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In N,N′-di-tert-butyl-N′′,N′′-dimethyl­phosphoric triamide, C10H26N3OP, (I), and N,N′,N′′,N′′′-tetra-tert-but­oxy­bis(phos­phonic diamide), C16H40N4O3P2, (II), the extended structures are mediated by P(O)...(H—N)2 inter­actions. The asymmetric unit of (I) consists of six independent mol­ecules which aggregate through P(O)...(H—N)2 hydrogen bonds, giving R21(6) loops and forming two independent chains parallel to the a axis. Of the 12 independent tert-butyl groups, five are disordered over two different positions with occupancies ranging from 1 \over 6 to 5 \over 6. In the structure of (II), the asymmetric unit contains one mol­ecule. P(O)...(H—N)2 hydrogen bonds give S(6) and R22(8) rings, and the mol­ecules form extended chains parallel to the c axis. The structures of (I) and (II), along with similar structures having (N)P(O)(NH)2 and (NH)2P(O)(O)P(O)(NH)2 skeletons extracted from the Cambridge Structural Database, are used to compare hydrogen-bond patterns in these families of phospho­ramidates. The strengths of P(O)[...H—N]x (x = 1, 2 or 3) hydrogen bonds are also analysed, using these compounds and previously reported structures with (N)2P(O)(NH) and P(O)(NH)3 fragments.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112008566/fa3268sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112008566/fa3268Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112008566/fa3268IIsup3.hkl
Contains datablock II

CCDC references: 879442; 879443

Comment top

The strengths of PO···H—N hydrogen bonds were investigated recently in compounds having C(O)NHP(O)[NH]2 and C(O)NHP(O)[N]2 skeletons (Pourayoubi, Tarahhomi et al., 2011). In another recent report by our group, the double hydrogen-bond acceptor capability of the P(O) unit in phosphoramidates, and the formation of the PO···[H—N][H—N] grouping, were discussed (Pourayoubi et al., 2012).

We report here a study of the hydrogen-bond patterns in new compounds having (N)P(O)(NH)2 and (NH)2P(O)(O)P(O)(NH)2 fragments [with n H-atom acceptors and 2n H-atom donor centres, with n = 1 and 2], with a double hydrogen-bond acceptor capability at the P(O) group. The observed hydrogen-bond patterns are compared with those of analogous structures. Moreover, the strengths of the PO···[H—N]x (x = 1, 2 or 3) hydrogen bonds are analysed for the new structures, for previously reported analogous compounds and also for compounds with (N)2P(O)(NH) and P(O)(NH)3 skeletons, for comparison.

A search of the Cambridge Structural Database (CSD, Version 5.32, May 2011 update; Allen, 2002; CSD refcodes will be given in capitals followed by the primary reference) shows that the N atom of the P(O)N group in phosphoramidate compounds does not usually act as a hydrogen-bond acceptor because of its weak Lewis base character; only one N—H···N—P hydrogen bond has been observed so far, in 4-I-C6H4NHP(O)[NHCH2CH2CH2NH] (HESCEO; Marsh, 1995).

In compounds having an (N)P(O)(NH)2 skeleton (six structures), three different linear arrangements were observed: (i) formed through PO···H—N hydrogen bonds, with one N—H unit not involved in hydrogen bonding (Fig. 1a) (NUVROL; Bourne et al., 1998); (ii) with molecules linked by an R21(6) ring (Fig. 1b) (MIFYIJ; Gholivand et al., 2002); and (iii) formed via an R22(8) ring (Fig. 1c) (IKASAP; Sabbaghi et al., 2011) [see Bernstein et al. (1995) for nomenclature of hydrogen-bond motifs]. In the two latter cases, with PO···(H—N)(H—N) groups, the phosphoryl O atom acts as a double hydrogen-bond acceptor.

In a compound with an (N)P(O)(NH)2 skeleton, but with one additional hydrogen-bond acceptor present (nitrogen) in the substituent (pyridine) linked to the amido N atom (HIVLII; Gholivand et al., 2008), the PO···H—N hydrogen bond also mediates a linear arrangement, although an intramolecular N—H···N hydrogen bond is also found in the structure.

The molecular structure of (I), with an (N)P(O)(NH)2 skeleton, is shown in Fig. 2. The asymmetric unit of (I) is composed of six independent molecules. The P atom exhibits a distorted tetrahedral environment which is reflected in its bond lengths and angles (Table 1), as has been noted for other phosphoramide derivatives (Pourayoubi, Tarahhomi et al., 2011). The PO and P—N bond lengths are comparable with those in similar compounds (IKASAP; Sabbaghi et al., 2011). In the (CH3)2NP(O) unit, the O—P—N—C torsion angles, which reflect the orientations of the methyl groups with respect to the phosphoryl group, are in the ranges -177.7 (4) to -168.1 (3)° and -9.5 (4) to 4.9 (4)°. Two independent one-dimensional chains are present in the extended structure, each chain containing three independent molecules. In each chain, adjacent molecules are linked via PO···[H—N]2 groups (Table 2), building R21(6) rings in a linear arrangement parallel to [100] (Fig. 3). In each of the independent molecules, the phosphoryl O atom acts as a double hydrogen-bond acceptor.

The hydrogen-bond pattern of a previously published structure, [CH3NH]P(O)[(CH3)NC(O)C(O)N(CH3)] (DIYMED; Hutton et al., 1986), is very similar to that of (I). The asymmetric unit contains four independent molecules which form two one-dimensional chains, each composed of two independent molecules.

Among the six independent molecules in the asymmetric unit of (I), five tert-butyl groups (of a total of 12) were found to be disordered. The relative site occupancies were refined to values in the range 0.1663–0.8337. Disorder in the tert-butyl groups was observed in some similar structures reported previously, even at low temperature (Chivers et al., 2003; Gholivand, Pourayoubi et al., 2005; Gholivand et al., 2009).

There are two previous examples of compounds having an (N)2P(O)(NH2) skeleton [BIXFOE (Kattuboina & Li, 2008) and GOMDOB (Hempel et al., 1999)], with hydrogen bonding mediating the formation of a one-dimensional chain for BIXFOE and a one-dimensional ladder with alternating R22(8) and R42(8) rings for GOMDOB. In the latter, the phosphoryl O atom acts as a double hydrogen-bond acceptor (Fig. 4).

The molecular structure of (II) is shown in Fig. 5. As in (I), the P atoms exhibit a distorted tetrahedral environment, with bond angles at P1 in the range 100.28 (8)–116.84 (7)°. The PO and P—N bond lengths are as expected in (II) (Table 3). The two [(CH3)3CNH]2P(O) units are bridged via an O atom [P—O—P = 126.85 (8)°]. The P1—O1 and P2—O1 bond lengths [1.619 (2) Å for both] are standard for the P—O—P moiety (Pourayoubi et al., 2010). The bridging O atom of the P—O—P fragment does not take part in hydrogen bonding. The hydrogen-bond motifs of this compound, which contains an (NH)2P(O)OP(O)(NH)2 skeleton, are similar to those found for compounds with an (N)P(O)(NH)2 core. Only one neutral molecular structure with this skeleton has been reported so far: [P(O)(NHC6H4(2-CH3))2]2O [OXPOTU (Cameron et al., 1978) and OXPOTU01 (Pourayoubi, Padělková et al., 2011)]. In the structure of (II), each of the phosphoryl O atoms acts as a double hydrogen-bond acceptor, but in this case it participates in one intra- and one intermolecular N—H···O hydrogen bond (Table 4), building S(6) and R22(8) rings which are further linked into an extended chain parallel to the c axis (Fig. 6). This hydrogen-bond pattern has also been observed in [P(O)(NHC6H4(2-CH3))2]2O (OXPOTU and OXPOTU01). Compounds containing an (NH)2P(O)OP(O)(NH)2 group, when crystallized as salts, show a diversity of hydrogen-bond patterns, as in the case of the hydrated salt C48H100N14O3P62+.2Cl-.0.5HCl.3.5H2O (GAHGAZ; Ledger et al., 2010), which has a complicated hydrogen-bond pattern, because H2O and Cl- are also involved.

In order to gauge the strengths of hydrogen bonds in this family of compounds, we have examined 58 previously reported neutral molecular structures (a few with unavailable CIFs were excluded) with the skeletons discussed in this work, and also compounds containing (N)2P(O)(NH) and P(O)(NH)3 skeletons for comparision. A scatter plot of donor···acceptor (D···A) distances versus D—H···A angles for 104 N—H···O and N—H···N hydrogen bonds in these compounds is shown in Fig. 7. Contacts with D—H···A angles smaller than 110° and D···A distances greater than 3.3 Å were not included in Fig. 7. Cocrystals and solvates were also excluded.

Double hydrogen-bond acceptor capability is also found in the structures of compounds having a P(O)(NH)3 skeleton [for example, in P(O)[NHC6H4(4-OCH3)]3 (WAWNIS; Li et al., 2005) and P(O)[NHCH2C6H5]3 (TOKXIB; Gholivand et al., 2006)]. A four-centred P(O)···[H—N]3 skeleton [for example, in P(O)[NHCH3]3 (KABVAL; Chivers et al., 2003)] has also been reported.

The data reveal weak hydrogen bonding for P(O)[NHCH3]3 [KABVAL (Chivers et al., 2003); N···O and N—H···O are 2.970 (2) Å/172 (2)°, 2.961 (2) Å/155 (2)° and 3.253 (2) Å/171 (3)°]. For P(O)[NHC(CH3)3]3 (KABVEP; Chivers et al., 2003), three weak N—H···O hydrogen bonds, in a P(O)···[H—N]3 grouping, were found: 3.255 (4) Å/111.1 (2)°, 3.159 (4) Å/123.0 (2)° and 3.294 (4) Å/93.4 (2)°; the last of these, with a low N—H···O angle and marginal character, is not included in Fig. 7.

All data to the right of the dashed vertical line in Fig. 7 (D···A > 3.1 Å) are from N—H···N and PO···[H—N]x (x = 2 or 3) assemblies. However, this type of hydrogen-bond grouping is also found on the left side of the line.

The maximum population of the distribution is found for hydrogen bonds in the region with D···A = 2.80–3.05 Å and D—H···A = 144–179°.

The shortest N···O distances are found in two hydrogen bonds of [(CH3)2N]P(O)Y, where Y = NHCH(C6H5)CH(C6H5)N(C10H7) (both D···A = 2.75 Å), with different angles (XAVXEY; Alcock et al., 2005). Also, a short distance with a relatively linear angle (2.77 Å and 170°) occurs in the N—H···OP hydrogen bond of P(O)[HNC6H4(4-NO2)][NC5H9(4-CH3)]2 (WALQUW; Gholivand, Shariatinia & Pourayoubi, 2005).

Interestingly, a long donor–acceptor distance [3.477 (2) Å] is observed with a nearly linear angle [171 (2)°] for the N—H···O—(CH3) hydrogen bond in P(O)[NHC6H4(4-OCH3)]3 (WAWNIS; Li et al., 2005), which is not included in Fig. 7.

Related literature top

For related literature, see: Alcock et al. (2005); Allen (2002); Bernstein et al. (1995); Bourne et al. (1998); Cameron et al. (1978); Chivers et al. (2003); Gholivand et al. (2002, 2006, 2008, 2009); Gholivand, Pourayoubi, Shariatinia & Molani (2005); Gholivand, Shariatinia & Pourayoubi (2005); Hempel et al. (1999); Hutton et al. (1986); Kattuboina & Li (2008); Ledger et al. (2010); Li et al. (2005); Marsh (1995); Pourayoubi et al. (2010, 2012); Pourayoubi, Padělková, Chaijan & Růžička (2011); Pourayoubi, Tarahhomi, Saneei, Rheingold & Golen (2011); Sabbaghi et al. (2011).

Experimental top

[(CH3)2N]P(O)Cl2 was prepared according to the literature method of Gholivand et al. (2002).

For the preparation of (I), a solution of tert-butylamine (2.7 g, 37.04 mmol) in chloroform (10 ml) was added at 273 K to a solution of [(CH3)2N]P(O)Cl2 (1.5 g, 9.26 mmol) in dry chloroform (15 ml). After stirring for 4 h, the solvent was removed [in vacuo? by heating?], and the product was washed with deionized water and recrystallized from chloroform–methanol (4:1 v/v) at room temperature.

For the preparation of (II), tert-butylamine (3.4 g, 46.8 mmol) was added to a solution of P(O)Cl3 (1.2 g, 7.8 mmol) in dry chloroform (30 ml) at 273 K. After stirring for 4 h, the solvent was evaporated [in vacuo? by heating?] and the product was washed with distilled water. Single crystals of (II) were obtained fortuitously from a reaction between (II), Zn(CH3COO)2.2H2O and piperazine in CH3OH under reflux, followed by slow evaporation of the filtered solution at room temperature.

