Download citation
Download citation
link to html
Reversed-phase chiral high-performance liquid chromatography (HPLC) is a potentially powerful technique for the enantiomeric resolution of racemic mixtures, although the elution order of enantiomers is only relative and it is necessary to fully characterize reference systems for this method to provide absolute configurational information. The enantiomeric resolution of a series of racemic di-spiro cyclotriphosphazene derivatives, N3P3X2[O(CH2)3NH]2 (X = Cl, Ph, SPh, NHPh, OPh) [(1)-(5), respectively] was carried out by reversed-phase chiral HPLC on a commercially available Pirkle-type chiral stationary phase (R,R)-Whelk-01 using 85:15 (v/v) hexane-thf as the mobile phase. The absolute configurations of the resulting enantiomers of compounds (3) (X = SPh) and (5) (X = OPh) were determined unambiguously by X-ray crystallography. For both (3) and (5) it was found that the SS enantiomer eluted before the RR enantiomer, indicating a convenient method to determine the absolute configurations of enantiomers of this series of cyclophosphazene derivatives and providing the first set of enantiomeric reference compounds for cyclophosphazene derivatives. These structures demonstrate an interesting anomaly in that the pair of enantiomers of (3) crystallize in enantiomorphically paired space groups whilst, under the same conditions, the solid-state forms of the enantiomers of (5) form structures in Sohncke space groups that are not enantiomorphous.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768109006120/ry5024sup1.cif
Contains datablocks 3a, 3b, 5, 5a, 5b

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109006120/ry50243asup2.hkl
Contains datablock 3a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109006120/ry50243bsup3.hkl
Contains datablock 3b

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109006120/ry50245sup4.hkl
Contains datablock 5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109006120/ry50245asup5.hkl
Contains datablock 5a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768109006120/ry50245bsup6.hkl
Contains datablock 5b

CCDC references: 654556; 654557; 654558; 654559; 654560

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998) for (3a), (5a). For all compounds, cell refinement: DENZO, COLLECT; data reduction: DENZO, COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: PLATON (Spek, 2003) for (3a), (5b); PLATON (Spek, 1990) for (3b), (5), (5a).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
(3a) top
Crystal data top
C18H24N5O2P3S2Dx = 1.496 Mg m3
Mr = 499.45Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41Cell parameters from 25190 reflections
a = 11.4912 (1) Åθ = 2.9–27.5°
c = 16.7890 (2) ŵ = 0.48 mm1
V = 2216.95 (4) Å3T = 120 K
Z = 4Prism, colourless
F(000) = 10400.45 × 0.45 × 0.40 mm
Data collection top
Bruker-Nonius KappaCCD Area Detector
diffractometer
5057 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode4976 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.5°
φ and ω scansh = 1414
Absorption correction: multi-scan
SADABS V2.10 (Sheldrick, G.M., 2003)
k = 1414
Tmin = 0.812, Tmax = 0.830l = 2121
41619 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.019H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.049 w = 1/[σ2(Fo2) + (0.0283P)2 + 0.4819P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.028
5057 reflectionsΔρmax = 0.16 e Å3
279 parametersΔρmin = 0.27 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (4)
Crystal data top
C18H24N5O2P3S2Z = 4
Mr = 499.45Mo Kα radiation
Tetragonal, P41µ = 0.48 mm1
a = 11.4912 (1) ÅT = 120 K
c = 16.7890 (2) Å0.45 × 0.45 × 0.40 mm
V = 2216.95 (4) Å3
Data collection top
Bruker-Nonius KappaCCD Area Detector
diffractometer
5057 independent reflections
Absorption correction: multi-scan
SADABS V2.10 (Sheldrick, G.M., 2003)
4976 reflections with I > 2σ(I)
Tmin = 0.812, Tmax = 0.830Rint = 0.031
41619 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.019H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.049Δρmax = 0.16 e Å3
S = 1.04Δρmin = 0.27 e Å3
5057 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
279 parametersAbsolute structure parameter: 0.01 (4)
1 restraint
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.82968 (12)0.70919 (12)0.03729 (9)0.0140 (3)
C20.84909 (14)0.70813 (13)0.11901 (9)0.0213 (3)
H20.79060.67990.15400.026*
C30.95378 (15)0.74816 (14)0.14949 (11)0.0279 (4)
H30.96740.74700.20530.033*
C41.03848 (14)0.78984 (15)0.09813 (13)0.0323 (4)
H41.11000.81800.11900.039*
C51.01959 (14)0.79083 (14)0.01660 (12)0.0298 (4)
H51.07860.81860.01820.036*
C60.91472 (13)0.75134 (12)0.01447 (10)0.0204 (3)
H60.90110.75300.07030.024*
C70.83701 (13)0.29119 (12)0.05502 (8)0.0167 (3)
C80.95653 (13)0.29214 (13)0.06857 (9)0.0218 (3)
H80.99240.35900.09100.026*
C91.02309 (14)0.19564 (15)0.04931 (11)0.0270 (3)
H91.10470.19630.05840.032*
C100.97048 (16)0.09819 (14)0.01675 (10)0.0286 (4)
H101.01620.03210.00340.034*
C110.85125 (15)0.09674 (14)0.00354 (10)0.0274 (3)
H110.81570.02950.01870.033*
C120.78345 (14)0.19330 (14)0.02264 (9)0.0226 (3)
H120.70180.19240.01370.027*
C131.06017 (12)0.55367 (13)0.19484 (10)0.0198 (3)
H13A1.08970.60450.23790.024*
H13B1.04610.60260.14730.024*
