.28819 (4)0.41540 (3)0.14543 (3)0.02698 (9)
O50.31962 (9)0.49069 (7)0.03001 (7)0.0318 (2)
O60.20563 (9)0.30975 (7)0.16752 (8)0.0358 (2)
C210.0785 (2)0.32298 (16)0.12818 (17)0.0359 (5)0.878 (3)
H21A0.09380.36940.04920.043*0.878 (3)
H21B0.00650.35890.17020.043*0.878 (3)
C220.03778 (15)0.20675 (13)0.14607 (13)0.0433 (4)0.878 (3)
H22A0.04650.21070.12120.065*0.878 (3)
H22B0.02330.16190.22450.065*0.878 (3)
H22C0.11020.17230.10420.065*0.878 (3)
C21A0.1268 (18)0.3010 (14)0.1041 (15)0.044 (5)*0.122 (3)
H21C0.18690.29970.03400.052*0.122 (3)
H21D0.06970.36950.08640.052*0.122 (3)
C22A0.03778 (15)0.20675 (13)0.14607 (13)0.0433 (4)0.122 (3)
H22D0.01390.21120.09140.065*0.122 (3)
H22E0.02540.20750.21420.065*0.122 (3)
H22F0.09220.13760.16110.065*0.122 (3)
O70.20462 (10)0.47239 (8)0.22701 (7)0.0373 (2)
C230.1966 (4)0.5895 (3)0.2029 (3)0.0407 (7)0.55331
H23A0.28660.62230.16150.049*0.55341
H23B0.17250.60530.27240.049*0.55341
C240.0926 (4)0.6419 (3)0.1366 (3)0.0600 (10)0.55341
H24A0.08860.72240.12130.090*0.55341
H24B0.00340.61000.17790.090*0.55341
H24C0.11740.62750.06720.090*0.55341
C23A0.1238 (5)0.5781 (4)0.1930 (4)0.0488 (11)0.44659
H23C0.09020.58350.12760.059*0.44659
H23D0.04380.57670.25320.059*0.44659
C24A0.2058 (5)0.6767 (4)0.1669 (5)0.0849 (17)0.44659
H24D0.15000.74440.14470.127*0.44659
H24E0.28440.67890.10660.127*0.44659
H24F0.23760.67240.23200.127*0.44659
C310.59945 (14)0.21126 (11)0.58563 (12)0.0336 (3)
H31A0.67280.21320.51970.040*
C320.66023 (17)0.17570 (14)0.68502 (12)0.0535 (5)
H32A0.73570.22460.67110.080*
H32B0.69410.09870.70030.080*
H32C0.59060.18060.74850.080*
C330.48880 (16)0.13581 (13)0.59736 (17)0.0589 (5)
H33A0.45070.16420.53160.088*
H33B0.41690.13340.66220.088*
H33C0.52650.06060.60600.088*
O310.54430 (10)0.32157 (7)0.57126 (7)0.0340 (2)
H310.53530.35280.50620.051*
O1W0.8669 (12)0.4473 (9)0.1058 (10)0.082 (5)*0.122 (3)
H1W0.81000.46550.06470.124*0.122 (3)
H2W0.84280.47710.15400.124*0.122 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0260 (7)0.0164 (6)0.0258 (7)0.0055 (5)0.0051 (5)0.0077 (5)
C20.0331 (8)0.0259 (7)0.0391 (8)0.0033 (6)0.0042 (6)0.0173 (6)
C30.0292 (8)0.0282 (7)0.0315 (7)0.0054 (5)0.0074 (6)0.0131 (6)
C40.0428 (9)0.0220 (7)0.0289 (7)0.0050 (6)0.0087 (6)0.0041 (6)
O10.0233 (5)0.0206 (4)0.0283 (5)0.0042 (3)0.0038 (4)0.0125 (4)
O20.0257 (5)0.0287 (5)0.0302 (5)0.0017 (4)0.0016 (4)0.0150 (4)
C50.0251 (7)0.0195 (6)0.0198 (6)0.0011 (5)0.0120 (5)0.0063 (5)
N10.0295 (6)0.0211 (5)0.0205 (5)0.0056 (5)0.0067 (4)0.0070 (4)
C60.0398 (8)0.0177 (6)0.0287 (7)0.0006 (5)0.0198 (6)0.0065 (5)
C70.0274 (7)0.0177 (6)0.0230 (6)0.0042 (5)0.0087 (5)0.0044 (5)
O30.0388 (6)0.0274 (5)0.0362 (5)0.0071 (4)0.0168 (4)0.0180 (4)
N20.0282 (6)0.0185 (5)0.0175 (5)0.0015 (4)0.0093 (4)0.0068 (4)
C80.0213 (6)0.0217 (6)0.0164 (6)0.0022 (5)0.0048 (5)0.0073 (5)
C90.0233 (7)0.0265 (7)0.0179 (6)0.0028 (5)0.0076 (5)0.0069 (5)
C100.0283 (7)0.0233 (6)0.0190 (6)0.0033 (5)0.0037 (5)0.0055 (5)
C110.0357 (8)0.0268 (7)0.0290 (7)0.0025 (6)0.0078 (6)0.0044 (6)
C120.0524 (10)0.0253 (7)0.0356 (8)0.0016 (7)0.0085 (7)0.0005 (6)
C130.0551 (10)0.0270 (8)0.0384 (9)0.0152 (7)0.0015 (7)0.0069 (7)
C140.0464 (9)0.0411 (9)0.0311 (8)0.0227 (7)0.0043 (7)0.0080 (7)
C150.0347 (8)0.0318 (7)0.0234 (7)0.0114 (6)0.0058 (6)0.0035 (6)
C160.0231 (7)0.0216 (6)0.0187 (6)0.0008 (5)0.0066 (5)0.0060 (5)
O40.0328 (5)0.0266 (5)0.0150 (4)0.0084 (4)0.0056 (4)0.0036 (4)
N30.0332 (7)0.0279 (6)0.0150 (5)0.0139 (5)0.0040 (5)0.0056 (4)
C170.0338 (8)0.0270 (7)0.0189 (6)0.0127 (5)0.0051 (5)0.0055 (5)
C180.0428 (9)0.0320 (7)0.0322 (8)0.0083 (6)0.0110 (6)0.0139 (6)
C190.0315 (10)0.0305 (9)0.0365 (10)0.0015 (7)0.0069 (8)0.0155 (8)
C200.0415 (11)0.0338 (9)0.0441 (11)0.0060 (7)0.0157 (8)0.0099 (8)
P10.0316 (2)0.03067 (19)0.01837 (17)0.01066 (15)0.00276 (14)0.00730 (14)
O50.0370 (6)0.0356 (5)0.0189 (5)0.0083 (4)0.0009 (4)0.0063 (4)