Refinement top

For (I), all H atoms belonging to nondisordered groups were located in a difference map, but those attached to C atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry, with C—H = 0.93–0.98 Å and N—H = 0.86–0.89 Å, and with Uiso(H) = 1.2–1.5Ueq(parent atom), after which the positions were refined with riding constraints. Geometric similarity restraints were used between the two different tert-butyl groups of each of the five disordered assemblies. Displacement similarity restraints were used for a number of the disordered groups in the tert-butyl assemblies. The occupancies of the disordered groups were initially refined, keeping the total occupancy fixed at 1 for each assembly, until the largest ratio of the final least-squares parameter shift to the final standard uncertainty was below 0.05. Then the occupancies were fixed, accelerating the final convergence. Despite the extensive modelling of the disorder in the tert-butyl assemblies, the final R residuals remain fairly large [R = 0.0961 for all reflections with I > -3σ(I) and R = 0.0609 for reflections with I > 2σ(I)]. This is most probably due to additional finer unresolved and unmodelled disorder, such as in the hitherto untreated tert-butyl assemblies, or splitting over more than two orientational sites for the five disordered tert-butyl assemblies.

For (II), all H atoms were discernible in difference Fourier maps and could be refined to reasonable geometries. In accord with common practice, H atoms attached to C atoms were kept in ideal positions during the refinement, with C—H = 0.96 Å. The methyl H atoms were allowed to rotate freely about the adjacent C—C bonds. The positions of the N-bound H atoms were restrained to 0.87 (2) Å. All H atoms were refined with Uiso(H) = 1.5Ueq(C) for the methyl groups or 1.2Ueq(N) for –NH– groups.

Computing details top

For both compounds, data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007). Program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003) for (I); JANA2006 (Petříček et al., 2006) for (II). For both compounds, molecular graphics: Mercury (Macrae et al., 2008). Software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003) and enCIFer (Allen et al., 2004) for (I); JANA2006 (Petříček et al., 2006) and enCIFer (Allen et al., 2004) for (II).

Figures top
[Figure 1] Fig. 1. Three different types of linear arrangement in compounds having an (N)P(O)(NH)2 skeleton; dashed lines indicate hydrogen bonds. (a) Through P(O)···H—N hydrogen bonds. (b) via a PO···(H—N)(H—N) grouping, building R21(6) rings. (c) via a PO···(H—N)(H—N) group, building R22(8) rings.
[Figure 2] Fig. 2. The asymmetric unit of (I), showing six independent molecules and the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The minor disordered components are not shown.
[Figure 3] Fig. 3. The packing in (I), showing two independent one-dimensional aggregates via PO···H—N hydrogen bonds (dotted lines) building R21(6) rings. Only H atoms involved in hydrogen bonds are shown. [Symmetry code: (i) x + 1, y, z.]
[Figure 4] Fig. 4. The one-dimensional ladder arrangement containing alternating R22(8) and R42(8) rings in the structure of P(O)[NH2][NCH2C(CH3)2]2. Dashed lines indicate hydrogen bonds. Non-interacting groups have been omitted for clarity.
[Figure 5] Fig. 5. The asymmetric unit of (II), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 6] Fig. 6. The packing in (II), with hydrogen bonds shown as dotted lines. Only H atoms involved in hydrogen bonds are shown. [Symmetry codes: (i) x, -y + 1/2, z - 1/2; (ii) x, -y + 1/2, z + 1/2.]
[Figure 7] Fig. 7. A scatter plot of N···X distances versus N—H···X angles (X = O, N) in phosphoramides with a P(O)(NH)m(N)3-m (m = 1, 2 or 3) or (NH)2P( O)OP(O)(NH)2 skeleton. [In the electronic version of the paper, the yellow and brown squares are data from compounds (I) and (II), respectively. The other squares denote compounds with (N)P(O)(NH)2 (red), (NH)2P( O)OP(O)(NH)2 (black), P(O)(NH)3 and (N)2P(O)(NH) (blue) skeletons.]
(I) tert-butyl[(tert-butylamino)(dimethylamino)phosphoryl]amine top
Crystal data top
C10H26N3OPF(000) = 1560.006
Mr = 235.31Dx = 1.064 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 11069 reflections
a = 12.0615 (4) Åθ = 1.5–29.1°
b = 21.2567 (7) ŵ = 0.17 mm1
c = 17.1877 (6) ÅT = 150 K
β = 90.529 (3)°Rod, colourless
V = 4406.5 (3) Å30.40 × 0.25 × 0.22 mm
Z = 12
Data collection top
Agilent Gemini-S with Sapphire3 detector
diffractometer
17386 independent reflections
Radiation source: Enhance (Mo) X-ray Source11821 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
Detector resolution: 16.0143 pixels mm-1θmax = 29.1°, θmin = 1.5°
ω scansh = 1615
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
k = 2426
Tmin = 0.558, Tmax = 1.000l = 2322
29385 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.061 Method = Modified Sheldrick w = 1/[σ2(F2) + ( 0.08P)2 + 1.62P],
where P = (max(Fo2,0) + 2Fc2)/3
wR(F2) = 0.161(Δ/σ)max = 0.006
S = 0.92Δρmax = 0.53 e Å3
17382 reflectionsΔρmin = 0.57 e Å3
947 parametersAbsolute structure: Flack (1983), with how many Friedel pairs?
207 restraintsAbsolute structure parameter: 0.00 (8)
Primary atom site location: structure-invariant direct methods
Crystal data top
C10H26N3OPV = 4406.5 (3) Å3
Mr = 235.31Z = 12
Monoclinic, P21Mo Kα radiation
a = 12.0615 (4) ŵ = 0.17 mm1
b = 21.2567 (7) ÅT = 150 K
c = 17.1877 (6) Å0.40 × 0.25 × 0.22 mm
β = 90.529 (3)°
Data collection top
Agilent Gemini-S with Sapphire3 detector
diffractometer
17386 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
11821 reflections with I > 2σ(I)
Tmin = 0.558, Tmax = 1.000Rint = 0.051
29385 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.161Δρmax = 0.53 e Å3
S = 0.92Δρmin = 0.57 e Å3
17382 reflectionsAbsolute structure: Flack (1983), with how many Friedel pairs?
947 parametersAbsolute structure parameter: 0.00 (8)
207 restraints
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat with a nominal stability of 0.1 K.