C141.15054 (12)0.46183 (13)0.17538 (9)0.0195 (3)
H14A1.17030.41850.22450.023*
H14B1.22220.50050.15610.023*
C151.10837 (12)0.37624 (13)0.11235 (9)0.0179 (3)
H15A1.09320.41780.06170.021*
H15B1.16870.31650.10250.021*
C160.48367 (12)0.21635 (12)0.14389 (9)0.0162 (3)
H16A0.46730.13190.14010.019*
H16B0.45780.25340.09370.019*
C170.41647 (12)0.26789 (12)0.21348 (9)0.0164 (3)
H17A0.43640.22490.26270.020*
H17B0.33200.25840.20390.020*
C180.44380 (12)0.39665 (12)0.22502 (9)0.0163 (3)
H18A0.41920.44110.17740.020*
H18B0.40060.42700.27160.020*
N10.86791 (10)0.48911 (10)0.07770 (7)0.0130 (2)
N20.78575 (10)0.35315 (10)0.19822 (7)0.0135 (2)
N30.63816 (10)0.43377 (10)0.08397 (7)0.0144 (2)
N40.99934 (10)0.31974 (10)0.14119 (7)0.0143 (2)
N50.57020 (10)0.41122 (10)0.23778 (7)0.0133 (2)
O10.95170 (8)0.49992 (9)0.21982 (6)0.0155 (2)
O20.60888 (8)0.23459 (8)0.15424 (6)0.01375 (19)
P10.74443 (3)0.48918 (3)0.03601 (2)0.01101 (7)
P20.89259 (3)0.41507 (3)0.156756 (19)0.01033 (7)
P30.65592 (3)0.36334 (3)0.166283 (19)0.01027 (7)
S10.69478 (3)0.65851 (3)0.00226 (2)0.01505 (7)
S20.75390 (3)0.41789 (3)0.07875 (2)0.01936 (8)
H4N0.9798 (15)0.2640 (10)0.1107 (8)0.016 (4)*
H5N0.5911 (16)0.4761 (8)0.2574 (11)0.027 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0146 (6)0.0114 (6)0.0160 (6)0.0026 (5)0.0010 (5)0.0026 (5)
C20.0246 (8)0.0206 (7)0.0188 (7)0.0014 (6)0.0034 (6)0.0022 (6)
C30.0326 (9)0.0262 (8)0.0248 (8)0.0065 (7)0.0136 (7)0.0063 (7)
C40.0184 (7)0.0234 (8)0.0552 (12)0.0043 (6)0.0110 (8)0.0163 (8)
C50.0201 (8)0.0218 (8)0.0475 (11)0.0046 (6)0.0104 (7)0.0089 (7)
C60.0236 (7)0.0163 (7)0.0213 (8)0.0004 (5)0.0045 (6)0.0023 (6)
C70.0213 (7)0.0166 (7)0.0123 (6)0.0006 (5)0.0004 (5)0.0044 (5)
C80.0230 (7)0.0202 (7)0.0222 (7)0.0042 (6)0.0049 (6)0.0068 (6)
C90.0230 (8)0.0278 (9)0.0301 (9)0.0033 (7)0.0024 (7)0.0095 (7)
C100.0388 (9)0.0190 (7)0.0280 (9)0.0076 (7)0.0048 (7)0.0062 (6)
C110.0387 (9)0.0180 (7)0.0256 (8)0.0063 (7)0.0012 (7)0.0008 (6)
C120.0239 (8)0.0227 (8)0.0212 (8)0.0047 (6)0.0039 (6)0.0036 (6)
C130.0143 (7)0.0207 (7)0.0243 (8)0.0051 (5)0.0045 (6)0.0030 (6)
C140.0107 (6)0.0236 (7)0.0241 (7)0.0020 (5)0.0046 (6)0.0033 (6)
C150.0102 (6)0.0200 (7)0.0235 (8)0.0023 (5)0.0017 (5)0.0020 (6)
C160.0145 (6)0.0147 (6)0.0193 (7)0.0038 (5)0.0046 (5)0.0006 (5)
C170.0110 (6)0.0166 (6)0.0217 (7)0.0023 (5)0.0009 (5)0.0016 (5)
C180.0094 (6)0.0168 (7)0.0226 (7)0.0009 (5)0.0004 (5)0.0017 (5)
N10.0096 (5)0.0147 (5)0.0146 (6)0.0004 (4)0.0019 (4)0.0025 (4)
N20.0102 (5)0.0174 (5)0.0128 (5)0.0007 (4)0.0016 (4)0.0029 (4)
N30.0104 (5)0.0173 (6)0.0155 (6)0.0018 (4)0.0037 (4)0.0043 (4)
N40.0113 (5)0.0126 (5)0.0189 (6)0.0008 (4)0.0003 (4)0.0003 (5)
N50.0100 (5)0.0134 (5)0.0164 (6)0.0009 (4)0.0004 (4)0.0040 (4)
O10.0127 (5)0.0189 (5)0.0150 (5)0.0020 (4)0.0034 (4)0.0043 (4)
O20.0133 (4)0.0106 (4)0.0173 (5)0.0009 (3)0.0000 (4)0.0024 (4)
P10.01067 (15)0.01207 (15)0.01030 (15)0.00029 (12)0.00227 (12)0.00081 (12)
P20.00858 (14)0.01161 (15)0.01080 (15)0.00057 (11)0.00205 (12)0.00041 (12)
P30.00929 (15)0.01051 (15)0.01102 (15)0.00029 (11)0.00140 (12)0.00001 (12)
S10.01338 (15)0.01561 (16)0.01615 (16)0.00377 (12)0.00195 (13)0.00466 (12)
S20.02553 (18)0.02081 (17)0.01174 (15)0.00217 (14)0.00373 (13)0.00313 (13)
Geometric parameters (Å, º) top
C1—C21.390 (2)C15—N41.4919 (17)
C1—C61.395 (2)C16—O21.4643 (16)
C1—S11.7841 (14)C16—C171.521 (2)
C2—C31.386 (2)C17—C181.5249 (19)
C3—C41.386 (3)C18—N51.4777 (17)
C4—C51.386 (3)N1—P11.5821 (11)
C5—C61.389 (2)N1—P21.6019 (12)
C7—C81.392 (2)N2—P21.5805 (12)
C7—C121.393 (2)N2—P31.5896 (11)
C7—S21.7861 (15)N3—P11.5954 (12)
C8—C91.385 (2)N3—P31.6144 (12)
C9—C101.385 (3)N4—P21.6653 (12)
C10—C111.388 (3)N5—P31.6474 (12)
C11—C121.393 (2)O1—P21.5916 (10)
C13—O11.4529 (17)O2—P31.5881 (9)
C13—C141.516 (2)P1—S22.0964 (5)
C14—C151.524 (2)P1—S12.1054 (5)
C2—C1—C6120.37 (14)C15—N4—P2112.53 (9)
C2—C1—S1120.26 (12)C18—N5—P3116.37 (9)
C6—C1—S1119.36 (11)C13—O1—P2115.76 (9)
C3—C2—C1120.05 (16)C16—O2—P3118.88 (8)
C2—C3—C4119.65 (16)N1—P1—N3117.58 (6)
C5—C4—C3120.49 (16)N1—P1—S2111.09 (5)
C4—C5—C6120.27 (16)N3—P1—S2110.34 (5)
C5—C6—C1119.16 (15)N1—P1—S1111.25 (5)
C8—C7—C12120.40 (14)N3—P1—S1107.29 (5)
C8—C7—S2118.99 (11)S2—P1—S197.35 (2)
C12—C7—S2120.61 (12)N2—P2—O1108.32 (6)
C9—C8—C7120.01 (14)N2—P2—N1117.81 (6)
C8—C9—C10119.89 (15)O1—P2—N1107.54 (6)
C9—C10—C11120.24 (16)N2—P2—N4110.19 (6)
C10—C11—C12120.37 (15)O1—P2—N4101.13 (6)
C7—C12—C11119.08 (15)N1—P2—N4110.47 (6)
O1—C13—C14110.73 (11)O2—P3—N2107.08 (6)
C13—C14—C15112.40 (11)O2—P3—N3108.37 (6)
N4—C15—C14108.82 (12)N2—P3—N3116.38 (6)
O2—C16—C17110.61 (11)O2—P3—N5101.56 (6)
C16—C17—C18111.77 (12)N2—P3—N5109.88 (6)
N5—C18—C17109.32 (11)N3—P3—N5112.38 (6)
P1—N1—P2121.71 (7)C1—S1—P199.58 (5)
P2—N2—P3123.18 (7)C7—S2—P198.12 (5)
P1—N3—P3122.37 (7)
(3b) top
Crystal data top
C18H24N5O2P3S2Dx = 1.497 Mg m3
Mr = 499.45Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43Cell parameters from 2618 reflections
a = 11.4899 (1) Åθ = 2.9–27.5°
c = 16.7827 (2) ŵ = 0.48 mm1
V = 2215.62 (4) Å3T = 120 K
Z = 4Block, colourless
F(000) = 10400.55 × 0.20 × 0.20 mm
Data collection top
Bruker-Nonius KappaCCD Area Detector
diffractometer
4532 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode4330 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.5°