O60.0382 (6)0.0365 (5)0.0338 (5)0.0163 (4)0.0143 (4)0.0051 (4)
C210.0274 (11)0.0446 (11)0.0392 (11)0.0054 (9)0.0124 (9)0.0142 (9)
C220.0361 (9)0.0550 (10)0.0447 (9)0.0180 (7)0.0050 (7)0.0221 (8)
C22A0.0361 (9)0.0550 (10)0.0447 (9)0.0180 (7)0.0050 (7)0.0221 (8)
O70.0439 (6)0.0421 (6)0.0235 (5)0.0004 (5)0.0016 (4)0.0126 (4)
C230.040 (2)0.0353 (19)0.0457 (19)0.0001 (16)0.0016 (17)0.0208 (14)
C240.057 (2)0.056 (2)0.045 (2)0.0245 (18)0.0035 (17)0.0044 (17)
C23A0.037 (3)0.071 (3)0.045 (3)0.006 (3)0.002 (2)0.034 (2)
C24A0.078 (4)0.058 (3)0.097 (4)0.017 (3)0.031 (3)0.030 (3)
C310.0298 (8)0.0356 (8)0.0332 (8)0.0028 (6)0.0030 (6)0.0128 (6)
C320.0494 (11)0.0645 (11)0.0314 (9)0.0207 (8)0.0101 (7)0.0037 (8)
C330.0382 (10)0.0448 (10)0.0931 (15)0.0039 (8)0.0012 (10)0.0312 (10)
O310.0476 (6)0.0310 (5)0.0226 (5)0.0060 (4)0.0108 (4)0.0082 (4)
Geometric parameters (Å, º) top
C1—O11.4715 (14)C19—H19A0.9900
C1—C31.5145 (18)C19—H19B0.9900
C1—C41.5149 (19)C20—H20A0.9800
C1—C21.5279 (18)C20—H20B0.9800
C2—H2A0.9800C20—H20C0.9800
C2—H2B0.9800C19A—C20A1.449 (19)
C2—H2C0.9800C19A—H19C0.9900
C3—H3A0.9800C19A—H19D0.9900
C3—H3B0.9800C20A—H20D0.9800
C3—H3C0.9800C20A—H20E0.9800
C4—H4A0.9800C20A—H20F0.9800
C4—H4B0.9800P1—O51.4727 (12)
C4—H4C0.9800P1—O71.5632 (12)
O1—C51.3558 (15)P1—O61.5681 (12)
O2—C51.2118 (15)O6—C21A1.336 (18)
C5—N11.3486 (17)O6—C211.478 (2)
N1—C61.4447 (16)C21—C221.511 (2)
N1—H10.817 (13)C21—H21A0.9900
C6—C71.5114 (17)C21—H21B0.9900
C6—H6A0.9900C22—H22A0.9800
C6—H6B0.9900C22—H22B0.9800
C7—O31.2218 (14)C22—H22C0.9800
C7—N21.3557 (17)C21A—H21C0.9900
N2—C81.4103 (15)C21A—H21D0.9900
N2—H20.833 (12)O7—C231.421 (3)
C8—C91.3360 (18)O7—C23A1.494 (5)
C8—C161.5009 (17)C23—C241.493 (5)
C9—C101.4694 (18)C23—H23A0.9900
C9—H90.9500C23—H23B0.9900
C10—C111.3954 (19)C24—H24A0.9800
C10—C151.4021 (18)C24—H24B0.9800
C11—C121.3822 (19)C24—H24C0.9800
C11—H110.9500C23A—C24A1.477 (6)
C12—C131.384 (2)C23A—H23C0.9900
C12—H120.9500C23A—H23D0.9900
C13—C141.382 (2)C24A—H24D0.9800
C13—H130.9500C24A—H24E0.9800
C14—C151.3847 (19)C24A—H24F0.9800
C14—H140.9500C31—O311.4340 (17)
C15—H150.9500C31—C331.501 (2)
C16—O41.2399 (15)C31—C321.502 (2)
C16—N31.3371 (15)C31—H31A1.0000
N3—C171.4635 (16)C32—H32A0.9800
N3—H30.830 (13)C32—H32B0.9800
C17—C181.5257 (19)C32—H32C0.9800
C17—P11.8066 (16)C33—H33A0.9800
C17—H171.0000C33—H33B0.9800
C18—C19A1.403 (15)C33—H33C0.9800
C18—C191.553 (2)O31—H310.8400
C18—H18A0.9900O1W—H1W0.8497
C18—H18B0.9900O1W—H2W0.8400
C19—C201.511 (3)
O1—C1—C3109.10 (10)C17—C18—H18B108.6
O1—C1—C4110.88 (10)C19—C18—H18B108.6
C3—C1—C4113.06 (11)H18A—C18—H18B107.6
O1—C1—C2102.19 (10)C20—C19—C18113.52 (16)
C3—C1—C2110.61 (11)C20—C19—H19A108.9
C4—C1—C2110.48 (11)C18—C19—H19A108.9
C1—C2—H2A109.5C20—C19—H19B108.9
C1—C2—H2B109.5C18—C19—H19B108.9
H2A—C2—H2B109.5H19A—C19—H19B107.7
C1—C2—H2C109.5C18—C19A—C20A99.9 (10)
H2A—C2—H2C109.5C18—C19A—H19C111.8
H2B—C2—H2C109.5C20A—C19A—H19C111.8
C1—C3—H3A109.5C18—C19A—H19D111.8
C1—C3—H3B109.5C20A—C19A—H19D111.8
H3A—C3—H3B109.5H19C—C19A—H19D109.5
C1—C3—H3C109.5C19A—C20A—H20D109.5
H3A—C3—H3C109.5C19A—C20A—H20E109.5
H3B—C3—H3C109.5H20D—C20A—H20E109.5
C1—C4—H4A109.5C19A—C20A—H20F109.5
C1—C4—H4B109.5H20D—C20A—H20F109.5
H4A—C4—H4B109.5H20E—C20A—H20F109.5
C1—C4—H4C109.5O5—P1—O7113.76 (6)
H4A—C4—H4C109.5O5—P1—O6114.89 (6)
H4B—C4—H4C109.5O7—P1—O6105.36 (7)
C5—O1—C1119.87 (10)O5—P1—C17114.24 (7)
O2—C5—N1124.49 (12)O7—P1—C17104.99 (7)
O2—C5—O1126.00 (11)O6—P1—C17102.38 (6)
N1—C5—O1109.50 (11)C21A—O6—P1125.3 (7)
C5—N1—C6120.92 (12)C21—O6—P1119.62 (10)
C5—N1—H1117.0 (9)O6—C21—C22106.03 (15)
C6—N1—H1122.0 (9)O6—C21—H21A110.5
N1—C6—C7116.34 (11)C22—C21—H21A110.5
N1—C6—H6A108.2O6—C21—H21B110.5
C7—C6—H6A108.2C22—C21—H21B110.5
N1—C6—H6B108.2H21A—C21—H21B108.7
C7—C6—H6B108.2O6—C21A—H21C107.7
H6A—C6—H6B107.4O6—C21A—H21D107.7