Absorption correction: CrysAlis PRO (Agilent, 2010), multi-scan using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. Five tert-butyl groups were found to be disordered: the additional group was located by Fourier difference maps and matched with the preponderant groups using SAME restraint instructions. The relative site occupancies were refined and found to be in between 0.166 and 0.834. In the final refinement cycles the occupancies were fixed. Geometrical restraints were used to have similar geometries for the disordered tert-butyl groups. In total 207 restraints were used. Two reflections (1 - 1 0; 1 2 1) were omitted from the refinement, because some of the symmetry related equivalents were masked by the (asymmetric) Gemini beamstop.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.77812 (8)0.42010 (6)1.09815 (7)0.0360
O20.6695 (2)0.44182 (15)1.06764 (17)0.0446
N30.7716 (3)0.42415 (19)1.1936 (2)0.0486
C40.6800 (4)0.4518 (3)1.2352 (3)0.0709
H410.66850.42981.28320.1079*
H420.69680.49521.24660.1081*
H430.61440.45021.20300.1079*
C50.8696 (4)0.4146 (4)1.2419 (3)0.0868
H510.85100.39161.28870.1273*
H520.89960.45471.25660.1270*
H530.92430.39151.21340.1269*
N60.8868 (3)0.45864 (15)1.0673 (2)0.0428
H610.93350.43651.04170.0529*
C70.8936 (3)0.5275 (2)1.0539 (3)0.0513
C81.0176 (4)0.5433 (2)1.0512 (3)0.0611
H811.05140.53351.10060.0915*
H821.05220.51981.01070.0918*
H831.02670.58741.04020.0920*
C90.8411 (4)0.5628 (2)1.1211 (4)0.0810
H910.87480.54971.16970.1249*
H920.85260.60711.11470.1249*
H930.76270.55461.12220.1249*
C100.8402 (5)0.5448 (3)0.9773 (4)0.0834
H1010.84910.58910.96740.1281*
H1020.76220.53490.97850.1279*
H1030.87490.52160.93600.1279*
N110.8172 (3)0.34884 (15)1.0769 (2)0.0495
H1110.87200.34621.04610.0606*
C120.7614 (3)0.28908 (13)1.0942 (2)0.0657
C130.6698 (8)0.2954 (3)1.1508 (6)0.11800.4789
H1310.63290.25551.15660.1749*0.4789
H1320.61760.32631.13160.1749*0.4789
H1330.70010.30881.20040.1751*0.4789
C140.7228 (9)0.2610 (4)1.0187 (5)0.10490.4789
H1410.77050.27320.97710.1569*0.4789
H1420.72270.21601.02280.1571*0.4789
H1430.64880.27521.00710.1570*0.4789
C150.8523 (7)0.2461 (4)1.1331 (7)0.12120.4789
H1510.81690.20261.14100.1659*0.4789
H1520.91700.24401.09460.1659*0.4789
H1530.87580.26651.18550.1661*0.4789
C4130.6381 (6)0.2963 (3)1.1090 (5)0.05030.5211
C4140.7837 (7)0.2449 (3)1.0300 (6)0.11850.5211
H41410.76240.20301.04710.1680*0.5211
H41420.86290.24571.01920.1680*0.5211
H41430.74100.25690.98370.1678*0.5211
C4150.8162 (6)0.2645 (3)1.1727 (6)0.10920.5211
H41510.78620.22371.18620.1460*0.5211
H41520.80040.29411.21390.1458*0.5211
H41530.89610.26171.16590.1461*0.5211
H41310.60530.25611.11910.0829*0.5211
H41320.62610.32301.15290.0830*0.5211
H41330.60340.31471.06430.0828*0.5211
P160.85943 (9)0.64004 (6)0.59774 (7)0.0411
O170.7457 (2)0.66017 (16)0.57819 (18)0.0511
N180.8681 (3)0.6366 (2)0.6926 (2)0.0567
C190.9725 (4)0.6211 (3)0.7318 (3)0.0749
H1910.95770.60370.78250.1101*
H1921.01740.65840.73700.1102*
H1931.01120.59110.70100.1102*
C200.7787 (5)0.6468 (4)0.7459 (3)0.1017
H2010.80710.65520.79760.1480*
H2020.73440.68170.72920.1481*
H2030.73350.60970.74660.1481*
N210.9617 (3)0.68386 (16)0.5663 (2)0.0411
H2111.00300.66670.53240.0517*
C220.9685 (4)0.7535 (2)0.5714 (3)0.0468
C231.0916 (4)0.7702 (2)0.5640 (3)0.0639
H2311.10050.81520.56610.0949*
H2321.11870.75440.51500.0949*
H2331.13210.75130.60660.0946*
C240.9015 (4)0.7833 (2)0.5058 (3)0.0616
H2410.93020.77000.45610.0920*
H2420.90690.82850.50970.0922*
H2430.82500.77090.51030.0919*
C250.9255 (5)0.7772 (3)0.6488 (3)0.0704
H2510.96660.75740.69100.1019*
H2520.84760.76750.65340.1018*
H2530.93610.82210.65140.1021*
N260.8986 (3)0.57148 (15)0.5632 (2)0.0506
H2610.95300.57250.53090.0628*
C270.8327 (2)0.51286 (13)0.56396 (17)0.0518
C280.7694 (5)0.5055 (2)0.6416 (3)0.07750.8337
H2810.82010.50820.68500.1148*0.8337
H2820.71540.53820.64570.1149*0.8337
H2830.73260.46540.64310.1150*0.8337
C290.7537 (4)0.5135 (2)0.4966 (3)0.07530.8337
H2910.70390.54850.50100.1099*0.8337
H2920.79480.51690.44910.1098*0.8337
H2930.71210.47480.49550.1101*0.8337
C300.9138 (4)0.4576 (2)0.5597 (3)0.06560.8337
H3010.87350.41860.56180.0970*0.8337
H3020.95370.45990.51180.0969*0.8337
H3030.96540.46050.60260.0970*0.8337
C4280.7099 (9)0.5260 (3)0.5855 (15)0.06970.1663
H42810.66820.48790.57970.0900*0.1663
H42820.70460.54070.63820.0900*0.1663
H42830.68020.55740.55080.0900*0.1663
C4290.8395 (17)0.4820 (7)0.4850 (7)0.08540.1663
H42910.82520.43700.49040.1340*0.1663
H42920.91340.48860.46380.1340*0.1663
H42930.78410.50070.45030.1340*0.1663
C4300.8800 (14)0.4710 (6)0.6281 (11)0.08370.1663
H43010.85370.42880.62090.1120*0.1663
H43020.85560.48670.67750.1120*0.1663
H43030.95950.47160.62670.1120*0.1663
P310.51417 (8)0.73870 (6)0.46963 (6)0.0348
O320.4065 (2)0.70654 (13)0.45762 (16)0.0392
N330.5575 (3)0.74708 (17)0.55954 (19)0.0462
H3310.61350.72460.57190.0558*
C340.4987 (2)0.77756 (15)0.62334 (18)0.0526
C350.3967 (5)0.8129 (4)0.6001 (3)0.08870.7278
H3510.35700.82580.64530.1378*0.7278
H3520.34940.78700.56860.1378*0.7278
H3530.41810.84950.57080.1382*0.7278
C360.5788 (5)0.8163 (4)0.6693 (5)0.15380.7278
H3620.54270.83010.71590.2309*0.7278
H3610.60260.85220.63980.2309*0.7278
H3630.64160.79070.68260.2311*0.7278
C370.4595 (8)0.7231 (4)0.6768 (5)0.17240.7278
H3710.43400.74060.72550.2560*0.7278
H3720.39910.70180.65140.2559*0.7278
H3730.51920.69400.68660.2561*0.7278
C4350.3768 (7)0.7771 (5)0.6166 (4)0.04510.2722
H43510.33700.77800.66520.0780*0.2722
H43520.42310.81570.60510.0800*0.2722
H43530.34600.75550.57180.0780*0.2722
C4360.5464 (8)0.8433 (5)0.6353 (6)0.05960.2722
H43610.51500.86170.68110.0909*0.2722
H43620.62530.84030.64160.0910*0.2722
H43630.53020.86950.59110.0909*0.2722
C4370.5284 (9)0.7383 (5)0.6978 (5)0.05680.2722
H43710.49800.75920.74290.0809*0.2722
H43720.60800.73570.70310.0809*0.2722
H43730.49760.69640.69340.0810*0.2722
N380.6242 (3)0.70515 (16)0.43239 (19)0.0388
H3810.67410.69420.46630.0467*
C390.6310 (3)0.6736 (2)0.3564 (2)0.0451
C400.5694 (4)0.6107 (2)0.3576 (3)0.0537
H4010.59860.58580.39930.0830*
H4020.49190.61800.36540.0828*
H4030.58030.58890.30910.0828*
C410.5804 (4)0.7155 (3)0.2938 (3)0.0607
H4110.61640.75560.29400.0908*
H4120.50200.72110.30340.0907*
H4130.58920.69620.24350.0906*
C420.7541 (4)0.6643 (3)0.3405 (3)0.0622
H4210.76340.64260.29180.0959*
H4220.78700.63980.38230.0957*
H4230.79080.70450.33810.0958*
N430.5001 (3)0.80862 (17)0.4305 (2)0.0509
C440.3972 (4)0.8321 (2)0.3984 (4)0.0719
H4410.38740.87480.41580.1061*
H4420.33520.80650.41590.1060*
H4430.39940.83130.34200.1062*
C450.5940 (5)0.8523 (2)0.4265 (4)0.0780
H4510.56960.89350.44630.1141*
H4520.65560.83540.45880.1140*
H4530.61770.85620.37210.1140*
P460.45278 (8)0.50924 (6)0.93811 (6)0.0351
O470.3430 (2)0.47949 (13)0.92945 (16)0.0398
N480.4900 (3)0.53223 (17)1.0250 (2)0.0410
H4810.54150.51101.04730.0504*
C490.4375 (3)0.5816 (2)1.0738 (3)0.0454
C500.3141 (3)0.5847 (2)1.0582 (3)0.0494
H5010.28190.61581.09150.0750*
H5020.29990.59561.00450.0748*
H5030.28080.54461.06840.0746*
C510.4890 (4)0.6463 (3)1.0556 (4)0.0799
H5110.56780.64401.06410.1180*
H5120.45730.67751.08950.1178*
H5130.47430.65761.00210.1177*
C520.4600 (5)0.5644 (3)1.1568 (3)0.0797
H5210.42720.52451.16800.1188*
H5220.42770.59571.19000.1189*
H5230.53860.56301.16550.1189*
N530.4512 (3)0.57281 (18)0.8829 (2)0.0471
C540.3617 (4)0.5867 (2)0.8277 (3)0.0592
H5410.34710.63120.82750.0861*
H5420.29500.56500.84290.0860*
H5430.38210.57390.77620.0858*
C550.5533 (4)0.6069 (3)0.8660 (3)0.0721
H5510.53940.65150.86600.1070*
H5520.60900.59680.90470.1070*
H5530.57930.59430.81560.1070*
N560.5611 (3)0.46559 (17)0.9172 (2)0.0420
H5610.60960.46050.95460.0512*
C570.5661 (4)0.4198 (2)0.8519 (3)0.0506
C580.6904 (4)0.4067 (3)0.8387 (3)0.0632
H5810.69920.37520.79960.0979*
H5820.72780.44440.82250.0979*
H5830.72360.39190.88670.0977*
C590.5082 (4)0.3599 (3)0.8731 (4)0.0793
H5910.54290.34200.91880.1176*
H5920.51430.33120.82980.1180*
H5930.43080.36840.88300.1180*
C600.5157 (5)0.4487 (3)0.7787 (3)0.0794
H6010.52070.41950.73610.1219*
H6020.43870.45870.78780.1219*
H6030.55560.48670.76560.1222*
P611.18574 (9)0.59160 (6)0.41617 (7)0.0398
O621.0727 (2)0.59868 (15)0.44844 (17)0.0475
N631.2299 (3)0.64756 (17)0.35813 (19)0.0406
H6311.28430.66970.37600.0522*
C641.1625 (4)0.6776 (3)0.2964 (3)0.0526
C651.2416 (4)0.7134 (3)0.2434 (3)0.0594
H6511.27900.74540.27360.0879*
H6521.29570.68510.22260.0879*
H6531.20030.73290.20100.0878*
C661.0798 (4)0.7241 (3)0.3318 (3)0.0844
H6611.11880.75800.35740.1269*
H6621.03220.74110.29160.1268*
H6631.03520.70210.36990.1268*
C671.1007 (5)0.6277 (3)0.2494 (3)0.0949
H6711.05800.64820.20930.1387*
H6721.05250.60480.28360.1390*
H6731.15360.59920.22610.1389*
N681.2898 (3)0.58920 (17)0.4767 (2)0.0412
H6811.33210.62150.47500.0510*
C691.2953 (4)0.5548 (2)0.5514 (3)0.0525
C701.4177 (4)0.5458 (2)0.5721 (3)0.0581
H7011.42590.52460.62100.0899*
H7021.45380.52110.53250.0899*
H7031.45490.58600.57680.0896*
C711.2344 (4)0.5905 (3)0.6147 (3)0.0754
H7111.26800.63160.62070.1148*
H7121.23870.56790.66350.1149*
H7131.15770.59570.59910.1150*
C721.2412 (4)0.4891 (2)0.5422 (4)0.0812
H7211.24750.46660.59040.1180*
H7221.16390.49400.52820.1179*
H7231.27800.46630.50140.1179*
N731.1872 (3)0.52511 (19)0.3667 (2)0.0584
C741.2886 (5)0.5036 (3)0.3301 (4)0.0826
H7411.27440.46800.29800.1263*
H7421.34290.49310.36910.1263*
H7431.31760.53680.29850.1260*
C751.0927 (5)0.4841 (3)0.3534 (4)0.1063
H7511.10160.46150.30490.1560*
H7521.08610.45430.39580.1561*
H7531.02600.50960.35000.1561*
P761.13177 (9)0.35437 (6)0.95440 (7)0.0401
O771.0194 (2)0.36291 (13)0.98729 (18)0.0492
N781.1415 (3)0.27985 (18)0.9281 (3)0.0616
C791.0536 (5)0.2352 (2)0.9373 (4)0.0914
H7911.05170.20770.89330.1381*