φ and ω scansh = 1214
Absorption correction: multi-scan
SADABS V2.10 (Sheldrick, G.M., 2003)
k = 1413
Tmin = 0.777, Tmax = 0.910l = 1821
15809 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.066 w = 1/[σ2(Fo2) + (0.0282P)2 + 0.916P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.004
4532 reflectionsΔρmax = 0.19 e Å3
279 parametersΔρmin = 0.33 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (5)
Crystal data top
C18H24N5O2P3S2Z = 4
Mr = 499.45Mo Kα radiation
Tetragonal, P43µ = 0.48 mm1
a = 11.4899 (1) ÅT = 120 K
c = 16.7827 (2) Å0.55 × 0.20 × 0.20 mm
V = 2215.62 (4) Å3
Data collection top
Bruker-Nonius KappaCCD Area Detector
diffractometer
4532 independent reflections
Absorption correction: multi-scan
SADABS V2.10 (Sheldrick, G.M., 2003)
4330 reflections with I > 2σ(I)
Tmin = 0.777, Tmax = 0.910Rint = 0.035
15809 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.066Δρmax = 0.19 e Å3
S = 1.03Δρmin = 0.33 e Å3
4532 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
279 parametersAbsolute structure parameter: 0.01 (5)
1 restraint
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.67032 (19)1.20914 (19)0.15183 (13)0.0160 (4)
C20.5854 (2)1.2512 (2)0.10010 (14)0.0226 (5)
H20.59911.25300.04430.027*
C30.4801 (2)1.2906 (2)0.13141 (18)0.0316 (6)
H30.42091.31810.09660.038*
C40.4615 (2)1.2900 (2)0.21254 (19)0.0340 (6)
H40.39001.31820.23340.041*
C50.5461 (2)1.2485 (2)0.26394 (16)0.0293 (6)
H50.53251.24780.31980.035*
C60.6513 (2)1.2079 (2)0.23359 (14)0.0230 (5)
H60.70971.17940.26860.028*
C70.6630 (2)0.79102 (19)0.16944 (13)0.0186 (5)
C80.5436 (2)0.7924 (2)0.18311 (14)0.0236 (5)
H80.50770.85920.20560.028*
C90.4771 (2)0.6955 (2)0.16371 (16)0.0286 (6)
H90.39550.69600.17280.034*
C100.5298 (2)0.5983 (2)0.13104 (15)0.0306 (6)
H100.48430.53220.11740.037*
C110.6488 (2)0.5971 (2)0.11818 (15)0.0290 (6)
H110.68450.52970.09620.035*
C120.7164 (2)0.6932 (2)0.13702 (14)0.0244 (5)
H120.79800.69220.12790.029*
C131.01646 (19)0.71621 (19)0.02928 (13)0.0175 (4)
H13A1.04230.75320.02100.021*
H13B1.03280.63180.02560.021*
C141.08356 (19)0.76804 (19)0.09898 (14)0.0183 (5)
H14A1.06370.72500.14820.022*
H14B1.16810.75860.08940.022*
C151.05628 (18)0.8966 (2)0.11072 (14)0.0182 (4)
H15A1.09920.92670.15750.022*
H15B1.08120.94120.06320.022*
C160.43990 (19)1.0535 (2)0.08011 (14)0.0210 (5)
H16A0.45401.10210.03240.025*
H16B0.41041.10460.12310.025*
C170.34959 (18)0.9619 (2)0.06095 (14)0.0210 (5)
H17A0.27791.00050.04170.025*
H17B0.32990.91870.11020.025*
C180.39203 (19)0.8761 (2)0.00217 (14)0.0204 (5)
H18A0.33180.81630.01200.024*
H18B0.40720.91770.05280.024*
N10.86200 (15)0.93390 (16)0.03041 (11)0.0159 (4)
N20.71425 (15)0.85306 (16)0.08384 (11)0.0151 (4)
N30.63220 (15)0.98896 (16)0.03661 (10)0.0152 (4)
N40.92980 (15)0.91119 (16)0.12314 (11)0.0152 (4)
N50.50092 (15)0.81992 (16)0.02673 (11)0.0158 (4)
O10.89091 (12)0.73456 (12)0.03975 (9)0.0151 (3)
O20.54848 (13)0.99991 (13)0.10528 (9)0.0176 (3)
P10.75563 (5)0.98916 (5)0.07845 (3)0.01310 (11)
P20.84409 (4)0.86326 (5)0.05180 (3)0.01232 (11)
P30.60744 (4)0.91504 (5)0.04231 (3)0.01243 (11)
S10.80527 (5)1.15848 (5)0.11231 (3)0.01700 (12)
S20.74609 (5)0.91785 (5)0.19321 (3)0.02108 (12)
H4N0.908 (2)0.9754 (11)0.1431 (15)0.024 (7)*
H5N0.519 (2)0.7646 (15)0.0045 (12)0.022 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0174 (10)0.0141 (10)0.0165 (10)0.0032 (8)0.0004 (8)0.0034 (8)
C20.0257 (12)0.0206 (11)0.0215 (12)0.0003 (9)0.0044 (9)0.0036 (9)
C30.0219 (12)0.0248 (13)0.0483 (17)0.0041 (10)0.0102 (12)0.0073 (12)
C40.0206 (12)0.0262 (13)0.0552 (18)0.0029 (10)0.0114 (12)0.0177 (13)
C50.0336 (14)0.0283 (14)0.0259 (13)0.0071 (11)0.0141 (11)0.0059 (11)
C60.0274 (13)0.0214 (12)0.0203 (11)0.0010 (10)0.0040 (10)0.0021 (9)
C70.0229 (11)0.0187 (11)0.0143 (10)0.0011 (9)0.0010 (9)0.0052 (9)
C80.0250 (12)0.0226 (12)0.0231 (12)0.0045 (9)0.0043 (10)0.0071 (10)
C90.0245 (13)0.0321 (14)0.0293 (13)0.0037 (11)0.0028 (11)0.0111 (11)
C100.0413 (15)0.0216 (12)0.0289 (13)0.0068 (11)0.0053 (12)0.0053 (10)
C110.0406 (15)0.0203 (12)0.0262 (13)0.0048 (11)0.0009 (12)0.0021 (10)
C120.0273 (13)0.0251 (13)0.0209 (12)0.0025 (10)0.0035 (10)0.0026 (10)
C130.0173 (11)0.0173 (10)0.0179 (11)0.0047 (8)0.0032 (9)0.0001 (9)
C140.0135 (10)0.0183 (11)0.0232 (12)0.0019 (9)0.0009 (9)0.0013 (9)
C150.0112 (10)0.0204 (11)0.0228 (11)0.0017 (9)0.0001 (9)0.0018 (9)
C160.0149 (11)0.0226 (11)0.0257 (12)0.0045 (9)0.0037 (9)0.0040 (10)
C170.0122 (10)0.0264 (12)0.0243 (12)0.0016 (9)0.0046 (9)0.0040 (10)
C180.0120 (10)0.0246 (12)0.0245 (12)0.0018 (9)0.0026 (9)0.0003 (10)
N10.0124 (8)0.0190 (9)0.0164 (9)0.0020 (7)0.0032 (7)0.0039 (7)
N20.0128 (9)0.0187 (9)0.0139 (8)0.0004 (7)0.0011 (7)0.0026 (7)
N30.0131 (8)0.0172 (9)0.0153 (9)0.0002 (7)0.0014 (7)0.0032 (7)
N40.0130 (9)0.0154 (9)0.0172 (9)0.0008 (7)0.0024 (7)0.0037 (7)
N50.0128 (9)0.0154 (9)0.0190 (9)0.0013 (7)0.0011 (7)0.0002 (8)
O10.0148 (7)0.0133 (7)0.0172 (7)0.0006 (6)0.0006 (6)0.0027 (6)
O20.0152 (7)0.0209 (8)0.0166 (7)0.0021 (6)0.0036 (6)0.0036 (6)
P10.0135 (3)0.0149 (3)0.0110 (2)0.0002 (2)0.0019 (2)0.0007 (2)
P20.0118 (2)0.0129 (2)0.0123 (2)0.00023 (19)0.0014 (2)0.0003 (2)
P30.0116 (2)0.0143 (3)0.0115 (2)0.0005 (2)0.0020 (2)0.0003 (2)
S10.0158 (3)0.0182 (3)0.0169 (2)0.0036 (2)0.0020 (2)0.0044 (2)
S20.0273 (3)0.0231 (3)0.0129 (2)0.0023 (2)0.0036 (2)0.0030 (2)