O3—C7—N2122.36 (11)H21C—C21A—H21D107.1
O3—C7—C6121.08 (11)C23—O7—P1123.81 (15)
N2—C7—C6116.54 (11)C23A—O7—P1123.98 (19)
C7—N2—C8120.66 (10)O7—C23—C24110.9 (3)
C7—N2—H2120.6 (9)O7—C23—H23A109.5
C8—N2—H2116.2 (9)C24—C23—H23A109.5
C9—C8—N2123.38 (11)O7—C23—H23B109.5
C9—C8—C16121.84 (11)C24—C23—H23B109.5
N2—C8—C16114.20 (10)H23A—C23—H23B108.0
C8—C9—C10129.91 (11)C23—C24—H24A109.5
C8—C9—H9115.0C23—C24—H24B109.5
C10—C9—H9115.0H24A—C24—H24B109.5
C11—C10—C15117.50 (12)C23—C24—H24C109.5
C11—C10—C9117.55 (12)H24A—C24—H24C109.5
C15—C10—C9124.95 (12)H24B—C24—H24C109.5
C12—C11—C10121.60 (13)C24A—C23A—O7111.6 (5)
C12—C11—H11119.2C24A—C23A—H23C109.3
C10—C11—H11119.2O7—C23A—H23C109.3
C11—C12—C13120.10 (14)C24A—C23A—H23D109.3
C11—C12—H12120.0O7—C23A—H23D109.3
C13—C12—H12120.0H23C—C23A—H23D108.0
C14—C13—C12119.35 (14)C23A—C24A—H24D109.5
C14—C13—H13120.3C23A—C24A—H24E109.5
C12—C13—H13120.3H24D—C24A—H24E109.5
C13—C14—C15120.72 (14)C23A—C24A—H24F109.5
C13—C14—H14119.6H24D—C24A—H24F109.5
C15—C14—H14119.6H24E—C24A—H24F109.5
C14—C15—C10120.73 (13)O31—C31—C33109.29 (12)
C14—C15—H15119.6O31—C31—C32107.05 (12)
C10—C15—H15119.6C33—C31—C32112.84 (14)
O4—C16—N3122.86 (11)O31—C31—H31A109.2
O4—C16—C8120.04 (11)C33—C31—H31A109.2
N3—C16—C8117.06 (11)C32—C31—H31A109.2
C16—N3—C17122.08 (11)C31—C32—H32A109.5
C16—N3—H3120.0 (9)C31—C32—H32B109.5
C17—N3—H3117.6 (9)H32A—C32—H32B109.5
N3—C17—C18111.88 (11)C31—C32—H32C109.5
N3—C17—P1106.27 (9)H32A—C32—H32C109.5
C18—C17—P1112.93 (9)H32B—C32—H32C109.5
N3—C17—H17108.5C31—C33—H33A109.5
C18—C17—H17108.5C31—C33—H33B109.5
P1—C17—H17108.5H33A—C33—H33B109.5
C19A—C18—C17100.9 (6)C31—C33—H33C109.5
C17—C18—C19114.55 (11)H33A—C33—H33C109.5
C19A—C18—H18A137.1H33B—C33—H33C109.5
C17—C18—H18A108.6C31—O31—H31109.5
C19—C18—H18A108.6H1W—O1W—H2W109.0
C19A—C18—H18B91.1
C3—C1—O1—C561.59 (13)C16—N3—C17—P1110.64 (12)
C4—C1—O1—C563.55 (14)N3—C17—C18—C19A77.6 (7)
C2—C1—O1—C5178.71 (10)P1—C17—C18—C19A162.5 (7)
C1—O1—C5—O210.36 (17)N3—C17—C18—C1950.86 (16)
C1—O1—C5—N1170.52 (10)P1—C17—C18—C19170.72 (11)
O2—C5—N1—C63.66 (18)C19A—C18—C19—C209.2 (12)
O1—C5—N1—C6177.20 (10)C17—C18—C19—C2057.30 (17)
C5—N1—C6—C792.40 (15)C17—C18—C19A—C20A178.1 (8)
N1—C6—C7—O3174.63 (11)C19—C18—C19A—C20A56.3 (11)
N1—C6—C7—N24.09 (17)N3—C17—P1—O555.17 (10)
O3—C7—N2—C89.25 (18)C18—C17—P1—O567.86 (10)
C6—C7—N2—C8172.05 (10)N3—C17—P1—O770.14 (10)
C7—N2—C8—C9133.21 (13)C18—C17—P1—O7166.83 (9)
C7—N2—C8—C1655.42 (15)N3—C17—P1—O6179.99 (8)
N2—C8—C9—C104.5 (2)C18—C17—P1—O656.98 (10)
C16—C8—C9—C10175.19 (12)O5—P1—O6—C21A23.1 (10)
C8—C9—C10—C11165.79 (13)O7—P1—O6—C21A102.9 (10)
C8—C9—C10—C1514.8 (2)C17—P1—O6—C21A147.5 (10)
C15—C10—C11—C120.1 (2)O5—P1—O6—C2151.83 (14)
C9—C10—C11—C12179.50 (12)O7—P1—O6—C2174.19 (13)
C10—C11—C12—C130.2 (2)C17—P1—O6—C21176.24 (12)
C11—C12—C13—C140.7 (2)C21A—O6—C21—C2260.4 (18)
C12—C13—C14—C150.9 (2)P1—O6—C21—C22171.12 (11)
C13—C14—C15—C100.6 (2)O5—P1—O7—C2319.8 (2)
C11—C10—C15—C140.1 (2)O6—P1—O7—C23146.5 (2)
C9—C10—C15—C14179.25 (13)C17—P1—O7—C23105.9 (2)
C9—C8—C16—O4141.68 (12)O5—P1—O7—C23A19.6 (2)
N2—C8—C16—O429.85 (16)O6—P1—O7—C23A107.1 (2)
C9—C8—C16—N335.90 (17)C17—P1—O7—C23A145.2 (2)
N2—C8—C16—N3152.57 (11)C23A—O7—C23—C2419.4 (4)
O4—C16—N3—C170.82 (19)P1—O7—C23—C2482.1 (3)
C8—C16—N3—C17176.69 (11)C23—O7—C23A—C24A10.3 (4)
C16—N3—C17—C18125.68 (13)P1—O7—C23A—C24A90.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.817 (13)2.083 (14)2.883 (2)166.5 (13)
N2—H2···O31i0.833 (12)2.201 (13)2.8991 (19)141.3 (11)
N3—H3···O5ii0.830 (13)1.978 (14)2.782 (2)162.8 (12)
O31—H31···O40.841.972.7993 (18)171
O1W—H2W···O30.841.982.630 (12)134
O1W—H1W···O5ii0.851.952.795 (12)179
C3—H3A···O20.982.493.0440 (18)115
C4—H4A···O20.982.382.9585 (19)118
C15—H15···N20.952.433.029 (2)121
C17—H17···O41.002.372.7943 (17)105
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z.