H7921.06580.21170.98410.1380*
H7930.98440.25730.94080.1381*
C801.2414 (4)0.2535 (2)0.8973 (4)0.0667
H8011.22280.22660.85410.0981*
H8021.27830.23010.93850.0982*
H8031.28790.28730.87950.0981*
N811.1620 (3)0.39666 (16)0.87966 (19)0.0426
H8111.21790.42100.88590.0523*
C821.1032 (3)0.40565 (16)0.80476 (19)0.0550
C831.1545 (5)0.3554 (4)0.7460 (4)0.08030.6635
H8311.12200.36070.69490.1190*0.6635
H8321.14100.31330.76480.1190*0.6635
H8331.23370.36270.74340.1190*0.6635
C840.9830 (5)0.3867 (4)0.8103 (3)0.07840.6635
H8410.94600.41480.84570.1219*0.6635
H8420.94840.38920.75970.1218*0.6635
H8430.97730.34420.82960.1219*0.6635
C851.1271 (7)0.4684 (3)0.7708 (4)0.10920.6635
H8511.19820.48500.77150.1299*0.6635
H8521.07640.48610.73640.1300*0.6635
H8531.07690.49890.83350.1720*0.6665
C4831.0316 (12)0.3439 (5)0.7909 (6)0.09420.3365
H48310.96960.35240.75620.1600*0.3365
H48321.08070.31330.76760.1600*0.3365
H48331.00420.32820.84000.1600*0.3365
C4841.0175 (12)0.4574 (6)0.8105 (5)0.12970.3365
H48410.95970.44890.77200.2071*0.3365
H48421.04870.49890.80160.2070*0.3365
H48430.98620.45610.86220.2069*0.3365
C4851.1806 (6)0.4090 (8)0.7398 (5)0.14390.3365
H48511.13320.41300.69040.1759*0.3365
H48521.22520.44920.74990.1760*0.3365
H48531.23040.37050.73840.1760*0.3365
N861.2366 (3)0.37155 (16)1.01107 (19)0.0457
H8611.27790.40130.99520.0549*
C871.2566 (3)0.35460 (16)1.09292 (18)0.0568
C881.1826 (7)0.3949 (4)1.1459 (3)0.09920.6788
H8811.20600.43801.14440.1530*0.6788
H8821.10680.39231.12840.1529*0.6788
H8831.18750.37971.19880.1530*0.6788
C891.3718 (6)0.3580 (4)1.1105 (3)0.13480.6788
H8911.38130.35251.16590.2069*0.6788
H8921.41430.32711.08270.2070*0.6788
H8931.39700.39951.09620.2068*0.6788
C901.2100 (8)0.2846 (4)1.1049 (4)0.12350.6788
H9011.25570.25501.07740.1741*0.6788
H9021.21170.27531.15980.1740*0.6788
H9031.13500.28191.08570.1740*0.6788
C4881.1450 (8)0.3445 (6)1.1345 (4)0.10080.3212
H48811.15370.31171.17250.1780*0.3212
H48821.19110.38481.13990.1310*0.3212
H48831.08660.34221.09600.1781*0.3212
C4891.3289 (10)0.4004 (4)1.1293 (4)0.09470.3212
H48911.33750.38861.18430.2100*0.3212
H48921.40240.40391.10560.2099*0.3212
H48931.28960.44081.12500.2101*0.3212
C4901.3122 (10)0.2856 (4)1.0935 (4)0.04580.3212
H49011.32940.27401.14630.0740*0.3212
H49021.37940.28771.06420.0740*0.3212
H49031.26420.25471.07050.0740*0.3212
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0331 (5)0.0333 (6)0.0416 (6)0.0022 (4)0.0001 (5)0.0010 (5)
O20.0312 (14)0.0569 (19)0.0455 (17)0.0021 (12)0.0057 (13)0.0061 (15)
N30.042 (2)0.059 (2)0.045 (2)0.0076 (18)0.0048 (17)0.003 (2)
C40.081 (4)0.077 (4)0.056 (3)0.017 (3)0.019 (3)0.003 (3)
C50.061 (4)0.136 (6)0.063 (4)0.012 (4)0.021 (3)0.005 (4)
N60.0366 (18)0.0280 (19)0.064 (2)0.0009 (14)0.0056 (17)0.0030 (18)
C70.038 (2)0.027 (2)0.089 (4)0.0056 (17)0.005 (2)0.002 (2)
C80.046 (3)0.037 (3)0.100 (4)0.006 (2)0.003 (3)0.000 (3)
C90.068 (3)0.032 (3)0.144 (6)0.007 (2)0.035 (4)0.019 (3)
C100.067 (4)0.054 (3)0.129 (6)0.012 (3)0.018 (4)0.038 (4)
N110.049 (2)0.0306 (19)0.069 (3)0.0070 (16)0.0208 (19)0.0044 (18)
C120.048 (3)0.031 (3)0.118 (5)0.0089 (19)0.018 (3)0.004 (3)
C130.136 (12)0.066 (10)0.153 (18)0.039 (8)0.107 (13)0.018 (9)
C140.079 (9)0.111 (13)0.125 (11)0.072 (8)0.002 (7)0.031 (9)
C150.096 (8)0.076 (8)0.191 (11)0.018 (6)0.021 (7)0.073 (8)
C4130.043 (4)0.044 (6)0.064 (7)0.013 (4)0.005 (4)0.009 (5)
C4140.084 (8)0.047 (6)0.225 (10)0.032 (5)0.071 (7)0.056 (6)
C4150.044 (5)0.074 (9)0.209 (9)0.010 (6)0.018 (7)0.084 (7)
P160.0347 (5)0.0439 (7)0.0448 (7)0.0006 (5)0.0024 (5)0.0016 (6)
O170.0316 (15)0.067 (2)0.054 (2)0.0025 (14)0.0013 (14)0.0043 (17)
N180.042 (2)0.078 (3)0.050 (2)0.002 (2)0.0073 (18)0.009 (2)
C190.068 (4)0.093 (5)0.064 (4)0.007 (3)0.017 (3)0.012 (3)
C200.075 (4)0.171 (8)0.060 (4)0.024 (4)0.020 (3)0.007 (4)
N210.0394 (19)0.036 (2)0.048 (2)0.0003 (15)0.0060 (16)0.0000 (17)
C220.046 (2)0.038 (3)0.056 (3)0.0015 (19)0.004 (2)0.003 (2)
C230.055 (3)0.049 (3)0.087 (4)0.014 (2)0.006 (3)0.001 (3)
C240.061 (3)0.043 (3)0.082 (4)0.002 (2)0.008 (3)0.005 (3)
C250.085 (4)0.050 (3)0.076 (4)0.007 (3)0.003 (3)0.025 (3)
N260.045 (2)0.037 (2)0.071 (3)0.0067 (16)0.0163 (19)0.0029 (19)
C270.048 (3)0.040 (3)0.067 (3)0.011 (2)0.005 (2)0.008 (3)
C280.081 (5)0.062 (4)0.090 (5)0.024 (4)0.019 (4)0.016 (4)
C290.068 (4)0.066 (5)0.091 (5)0.026 (4)0.035 (4)0.018 (4)
C300.065 (4)0.036 (3)0.096 (5)0.007 (3)0.012 (4)0.013 (4)
C4280.065 (16)0.035 (15)0.11 (2)0.021 (12)0.008 (17)0.020 (16)
C4290.12 (3)0.017 (14)0.12 (2)0.022 (16)0.04 (2)0.007 (17)
C4300.08 (2)0.030 (14)0.14 (2)0.003 (14)0.00 (2)0.011 (14)
P310.0363 (5)0.0311 (5)0.0371 (6)0.0032 (4)0.0021 (5)0.0007 (5)
O320.0374 (15)0.0349 (16)0.0453 (17)0.0078 (12)0.0043 (13)0.0016 (13)
N330.0404 (19)0.054 (2)0.044 (2)0.0065 (17)0.0012 (16)0.0094 (19)
C340.053 (3)0.052 (3)0.053 (3)0.007 (2)0.003 (2)0.022 (2)
C350.058 (5)0.116 (8)0.092 (7)0.040 (5)0.014 (4)0.052 (5)
C360.066 (6)0.200 (11)0.194 (12)0.038 (6)0.045 (6)0.168 (11)
C370.248 (14)0.123 (8)0.149 (11)0.060 (7)0.152 (10)0.044 (6)
C4350.038 (8)0.048 (11)0.050 (11)0.004 (6)0.001 (6)0.026 (8)
C4360.021 (6)0.063 (6)0.094 (12)0.005 (6)0.008 (8)0.033 (6)
C4370.047 (9)0.084 (10)0.039 (5)0.004 (9)0.006 (7)0.026 (6)
N380.0395 (18)0.044 (2)0.0326 (19)0.0010 (15)0.0046 (15)0.0044 (17)
C390.044 (2)0.058 (3)0.033 (2)0.004 (2)0.0003 (19)0.001 (2)
C400.060 (3)0.056 (3)0.045 (3)0.000 (2)0.000 (2)0.017 (2)
C410.066 (3)0.080 (4)0.036 (3)0.002 (3)0.001 (2)0.005 (3)
C420.046 (3)0.091 (4)0.050 (3)0.008 (3)0.006 (2)0.016 (3)
N430.049 (2)0.033 (2)0.071 (3)0.0057 (17)0.001 (2)0.008 (2)
C440.073 (4)0.045 (3)0.098 (5)0.009 (3)0.012 (3)0.023 (3)
C450.086 (4)0.041 (3)0.107 (5)0.028 (3)0.001 (3)0.019 (3)
P460.0355 (5)0.0371 (6)0.0327 (6)0.0029 (4)0.0009 (4)0.0013 (5)
O470.0376 (15)0.0433 (17)0.0385 (16)0.0054 (12)0.0038 (13)0.0026 (14)
N480.0412 (19)0.043 (2)0.039 (2)0.0065 (15)0.0005 (16)0.0049 (17)
C490.039 (2)0.051 (3)0.047 (3)0.0034 (19)0.007 (2)0.017 (2)
C500.044 (2)0.050 (3)0.054 (3)0.009 (2)0.003 (2)0.013 (2)
C510.058 (3)0.058 (4)0.124 (5)0.011 (3)0.004 (3)0.043 (4)
C520.081 (4)0.112 (5)0.046 (3)0.050 (4)0.011 (3)0.034 (3)
N530.041 (2)0.053 (2)0.048 (2)0.0031 (16)0.0018 (17)0.0132 (19)
C540.062 (3)0.059 (3)0.057 (3)0.008 (3)0.005 (3)0.005 (3)
C550.062 (3)0.066 (4)0.089 (4)0.012 (3)0.015 (3)0.028 (3)
N560.0404 (19)0.050 (2)0.0351 (19)0.0002 (16)0.0051 (16)0.0079 (18)
C570.050 (3)0.060 (3)0.042 (3)0.007 (2)0.002 (2)0.017 (2)
C580.052 (3)0.083 (4)0.055 (3)0.010 (3)0.006 (2)0.020 (3)
C590.065 (3)0.068 (4)0.104 (5)0.002 (3)0.011 (3)0.040 (4)
C600.081 (4)0.109 (5)0.048 (3)0.035 (4)0.011 (3)0.031 (3)
P610.0364 (6)0.0392 (6)0.0438 (7)0.0027 (5)0.0005 (5)0.0062 (5)
O620.0362 (15)0.0534 (19)0.0530 (19)0.0028 (13)0.0023 (14)0.0024 (16)
N630.0357 (18)0.049 (2)0.037 (2)0.0009 (15)0.0093 (15)0.0026 (17)
C640.049 (3)0.077 (4)0.032 (2)0.006 (2)0.008 (2)0.005 (2)
C650.066 (3)0.070 (3)0.042 (3)0.002 (3)0.005 (2)0.015 (3)
C660.060 (3)0.125 (6)0.068 (4)0.046 (3)0.008 (3)0.023 (4)
C670.091 (4)0.138 (6)0.055 (4)0.041 (4)0.038 (3)0.018 (4)
N680.0345 (17)0.0386 (19)0.050 (2)0.0055 (15)0.0026 (16)0.0093 (18)
C690.043 (2)0.051 (3)0.063 (3)0.004 (2)0.002 (2)0.026 (3)
C700.047 (3)0.065 (3)0.062 (3)0.008 (2)0.007 (2)0.023 (3)
C710.063 (3)0.104 (5)0.059 (3)0.028 (3)0.008 (3)0.030 (3)
C720.058 (3)0.055 (3)0.130 (5)0.011 (2)0.005 (3)0.052 (4)
N730.052 (2)0.055 (3)0.068 (3)0.0129 (19)0.004 (2)0.032 (2)
C740.079 (4)0.065 (4)0.104 (5)0.008 (3)0.024 (3)0.040 (4)
C750.083 (4)0.095 (5)0.141 (6)0.046 (4)0.033 (4)0.058 (5)
P760.0410 (6)0.0255 (5)0.0539 (7)0.0003 (4)0.0110 (5)0.0012 (5)
O770.0471 (17)0.0312 (16)0.070 (2)0.0015 (12)0.0217 (15)0.0049 (15)
N780.052 (2)0.028 (2)0.105 (4)0.0002 (17)0.028 (2)0.012 (2)
C790.079 (4)0.035 (3)0.161 (7)0.015 (3)0.046 (4)0.018 (4)
C800.059 (3)0.044 (3)0.097 (4)0.010 (2)0.026 (3)0.010 (3)
N810.0399 (19)0.042 (2)0.045 (2)0.0091 (15)0.0060 (17)0.0024 (17)
C820.052 (3)0.055 (3)0.058 (3)0.011 (2)0.018 (2)0.005 (3)
C830.064 (5)0.100 (8)0.077 (6)0.012 (5)0.005 (5)0.015 (6)
C840.046 (5)0.125 (9)0.065 (6)0.005 (5)0.007 (4)0.002 (6)
C850.128 (9)0.115 (9)0.083 (7)0.066 (7)0.075 (7)0.076 (7)
C4830.092 (15)0.120 (19)0.070 (13)0.029 (12)0.024 (10)0.036 (12)
C4840.123 (17)0.035 (10)0.23 (3)0.025 (11)0.053 (15)0.014 (14)
C4850.083 (13)0.30 (3)0.051 (6)0.048 (16)0.013 (6)0.035 (19)
N860.048 (2)0.045 (2)0.044 (2)0.0033 (16)0.0012 (17)0.0170 (18)
C870.076 (3)0.047 (3)0.047 (3)0.003 (2)0.004 (2)0.012 (2)
C880.086 (7)0.172 (12)0.039 (5)0.017 (7)0.004 (5)0.024 (6)
C890.067 (6)0.274 (18)0.063 (7)0.033 (9)0.013 (5)0.069 (10)
C900.191 (13)0.088 (8)0.092 (8)0.030 (8)0.005 (8)0.055 (7)
C4880.148 (17)0.077 (16)0.078 (15)0.019 (12)0.024 (14)0.016 (13)
C4890.19 (2)0.044 (8)0.050 (10)0.016 (10)0.038 (11)0.006 (8)
C4900.054 (8)0.037 (6)0.047 (9)0.009 (6)0.005 (7)0.017 (6)
Geometric parameters (Å, º) top
P1—O21.481 (3)C44—H4410.964
P1—N31.646 (4)C44—H4420.974
P1—N61.639 (3)C44—H4430.971
P1—N111.629 (3)C45—H4510.985
N3—C41.447 (5)C45—H4520.990
N3—C51.452 (6)C45—H4530.983
C4—H410.960P46—O471.474 (3)
C4—H420.963P46—N481.631 (4)
C4—H430.962P46—N531.651 (4)
C5—H510.968P46—N561.645 (3)
C5—H520.960N48—H4810.855
C5—H530.960N48—C491.488 (5)
N6—H610.858C49—C501.511 (5)
N6—C71.485 (5)C49—C511.543 (7)
C7—C81.534 (6)C49—C521.496 (7)
C7—C91.520 (7)C50—H5010.959
C7—C101.506 (7)C50—H5020.964
C8—H810.961C50—H5030.961
C8—H820.956C51—H5110.961
C8—H830.963C51—H5120.963
C9—H910.965C51—H5130.965
C9—H920.959C52—H5210.955
C9—H930.962C52—H5220.961
C10—H1010.962C52—H5230.959
C10—H1020.964N53—C541.460 (5)
C10—H1030.963N53—C551.460 (5)
N11—H1110.852C54—H5410.962
N11—C121.469 (4)C54—H5420.965
C12—C131.485 (8)C54—H5430.961
C12—C141.499 (8)C55—H5510.964
C12—C151.572 (8)C55—H5520.965