Geometric parameters (Å, º) top
C1—C61.390 (3)C15—N41.478 (3)
C1—C21.392 (3)C16—O21.454 (3)
C1—S11.784 (2)C16—C171.512 (3)
C2—C31.395 (4)C17—C181.527 (3)
C3—C41.378 (4)C18—N51.489 (3)
C4—C51.384 (4)N1—P11.5959 (18)
C5—C61.391 (4)N1—P21.6140 (19)
C7—C81.391 (3)N2—P31.5809 (18)
C7—C121.392 (3)N2—P21.5901 (18)
C7—S21.787 (2)N3—P11.5825 (18)
C8—C91.389 (4)N3—P31.5989 (18)
C9—C101.385 (4)N4—P21.6451 (19)
C10—C111.384 (4)N5—P31.6615 (19)
C11—C121.387 (4)O1—P21.5865 (15)
C13—O11.468 (2)O2—P31.5896 (15)
C13—C141.522 (3)P1—S22.0959 (8)
C14—C151.522 (3)P1—S12.1055 (8)
C6—C1—C2120.6 (2)C15—N4—P2116.62 (14)
C6—C1—S1120.04 (18)C18—N5—P3112.63 (14)
C2—C1—S1119.36 (18)C13—O1—P2118.83 (13)
C1—C2—C3119.0 (2)C16—O2—P3115.61 (13)
C4—C3—C2120.3 (2)N3—P1—N1117.49 (10)
C3—C4—C5120.6 (2)N3—P1—S2111.12 (7)
C4—C5—C6119.8 (2)N1—P1—S2110.41 (7)
C1—C6—C5119.7 (2)N3—P1—S1111.34 (7)
C8—C7—C12120.6 (2)N1—P1—S1107.25 (7)
C8—C7—S2118.74 (18)S2—P1—S197.31 (3)
C12—C7—S2120.69 (19)O1—P2—N2107.01 (9)
C9—C8—C7119.7 (2)O1—P2—N1108.45 (9)
C10—C9—C8119.9 (2)N2—P2—N1116.47 (9)
C11—C10—C9120.1 (2)O1—P2—N4101.64 (9)
C10—C11—C12120.7 (2)N2—P2—N4109.89 (9)
C11—C12—C7119.0 (2)N1—P2—N4112.17 (9)
O1—C13—C14110.45 (17)N2—P3—O2108.30 (9)
C15—C14—C13112.00 (18)N2—P3—N3117.80 (10)
N4—C15—C14109.33 (17)O2—P3—N3107.50 (9)
O2—C16—C17110.85 (18)N2—P3—N5110.18 (9)
C16—C17—C18112.17 (18)O2—P3—N5101.20 (9)
N5—C18—C17108.80 (18)N3—P3—N5110.49 (10)
P1—N1—P2122.29 (11)C1—S1—P199.57 (7)
P3—N2—P2123.09 (11)C7—S2—P198.14 (7)
P1—N3—P3121.86 (11)
(5) top
Crystal data top
C18H24N5O4P3Dx = 1.495 Mg m3
Mr = 467.33Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcnCell parameters from 4837 reflections
a = 38.7541 (16) Åθ = 2.9–27.5°
b = 10.1505 (4) ŵ = 0.32 mm1
c = 10.5550 (5) ÅT = 120 K
V = 4152.1 (3) Å3Needle, colourless
Z = 80.65 × 0.02 × 0.01 mm
F(000) = 1952
Data collection top
Bruker APEX2
diffractometer
4703 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode3961 reflections with I > 2σ(I)
10cm confocal mirrors monochromatorRint = 0.055
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.5°
φ and ω scansh = 5050
Absorption correction: multi-scan
SADABS V2.10 (Sheldrick, G.M., 2003)
k = 1311
Tmin = 0.817, Tmax = 0.997l = 1311
19961 measured reflections
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.P)2 + 15.046P]
where P = (Fo2 + 2Fc2)/3
4703 reflections(Δ/σ)max < 0.001
279 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C18H24N5O4P3V = 4152.1 (3) Å3
Mr = 467.33Z = 8
Orthorhombic, PbcnMo Kα radiation
a = 38.7541 (16) ŵ = 0.32 mm1
b = 10.1505 (4) ÅT = 120 K
c = 10.5550 (5) Å0.65 × 0.02 × 0.01 mm
Data collection top
Bruker APEX2
diffractometer
4703 independent reflections
Absorption correction: multi-scan
SADABS V2.10 (Sheldrick, G.M., 2003)
3961 reflections with I > 2σ(I)
Tmin = 0.817, Tmax = 0.997Rint = 0.055
19961 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.P)2 + 15.046P]
where P = (Fo2 + 2Fc2)/3
4703 reflectionsΔρmax = 0.55 e Å3
279 parametersΔρmin = 0.43 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.36017 (9)0.3751 (3)0.5506 (3)0.0302 (8)
H1A0.36130.37940.45700.036*
H1B0.38390.38260.58440.036*
C20.33821 (9)0.4871 (4)0.6006 (4)0.0327 (8)
H2A0.34890.57240.57730.039*
H2B0.31500.48320.56160.039*
C30.33495 (9)0.4781 (3)0.7433 (4)0.0326 (8)
H3A0.35820.48340.78220.039*
H3B0.32110.55320.77490.039*
C40.25752 (9)0.0680 (4)0.9491 (5)0.0467 (12)
H4A0.24410.01040.89160.056*
H4B0.24470.07501.03000.056*
C50.26078 (10)0.2034 (4)0.8906 (5)0.0519 (13)
H5A0.27290.26290.95010.062*
H5B0.23750.23990.87450.062*
C60.28041 (11)0.1963 (4)0.7688 (5)0.0502 (13)
H6A0.28120.28490.72960.060*
H6B0.26830.13640.70950.060*
C70.44017 (7)0.0336 (3)0.9473 (3)0.0209 (6)
C80.43182 (8)0.0875 (3)1.0632 (3)0.0237 (7)
H80.41160.06061.10700.028*
C90.45373 (9)0.1825 (3)1.1146 (3)0.0263 (7)
H90.44830.22121.19410.032*
C100.48323 (8)0.2209 (3)1.0513 (3)0.0276 (7)
H100.49810.28481.08770.033*
C110.49106 (8)0.1657 (3)0.9342 (3)0.0276 (7)
H110.51130.19230.89020.033*
C120.46941 (8)0.0723 (3)0.8818 (3)0.0238 (7)
H120.47460.03490.80140.029*
C130.40613 (7)0.2587 (3)1.1054 (3)0.0206 (6)
C140.40683 (8)0.2685 (3)1.2360 (3)0.0268 (7)
H140.39320.21171.28700.032*
C150.42782 (9)0.3629 (4)1.2911 (4)0.0328 (8)
H150.42850.37061.38080.039*
C160.44778 (9)0.4462 (4)1.2174 (4)0.0318 (8)
H160.46220.51041.25610.038*
C170.44651 (9)0.4350 (3)1.0862 (4)0.0292 (7)
H170.46010.49201.03520.035*
C180.42556 (8)0.3414 (3)1.0289 (3)0.0250 (7)
H180.42460.33420.93920.030*
N10.31327 (7)0.1027 (3)0.7586 (3)0.0245 (6)
N20.35745 (6)0.0157 (3)0.9234 (3)0.0222 (6)
N30.37388 (6)0.2199 (3)0.8187 (3)0.0218 (6)
N40.34500 (7)0.2495 (3)0.5898 (3)0.0228 (6)
N50.29128 (7)0.0080 (3)0.9732 (3)0.0309 (7)
O10.31856 (6)0.3554 (2)0.7800 (2)0.0251 (5)
O20.31564 (6)0.1487 (2)0.7892 (3)0.0332 (6)
O30.42063 (5)0.0639 (2)0.8864 (2)0.0225 (5)
O40.38410 (5)0.1615 (2)1.0584 (2)0.0222 (5)
P10.338309 (19)0.22429 (8)0.74061 (8)0.01890 (18)
P20.320197 (19)0.01163 (8)0.85954 (8)0.02149 (19)
P30.382158 (19)0.10819 (8)0.91629 (8)0.01875 (18)
H5N0.2998 (9)0.035 (3)1.0427 (18)0.026 (10)*
H4N0.3529 (10)0.185 (3)0.548 (4)0.046 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0302 (17)0.0336 (19)0.0267 (18)0.0035 (14)0.0011 (14)0.0095 (15)