(III) tert-butoxycarbonylglycyl-α,β-(Z)- dehydrophenylalanyl-˘1-aminobutyl)phosphonic acid diethyl ester ethanol water solvate top
Crystal data top
C24H38N3O7P·C2H6O·0.076H2OZ = 2
Mr = 558.97F(000) = 601.5
Triclinic, P1Dx = 1.189 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.047 (3) ÅCell parameters from 16877 reflections
b = 12.667 (4) Åθ = 2–35°
c = 13.499 (4) ŵ = 0.14 mm1
α = 69.16 (4)°T = 180 K
β = 76.54 (4)°Parallelepiped, colourless
γ = 83.89 (4)°0.47 × 0.22 × 0.21 mm
V = 1560.9 (10) Å3
Data collection top
Oxford Xcalibur PX κ-geometry
diffractometer with CCD area detector
7581 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 35.0°, θmin = 2.7°
ω and ϕ scansh = 1314
21697 measured reflectionsk = 1720
11597 independent reflectionsl = 2119
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.072P)2]
where P = (Fo2 + 2Fc2)/3
11597 reflections(Δ/σ)max < 0.001
380 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C24H38N3O7P·C2H6O·0.076H2Oγ = 83.89 (4)°
Mr = 558.97V = 1560.9 (10) Å3
Triclinic, P1Z = 2
a = 10.047 (3) ÅMo Kα radiation
b = 12.667 (4) ŵ = 0.14 mm1
c = 13.499 (4) ÅT = 180 K
α = 69.16 (4)°0.47 × 0.22 × 0.21 mm
β = 76.54 (4)°
Data collection top
Oxford Xcalibur PX κ-geometry
diffractometer with CCD area detector
7581 reflections with I > 2σ(I)
21697 measured reflectionsRint = 0.017
11597 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.42 e Å3
11597 reflectionsΔρmin = 0.25 e Å3
380 parameters
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*/UeqOcc. (<1)
C10.87156 (12)0.83991 (8)0.49273 (9)0.0337 (2)
C20.77336 (15)0.89573 (10)0.56450 (11)0.0499 (3)
H2A0.75920.84470.64000.075*
H2B0.68550.91220.54160.075*
H2C0.81200.96630.55820.075*
C31.00486 (15)0.80511 (11)0.53146 (12)0.0511 (3)
H3A1.07140.77960.47840.077*
H3B0.98850.74340.60150.077*
H3C1.04090.86980.53960.077*
C40.89389 (18)0.91542 (11)0.37463 (11)0.0572 (4)
H4A0.95990.87870.33040.086*
H4B0.92940.98780.36650.086*
H4C0.80680.92850.35070.086*
O10.79888 (8)0.73782 (6)0.51125 (6)0.03548 (17)
O20.95622 (8)0.67825 (7)0.38888 (6)0.03872 (19)
C50.85424 (11)0.66428 (8)0.46007 (8)0.0282 (2)
N10.77711 (10)0.57145 (7)0.49982 (7)0.03015 (18)
H10.7089 (14)0.5656 (10)0.5508 (10)0.036*
C60.81542 (13)0.47790 (8)0.46094 (8)0.0340 (2)
H6A0.77830.40820.51950.041*
H6B0.91650.46940.44670.041*
C70.76828 (11)0.48629 (8)0.35917 (8)0.0286 (2)
O30.80442 (10)0.41511 (7)0.31631 (7)0.0440 (2)
N20.68664 (9)0.57629 (7)0.31933 (6)0.02612 (17)
H20.6517 (13)0.6174 (10)0.3563 (9)0.031*
C80.62200 (10)0.57979 (8)0.23573 (7)0.02560 (19)
C90.61901 (11)0.67056 (9)0.14653 (7)0.0298 (2)
H90.56590.66300.09980.036*
C100.68509 (12)0.77982 (9)0.10977 (8)0.0319 (2)
C110.63968 (14)0.86821 (9)0.02642 (9)0.0409 (3)
H110.56910.85510.00370.049*
C120.69563 (16)0.97443 (10)0.01303 (11)0.0518 (3)
H120.66301.03330.06940.062*
C130.79850 (16)0.99482 (11)0.02932 (10)0.0516 (3)
H130.83651.06770.00280.062*
C140.84601 (16)0.90831 (11)0.11084 (10)0.0503 (3)
H140.91770.92200.13950.060*
C150.79046 (13)0.80187 (10)0.15127 (9)0.0409 (3)
H150.82400.74350.20750.049*
C160.53736 (10)0.47875 (8)0.26216 (7)0.02578 (19)
O40.48229 (8)0.42769 (6)0.35797 (5)0.03334 (17)
N30.52000 (9)0.45069 (7)0.17953 (6)0.02808 (18)
H30.5669 (13)0.4798 (10)0.1182 (10)0.034*
C170.43245 (11)0.35834 (8)0.19640 (7)0.0286 (2)
H170.40260.31820.27610.034*
C180.50870 (13)0.27315 (10)0.14465 (9)0.0384 (2)
H18A0.44860.20880.16360.046*
H18B0.52780.30980.06480.046*
C190.64300 (15)0.22817 (12)0.18016 (12)0.0503 (3)
H19A0.68650.17510.14240.060*
H19B0.70520.29210.15690.060*
C200.6282 (2)0.16846 (15)0.30059 (14)0.0712 (5)
H20A0.71850.14160.31690.107*
H20B0.56840.10400.32440.107*
H20C0.58830.22100.33880.107*