C12—C4131.519 (7)C55—H5530.961
C12—C4141.475 (8)N56—H5610.873
C12—C4151.585 (8)N56—C571.487 (5)
C13—H1310.964C57—C581.543 (6)
C13—H1320.966C57—C591.500 (7)
C13—H1330.968C57—C601.522 (7)
C14—H1410.958C58—H5810.955
C14—H1420.957C58—H5820.963
C14—H1430.961C58—H5830.965
C15—H1511.027C59—H5910.965
C15—H1521.029C59—H5920.965
C15—H1531.037C59—H5930.968
C413—H41310.958C60—H6010.961
C413—H41320.957C60—H6020.967
C413—H41330.955C60—H6030.967
C414—H41410.972P61—O621.484 (3)
C414—H41420.975P61—N631.644 (4)
C414—H41430.978P61—N681.624 (3)
C415—H41510.969P61—N731.650 (4)
C415—H41520.967N63—H6310.862
C415—H41530.974N63—C641.476 (5)
P16—O171.472 (3)C64—C651.528 (6)
P16—N181.635 (4)C64—C661.533 (7)
P16—N211.641 (3)C64—C671.525 (8)
P16—N261.645 (3)C65—H6510.966
N18—C191.460 (6)C65—H6520.959
N18—C201.438 (6)C65—H6530.972
C19—H1910.965C66—H6610.965
C19—H1920.964C66—H6620.965
C19—H1930.954C66—H6630.971
C20—H2010.966C67—H6710.961
C20—H2020.956C67—H6720.962
C20—H2030.960C67—H6730.969
N21—H2110.853N68—H6810.855
N21—C221.485 (5)N68—C691.478 (5)
C22—C231.533 (6)C69—C701.528 (6)
C22—C241.520 (7)C69—C711.521 (7)
C22—C251.519 (7)C69—C721.548 (7)
C23—H2310.963C70—H7010.959
C23—H2320.966C70—H7020.965
C23—H2330.965C70—H7030.969
C24—H2410.967C71—H7110.967
C24—H2420.965C71—H7120.967
C24—H2430.963C71—H7130.967
C25—H2510.971C72—H7210.959
C25—H2520.965C72—H7220.965
C25—H2530.963C72—H7230.965
N26—H2610.864N73—C741.453 (6)
N26—C271.478 (4)N73—C751.451 (6)
C27—C281.552 (6)C74—H7410.951
C27—C291.492 (5)C74—H7420.959
C27—C301.530 (5)C74—H7430.958
C27—C4281.556 (9)C75—H7510.969
C27—C4291.510 (10)C75—H7520.969
C27—C4301.523 (10)C75—H7530.972
C28—H2810.962P76—O771.484 (3)
C28—H2820.957P76—N781.652 (4)
C28—H2830.961P76—N811.612 (3)
C29—H2910.960P76—N861.630 (4)
C29—H2920.962N78—C791.433 (6)
C29—H2930.963N78—C801.433 (5)
C30—H3010.963C79—H7910.956
C30—H3020.959C79—H7920.957
C30—H3030.963C79—H7930.960
C428—H42810.959C80—H8010.963
C428—H42820.961C80—H8020.970
C428—H42830.962C80—H8030.963
C429—H42910.976N81—H8110.856
C429—H42920.976N81—C821.476 (4)
C429—H42930.976C82—C831.598 (7)
C430—H43010.960C82—C841.509 (6)
C430—H43020.961C82—C851.485 (7)
C430—H43030.960C82—C4831.587 (9)
P31—O321.481 (3)C82—C4841.513 (9)
P31—N331.636 (3)C82—C4851.464 (9)
P31—N381.642 (3)C83—H8310.966
P31—N431.640 (4)C83—H8320.965
N33—H3310.854C83—H8330.968
N33—C341.463 (4)C84—H8410.965
C34—C351.492 (6)C84—H8420.963
C34—C361.490 (7)C84—H8430.963
C34—C371.554 (7)C85—H8510.928
C34—C4351.474 (9)C85—H8520.927
C34—H43521.257H853—C4841.201
C34—C4361.524 (9)H853—H48420.644
C34—C4371.567 (9)C483—H48310.969
C35—H3510.956C483—H48320.969
C35—H3520.957C483—H48330.970
C35—H3530.963C484—H48410.974
C36—H3620.961C484—H48420.972
C36—H3610.962C484—H48430.970
C36—H3630.959C485—H48511.023
C37—H3710.968C485—H48521.023
C37—H3720.960C485—H48531.016
C37—H3730.964N86—H8610.852
C435—H43510.968N86—C871.470 (4)
C435—H43521.014C87—C881.540 (7)
C435—H43530.967C87—C891.421 (7)
C436—H43610.961C87—C901.604 (7)
C436—H43620.959C87—C4881.545 (9)
C436—H43630.961C87—C4891.446 (9)
C437—H43710.969C87—C4901.612 (8)
C437—H43720.965C88—H8810.960
C437—H43730.967C88—H8820.961
N38—H3810.866C88—H8830.966
N38—C391.471 (5)C89—H8910.966
C39—C401.529 (6)C89—H8920.964
C39—C411.521 (6)C89—H8930.966
C39—C421.525 (6)C90—H9010.964
C40—H4010.956C90—H9020.963
C40—H4020.959C90—H9030.962
C40—H4030.964C488—H48810.960
C41—H4110.957C488—H48821.026
C41—H4120.969C488—H48830.964
C41—H4130.963C489—H48910.982
C42—H4210.965C489—H48920.982
C42—H4220.970C489—H48930.984
C42—H4230.963C490—H49010.961
N43—C441.442 (6)C490—H49020.959
N43—C451.467 (5)C490—H49030.959
O2—P1—N3106.67 (17)N43—C44—H441108.4
O2—P1—N6115.95 (18)N43—C44—H442110.5
N3—P1—N6110.01 (19)H441—C44—H442109.5
O2—P1—N11117.89 (18)N43—C44—H443110.2
N3—P1—N11106.8 (2)H441—C44—H443109.2
N6—P1—N1199.08 (17)H442—C44—H443109.1
P1—N3—C4123.9 (3)N43—C45—H451108.3
P1—N3—C5121.1 (3)N43—C45—H452108.6
C4—N3—C5113.3 (4)H451—C45—H452110.8
N3—C4—H41110.1N43—C45—H453109.1
N3—C4—H42109.2H451—C45—H453110.2
H41—C4—H42109.0H452—C45—H453109.9
N3—C4—H43109.2O47—P46—N48117.44 (17)
H41—C4—H43110.6O47—P46—N53106.71 (17)
H42—C4—H43108.7N48—P46—N53106.44 (19)
N3—C5—H51110.6O47—P46—N56116.76 (18)
N3—C5—H52109.2N48—P46—N5699.03 (17)
H51—C5—H52108.7N53—P46—N56109.93 (19)
N3—C5—H53109.8P46—N48—H481116.4
H51—C5—H53109.3P46—N48—C49127.7 (3)
H52—C5—H53109.2H481—N48—C49115.5
P1—N6—H61115.0N48—C49—C50110.8 (3)
P1—N6—C7126.0 (3)N48—C49—C51109.9 (4)
H61—N6—C7115.1C50—C49—C51108.8 (4)
N6—C7—C8105.9 (3)N48—C49—C52106.9 (4)
N6—C7—C9110.2 (4)C50—C49—C52110.5 (4)
C8—C7—C9109.2 (4)C51—C49—C52110.0 (4)
N6—C7—C10110.6 (4)C49—C50—H501109.2
C8—C7—C10109.2 (4)C49—C50—H502110.3
C9—C7—C10111.5 (5)H501—C50—H502109.8
C7—C8—H81109.4C49—C50—H503109.9
C7—C8—H82109.9H501—C50—H503109.3
H81—C8—H82110.3H502—C50—H503108.4
C7—C8—H83109.4C49—C51—H511108.9
H81—C8—H83109.5C49—C51—H512109.2
H82—C8—H83108.4H511—C51—H512109.9
C7—C9—H91109.8C49—C51—H513110.2
C7—C9—H92109.6H511—C51—H513109.2
H91—C9—H92108.9H512—C51—H513109.5
C7—C9—H93109.9C49—C52—H521109.7
H91—C9—H93109.7C49—C52—H522109.0
H92—C9—H93108.8H521—C52—H522108.9
C7—C10—H101110.2C49—C52—H523109.1
C7—C10—H102109.7H521—C52—H523110.7
H101—C10—H102109.2H522—C52—H523109.5
C7—C10—H103109.5P46—N53—C54122.9 (3)
H101—C10—H103108.7P46—N53—C55121.0 (3)
H102—C10—H103109.6C54—N53—C55113.0 (4)
P1—N11—H111115.4N53—C54—H541109.7
P1—N11—C12128.6 (2)N53—C54—H542109.9
H111—N11—C12115.3H541—C54—H542108.6
N11—C12—C13113.52 (9)N53—C54—H543110.3
N11—C12—C14108.01 (9)H541—C54—H543108.9
C13—C12—C14112.05 (9)H542—C54—H543109.5
N11—C12—C15105.66 (9)N53—C55—H551109.9
C13—C12—C15107.07 (9)N53—C55—H552109.6
C14—C12—C15110.32 (9)H551—C55—H552109.8
N11—C12—C413113.43 (9)N53—C55—H553108.9
N11—C12—C414108.22 (9)H551—C55—H553109.4
C413—C12—C414112.03 (9)H552—C55—H553109.3
N11—C12—C415105.60 (9)P46—N56—H561116.0
C413—C12—C415106.92 (9)P46—N56—C57124.9 (3)
C414—C12—C415110.44 (9)H561—N56—C57116.3
C12—C13—H131109.6N56—C57—C58106.0 (4)
C12—C13—H132109.0N56—C57—C59110.5 (4)
H131—C13—H132109.5C58—C57—C59109.7 (4)
C12—C13—H133109.0N56—C57—C60109.9 (4)
H131—C13—H133109.8C58—C57—C60109.5 (4)
H132—C13—H133109.9C59—C57—C60111.1 (5)
C12—C14—H141110.7C57—C58—H581110.2
C12—C14—H142109.5C57—C58—H582110.5
H141—C14—H142109.0H581—C58—H582108.8
C12—C14—H143109.6C57—C58—H583109.3
H141—C14—H143108.9H581—C58—H583109.0
H142—C14—H143109.1H582—C58—H583109.0
C12—C15—H151106.9C57—C59—H591109.4
C12—C15—H152106.3C57—C59—H592108.2
H151—C15—H152111.4H591—C59—H592110.0
C12—C15—H153108.1C57—C59—H593109.6
H151—C15—H153111.9H591—C59—H593110.0
H152—C15—H153111.9H592—C59—H593109.6
C12—C413—H4131110.3C57—C60—H601110.0
C12—C413—H4132110.4C57—C60—H602109.3
H4131—C413—H4132108.7H601—C60—H602109.4
C12—C413—H4133109.2C57—C60—H603109.4
H4131—C413—H4133109.4H601—C60—H603109.0
H4132—C413—H4133108.8H602—C60—H603109.7
C12—C414—H4141107.9O62—P61—N63117.21 (18)
C12—C414—H4142108.5O62—P61—N68118.09 (18)
H4141—C414—H4142109.6N63—P61—N6899.12 (17)
C12—C414—H4143110.2O62—P61—N73107.09 (19)
H4141—C414—H4143110.2N63—P61—N73107.6 (2)
H4142—C414—H4143110.5N68—P61—N73107.0 (2)
C12—C415—H4151110.2P61—N63—H631115.4
C12—C415—H4152109.0P61—N63—C64124.7 (3)
H4151—C415—H4152109.3H631—N63—C64115.6
C12—C415—H4153108.9N63—C64—C65107.6 (4)
H4151—C415—H4153110.2N63—C64—C66110.5 (4)
H4152—C415—H4153109.2C65—C64—C66109.2 (5)
O17—P16—N18106.97 (18)N63—C64—C67110.1 (4)
O17—P16—N21117.46 (19)C65—C64—C67109.5 (4)
N18—P16—N21108.2 (2)C66—C64—C67110.0 (5)
O17—P16—N26116.42 (19)C64—C65—H651108.7
N18—P16—N26107.7 (2)C64—C65—H652110.0
N21—P16—N2699.50 (17)H651—C65—H652109.0
P16—N18—C19121.2 (3)C64—C65—H653110.0
P16—N18—C20125.9 (4)H651—C65—H653109.6
C19—N18—C20112.9 (4)H652—C65—H653109.5
N18—C19—H191109.8C64—C66—H661110.3
N18—C19—H192109.8C64—C66—H662110.1
H191—C19—H192109.9H661—C66—H662109.3
N18—C19—H193108.6C64—C66—H663108.9
H191—C19—H193110.0H661—C66—H663108.8
H192—C19—H193108.8H662—C66—H663109.4
N18—C20—H201110.6C64—C67—H671108.7
N18—C20—H202110.3C64—C67—H672108.8
H201—C20—H202109.1H671—C67—H672110.1
N18—C20—H203108.2C64—C67—H673109.5
H201—C20—H203109.6H671—C67—H673109.8
H202—C20—H203108.9H672—C67—H673109.9
P16—N21—H211115.4P61—N68—H681114.2
P16—N21—C22126.0 (3)P61—N68—C69126.9 (3)
H211—N21—C22115.7H681—N68—C69113.9
N21—C22—C23106.2 (4)N68—C69—C70107.4 (4)
N21—C22—C24110.0 (4)N68—C69—C71110.9 (4)
C23—C22—C24110.5 (4)C70—C69—C71111.6 (4)
N21—C22—C25111.3 (4)N68—C69—C72110.0 (4)
C23—C22—C25109.6 (4)C70—C69—C72108.4 (4)
C24—C22—C25109.1 (4)C71—C69—C72108.5 (4)
C22—C23—H231109.6C69—C70—H701110.7
C22—C23—H232109.1C69—C70—H702110.2
H231—C23—H232109.9H701—C70—H702108.6
C22—C23—H233108.9C69—C70—H703110.7
H231—C23—H233109.3H701—C70—H703107.4
H232—C23—H233110.1H702—C70—H703109.1
C22—C24—H241109.9C69—C71—H711108.8
C22—C24—H242109.1C69—C71—H712110.4
H241—C24—H242109.2H711—C71—H712109.7
C22—C24—H243109.2C69—C71—H713109.0
H241—C24—H243110.1H711—C71—H713109.0
H242—C24—H243109.3H712—C71—H713109.9
C22—C25—H251109.4C69—C72—H721109.4
C22—C25—H252109.9C69—C72—H722109.5
H251—C25—H252109.8H721—C72—H722109.7
C22—C25—H253108.9C69—C72—H723109.4
H251—C25—H253109.1H721—C72—H723110.0
H252—C25—H253109.7H722—C72—H723108.8
P16—N26—H261115.6P61—N73—C74120.3 (3)
P16—N26—C27126.0 (2)P61—N73—C75125.7 (4)
H261—N26—C27116.1C74—N73—C75113.9 (4)
N26—C27—C28111.24 (9)N73—C74—H741110.7
N26—C27—C29108.95 (9)N73—C74—H742110.1
C28—C27—C29110.61 (9)H741—C74—H742109.7
N26—C27—C30107.60 (9)N73—C74—H743109.1
C28—C27—C30106.46 (9)H741—C74—H743108.7
C29—C27—C30111.93 (9)H742—C74—H743108.4
N26—C27—C428111.31 (9)N73—C75—H751109.8
N26—C27—C429108.93 (9)N73—C75—H752110.2
C428—C27—C429110.60 (9)H751—C75—H752109.6
N26—C27—C430107.55 (9)N73—C75—H753108.8
C428—C27—C430106.47 (9)H751—C75—H753108.7