C20.0302 (17)0.0254 (18)0.042 (2)0.0015 (14)0.0065 (16)0.0089 (16)
C30.0325 (18)0.0205 (17)0.045 (2)0.0040 (14)0.0033 (16)0.0077 (16)
C40.0157 (16)0.048 (2)0.076 (3)0.0015 (16)0.0007 (17)0.026 (2)
C50.0249 (18)0.036 (2)0.095 (4)0.0091 (16)0.020 (2)0.026 (2)
C60.050 (2)0.0242 (19)0.076 (3)0.0015 (17)0.041 (2)0.001 (2)
C70.0168 (13)0.0218 (15)0.0243 (16)0.0015 (11)0.0019 (12)0.0010 (13)
C80.0189 (14)0.0266 (16)0.0256 (17)0.0002 (12)0.0026 (12)0.0005 (14)
C90.0298 (16)0.0267 (17)0.0225 (17)0.0016 (13)0.0002 (13)0.0032 (14)
C100.0252 (16)0.0240 (17)0.0335 (19)0.0013 (13)0.0037 (14)0.0010 (14)
C110.0203 (15)0.0304 (18)0.0321 (19)0.0014 (13)0.0033 (13)0.0014 (15)
C120.0173 (14)0.0284 (17)0.0258 (17)0.0020 (12)0.0040 (12)0.0004 (14)
C130.0160 (13)0.0206 (15)0.0250 (16)0.0041 (11)0.0012 (12)0.0008 (13)
C140.0255 (16)0.0301 (18)0.0249 (17)0.0012 (13)0.0007 (13)0.0009 (14)
C150.0341 (18)0.036 (2)0.0282 (18)0.0028 (15)0.0054 (15)0.0047 (16)
C160.0294 (17)0.0278 (18)0.038 (2)0.0002 (14)0.0080 (15)0.0074 (16)
C170.0257 (16)0.0263 (17)0.0356 (19)0.0000 (13)0.0027 (14)0.0036 (15)
C180.0246 (15)0.0279 (17)0.0224 (16)0.0012 (13)0.0014 (13)0.0002 (14)
N10.0195 (12)0.0249 (14)0.0291 (15)0.0024 (10)0.0058 (11)0.0062 (12)
N20.0184 (12)0.0221 (13)0.0261 (14)0.0018 (10)0.0015 (11)0.0034 (11)
N30.0183 (12)0.0239 (14)0.0233 (14)0.0013 (10)0.0035 (10)0.0043 (11)
N40.0260 (13)0.0247 (14)0.0176 (13)0.0001 (11)0.0007 (11)0.0003 (12)
N50.0186 (13)0.0371 (17)0.0369 (18)0.0016 (12)0.0025 (12)0.0130 (14)
O10.0225 (11)0.0247 (12)0.0282 (12)0.0026 (9)0.0021 (9)0.0036 (10)
O20.0367 (14)0.0238 (12)0.0391 (15)0.0013 (10)0.0123 (11)0.0028 (11)
O30.0164 (10)0.0286 (12)0.0227 (11)0.0018 (9)0.0024 (8)0.0060 (10)
O40.0205 (10)0.0257 (11)0.0206 (11)0.0036 (9)0.0001 (9)0.0003 (9)
P10.0174 (4)0.0202 (4)0.0191 (4)0.0011 (3)0.0007 (3)0.0001 (3)
P20.0174 (4)0.0205 (4)0.0266 (4)0.0015 (3)0.0029 (3)0.0025 (3)
P30.0149 (3)0.0222 (4)0.0192 (4)0.0003 (3)0.0001 (3)0.0012 (3)
Geometric parameters (Å, º) top
C1—N41.463 (4)C13—O41.395 (4)
C1—C21.515 (5)C14—C151.385 (5)
C2—C31.514 (5)C15—C161.385 (5)
C3—O11.451 (4)C16—C171.390 (5)
C4—N51.465 (4)C17—C181.388 (5)
C4—C51.512 (7)N1—P11.582 (3)
C5—C61.496 (7)N1—P21.598 (3)
C6—O21.464 (4)N2—P31.582 (3)
C7—C81.378 (4)N2—P21.594 (3)
C7—C121.385 (4)N3—P31.565 (3)
C7—O31.402 (4)N3—P11.606 (3)
C8—C91.395 (5)N4—P11.633 (3)
C9—C101.380 (5)N5—P21.642 (3)
C10—C111.391 (5)O1—P11.590 (2)
C11—C121.382 (5)O2—P21.587 (3)
C13—C141.383 (5)O3—P31.589 (2)
C13—C181.387 (4)O4—P31.597 (2)
N4—C1—C2109.3 (3)C1—N4—P1118.4 (2)
C3—C2—C1110.3 (3)C4—N5—P2118.2 (3)
O1—C3—C2110.7 (3)C3—O1—P1116.0 (2)
N5—C4—C5112.0 (3)C6—O2—P2117.5 (2)
C6—C5—C4110.5 (3)C7—O3—P3128.0 (2)
O2—C6—C5111.3 (3)C13—O4—P3127.0 (2)
C8—C7—C12121.5 (3)N1—P1—O1109.05 (14)
C8—C7—O3124.1 (3)N1—P1—N3116.29 (14)
C12—C7—O3114.4 (3)O1—P1—N3107.59 (14)
C7—C8—C9118.5 (3)N1—P1—N4109.70 (15)
C10—C9—C8120.7 (3)O1—P1—N4101.53 (14)
C9—C10—C11119.8 (3)N3—P1—N4111.59 (14)
C12—C11—C10120.0 (3)O2—P2—N2106.02 (14)
C11—C12—C7119.5 (3)O2—P2—N1107.81 (15)
C14—C13—C18121.7 (3)N2—P2—N1116.93 (14)
C14—C13—O4114.6 (3)O2—P2—N5106.60 (16)
C18—C13—O4123.6 (3)N2—P2—N5108.05 (15)
C13—C14—C15118.7 (3)N1—P2—N5110.86 (15)
C14—C15—C16120.9 (3)N3—P3—N2118.87 (14)
C15—C16—C17119.3 (3)N3—P3—O3105.48 (13)
C18—C17—C16120.7 (3)N2—P3—O3110.61 (13)
C13—C18—C17118.6 (3)N3—P3—O4112.51 (14)
P1—N1—P2122.95 (17)N2—P3—O4104.68 (13)
P3—N2—P2120.48 (17)O3—P3—O4103.77 (12)
P3—N3—P1122.26 (17)
(5a) top
Crystal data top
C18H24N5O4P3Dx = 1.465 Mg m3
Mr = 467.33Mo Kα radiation, λ = 0.71073 Å
Trigonal, P32Cell parameters from 2347 reflections
a = 10.4920 (1) Åθ = 2.9–27.5°
c = 16.6645 (3) ŵ = 0.32 mm1
V = 1588.69 (4) Å3T = 120 K
Z = 3Block, colourless
F(000) = 7320.50 × 0.40 × 0.34 mm
Data collection top
Bruker-Nonius KappaCCD Area Detector
diffractometer
4848 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode4802 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.3°
φ and ω scansh = 1313
Absorption correction: multi-scan
SADABS V2.10 (Sheldrick, G.M., 2003)
k = 1111
Tmin = 0.858, Tmax = 0.900l = 2121
4871 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.072 w = 1/[σ2(Fo2) + (0.0389P)2 + 0.8904P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.021
4848 reflectionsΔρmax = 0.18 e Å3
280 parametersΔρmin = 0.38 e Å3
3 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (8)
Crystal data top
C18H24N5O4P3Z = 3
Mr = 467.33Mo Kα radiation
Trigonal, P32µ = 0.32 mm1
a = 10.4920 (1) ÅT = 120 K
c = 16.6645 (3) Å0.50 × 0.40 × 0.34 mm
V = 1588.69 (4) Å3
Data collection top
Bruker-Nonius KappaCCD Area Detector
diffractometer
4848 independent reflections
Absorption correction: multi-scan
SADABS V2.10 (Sheldrick, G.M., 2003)
4802 reflections with I > 2σ(I)
Tmin = 0.858, Tmax = 0.900Rint = 0.048
4871 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.072Δρmax = 0.18 e Å3
S = 1.02Δρmin = 0.38 e Å3
4848 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
280 parametersAbsolute structure parameter: 0.06 (8)
3 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.5989 (3)1.0664 (3)0.99501 (16)0.0175 (5)
C20.6981 (3)1.2019 (3)0.96413 (18)0.0249 (6)
H20.69801.22150.90850.030*
C30.7981 (4)1.3094 (4)1.0152 (2)0.0316 (7)
H30.86641.40390.99470.038*
C40.7987 (4)1.2796 (4)1.0961 (2)0.0315 (7)