P10.28278 (3)0.42088 (2)0.142084 (19)0.02960 (7)
O50.31129 (8)0.49481 (7)0.02755 (5)0.03827 (19)
O60.19809 (9)0.31408 (7)0.16625 (7)0.0457 (2)
C210.07167 (19)0.32449 (16)0.12762 (16)0.0550 (4)0.924 (4)
H21A0.08660.36990.04940.066*0.924 (4)
H21B0.00090.36240.16760.066*0.924 (4)
C220.03020 (17)0.20850 (15)0.14626 (15)0.0719 (5)
H22A0.05220.21300.11770.108*
H22B0.01110.16560.22420.108*
H22C0.10440.17050.10910.108*
C21A0.120 (3)0.292 (2)0.105 (2)0.056 (6)*0.076 (4)
H21C0.06740.36300.07490.067*0.076 (4)
H21D0.18390.27900.04240.067*0.076 (4)
O70.20497 (10)0.48232 (7)0.22160 (6)0.0465 (2)
C230.1316 (2)0.58995 (16)0.18940 (15)0.0527 (5)0.868 (5)
H23A0.04380.58670.24210.063*0.868 (5)
H23B0.11060.60500.11740.063*0.868 (5)
C240.2141 (2)0.68300 (18)0.1844 (2)0.0857 (9)0.868 (5)
H24A0.16290.75490.16210.129*0.868 (5)
H24B0.30060.68660.13170.129*0.868 (5)
H24C0.23320.66890.25610.129*0.868 (5)
C23A0.195 (2)0.5981 (14)0.1979 (13)0.069 (5)*0.132 (5)
H23C0.28490.63110.15680.082*0.132 (5)
H23D0.17290.61430.26650.082*0.132 (5)
C24A0.0929 (19)0.6520 (15)0.1359 (14)0.087 (6)*0.132 (5)
H24D0.09090.73360.12160.131*0.132 (5)
H24E0.00300.62140.17690.131*0.132 (5)
H24F0.11500.63790.06700.131*0.132 (5)
O310.5212 (2)0.30183 (13)0.56798 (8)0.0519 (6)0.924 (6)
H310.51210.33580.50390.078*0.924 (6)
C310.56670 (19)0.18897 (13)0.58014 (12)0.0635 (4)0.924 (6)
H31B0.65200.18880.52580.076*0.924 (6)
H31C0.49650.14890.56740.076*0.924 (6)
C320.5921 (2)0.13020 (15)0.68955 (13)0.0864 (7)
H32A0.62300.05220.69700.130*
H32B0.50740.12990.74320.130*
H32C0.66280.16920.70150.130*
O31A0.4590 (18)0.2669 (12)0.5744 (9)0.036 (4)*0.076 (6)
H31A0.49000.32500.52280.054*0.076 (6)
C31B0.56670 (19)0.18897 (13)0.58014 (12)0.0635 (4)0.076 (6)
H31D0.65090.22820.53320.076*0.076 (6)
H31F0.54840.13200.55070.076*0.076 (6)
O1W0.889 (2)0.4733 (16)0.0989 (17)0.102 (8)*0.076 (4)
H1W0.86280.45470.16730.153*0.076 (4)
H2W0.82930.48260.06110.153*0.076 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0395 (6)0.0257 (5)0.0367 (5)0.0054 (4)0.0049 (4)0.0122 (4)
C20.0576 (9)0.0380 (6)0.0576 (7)0.0055 (6)0.0006 (6)0.0272 (6)
C30.0509 (9)0.0454 (7)0.0692 (9)0.0054 (6)0.0234 (7)0.0261 (6)
C40.0867 (12)0.0342 (6)0.0421 (7)0.0011 (6)0.0099 (7)0.0060 (5)
O10.0348 (4)0.0347 (4)0.0413 (4)0.0079 (3)0.0004 (3)0.0215 (3)
O20.0343 (5)0.0421 (4)0.0415 (4)0.0030 (3)0.0003 (3)0.0210 (3)
C50.0308 (6)0.0298 (5)0.0281 (4)0.0013 (4)0.0110 (4)0.0123 (4)
N10.0363 (5)0.0309 (4)0.0263 (4)0.0045 (4)0.0082 (3)0.0115 (3)
C60.0479 (7)0.0263 (5)0.0338 (5)0.0030 (4)0.0216 (5)0.0105 (4)
C70.0321 (6)0.0278 (5)0.0290 (4)0.0014 (4)0.0104 (4)0.0110 (4)
O30.0522 (6)0.0446 (5)0.0492 (5)0.0145 (4)0.0226 (4)0.0298 (4)
N20.0323 (5)0.0270 (4)0.0226 (3)0.0003 (3)0.0096 (3)0.0105 (3)
C80.0264 (5)0.0307 (5)0.0214 (4)0.0016 (4)0.0059 (3)0.0101 (3)
C90.0315 (6)0.0347 (5)0.0245 (4)0.0037 (4)0.0086 (4)0.0090 (4)
C100.0370 (6)0.0320 (5)0.0247 (4)0.0039 (4)0.0055 (4)0.0071 (4)
C110.0493 (8)0.0359 (6)0.0353 (5)0.0010 (5)0.0144 (5)0.0062 (4)
C120.0668 (10)0.0351 (6)0.0437 (6)0.0000 (6)0.0103 (6)0.0029 (5)
C130.0674 (10)0.0369 (6)0.0446 (7)0.0163 (6)0.0005 (6)0.0095 (5)
C140.0576 (9)0.0519 (7)0.0401 (6)0.0242 (6)0.0076 (6)0.0093 (5)
C150.0448 (7)0.0434 (6)0.0303 (5)0.0145 (5)0.0093 (5)0.0027 (4)
C160.0268 (5)0.0305 (4)0.0212 (4)0.0024 (4)0.0051 (3)0.0098 (3)
O40.0387 (4)0.0404 (4)0.0197 (3)0.0106 (3)0.0017 (3)0.0089 (3)
N30.0303 (5)0.0362 (4)0.0189 (3)0.0095 (3)0.0018 (3)0.0105 (3)
C170.0298 (5)0.0334 (5)0.0245 (4)0.0060 (4)0.0043 (4)0.0118 (4)
C180.0407 (7)0.0404 (6)0.0408 (6)0.0010 (5)0.0078 (5)0.0226 (5)
C190.0444 (8)0.0503 (7)0.0628 (8)0.0093 (6)0.0132 (6)0.0290 (6)
C200.0671 (12)0.0713 (10)0.0716 (10)0.0286 (9)0.0263 (9)0.0212 (8)