C429—C27—C430111.95 (9)H752—C75—H753109.7
C27—C28—H281110.2O77—P76—N78106.81 (17)
C27—C28—H282109.3O77—P76—N81116.69 (18)
H281—C28—H282109.0N78—P76—N81107.4 (2)
C27—C28—H283110.2O77—P76—N86116.79 (18)
H281—C28—H283108.9N78—P76—N86108.8 (2)
H282—C28—H283109.2N81—P76—N8699.87 (16)
C27—C29—H291110.1P76—N78—C79123.4 (3)
C27—C29—H292109.2P76—N78—C80122.5 (3)
H291—C29—H292109.5C79—N78—C80114.1 (4)
C27—C29—H293109.6N78—C79—H791109.2
H291—C29—H293109.7N78—C79—H792109.3
H292—C29—H293108.7H791—C79—H792110.4
C27—C30—H301109.7N78—C79—H793109.1
C27—C30—H302109.2H791—C79—H793109.5
H301—C30—H302109.4H792—C79—H793109.2
C27—C30—H303109.0N78—C80—H801109.0
H301—C30—H303110.3N78—C80—H802108.2
H302—C30—H303109.2H801—C80—H802111.2
C27—C428—H4281108.8N78—C80—H803108.7
C27—C428—H4282110.8H801—C80—H803109.2
H4281—C428—H4282109.5H802—C80—H803110.5
C27—C428—H4283109.1P76—N81—H811114.9
H4281—C428—H4283109.3P76—N81—C82131.0 (2)
H4282—C428—H4283109.4H811—N81—C82113.7
C27—C429—H4291109.2N81—C82—C83106.16 (9)
C27—C429—H4292109.3N81—C82—C84111.36 (9)
H4291—C429—H4292109.8C83—C82—C84103.86 (9)
C27—C429—H4293109.3N81—C82—C85111.45 (9)
H4291—C429—H4293109.8C83—C82—C85105.91 (9)
H4292—C429—H4293109.6C84—C82—C85117.07 (9)
C27—C430—H4301109.4N81—C82—C483106.29 (9)
C27—C430—H4302108.8N81—C82—C484111.11 (9)
H4301—C430—H4302109.6C483—C82—C484103.86 (9)
C27—C430—H4303110.0N81—C82—C485111.50 (9)
H4301—C430—H4303109.7C483—C82—C485106.02 (9)
H4302—C430—H4303109.3C484—C82—C485117.07 (9)
O32—P31—N33116.98 (17)C82—C83—H831109.9
O32—P31—N38117.15 (17)C82—C83—H832109.9
N33—P31—N3899.41 (17)H831—C83—H832110.0
O32—P31—N43105.90 (18)C82—C83—H833108.1
N33—P31—N43108.7 (2)H831—C83—H833109.3
N38—P31—N43108.34 (19)H832—C83—H833109.5
P31—N33—H331114.8C82—C84—H841108.9
P31—N33—C34127.1 (2)C82—C84—H842109.6
H331—N33—C34116.7H841—C84—H842109.6
N33—C34—C35115.24 (9)C82—C84—H843110.1
N33—C34—C36108.99 (9)H841—C84—H843109.3
C35—C34—C36113.12 (9)H842—C84—H843109.4
N33—C34—C37105.43 (9)C82—C85—H851121.3
C35—C34—C37106.20 (9)C82—C85—H852119.2
C36—C34—C37107.24 (9)H851—C85—H852117.3
N33—C34—C435115.33 (9)C484—H853—H484253.9
N33—C34—H4352117.0C82—C483—H4831110.8
N33—C34—C436108.77 (9)C82—C483—H4832106.5
C435—C34—C436113.10 (9)H4831—C483—H4832110.0
N33—C34—C437105.49 (9)C82—C483—H4833110.1
C435—C34—C437106.37 (9)H4831—C483—H4833109.4
H4352—C34—C437135.0H4832—C483—H4833110.0
C436—C34—C437107.16 (9)C82—C484—H85398.6
C34—C35—H351110.1C82—C484—H4841107.8
C34—C35—H352110.3H853—C484—H4841141.4
H351—C35—H352108.9C82—C484—H4842112.6
C34—C35—H353108.8H4841—C484—H4842109.7
H351—C35—H353109.5C82—C484—H4843108.1
H352—C35—H353109.2H4841—C484—H4843109.6
C34—C36—H362108.3H4842—C484—H4843109.0
C34—C36—H361110.8C82—C485—H4851106.3
H362—C36—H361109.6C82—C485—H4852104.5
C34—C36—H363108.7H4851—C485—H4852111.1
H362—C36—H363109.7C82—C485—H4853111.1
H361—C36—H363109.7H4851—C485—H4853111.9
C34—C37—H371109.1H4852—C485—H4853111.5
C34—C37—H372108.4P76—N86—H861115.4
H371—C37—H372109.1P76—N86—C87129.5 (2)
C34—C37—H373110.6H861—N86—C87113.3
H371—C37—H373109.8N86—C87—C88109.76 (9)
H372—C37—H373109.8N86—C87—C89110.04 (9)
C34—C435—H4351115.8C88—C87—C89114.63 (9)
H4351—C435—H4352115.4N86—C87—C90107.21 (9)
C34—C435—H4353116.2C88—C87—C90103.49 (9)
H4351—C435—H4353120.4C89—C87—C90111.31 (9)
H4352—C435—H4353116.1N86—C87—C488109.95 (9)
C34—C436—H4361109.4N86—C87—H4882112.1
C34—C436—H4362109.2N86—C87—C489109.99 (9)
H4361—C436—H4362109.4C488—C87—C489114.70 (9)
C34—C436—H4363110.6N86—C87—C490107.08 (9)
H4361—C436—H4363109.4C488—C87—C490103.57 (9)
H4362—C436—H4363108.8C489—C87—C490111.15 (9)
C34—C437—H4371108.8C87—C88—H881110.1
C34—C437—H4372109.1C87—C88—H882109.8
H4371—C437—H4372109.6H881—C88—H882109.0
C34—C437—H4373110.0C87—C88—H883109.9
H4371—C437—H4373109.7H881—C88—H883109.1
H4372—C437—H4373109.6H882—C88—H883109.0
P31—N38—H381114.5C87—C89—H891108.1
P31—N38—C39126.6 (3)C87—C89—H892112.5
H381—N38—C39115.5H891—C89—H892110.3
N38—C39—C40110.9 (3)C87—C89—H893107.6
N38—C39—C41109.6 (4)H891—C89—H893109.1
C40—C39—C41109.3 (4)H892—C89—H893109.1
N38—C39—C42106.3 (3)C87—C90—H901109.8
C40—C39—C42111.3 (4)C87—C90—H902108.2
C41—C39—C42109.5 (4)H901—C90—H902109.8
C39—C40—H401108.6C87—C90—H903110.0
C39—C40—H402109.5H901—C90—H903109.4
H401—C40—H402109.8H902—C90—H903109.7
C39—C40—H403109.8C87—C488—H4881109.0
H401—C40—H403109.3H4881—C488—H4882119.4
H402—C40—H403109.8C87—C488—H4883108.9
C39—C41—H411109.9H4881—C488—H4883120.3
C39—C41—H412109.7H4882—C488—H4883119.7
H411—C41—H412109.5C87—C489—H4891107.5
C39—C41—H413109.8C87—C489—H4892114.4
H411—C41—H413109.2H4891—C489—H4892109.4
H412—C41—H413108.7C87—C489—H4893105.5
C39—C42—H421109.8H4891—C489—H4893110.1
C39—C42—H422109.2H4892—C489—H4893109.9
H421—C42—H422109.6C87—C490—H4901109.0
C39—C42—H423110.0C87—C490—H4902108.0
H421—C42—H423109.3H4901—C490—H4902109.4
H422—C42—H423108.9C87—C490—H4903111.8
P31—N43—C44123.7 (3)H4901—C490—H4903109.8
P31—N43—C45121.1 (3)H4902—C490—H4903108.9
C44—N43—C45115.2 (4)
O77—P76—N78—C790.2 (5)N56—P46—N53—C54118.0 (4)
O77—P76—N78—C80176.8 (4)O47—P46—N53—C549.5 (4)
N81—P76—N78—C79125.8 (5)O47—P46—N53—C55168.1 (3)
N81—P76—N78—C8057.3 (5)N56—P46—N48—C49169.5 (3)
N86—P76—N78—C79127.0 (5)O47—P46—N48—C4963.9 (4)
N86—P76—N78—C8049.9 (5)N53—P46—N48—C4955.5 (4)
O77—P76—N81—C8252.4 (4)N73—P61—N68—C6978.6 (4)
N78—P76—N81—C8267.4 (4)O62—P61—N68—C6942.2 (4)
N86—P76—N81—C82179.2 (3)O62—P61—N73—C74177.7 (4)
O77—P76—N86—C8745.9 (4)N63—P61—N73—C7455.5 (4)
N78—P76—N86—C8775.0 (4)N63—P61—N73—C75123.0 (4)
N81—P76—N86—C87172.7 (3)N63—P61—N68—C69169.8 (4)
O2—P1—N11—C1258.9 (4)N68—P61—N73—C75131.4 (4)
N3—P1—N11—C1260.9 (4)N73—P61—N63—C6478.0 (4)
N6—P1—N11—C12175.2 (3)O62—P61—N63—C6442.7 (4)
N11—P1—N3—C4134.0 (4)N68—P61—N73—C7450.2 (4)
N11—P1—N3—C561.9 (5)N68—P61—N63—C64170.9 (4)
O2—P1—N6—C738.3 (4)O62—P61—N73—C753.9 (5)
O2—P1—N3—C47.1 (5)P76—N81—C82—C8419.3 (6)
O2—P1—N3—C5171.3 (5)P76—N81—C82—C85152.0 (4)
N6—P1—N3—C4119.4 (4)P76—N81—C82—C8393.1 (4)
N6—P1—N3—C544.8 (5)P76—N86—C87—C8875.0 (5)
N3—P1—N6—C782.8 (4)P76—N86—C87—C9036.8 (5)
N11—P1—N6—C7165.5 (4)P76—N86—C87—C89158.0 (4)
N21—P16—N18—C1949.4 (5)P1—N6—C7—C1079.4 (5)
N18—P16—N26—C2775.3 (3)P1—N6—C7—C944.4 (5)
N21—P16—N26—C27172.0 (3)P1—N6—C7—C8162.3 (3)
N18—P16—N21—C2274.9 (4)P1—N11—C12—C41321.7 (6)
N26—P16—N21—C22172.8 (4)P1—N11—C12—C41595.1 (4)
O17—P16—N26—C2744.8 (4)P1—N11—C12—C414146.7 (4)
O17—P16—N18—C204.2 (6)P16—N21—C22—C2481.2 (5)
N26—P16—N18—C20121.6 (5)P16—N21—C22—C2540.0 (5)
N21—P16—N18—C20131.7 (5)P16—N21—C22—C23159.2 (3)
N26—P16—N18—C1957.3 (4)P16—N26—C27—C30156.1 (3)
O17—P16—N21—C2246.3 (4)P16—N26—C27—C2839.9 (4)
O17—P16—N18—C19176.8 (4)P16—N26—C27—C2982.3 (4)
N33—P31—N43—C4558.0 (4)P31—N33—C34—C37106.7 (5)
O32—P31—N43—C45175.5 (4)P31—N33—C34—C3510.0 (5)
N33—P31—N43—C44121.5 (4)P31—N33—C34—C36138.4 (4)
N43—P31—N33—C3463.6 (4)P31—N38—C39—C4148.7 (5)
N38—P31—N43—C44131.4 (4)P31—N38—C39—C42167.0 (3)
N38—P31—N43—C4549.0 (4)P31—N38—C39—C4072.0 (4)
O32—P31—N43—C444.9 (4)P46—N48—C49—C5031.7 (5)
N33—P31—N38—C39166.7 (3)P46—N48—C49—C52152.1 (4)
N43—P31—N38—C3980.0 (4)P46—N48—C49—C5188.6 (4)
N38—P31—N33—C34176.7 (3)P46—N56—C57—C5979.0 (5)
O32—P31—N33—C3456.2 (4)P46—N56—C57—C6044.1 (5)
O32—P31—N38—C3939.6 (4)P46—N56—C57—C58162.2 (3)
N48—P46—N53—C5565.8 (4)P61—N63—C64—C65165.3 (4)
N56—P46—N53—C5540.6 (4)P61—N63—C64—C6675.8 (5)
O47—P46—N56—C5738.6 (4)P61—N63—C64—C6745.9 (5)
N48—P46—N56—C57165.7 (3)P61—N68—C69—C70159.1 (3)
N53—P46—N56—C5783.1 (4)P61—N68—C69—C7178.7 (5)
N48—P46—N53—C54135.7 (3)P61—N68—C69—C7241.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H61···O770.862.102.937 (9)165
N11—H111···O770.852.082.911 (9)164
N21—H211···O620.852.213.038 (9)162
N26—H261···O620.862.112.952 (9)166
N33—H331···O170.852.102.943 (9)167
N38—H381···O170.872.223.046 (9)159
N48—H481···O20.862.162.981 (9)161
N56—H561···O20.872.102.931 (9)158
N63—H631···O32i0.862.172.994 (9)160
N68—H681···O32i0.862.042.884 (9)168
N81—H811···O47i0.862.092.927 (9)166
N86—H861···O47i0.852.162.986 (9)163
Symmetry code: (i) x+1, y, z.
(II) ({[bis(tert-butylamino)phosphoryl]oxy}(tert- butylamino)phosphoryl)(tert-butyl)amine top
Crystal data top
C16H40N4O3P2F(000) = 872
Mr = 398.5Dx = 1.097 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybcCell parameters from 9398 reflections
a = 11.3715 (4) Åθ = 3.7–67.1°
b = 17.7755 (7) ŵ = 1.80 mm1
c = 13.6956 (5) ÅT = 150 K
β = 119.371 (4)°Prism, colourless
V = 2412.51 (18) Å30.37 × 0.22 × 0.09 mm
Z = 4
Data collection top
Gemini Ultra
diffractometer with Atlas detector
4265 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source3420 reflections with I > 3σ(I)
Mirror monochromatorRint = 0.033
Detector resolution: 10.3784 pixels mm-1θmax = 67.2°, θmin = 4.5°
Rotation method data acquisition using ω scansh = 1311
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
k = 2121
Tmin = 0.746, Tmax = 1.000l = 1216
15622 measured reflections
Refinement top
Refinement on F2148 constraints
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
S = 1.60(Δ/σ)max = 0.002
4265 reflectionsΔρmax = 0.33 e Å3
238 parametersΔρmin = 0.21 e Å3
4 restraints
Crystal data top
C16H40N4O3P2V = 2412.51 (18) Å3
Mr = 398.5Z = 4
Monoclinic, P21/cCu Kα radiation
a = 11.3715 (4) ŵ = 1.80 mm1
b = 17.7755 (7) ÅT = 150 K
c = 13.6956 (5) Å0.37 × 0.22 × 0.09 mm
β = 119.371 (4)°
Data collection top
Gemini Ultra
diffractometer with Atlas detector
4265 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2010)
3420 reflections with I > 3σ(I)
Tmin = 0.746, Tmax = 1.000Rint = 0.033
15622 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0404 restraints
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.60Δρmax = 0.33 e Å3
4265 reflectionsΔρmin = 0.21 e Å3
238 parameters
Special details top