H40.86721.35401.13100.038*
C50.7003 (4)1.1423 (4)1.12636 (18)0.0302 (7)
H50.70201.12201.18180.036*
C60.5991 (3)1.0343 (3)1.07577 (18)0.0251 (6)
H60.53090.93961.09610.030*
C70.3613 (3)0.6262 (3)0.81817 (16)0.0148 (5)
C80.3212 (3)0.4953 (3)0.85581 (17)0.0232 (6)
H80.30980.48690.91250.028*
C90.2974 (4)0.3749 (3)0.80942 (19)0.0277 (7)
H90.26960.28340.83460.033*
C100.3140 (3)0.3878 (3)0.72724 (18)0.0218 (6)
H100.29910.30580.69600.026*
C110.3523 (3)0.5202 (3)0.69040 (16)0.0235 (6)
H110.36210.52850.63370.028*
C120.3765 (3)0.6414 (3)0.73619 (16)0.0221 (6)
H120.40290.73280.71130.026*
C130.6087 (3)0.5161 (3)1.02805 (18)0.0235 (6)
H13A0.58770.41371.02090.028*
H13B0.51370.51481.02850.028*
C140.6869 (4)0.5755 (4)1.10715 (19)0.0261 (7)
H14A0.77620.56621.10870.031*
H14B0.62150.51541.15140.031*
C150.7306 (3)0.7351 (4)1.12042 (16)0.0231 (6)
H15A0.64140.74371.12640.028*
H15B0.78940.77181.17020.028*
N40.8183 (3)0.8242 (3)1.05117 (13)0.0173 (5)
C160.9219 (3)1.1999 (3)0.76421 (16)0.0200 (6)
H16A1.00101.30350.77050.024*
H16B0.82611.19660.76740.024*
C170.9363 (3)1.1422 (3)0.68278 (17)0.0221 (6)
H17A0.92311.20000.64000.027*
H17B1.03671.15680.67750.027*
C180.8257 (3)0.9813 (3)0.67088 (15)0.0207 (6)
H18A0.72500.96690.66980.025*
H18B0.84400.94740.61890.025*
N50.8383 (3)0.8942 (3)0.73720 (13)0.0160 (4)
N10.5814 (2)0.7685 (3)0.96406 (13)0.0139 (4)
N20.8474 (2)0.8609 (3)0.89470 (14)0.0147 (4)
N30.6528 (2)0.9339 (3)0.83125 (13)0.0151 (4)
O10.4938 (2)0.9583 (2)0.94427 (11)0.0155 (4)
O20.3803 (2)0.7472 (2)0.86408 (11)0.0151 (4)
O30.6979 (2)0.6057 (2)0.96134 (11)0.0178 (4)
O40.9321 (2)1.1113 (2)0.82846 (11)0.0165 (4)
P10.53976 (7)0.85171 (7)0.90071 (4)0.01200 (11)
P20.73541 (7)0.77205 (7)0.96437 (3)0.01212 (12)
P30.80971 (7)0.94302 (7)0.82731 (4)0.01249 (12)
H5N0.794 (4)0.8026 (13)0.732 (3)0.041 (12)*
H4N0.857 (4)0.9153 (14)1.060 (2)0.035 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0160 (12)0.0191 (13)0.0214 (12)0.0118 (11)0.0040 (10)0.0082 (10)
C20.0271 (16)0.0191 (14)0.0267 (13)0.0103 (12)0.0050 (12)0.0018 (12)
C30.0310 (17)0.0196 (14)0.0425 (18)0.0113 (13)0.0112 (14)0.0099 (13)
C40.0319 (16)0.0321 (17)0.0393 (18)0.0225 (15)0.0182 (14)0.0193 (14)
C50.0345 (18)0.0441 (19)0.0206 (13)0.0262 (15)0.0102 (12)0.0123 (13)
C60.0265 (15)0.0297 (16)0.0225 (13)0.0166 (13)0.0038 (12)0.0050 (12)
C70.0121 (12)0.0128 (12)0.0209 (12)0.0073 (10)0.0020 (10)0.0028 (10)
C80.0298 (15)0.0167 (13)0.0224 (13)0.0112 (12)0.0060 (12)0.0038 (11)
C90.0343 (17)0.0118 (12)0.0349 (16)0.0100 (12)0.0113 (13)0.0051 (11)
C100.0164 (13)0.0167 (13)0.0308 (14)0.0071 (12)0.0041 (11)0.0072 (11)
C110.0336 (16)0.0256 (15)0.0176 (12)0.0195 (13)0.0071 (11)0.0048 (11)
C120.0311 (16)0.0210 (14)0.0188 (13)0.0165 (12)0.0045 (12)0.0001 (11)
C130.0165 (13)0.0173 (13)0.0375 (16)0.0089 (11)0.0091 (12)0.0114 (12)
C140.0265 (16)0.0315 (17)0.0252 (14)0.0181 (14)0.0115 (12)0.0177 (13)
C150.0239 (15)0.0343 (17)0.0155 (12)0.0180 (13)0.0065 (11)0.0064 (11)
N40.0177 (11)0.0195 (12)0.0144 (11)0.0092 (10)0.0002 (9)0.0010 (9)
C160.0220 (14)0.0163 (13)0.0209 (13)0.0090 (11)0.0018 (11)0.0067 (11)
C170.0218 (14)0.0267 (14)0.0198 (13)0.0135 (12)0.0069 (11)0.0093 (11)
C180.0233 (14)0.0296 (16)0.0126 (11)0.0158 (13)0.0003 (10)0.0016 (10)
N50.0186 (11)0.0160 (11)0.0133 (10)0.0087 (9)0.0009 (9)0.0004 (8)
N10.0128 (10)0.0175 (11)0.0138 (10)0.0094 (9)0.0025 (8)0.0037 (8)
N20.0145 (10)0.0175 (10)0.0139 (9)0.0093 (9)0.0010 (8)0.0022 (7)
N30.0150 (10)0.0184 (11)0.0142 (9)0.0099 (9)0.0003 (8)0.0026 (8)
O10.0149 (9)0.0165 (9)0.0185 (9)0.0103 (8)0.0031 (7)0.0044 (7)
O20.0134 (8)0.0141 (9)0.0190 (8)0.0079 (7)0.0037 (7)0.0040 (7)
O30.0198 (9)0.0148 (9)0.0216 (9)0.0108 (8)0.0038 (8)0.0028 (8)
O40.0163 (9)0.0142 (9)0.0168 (9)0.0059 (8)0.0007 (7)0.0024 (7)
P10.0109 (3)0.0124 (3)0.0134 (2)0.0064 (3)0.0003 (2)0.0003 (2)
P20.0115 (3)0.0132 (3)0.0129 (3)0.0070 (3)0.0015 (2)0.0020 (2)
P30.0121 (3)0.0129 (3)0.0116 (3)0.0056 (3)0.0008 (2)0.0010 (2)
Geometric parameters (Å, º) top
C1—C21.375 (4)C15—N41.480 (3)
C1—C61.388 (4)N4—P21.635 (2)
C1—O11.403 (3)C16—O41.456 (3)
C2—C31.383 (4)C16—C171.524 (4)
C3—C41.386 (5)C17—C181.509 (4)
C4—C51.381 (5)C18—N51.482 (3)
C5—C61.386 (4)N5—P31.662 (2)
C7—C81.370 (4)N1—P11.565 (2)
C7—C121.376 (4)N1—P21.597 (2)
C7—O21.408 (3)N2—P31.582 (2)
C8—C91.393 (4)N2—P21.582 (2)
C9—C101.379 (4)N3—P11.571 (2)
C10—C111.382 (4)N3—P31.602 (2)
C11—C121.393 (4)O1—P11.5969 (19)
C13—O31.455 (3)O2—P11.5936 (18)
C13—C141.512 (5)O3—P21.5862 (19)
C14—C151.514 (5)O4—P31.5805 (19)
C2—C1—C6121.5 (3)P3—N2—P2121.82 (13)
C2—C1—O1119.6 (2)P1—N3—P3122.32 (14)
C6—C1—O1119.0 (3)C1—O1—P1116.74 (16)
C1—C2—C3119.1 (3)C7—O2—P1117.07 (16)
C2—C3—C4120.2 (3)C13—O3—P2114.37 (17)
C5—C4—C3120.3 (3)C16—O4—P3115.24 (16)
C4—C5—C6119.9 (3)N1—P1—N3117.27 (11)
C5—C6—C1119.0 (3)N1—P1—O2111.37 (12)
C8—C7—C12122.1 (3)N3—P1—O2109.89 (11)
C8—C7—O2119.3 (2)N1—P1—O1110.52 (11)
C12—C7—O2118.6 (2)N3—P1—O1111.13 (11)
C7—C8—C9118.7 (3)O2—P1—O194.31 (9)
C10—C9—C8120.4 (3)N2—P2—O3109.11 (12)
C9—C10—C11119.9 (3)N2—P2—N1117.16 (11)
C10—C11—C12120.2 (3)O3—P2—N1106.41 (12)
C7—C12—C11118.7 (3)N2—P2—N4109.75 (12)
O3—C13—C14111.0 (2)O3—P2—N4101.20 (11)
C13—C14—C15112.7 (2)N1—P2—N4111.92 (12)
N4—C15—C14109.5 (2)O4—P3—N2108.37 (11)
C15—N4—P2114.82 (19)O4—P3—N3107.64 (12)