P10.02777 (15)0.03788 (14)0.02264 (11)0.00503 (10)0.00243 (9)0.01036 (10)
O50.0358 (5)0.0519 (5)0.0220 (3)0.0024 (3)0.0018 (3)0.0088 (3)
O60.0386 (5)0.0484 (5)0.0510 (5)0.0146 (4)0.0179 (4)0.0089 (4)
C210.0339 (9)0.0702 (11)0.0725 (11)0.0054 (8)0.0195 (8)0.0320 (9)
C220.0459 (9)0.0940 (13)0.0903 (12)0.0261 (8)0.0039 (8)0.0487 (10)
C22A0.0459 (9)0.0940 (13)0.0903 (12)0.0261 (8)0.0039 (8)0.0487 (10)
O70.0529 (6)0.0524 (5)0.0282 (4)0.0117 (4)0.0004 (3)0.0152 (3)
C230.0475 (12)0.0611 (11)0.0508 (9)0.0169 (9)0.0087 (8)0.0271 (8)
C240.0759 (16)0.0537 (12)0.1023 (17)0.0077 (10)0.0188 (12)0.0185 (11)
O310.0659 (11)0.0550 (8)0.0320 (5)0.0163 (7)0.0118 (5)0.0157 (4)
C310.0810 (12)0.0622 (9)0.0529 (8)0.0185 (8)0.0195 (8)0.0288 (7)
C320.1257 (18)0.0748 (12)0.0534 (9)0.0465 (12)0.0269 (10)0.0240 (8)
C31B0.0810 (12)0.0622 (9)0.0529 (8)0.0185 (8)0.0195 (8)0.0288 (7)
C32B0.1257 (18)0.0748 (12)0.0534 (9)0.0465 (12)0.0269 (10)0.0240 (8)
Geometric parameters (Å, º) top
C1—O11.4676 (13)C18—H18A0.9900
C1—C31.5159 (19)C18—H18B0.9900
C1—C41.5168 (18)C19—C201.508 (2)
C1—C21.5185 (17)C19—H19A0.9900
C2—H2A0.9800C19—H19B0.9900
C2—H2B0.9800C20—H20A0.9800
C2—H2C0.9800C20—H20B0.9800
C3—H3A0.9800C20—H20C0.9800
C3—H3B0.9800P1—O51.4731 (11)
C3—H3C0.9800P1—O71.5631 (11)
C4—H4A0.9800P1—O61.5692 (11)
C4—H4B0.9800O6—C21A1.38 (2)
C4—H4C0.9800O6—C211.4582 (18)
O1—C51.3502 (13)C21—C221.488 (2)
O2—C51.2098 (14)C21—H21A0.9900
C5—N11.3501 (14)C21—H21B0.9900
N1—C61.4420 (14)C22—H22A0.9800
N1—H10.839 (13)C22—H22B0.9800
C6—C71.5202 (14)C22—H22C0.9800
C6—H6A0.9900C21A—H21C0.9900
C6—H6B0.9900C21A—H21D0.9900
C7—O31.2179 (13)O7—C23A1.384 (17)
C7—N21.3534 (15)O7—C231.451 (2)
N2—C81.4130 (12)C23—C241.485 (3)
N2—H20.841 (13)C23—H23A0.9900
C8—C91.3405 (15)C23—H23B0.9900
C8—C161.5014 (15)C24—H24A0.9800
C9—C101.4683 (16)C24—H24B0.9800
C9—H90.9500C24—H24C0.9800
C10—C111.4006 (17)C23A—C24A1.44 (3)
C10—C151.4011 (16)C23A—H23C0.9900
C11—C121.3863 (18)C23A—H23D0.9900
C11—H110.9500C24A—H24D0.9800
C12—C131.378 (2)C24A—H24E0.9800
C12—H120.9500C24A—H24F0.9800
C13—C141.384 (2)O31—C311.4171 (19)
C13—H130.9500O31—H310.8400
C14—C151.3863 (17)O31—H31A0.7065
C14—H140.9500C31—C321.467 (2)
C15—H150.9500C31—H31B0.9900
C16—O41.2430 (13)C31—H31C0.9900
C16—N31.3367 (12)C32—H32A0.9800
N3—C171.4595 (14)C32—H32B0.9800
N3—H30.826 (12)C32—H32C0.9800
C17—C181.5332 (16)O31A—H311.1058
C17—P11.8091 (13)O31A—H31A0.8400
C17—H171.0000O1W—H1W0.8498
C18—C191.523 (2)O1W—H2W0.8508
O1—C1—C3108.83 (9)P1—C17—H17108.5
O1—C1—C4111.12 (10)C19—C18—C17113.63 (10)
C3—C1—C4112.25 (12)C19—C18—H18A108.8
O1—C1—C2102.33 (10)C17—C18—H18A108.8
C3—C1—C2110.81 (11)C19—C18—H18B108.8
C4—C1—C2111.06 (11)C17—C18—H18B108.8
C1—C2—H2A109.5H18A—C18—H18B107.7
C1—C2—H2B109.5C20—C19—C18114.33 (13)
H2A—C2—H2B109.5C20—C19—H19A108.7
C1—C2—H2C109.5C18—C19—H19A108.7
H2A—C2—H2C109.5C20—C19—H19B108.7
H2B—C2—H2C109.5C18—C19—H19B108.7
C1—C3—H3A109.5H19A—C19—H19B107.6
C1—C3—H3B109.5C19—C20—H20A109.5
H3A—C3—H3B109.5C19—C20—H20B109.5
C1—C3—H3C109.5H20A—C20—H20B109.5
H3A—C3—H3C109.5C19—C20—H20C109.5
H3B—C3—H3C109.5H20A—C20—H20C109.5
C1—C4—H4A109.5H20B—C20—H20C109.5
C1—C4—H4B109.5O5—P1—O7113.72 (6)
H4A—C4—H4B109.5O5—P1—O6114.54 (6)
C1—C4—H4C109.5O7—P1—O6106.43 (6)
H4A—C4—H4C109.5O5—P1—C17115.12 (6)
H4B—C4—H4C109.5O7—P1—C17103.74 (6)
C5—O1—C1120.52 (9)O6—P1—C17101.98 (6)
O2—C5—N1124.43 (10)C21A—O6—P1129.8 (9)
O2—C5—O1126.15 (10)C21—O6—P1120.94 (10)
N1—C5—O1109.42 (9)O6—C21—C22107.64 (15)
C5—N1—C6120.88 (10)O6—C21—H21A110.2
C5—N1—H1120.1 (9)C22—C21—H21A110.2
C6—N1—H1118.9 (9)O6—C21—H21B110.2
N1—C6—C7116.29 (9)C22—C21—H21B110.2
N1—C6—H6A108.2H21A—C21—H21B108.5
C7—C6—H6A108.2O6—C21A—H21C106.8