Experimental. Absorption correction: CrysAlis PRO (Agilent, 2010), multi-scan using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.

The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.27512 (5)0.23253 (3)0.54865 (4)0.02780 (19)
P20.12827 (4)0.24723 (2)0.67070 (4)0.02659 (18)
O10.21004 (12)0.28033 (7)0.61111 (9)0.0287 (5)
O20.17179 (13)0.18682 (7)0.45603 (10)0.0339 (5)
O30.21375 (13)0.19473 (7)0.76223 (10)0.0315 (5)
N10.39326 (16)0.18678 (8)0.65511 (12)0.0311 (6)
N20.33956 (16)0.29241 (9)0.50011 (12)0.0317 (6)
N30.00300 (16)0.21182 (9)0.56138 (12)0.0309 (6)
N40.08569 (16)0.31779 (9)0.71999 (12)0.0320 (6)
C10.4652 (2)0.11921 (11)0.64637 (18)0.0398 (9)
C20.4887 (3)0.12659 (14)0.54571 (19)0.0503 (10)
C30.6012 (2)0.11542 (15)0.7536 (2)0.0540 (11)
C40.3821 (3)0.04932 (13)0.6338 (3)0.0644 (15)
C50.4264 (2)0.35926 (11)0.55199 (16)0.0389 (8)
C60.5158 (3)0.36650 (18)0.4992 (2)0.0685 (13)
C70.5122 (3)0.35142 (15)0.67740 (19)0.0676 (12)
C80.3361 (3)0.42794 (14)0.5241 (3)0.0700 (15)
C90.0964 (2)0.15571 (11)0.56689 (17)0.0385 (8)
C100.0349 (3)0.07749 (13)0.5816 (2)0.0573 (13)
C110.2274 (2)0.16068 (16)0.4558 (2)0.0576 (11)
C120.1228 (3)0.17341 (14)0.6630 (2)0.0521 (11)
C130.0167 (2)0.39025 (10)0.67141 (16)0.0374 (8)
C140.1236 (3)0.45200 (12)0.7124 (2)0.0553 (12)
C150.0599 (3)0.38826 (13)0.54431 (18)0.0570 (11)
C160.0804 (2)0.40471 (13)0.7163 (2)0.0500 (10)
H2A0.5366630.0832190.5419870.0755*
H2B0.4033790.1301420.4780890.0755*
H2C0.5408070.171020.5540290.0755*
H3A0.649340.0715620.7518950.0811*
H3B0.6527440.1596070.7594480.0811*
H3C0.586980.1127140.8171280.0811*
H4A0.4298690.0056320.6308050.0966*
H4B0.3669120.0453780.6966320.0966*
H4C0.2969940.0527660.5659290.0966*
H6A0.5733910.4095620.5298470.1028*
H6B0.5699660.3220310.5146820.1028*
H6C0.4606120.3725060.4196560.1028*
H7A0.5655080.3960440.7076020.1014*
H7B0.4550520.3445320.7099990.1014*
H7C0.5707190.3086960.6943770.1014*
H8A0.3903180.4714540.5597170.1051*
H8B0.2880990.4353230.4443830.1051*
H8C0.2727490.4204790.5504170.1051*
H10A0.0978970.0405610.5791810.0859*
H10B0.0147740.0679590.5223670.0859*
H10C0.046580.0747070.6524940.0859*
H11A0.2913170.1253060.4555920.0864*
H11B0.2634730.2106430.4462180.0864*
H11C0.2099980.1492090.3955540.0864*
H12A0.185160.1373830.6638840.0782*
H12B0.0394970.1710060.7326470.0782*
H12C0.1602920.2230110.6533420.0782*
H14A0.0806990.4998320.6850890.0829*
H14B0.1718320.4525360.7928120.0829*
H14C0.1853950.4424760.6850410.0829*
H15A0.1050010.4354490.5161570.0855*
H15B0.0022220.3796450.5169610.0855*
H15C0.1252420.348430.519410.0855*
H16A0.1226020.4528770.6905850.0751*
H16B0.1482160.3661640.6897610.0751*
H16C0.0314190.4041930.7966870.0751*
H1N0.375 (2)0.1808 (12)0.7090 (14)0.0373*
H2N0.298 (2)0.2962 (12)0.4276 (8)0.038*
H3N0.015 (2)0.1989 (12)0.5088 (14)0.0371*
H4N0.116 (2)0.3165 (13)0.7917 (9)0.0384*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0304 (2)0.0325 (2)0.0193 (2)0.00433 (17)0.01126 (19)0.00167 (16)
P20.0287 (2)0.0304 (2)0.0181 (2)0.00091 (17)0.00953 (19)0.00071 (16)
O10.0312 (6)0.0319 (6)0.0197 (6)0.0012 (5)0.0100 (5)0.0001 (5)
O20.0382 (7)0.0402 (7)0.0241 (6)0.0110 (6)0.0158 (6)0.0067 (5)
O30.0369 (7)0.0343 (6)0.0212 (6)0.0061 (5)0.0126 (5)0.0033 (5)
N10.0362 (8)0.0331 (8)0.0259 (8)0.0034 (6)0.0166 (7)0.0023 (6)
N20.0347 (8)0.0393 (8)0.0171 (7)0.0097 (7)0.0097 (6)0.0014 (6)
N30.0317 (8)0.0370 (8)0.0234 (8)0.0054 (6)0.0131 (6)0.0027 (6)
N40.0363 (8)0.0353 (8)0.0195 (7)0.0068 (7)0.0099 (7)0.0028 (6)
C10.0443 (11)0.0381 (10)0.0427 (12)0.0074 (8)0.0257 (10)0.0026 (8)
C20.0556 (14)0.0560 (13)0.0458 (13)0.0093 (11)0.0300 (11)0.0034 (10)
C30.0503 (13)0.0684 (15)0.0452 (13)0.0245 (12)0.0248 (11)0.0131 (11)
C40.0758 (18)0.0363 (11)0.096 (2)0.0005 (11)0.0537 (17)0.0013 (12)
C50.0433 (11)0.0373 (10)0.0282 (10)0.0144 (8)0.0115 (9)0.0007 (8)
C60.0612 (16)0.0857 (19)0.0644 (17)0.0396 (15)0.0352 (14)0.0163 (14)
C70.0816 (19)0.0660 (16)0.0291 (12)0.0428 (15)0.0070 (12)0.0053 (11)
C80.0792 (19)0.0393 (12)0.083 (2)0.0076 (12)0.0330 (16)0.0003 (13)
C90.0376 (10)0.0418 (10)0.0354 (11)0.0096 (8)0.0174 (9)0.0041 (8)
C100.0674 (16)0.0363 (11)0.0756 (18)0.0092 (10)0.0408 (15)0.0015 (11)
C110.0414 (12)0.0763 (17)0.0444 (13)0.0210 (12)0.0128 (10)0.0058 (11)
C120.0524 (13)0.0648 (15)0.0505 (13)0.0164 (11)0.0340 (12)0.0060 (11)
C130.0446 (11)0.0330 (9)0.0306 (10)0.0099 (8)0.0154 (9)0.0040 (7)
C140.0683 (16)0.0361 (11)0.0617 (15)0.0015 (10)0.0321 (13)0.0009 (10)
C150.0770 (17)0.0474 (12)0.0304 (11)0.0249 (12)0.0138 (11)0.0092 (9)
C160.0494 (13)0.0493 (12)0.0509 (13)0.0179 (10)0.0241 (11)0.0058 (10)
Geometric parameters (Å, º) top
P1—O11.6194 (16)C6—H6B0.96
P1—O21.4791 (12)C6—H6C0.96
P1—N11.6341 (14)C7—H7A0.96
P1—N21.609 (2)C7—H7B0.96
P2—O11.6191 (17)C7—H7C0.96
P2—O31.4806 (12)C8—H8A0.96
P2—N31.6351 (13)C8—H8B0.96
P2—N41.6075 (18)C8—H8C0.96
N1—C11.490 (3)C9—C101.524 (3)
N1—H1N0.87 (3)C9—C111.523 (3)
N2—C51.484 (2)C9—C121.520 (4)
N2—H2N0.868 (10)C10—H10A0.96
N3—C91.485 (3)C10—H10B0.96
N3—H3N0.87 (3)C10—H10C0.96
N4—C131.485 (2)C11—H11A0.96
N4—H4N0.866 (12)C11—H11B0.96
C1—C21.533 (4)C11—H11C0.96
C1—C31.525 (3)C12—H12A0.96
C1—C41.518 (4)C12—H12B0.96
C2—H2A0.96C12—H12C0.96
C2—H2B0.96C13—C141.526 (3)
C2—H2C0.96C13—C151.517 (3)
C3—H3A0.96C13—C161.526 (4)
C3—H3B0.96C14—H14A0.96
C3—H3C0.96C14—H14B0.96
C4—H4A0.96C14—H14C0.96
C4—H4B0.96C15—H15A0.96
C4—H4C0.96C15—H15B0.96
C5—C61.514 (5)C15—H15C0.96
C5—C71.509 (3)C16—H16A0.96
C5—C81.518 (3)C16—H16B0.96
C6—H6A0.96C16—H16C0.96
P1—O1—P2126.85 (8)C5—C7—H7A109.4718
O1—P1—O2111.38 (8)C5—C7—H7B109.4709
O1—P1—N1100.28 (8)C5—C7—H7C109.471
O1—P1—N2106.84 (8)H7A—C7—H7B109.4712
O2—P1—N1116.84 (7)H7A—C7—H7C109.4708
O2—P1—N2109.89 (8)H7B—C7—H7C109.4715
N1—P1—N2110.86 (9)C5—C8—H8A109.4718
O1—P2—O3110.79 (8)C5—C8—H8B109.4714
O1—P2—N399.81 (8)C5—C8—H8C109.4699
O1—P2—N4107.09 (9)H8A—C8—H8B109.4718
O3—P2—N3117.26 (7)H8A—C8—H8C109.4709
O3—P2—N4110.13 (8)H8B—C8—H8C109.4716
N3—P2—N4110.93 (8)N3—C9—C10109.0 (2)
P1—N1—C1124.93 (13)N3—C9—C11106.49 (18)
P1—N1—H1N112.6 (14)N3—C9—C12110.78 (17)
C1—N1—H1N109.9 (15)C10—C9—C11110.20 (18)
P1—N2—C5131.48 (15)C10—C9—C12110.3 (2)
P1—N2—H2N115.1 (15)C11—C9—C12110.0 (2)
C5—N2—H2N110.2 (15)C9—C10—H10A109.4709
P2—N3—C9124.49 (14)C9—C10—H10B109.4713
P2—N3—H3N112.4 (14)C9—C10—H10C109.4703
C9—N3—H3N109.1 (15)H10A—C10—H10B109.4709
P2—N4—C13133.65 (15)H10A—C10—H10C109.4725
P2—N4—H4N114.7 (15)H10B—C10—H10C109.4714
C13—N4—H4N111.2 (15)C9—C11—H11A109.4714
N1—C1—C2110.36 (17)C9—C11—H11B109.4711
N1—C1—C3107.17 (17)C9—C11—H11C109.4709
N1—C1—C4109.5 (2)H11A—C11—H11B109.472
C2—C1—C3109.2 (2)H11A—C11—H11C109.4712
C2—C1—C4109.9 (2)H11B—C11—H11C109.4707
C3—C1—C4110.71 (19)C9—C12—H12A109.4707
C1—C2—H2A109.4703C9—C12—H12B109.471
C1—C2—H2B109.4716C9—C12—H12C109.4721
C1—C2—H2C109.472H12A—C12—H12B109.4706
H2A—C2—H2B109.4709H12A—C12—H12C109.4716
H2A—C2—H2C109.4714H12B—C12—H12C109.4712
H2B—C2—H2C109.4712N4—C13—C14107.98 (16)
C1—C3—H3A109.4714N4—C13—C15111.94 (17)
C1—C3—H3B109.4712N4—C13—C16107.05 (19)
C1—C3—H3C109.4713C14—C13—C15110.1 (2)
H3A—C3—H3B109.4718C14—C13—C16109.5 (2)
H3A—C3—H3C109.471C15—C13—C16110.2 (2)
H3B—C3—H3C109.4706C13—C14—H14A109.4718
C1—C4—H4A109.4713C13—C14—H14B109.4713
C1—C4—H4B109.4713C13—C14—H14C109.4706
C1—C4—H4C109.4717H14A—C14—H14B109.4713
H4A—C4—H4B109.4713H14A—C14—H14C109.4713
H4A—C4—H4C109.4706H14B—C14—H14C109.471
H4B—C4—H4C109.4712C13—C15—H15A109.4714
N2—C5—C6106.5 (2)C13—C15—H15B109.4713
N2—C5—C7112.21 (19)C13—C15—H15C109.4712
N2—C5—C8108.33 (17)H15A—C15—H15B109.4703
C6—C5—C7109.9 (2)H15A—C15—H15C109.4711
C6—C5—C8109.9 (2)H15B—C15—H15C109.4721
C7—C5—C8109.9 (2)C13—C16—H16A109.4713
C5—C6—H6A109.4718C13—C16—H16B109.471
C5—C6—H6B109.4713C13—C16—H16C109.4709
C5—C6—H6C109.4716H16A—C16—H16B109.4709
H6A—C6—H6B109.4706H16A—C16—H16C109.4717
H6A—C6—H6C109.4711H16B—C16—H16C109.4715
H6B—C6—H6C109.4709
O2—P1—O1—P257.79 (11)O1—P2—N4—C1350.9 (2)
N1—P1—O1—P266.53 (11)O3—P2—N4—C13171.4 (2)
N2—P1—O1—P2177.81 (10)N3—P2—N4—C1357.1 (2)
O1—P1—N1—C1163.63 (17)P1—N1—C1—C236.9 (3)
O2—P1—N1—C143.2 (2)P1—N1—C1—C3155.68 (16)
N2—P1—N1—C183.77 (18)P1—N1—C1—C484.2 (2)
O1—P1—N2—C546.3 (2)P1—N2—C5—C6148.66 (19)
O2—P1—N2—C5167.22 (18)P1—N2—C5—C728.4 (3)
N1—P1—N2—C562.1 (2)P1—N2—C5—C893.1 (2)
O3—P2—O1—P159.76 (11)P2—N3—C9—C1082.0 (2)
N3—P2—O1—P164.50 (11)P2—N3—C9—C11159.08 (16)
N4—P2—O1—P1179.88 (10)P2—N3—C9—C1239.5 (3)
O1—P2—N3—C9162.53 (16)P2—N4—C13—C14102.9 (2)
O3—P2—N3—C942.9 (2)P2—N4—C13—C1518.6 (3)
N4—P2—N3—C984.80 (18)P2—N4—C13—C16139.33 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O30.87 (3)2.29 (3)3.046 (3)145 (2)
N2—H2N···O3i0.87 (1)1.99 (1)2.8531 (19)177 (2)
N3—H3N···O20.87 (3)2.24 (3)3.007 (3)147 (2)
N4—H4N···O2ii0.87 (1)2.02 (1)2.883 (2)175 (2)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+1/2, z+1/2.

Experimental details

(I)(II)
Crystal data
Chemical formulaC10H26N3OPC16H40N4O3P2
Mr235.31398.5
Crystal system, space groupMonoclinic, P21Monoclinic, P21/c
Temperature (K)150150
a, b, c (Å)12.0615 (4), 21.2567 (7), 17.1877 (6)11.3715 (4), 17.7755 (7), 13.6956 (5)
β (°) 90.529 (3) 119.371 (4)
V3)4406.5 (3)2412.51 (18)
Z124
Radiation typeMo KαCu Kα
µ (mm1)0.171.80
Crystal size (mm)0.40 × 0.25 × 0.220.37 × 0.22 × 0.09
Data collection
DiffractometerAgilent Gemini-S with Sapphire3 detector
diffractometer
Gemini Ultra
diffractometer with Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2010)
Multi-scan
(CrysAlis PRO; Agilent, 2010)
Tmin, Tmax0.558, 1.0000.746, 1.000
No. of measured, independent and
observed reflections
29385, 17386, 11821 [I > 2σ(I)]15622, 4265, 3420 [I > 3σ(I)]
Rint0.0510.033
(sin θ/λ)max1)0.6850.598
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.161, 0.92 0.040, 0.107, 1.60
No. of reflections173824265
No. of parameters947238
No. of restraints2074
H-atom treatmentH-atom parameters constrainedH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.53, 0.570.33, 0.21
Absolute structureFlack (1983), with how many Friedel pairs??
Absolute structure parameter0.00 (8)?

Computer programs: CrysAlis PRO (Agilent, 2010), SUPERFLIP (Palatinus & Chapuis, 2007), Mercury (Macrae et al., 2008), CRYSTALS (Betteridge et al., 2003) and enCIFer (Allen et al., 2004), JANA2006 (Petříček et al., 2006) and enCIFer (Allen et al., 2004).

Selected geometric parameters (Å, º) for (I) top
P1—O21.481 (3)P46—O471.474 (3)
P1—N31.646 (4)P46—N481.631 (4)
P1—N61.639 (3)P46—N531.651 (4)
P1—N111.629 (3)P46—N561.645 (3)
P16—O171.472 (3)P61—O621.484 (3)
P16—N181.635 (4)P61—N631.644 (4)
P16—N211.641 (3)P61—N681.624 (3)
P16—N261.645 (3)P61—N731.650 (4)
P31—O321.481 (3)P76—O771.484 (3)
P31—N331.636 (3)P76—N781.652 (4)
P31—N381.642 (3)P76—N811.612 (3)
P31—N431.640 (4)P76—N861.630 (4)
O2—P1—N3106.67 (17)O47—P46—N48117.44 (17)
O2—P1—N6115.95 (18)O47—P46—N53106.71 (17)
N3—P1—N6110.01 (19)N48—P46—N53106.44 (19)
O2—P1—N11117.89 (18)O47—P46—N56116.76 (18)
N3—P1—N11106.8 (2)N48—P46—N5699.03 (17)
N6—P1—N1199.08 (17)N53—P46—N56109.93 (19)
O17—P16—N18106.97 (18)O62—P61—N63117.21 (18)
O17—P16—N21117.46 (19)O62—P61—N68118.09 (18)
N18—P16—N21108.2 (2)N63—P61—N6899.12 (17)
O17—P16—N26116.42 (19)O62—P61—N73107.09 (19)
N18—P16—N26107.7 (2)N63—P61—N73107.6 (2)
N21—P16—N2699.50 (17)N68—P61—N73107.0 (2)
O32—P31—N33116.98 (17)O77—P76—N78106.81 (17)
O32—P31—N38117.15 (17)O77—P76—N81116.69 (18)
N33—P31—N3899.41 (17)N78—P76—N81107.4 (2)
O32—P31—N43105.90 (18)O77—P76—N86116.79 (18)
N33—P31—N43108.7 (2)N78—P76—N86108.8 (2)
N38—P31—N43108.34 (19)N81—P76—N8699.87 (16)
O77—P76—N78—C790.2 (5)O32—P31—N43—C45175.5 (4)
O77—P76—N78—C80176.8 (4)O32—P31—N43—C444.9 (4)
O2—P1—N3—C47.1 (5)O47—P46—N53—C549.5 (4)
O2—P1—N3—C5171.3 (5)O47—P46—N53—C55168.1 (3)
O17—P16—N18—C204.2 (6)O62—P61—N73—C74177.7 (4)
O17—P16—N18—C19176.8 (4)O62—P61—N73—C753.9 (5)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N6—H61···O770.862.102.937 (9)165
N11—H111···O770.852.082.911 (9)164
N21—H211···O620.852.213.038 (9)162
N26—H261···O620.862.112.952 (9)166
N33—H331···O170.852.102.943 (9)167
N38—H381···O170.872.223.046 (9)159
N48—H481···O20.862.162.981 (9)161
N56—H561···O20.872.102.931 (9)158
N63—H631···O32i0.862.172.994 (9)160
N68—H681···O32i0.862.042.884 (9)168
N81—H811···O47i0.862.092.927 (9)166
N86—H861···O47i0.852.162.986 (9)163
Symmetry code: (i) x+1, y, z.
Selected geometric parameters (Å, º) for (II) top
P1—O11.6194 (16)P2—O11.6191 (17)
P1—O21.4791 (12)P2—O31.4806 (12)
P1—N11.6341 (14)P2—N31.6351 (13)
P1—N21.609 (2)P2—N41.6075 (18)
P1—O1—P2126.85 (8)O1—P2—O3110.79 (8)
O1—P1—O2111.38 (8)O1—P2—N399.81 (8)
O1—P1—N1100.28 (8)O1—P2—N4107.09 (9)
O1—P1—N2106.84 (8)O3—P2—N3117.26 (7)
O2—P1—N1116.84 (7)O3—P2—N4110.13 (8)
O2—P1—N2109.89 (8)N3—P2—N4110.93 (8)
N1—P1—N2110.86 (9)
O2—P1—O1—P257.79 (11)O3—P2—O1—P159.76 (11)
N1—P1—O1—P266.53 (11)N3—P2—O1—P164.50 (11)
N2—P1—O1—P2177.81 (10)N4—P2—O1—P1179.88 (10)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O30.87 (3)2.29 (3)3.046 (3)145.2 (16)
N2—H2N···O3i0.868 (10)1.986 (11)2.8531 (19)177 (2)
N3—H3N···O20.87 (3)2.24 (3)3.007 (3)147.1 (16)
N4—H4N···O2ii0.866 (12)2.019 (13)2.883 (2)175 (2)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y+1/2, z+1/2.
 

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