O4—C16—C17110.3 (2)N2—P3—N3117.90 (12)
C18—C17—C16112.8 (2)O4—P3—N5100.61 (11)
N5—C18—C17109.6 (2)N2—P3—N5109.91 (12)
C18—N5—P3113.47 (18)N3—P3—N5110.93 (12)
P1—N1—P2123.40 (14)
(5b) top
Crystal data top
C18H24N5O4P3F(000) = 488
Mr = 467.33Dx = 1.470 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 6.3073 (1) ÅCell parameters from 10282 reflections
b = 17.6438 (4) Åθ = 2.9–27.5°
c = 9.5481 (2) ŵ = 0.32 mm1
β = 96.552 (1)°T = 120 K
V = 1055.62 (4) Å3Plate, colourless
Z = 20.22 × 0.18 × 0.04 mm
Data collection top
Bruker-Nonius APEX2 Area Detector
diffractometer
4543 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode4430 reflections with I > 2σ(I)
10cm confocal mirrors monochromatorRint = 0.030
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.2°
φ and ω scansh = 88
Absorption correction: multi-scan
SADABS V2.10 (Sheldrick, G.M., 2003)
k = 2222
Tmin = 0.933, Tmax = 0.987l = 1012
12391 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.065 w = 1/[σ2(Fo2) + (0.0168P)2 + 0.620P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.002
4543 reflectionsΔρmax = 0.26 e Å3
279 parametersΔρmin = 0.29 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (6)
Crystal data top
C18H24N5O4P3V = 1055.62 (4) Å3
Mr = 467.33Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.3073 (1) ŵ = 0.32 mm1
b = 17.6438 (4) ÅT = 120 K
c = 9.5481 (2) Å0.22 × 0.18 × 0.04 mm
β = 96.552 (1)°
Data collection top
Bruker-Nonius APEX2 Area Detector
diffractometer
4543 independent reflections
Absorption correction: multi-scan
SADABS V2.10 (Sheldrick, G.M., 2003)
4430 reflections with I > 2σ(I)
Tmin = 0.933, Tmax = 0.987Rint = 0.030
12391 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.065Δρmax = 0.26 e Å3
S = 1.01Δρmin = 0.29 e Å3
4543 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
279 parametersAbsolute structure parameter: 0.02 (6)
1 restraint
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
H5N0.060 (8)0.2157 (15)0.767 (4)0.011 (13)*
H4N0.824 (6)0.325 (4)0.650 (4)0.05 (2)*
C10.5718 (8)0.5162 (3)1.0131 (5)0.0240 (11)
C20.7612 (9)0.4796 (3)0.9996 (5)0.0252 (11)
H20.77720.44980.91850.030*
C30.9284 (9)0.4870 (3)1.1067 (6)0.0331 (13)
H31.05950.46151.09900.040*
C40.9071 (10)0.5309 (4)1.2245 (6)0.0371 (14)
H41.02330.53651.29640.044*
C50.7132 (11)0.5666 (3)1.2361 (6)0.0364 (14)
H50.69550.59581.31770.044*
C60.5471 (10)0.5600 (3)1.1303 (6)0.0326 (13)
H60.41580.58531.13770.039*
C70.0591 (8)0.5483 (3)0.6743 (5)0.0218 (10)
C80.1485 (8)0.5741 (3)0.6558 (5)0.0240 (11)
H80.25900.54520.68990.029*
C90.1957 (8)0.6417 (3)0.5880 (5)0.0246 (11)
H90.33880.65960.57640.030*
C100.0366 (8)0.6839 (3)0.5366 (5)0.0251 (11)
H100.06980.73060.48930.030*
C110.1725 (9)0.6574 (3)0.5549 (6)0.0325 (13)
H110.28280.68650.52090.039*
C120.2213 (9)0.5895 (3)0.6216 (6)0.0290 (12)
H120.36380.57100.63170.035*
C130.4031 (9)0.3921 (3)0.3723 (5)0.0274 (12)
H13A0.40940.44580.40290.033*
H13B0.29600.38790.28820.033*
C140.6196 (8)0.3674 (3)0.3349 (6)0.0298 (12)
H14A0.65940.39840.25530.036*
H14B0.61340.31360.30500.036*
C150.7891 (8)0.3770 (3)0.4632 (5)0.0257 (11)
H15A0.92950.35920.43930.031*
H15B0.80240.43130.48950.031*
C160.2693 (9)0.2276 (4)1.0966 (5)0.0314 (13)
H16A0.24930.27561.14710.038*
H16B0.34920.19221.16390.038*
C170.0529 (9)0.1938 (3)1.0471 (5)0.0291 (12)
H17A0.02930.18761.12890.035*
H17B0.07240.14291.00650.035*
C180.0730 (9)0.2438 (3)0.9365 (6)0.0288 (12)
H18A0.21180.21940.90500.035*
H18B0.10250.29330.97940.035*
N10.4701 (7)0.4303 (2)0.6981 (4)0.0225 (9)
N20.4243 (7)0.2792 (3)0.7259 (4)0.0226 (9)
N30.2623 (7)0.3763 (3)0.9082 (5)0.0271 (10)
O30.3398 (5)0.3445 (2)0.4854 (3)0.0244 (8)
O40.3944 (6)0.2423 (2)0.9801 (4)0.0251 (8)
O10.3971 (6)0.5162 (2)0.9090 (3)0.0245 (8)
O20.0902 (6)0.4801 (2)0.7469 (4)0.0239 (8)
N40.7256 (7)0.3328 (3)0.5827 (4)0.0236 (9)
N50.0454 (7)0.2567 (2)0.8122 (5)0.0263 (10)
P10.3157 (2)0.44552 (9)0.81351 (13)0.0207 (3)
P20.4893 (2)0.34742 (9)0.63165 (13)0.0201 (3)
P30.2884 (2)0.29211 (9)0.85345 (13)0.0209 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.025 (3)0.024 (3)0.022 (2)0.009 (2)0.003 (2)0.000 (2)
C20.030 (3)0.027 (3)0.019 (2)0.000 (2)0.002 (2)0.003 (2)
C30.032 (3)0.034 (3)0.032 (3)0.006 (3)0.002 (2)0.011 (2)
C40.045 (4)0.037 (3)0.027 (3)0.014 (3)0.009 (2)0.004 (2)
C50.053 (4)0.030 (3)0.026 (3)0.003 (3)0.005 (3)0.003 (2)
C60.032 (3)0.032 (3)0.034 (3)0.001 (3)0.003 (2)0.004 (2)
C70.020 (3)0.018 (2)0.027 (2)0.002 (2)0.003 (2)0.001 (2)
C80.016 (3)0.034 (3)0.022 (2)0.001 (2)0.0041 (19)0.001 (2)
C90.021 (3)0.032 (3)0.021 (2)0.001 (2)0.002 (2)0.003 (2)
C100.025 (3)0.024 (3)0.024 (2)0.003 (2)0.004 (2)0.003 (2)
C110.025 (3)0.026 (3)0.046 (3)0.009 (2)0.005 (2)0.012 (2)
C120.019 (3)0.028 (3)0.041 (3)0.001 (2)0.006 (2)0.004 (2)
C130.029 (3)0.031 (3)0.021 (2)0.001 (2)0.004 (2)0.005 (2)
C140.027 (3)0.034 (3)0.029 (3)0.005 (2)0.004 (2)0.004 (2)
C150.026 (3)0.027 (3)0.024 (3)0.003 (2)0.005 (2)0.004 (2)
C160.028 (3)0.044 (3)0.022 (2)0.000 (3)0.002 (2)0.011 (2)
C170.026 (3)0.036 (3)0.026 (3)0.005 (2)0.006 (2)0.004 (2)
C180.025 (3)0.031 (3)0.031 (3)0.000 (2)0.004 (2)0.009 (2)
N10.017 (2)0.024 (2)0.026 (2)0.0025 (17)0.0010 (16)0.0050 (17)
N20.019 (2)0.025 (2)0.024 (2)0.0000 (17)0.0055 (17)0.0034 (17)
N30.023 (2)0.026 (2)0.032 (2)0.0002 (19)0.0017 (19)0.0056 (19)