N1—C6—H6B108.2O6—C21A—H21D106.8
C7—C6—H6B108.2H21C—C21A—H21D106.6
H6A—C6—H6B107.4C23A—O7—P1125.3 (7)
O3—C7—N2122.63 (9)C23—O7—P1124.72 (9)
O3—C7—C6120.62 (10)O7—C23—C24110.81 (19)
N2—C7—C6116.75 (9)O7—C23—H23A109.5
C7—N2—C8119.38 (9)C24—C23—H23A109.5
C7—N2—H2120.4 (8)O7—C23—H23B109.5
C8—N2—H2116.7 (8)C24—C23—H23B109.5
C9—C8—N2123.99 (9)H23A—C23—H23B108.1
C9—C8—C16121.30 (9)C23—C24—H24A109.5
N2—C8—C16114.09 (8)C23—C24—H24B109.5
C8—C9—C10130.07 (10)H24A—C24—H24B109.5
C8—C9—H9115.0C23—C24—H24C109.5
C10—C9—H9115.0H24A—C24—H24C109.5
C11—C10—C15117.74 (11)H24B—C24—H24C109.5
C11—C10—C9117.33 (10)O7—C23A—C24A113.3 (14)
C15—C10—C9124.93 (10)O7—C23A—H23C108.9
C12—C11—C10121.33 (12)C24A—C23A—H23C108.9
C12—C11—H11119.3O7—C23A—H23D108.9
C10—C11—H11119.3C24A—C23A—H23D108.9
C13—C12—C11120.13 (12)H23C—C23A—H23D107.7
C13—C12—H12119.9C23A—C24A—H24D109.5
C11—C12—H12119.9C23A—C24A—H24E109.5
C12—C13—C14119.48 (12)H24D—C24A—H24E109.5
C12—C13—H13120.3C23A—C24A—H24F109.5
C14—C13—H13120.3H24D—C24A—H24F109.5
C13—C14—C15120.90 (13)H24E—C24A—H24F109.5
C13—C14—H14119.5C31—O31—H31109.4
C15—C14—H14119.5C31—O31—H31A110.5
C14—C15—C10120.40 (11)O31—C31—C32110.27 (13)
C14—C15—H15119.8O31—C31—H31B109.6
C10—C15—H15119.8C32—C31—H31B109.6
O4—C16—N3122.75 (9)O31—C31—H31C109.6
O4—C16—C8119.57 (9)C32—C31—H31C109.6
N3—C16—C8117.62 (8)H31B—C31—H31C108.1
C16—N3—C17121.69 (8)C31—C32—H32A109.5
C16—N3—H3120.2 (9)C31—C32—H32B109.5
C17—N3—H3117.6 (9)H32A—C32—H32B109.5
N3—C17—C18111.55 (9)C31—C32—H32C109.5
N3—C17—P1107.22 (7)H32A—C32—H32C109.5
C18—C17—P1112.44 (7)H32B—C32—H32C109.5
N3—C17—H17108.5H1W—O1W—H2W118.3
C18—C17—H17108.5
C3—C1—O1—C562.98 (13)C8—C16—N3—C17176.06 (9)
C4—C1—O1—C561.12 (14)C16—N3—C17—C18126.77 (11)
C2—C1—O1—C5179.72 (9)C16—N3—C17—P1109.72 (10)
C1—O1—C5—O28.00 (16)N3—C17—C18—C1953.53 (13)
C1—O1—C5—N1172.61 (8)P1—C17—C18—C19174.04 (9)
O2—C5—N1—C62.15 (15)C17—C18—C19—C2059.42 (16)
O1—C5—N1—C6178.44 (8)N3—C17—P1—O555.92 (9)
C5—N1—C6—C785.37 (13)C18—C17—P1—O567.05 (9)
N1—C6—C7—O3174.65 (10)N3—C17—P1—O768.98 (8)
N1—C6—C7—N24.71 (15)C18—C17—P1—O7168.05 (8)
O3—C7—N2—C810.60 (16)N3—C17—P1—O6179.44 (6)
C6—C7—N2—C8170.05 (9)C18—C17—P1—O657.59 (9)
C7—N2—C8—C9133.76 (11)O5—P1—O6—C21A17.4 (15)
C7—N2—C8—C1655.14 (13)O7—P1—O6—C21A109.2 (15)
N2—C8—C9—C104.74 (18)C17—P1—O6—C21A142.4 (15)
C16—C8—C9—C10175.23 (10)O5—P1—O6—C2149.97 (14)
C8—C9—C10—C11165.79 (12)O7—P1—O6—C2176.60 (13)
C8—C9—C10—C1514.66 (19)C17—P1—O6—C21175.00 (12)
C15—C10—C11—C120.76 (19)C21A—O6—C21—C2253 (2)
C9—C10—C11—C12179.66 (11)P1—O6—C21—C22170.15 (11)
C10—C11—C12—C130.3 (2)O5—P1—O7—C23A17.6 (10)
C11—C12—C13—C140.5 (2)O6—P1—O7—C23A144.7 (9)
C12—C13—C14—C150.7 (2)C17—P1—O7—C23A108.1 (10)
C13—C14—C15—C100.3 (2)O5—P1—O7—C2317.13 (16)
C11—C10—C15—C140.49 (18)O6—P1—O7—C23109.93 (15)
C9—C10—C15—C14179.97 (12)C17—P1—O7—C23142.92 (15)
C9—C8—C16—O4141.62 (11)C23A—O7—C23—C240.1 (15)
N2—C8—C16—O429.75 (13)P1—O7—C23—C24101.27 (17)
C9—C8—C16—N335.57 (15)C23—O7—C23A—C24A19.1 (9)
N2—C8—C16—N3153.06 (10)P1—O7—C23A—C24A79.9 (16)
O4—C16—N3—C171.03 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.839 (13)2.038 (14)2.8561 (18)165.0 (12)
N2—H2···O31Ai0.841 (13)2.099 (18)2.928 (12)168.8 (12)
N2—H2···O31i0.841 (13)2.156 (13)2.9267 (19)152.2 (11)
N3—H3···O5ii0.826 (12)1.996 (13)2.7990 (18)164.0 (12)
O31—H31···O40.841.972.8106 (17)175
O31A—H31A···O40.842.162.879 (12)144
O1W—H1W···O30.851.852.70 (2)180
O1W—H2W···O5ii0.851.992.84 (2)180
C3—H3A···O20.982.553.0548 (18)112
C4—H4A···O20.982.382.9494 (19)117
C15—H15···N20.952.463.053 (2)120
C17—H17···O41.002.352.7829 (14)105
C23—H23A···O2iii0.992.583.335 (2)133
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z; (iii) x1, y, z.

Experimental details

(I)(II)(III)
Crystal data
Chemical formulaC21H32N3O7PC24H38N3O7P·C3H8O·0.122H2OC24H38N3O7P·C2H6O·0.076H2O
Mr469.47573.80558.97
Crystal system, space groupOrthorhombic, Pna21Triclinic, P1Triclinic, P1
Temperature (K)100110180
a, b, c (Å)8.597 (3), 18.023 (4), 15.852 (4)10.131 (4), 12.866 (5), 13.368 (5)10.047 (3), 12.667 (4), 13.499 (4)
α, β, γ (°)90, 90, 9068.90 (4), 75.94 (4), 84.11 (4)69.16 (4), 76.54 (4), 83.89 (4)
V3)2456.2 (12)1576.7 (11)1560.9 (10)
Z422
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.160.140.14
Crystal size (mm)0.30 × 0.15 × 0.080.44 × 0.08 × 0.070.47 × 0.22 × 0.21
Data collection
DiffractometerOxford Xcalibur PX κ-geometry
diffractometer with CCD area detector
Oxford Xcalibur PX κ-geometry
diffractometer with CCD area detector
Oxford Xcalibur PX κ-geometry
diffractometer with CCD area detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
30498, 3370, 3134 23109, 10752, 5951 21697, 11597, 7581
Rint0.0980.0340.017
(sin θ/λ)max1)0.6820.7570.807
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.126, 1.23 0.045, 0.091, 1.01 0.044, 0.131, 1.04
No. of reflections33701075211597
No. of parameters334406380
No. of restraints2300
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.29, 0.250.35, 0.450.42, 0.25

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) for (I) top
N2—C81.413 (5)C9—C101.468 (6)
C8—C91.329 (5)C17—P11.811 (4)
C8—C161.515 (5)
C9—C8—N2126.8 (3)O5—P1—O6113.8 (2)
N2—C8—C16115.5 (3)O5—P1—O7116.35 (17)
C8—C9—C10130.4 (4)O6—P1—O7102.7 (2)
C6—C7—N2—C8168.4 (3)C8—C9—C10—C1524.2 (7)
N2—C8—C9—C103.1 (7)C8—C16—N3—C17179.2 (3)
C8—C9—C10—C11154.2 (4)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O5i0.87 (5)2.04 (5)2.830 (5)152 (4)
N2—H2···O4ii0.81 (5)2.21 (5)2.942 (4)149 (4)
N3—H3···O3ii0.74 (5)2.23 (5)2.955 (4)168 (5)
C3—H3C···O20.982.402.987 (6)118
C6—H6A···O4ii0.992.533.210 (5)126
C9—H9···O40.952.482.825 (5)101
C15—H15···O4ii0.952.593.537 (5)173
C17—H17···O41.002.442.825 (5)103
C20—H20C···O50.982.513.001 (7)111
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x+1/2, y+3/2, z.
Selected geometric parameters (Å, º) for (II) top
N2—C81.4103 (15)C9—C101.4694 (18)
C8—C91.3360 (18)C17—P11.8066 (16)
C8—C161.5009 (17)
C9—C8—N2123.38 (11)O5—P1—O7113.76 (6)
N2—C8—C16114.20 (10)O5—P1—O6114.89 (6)
C8—C9—C10129.91 (11)O7—P1—O6105.36 (7)
C6—C7—N2—C8172.05 (10)C8—C9—C10—C1514.8 (2)
N2—C8—C9—C104.5 (2)C8—C16—N3—C17176.69 (11)
C8—C9—C10—C11165.79 (13)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.817 (13)2.083 (14)2.883 (2)166.5 (13)
N2—H2···O31i0.833 (12)2.201 (13)2.8991 (19)141.3 (11)
N3—H3···O5ii0.830 (13)1.978 (14)2.782 (2)162.8 (12)
O31—H31···O40.841.972.7993 (18)171
O1W—H2W···O30.841.982.630 (12)134
O1W—H1W···O5ii0.851.952.795 (12)179
C3—H3A···O20.982.493.0440 (18)115
C4—H4A···O20.982.382.9585 (19)118
C15—H15···N20.952.433.029 (2)121
C17—H17···O41.002.372.7943 (17)105
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z.
Selected geometric parameters (Å, º) for (III) top
N2—C81.4130 (12)C9—C101.4683 (16)
C8—C91.3405 (15)C17—P11.8091 (13)
C8—C161.5014 (15)
C9—C8—N2123.99 (9)O5—P1—O7113.72 (6)
N2—C8—C16114.09 (8)O5—P1—O6114.54 (6)
C8—C9—C10130.07 (10)O7—P1—O6106.43 (6)
C6—C7—N2—C8170.05 (9)C8—C9—C10—C1514.66 (19)
N2—C8—C9—C104.74 (18)C8—C16—N3—C17176.06 (9)
C8—C9—C10—C11165.79 (12)
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.839 (13)2.038 (14)2.8561 (18)165.0 (12)
N2—H2···O31Ai0.841 (13)2.099 (18)2.928 (12)168.8 (12)
N2—H2···O31i0.841 (13)2.156 (13)2.9267 (19)152.2 (11)
N3—H3···O5ii0.826 (12)1.996 (13)2.7990 (18)164.0 (12)
O31—H31···O40.841.972.8106 (17)175
O31A—H31A···O40.842.162.879 (12)144
O1W—H1W···O30.851.852.70 (2)180
O1W—H2W···O5ii0.851.992.84 (2)180
C3—H3A···O20.982.553.0548 (18)112
C4—H4A···O20.982.382.9494 (19)117
C15—H15···N20.952.463.053 (2)120
C17—H17···O41.002.352.7829 (14)105
C23—H23A···O2iii0.992.583.335 (2)133
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z; (iii) x1, y, z.
 

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