O30.0213 (18)0.0297 (19)0.0208 (16)0.0038 (16)0.0037 (13)0.0007 (15)
O40.0211 (19)0.028 (2)0.0259 (18)0.0004 (16)0.0017 (14)0.0087 (15)
O10.026 (2)0.0230 (19)0.0241 (17)0.0017 (15)0.0014 (14)0.0024 (14)
O20.0207 (19)0.0194 (18)0.0318 (19)0.0012 (15)0.0036 (14)0.0030 (15)
N40.015 (2)0.033 (3)0.023 (2)0.0015 (18)0.0042 (17)0.0011 (18)
N50.023 (2)0.026 (2)0.028 (2)0.001 (2)0.0018 (18)0.0024 (19)
P10.0203 (6)0.0191 (6)0.0225 (6)0.0006 (5)0.0021 (5)0.0006 (5)
P20.0178 (6)0.0216 (7)0.0207 (6)0.0012 (5)0.0006 (5)0.0003 (5)
P30.0201 (7)0.0188 (6)0.0236 (6)0.0005 (5)0.0015 (5)0.0029 (5)
Geometric parameters (Å, º) top
C1—C21.375 (8)C15—N41.473 (6)
C1—C61.382 (8)C16—O41.457 (6)
C1—O11.395 (6)C16—C171.513 (8)
C2—C31.387 (7)C17—C181.527 (7)
C3—C41.384 (8)C18—N51.488 (7)
C4—C51.390 (9)N1—P11.573 (4)
C5—C61.374 (8)N1—P21.602 (4)
C7—C81.378 (7)N2—P31.582 (4)
C7—O21.390 (6)N2—P21.583 (4)
C7—C121.394 (7)N3—P11.577 (5)
C8—C91.371 (7)N3—P31.588 (5)
C9—C101.382 (7)O3—P21.593 (3)
C10—C111.390 (8)O4—P31.578 (3)
C11—C121.374 (8)O1—P11.593 (4)
C13—O31.458 (6)O2—P11.608 (4)
C13—C141.513 (7)N4—P21.631 (4)
C14—C151.539 (7)N5—P31.658 (5)
C2—C1—C6121.1 (5)C13—O3—P2116.4 (3)
C2—C1—O1123.8 (4)C16—O4—P3117.7 (3)
C6—C1—O1115.0 (5)C1—O1—P1125.7 (3)
C1—C2—C3118.8 (5)C7—O2—P1126.3 (3)
C4—C3—C2121.0 (6)C15—N4—P2118.3 (4)
C3—C4—C5119.1 (5)C18—N5—P3113.7 (3)
C6—C5—C4120.4 (5)N1—P1—N3117.2 (2)
C5—C6—C1119.7 (6)N1—P1—O1110.4 (2)
C8—C7—O2115.4 (4)N3—P1—O1110.7 (2)
C8—C7—C12120.3 (5)N1—P1—O2112.2 (2)
O2—C7—C12124.3 (5)N3—P1—O2106.5 (2)
C9—C8—C7120.0 (5)O1—P1—O298.18 (19)
C8—C9—C10120.5 (5)N2—P2—O3107.9 (2)
C9—C10—C11119.3 (5)N2—P2—N1115.6 (2)
C12—C11—C10120.6 (5)O3—P2—N1108.2 (2)
C11—C12—C7119.2 (5)N2—P2—N4110.3 (2)
O3—C13—C14109.8 (4)O3—P2—N4102.2 (2)
C13—C14—C15110.1 (4)N1—P2—N4111.7 (2)
N4—C15—C14109.4 (4)O4—P3—N2106.9 (2)
O4—C16—C17112.2 (4)O4—P3—N3108.5 (2)
C16—C17—C18111.5 (5)N2—P3—N3118.2 (2)
N5—C18—C17111.8 (4)O4—P3—N5105.7 (2)
P1—N1—P2120.9 (3)N2—P3—N5109.2 (2)
P3—N2—P2121.7 (3)N3—P3—N5107.6 (2)
P1—N3—P3119.9 (3)

Experimental details

(3a)(3b)(5)(5a)
Crystal data
Chemical formulaC18H24N5O2P3S2C18H24N5O2P3S2C18H24N5O4P3C18H24N5O4P3
Mr499.45499.45467.33467.33
Crystal system, space groupTetragonal, P41Tetragonal, P43Orthorhombic, PbcnTrigonal, P32
Temperature (K)120120120120
a, b, c (Å)11.4912 (1), 11.4912 (1), 16.7890 (2)11.4899 (1), 11.4899 (1), 16.7827 (2)38.7541 (16), 10.1505 (4), 10.5550 (5)10.4920 (1), 10.4920 (1), 16.6645 (3)
α, β, γ (°)90, 90, 9090, 90, 9090, 90, 9090, 90, 120
V3)2216.95 (4)2215.62 (4)4152.1 (3)1588.69 (4)
Z4483
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.480.480.320.32
Crystal size (mm)0.45 × 0.45 × 0.400.55 × 0.20 × 0.200.65 × 0.02 × 0.010.50 × 0.40 × 0.34
Data collection
DiffractometerBruker-Nonius KappaCCD Area Detector
diffractometer
Bruker-Nonius KappaCCD Area Detector
diffractometer
Bruker APEX2
diffractometer
Bruker-Nonius KappaCCD Area Detector
diffractometer
Absorption correctionMulti-scan
SADABS V2.10 (Sheldrick, G.M., 2003)
Multi-scan
SADABS V2.10 (Sheldrick, G.M., 2003)
Multi-scan
SADABS V2.10 (Sheldrick, G.M., 2003)
Multi-scan
SADABS V2.10 (Sheldrick, G.M., 2003)
Tmin, Tmax0.812, 0.8300.777, 0.9100.817, 0.9970.858, 0.900
No. of measured, independent and
observed [I > 2σ(I)] reflections
41619, 5057, 4976 15809, 4532, 4330 19961, 4703, 3961 4871, 4848, 4802
Rint0.0310.0350.0550.048
(sin θ/λ)max1)0.6500.6490.6500.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.019, 0.049, 1.04 0.028, 0.066, 1.03 0.062, 0.135, 1.08 0.029, 0.072, 1.02
No. of reflections5057453247034848
No. of parameters279279279280
No. of restraints1103
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 refinementH atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(Fo2) + (0.0283P)2 + 0.4819P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0282P)2 + 0.916P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.P)2 + 15.046P]
where P = (Fo2 + 2Fc2)/3
w = 1/[σ2(Fo2) + (0.0389P)2 + 0.8904P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.16, 0.270.19, 0.330.55, 0.430.18, 0.38
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881?Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter0.01 (4)0.01 (5)?0.06 (8)


(5b)
Crystal data
Chemical formulaC18H24N5O4P3
Mr467.33
Crystal system, space groupMonoclinic, P21
Temperature (K)120
a, b, c (Å)6.3073 (1), 17.6438 (4), 9.5481 (2)
α, β, γ (°)90, 96.552 (1), 90
V3)1055.62 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.32
Crystal size (mm)0.22 × 0.18 × 0.04
Data collection
DiffractometerBruker-Nonius APEX2 Area Detector
diffractometer
Absorption correctionMulti-scan
SADABS V2.10 (Sheldrick, G.M., 2003)
Tmin, Tmax0.933, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
12391, 4543, 4430
Rint0.030
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.065, 1.01
No. of reflections4543
No. of parameters279
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(Fo2) + (0.0168P)2 + 0.620P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.26, 0.29
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter0.02 (6)

Computer programs: DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998), DENZO, COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON (Spek, 1990).

 

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds