Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
Five new compounds belonging to the phosphoric triamide family have been synthesized: two of them with the formula XC(O)NHP(O)Y [X = CF3 (1) and CClF2 (2), Y = NHCH2C(CH3)2CH2NH] involving a 1,3-diazaphosphorinane ring part, and three 2,6-Cl2C6H3C(O)NHP(O)Z2 phosphoric triamides [Z = NHC(CH3)3 (3), N(CH3)(C6H11) (4) and N(CH3)(CH2C6H5) (5)]. The characterization was performed by 31P{1H}, 1H, 13C NMR, IR spectroscopy besides 19F NMR for fluorine containing compounds (1) and (2), and X-ray single-crystal structure analysis for (1), (3), (4) and (5). In each molecule the P atom has a distorted tetrahedral environment. The N atoms bonded to P atom have mainly sp2 character with a very slight tendency to a pyramidal coordination for some amido groups. Different types of N—H...O hydrogen bonds have been analyzed for (1), (3), (4) and (5) and 118 other structures (including 194 hydrogen bonds) deposited in the Cambridge Structural Database, containing either C(O)—NH—P(O)[N(C)(C)]2 or C(O)—NH—P(O)[NH(C)]2. The participation of NCP—H...O=P [NCP = the nitrogen atom of the C(O)—NH—P(O) fragment], N—H...O=P, N—H...O=C and NCP—H...O=C hydrogen bonds in different hydrogen-bonded motifs are discussed. Moreover, the involvement of the O atoms of C=O or P=O in the [NCP—H][N—H]...O=P, [N—H]2...O=P, [N—H]2...O=C and [N—H]3...O=C groups are considered. A histogram of N...O distances, the distribution of N—H...O angles and the scatterplot of N—H...O angles versus N...O distances are studied.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052519213002650/dk5007sup1.cif
Contains datablocks global, I, IV, V, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213002650/dk5007Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213002650/dk5007IIIsup3.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213002650/dk5007IVsup4.hkl
Contains datablock IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213002650/dk5007Vsup5.hkl
Contains datablock V

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052519213002650/dk5007sup6.pdf
Spectroscopic data

Computing details top

Data collection: Collect (Bruker AXS BV, 1997-2004) for (I); CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) for (IV), (V); CrysAlis PRO, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) for (III). Cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997) for (I); CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) for (IV), (V); CrysAlis PRO, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) for (III). Data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997) for (I); CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) for (IV), (V); CrysAlis PRO, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) for (III). Program(s) used to solve structure: SIR2002 (Giacovazzo et al., 2003) for (I); SIR92 (Altomare et al., 1993) for (IV), (V); Superflip (Palatinus & Chapuis, 2007) for (III). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for (I); SHELXL97 (Sheldrick, 2008) for (IV), (V); CRYSTALS (Betteridge et al., 2003) for (III). Molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) for (I); Mercury (Macrae et al., 2008) for (IV), (V); CAMERON (Watkin et al., 1996) for (III). Software used to prepare material for publication: WinGX publication routines (Farrugia, 1999) for (I); SHELXL97 (Sheldrick, 2008) for (IV), (V); CRYSTALS (Betteridge et al., 2003) for (III).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
[Figure 12]
[Figure 13]
[Figure 14]
[Figure 15]
[Figure 16]
[Figure 17]
[Figure 18]
[Figure 19]
[Figure 20]
(I) top
Crystal data top
C7H13F3N3O2PF(000) = 536
Mr = 259.17Dx = 1.506 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yabCell parameters from 600 reflections
a = 11.3416 (3) Åθ = 1–14°
b = 9.0552 (3) ŵ = 0.27 mm1
c = 11.8030 (4) ÅT = 295 K
β = 109.413 (2)°Prism, colourless
V = 1143.26 (6) Å30.41 × 0.35 × 0.24 mm
Z = 4
Data collection top
KappaCCD
diffractometer
1748 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590Rint = 0.000
Graphite monochromatorθmax = 25.0°, θmin = 2.9°
Detector resolution: 9 pixels mm-1h = 1312
CCD rotation images, thick slices scansk = 010
1977 measured reflectionsl = 014
1977 independent 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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0413P)2 + 0.5607P]
where P = (Fo2 + 2Fc2)/3
1977 reflections(Δ/σ)max < 0.001
156 parametersΔρmax = 0.26 e Å3
3 restraintsΔρmin = 0.28 e Å3
Crystal data top
C7H13F3N3O2PV = 1143.26 (6) Å3
Mr = 259.17Z = 4
Monoclinic, P21/aMo Kα radiation
a = 11.3416 (3) ŵ = 0.27 mm1
b = 9.0552 (3) ÅT = 295 K
c = 11.8030 (4) Å0.41 × 0.35 × 0.24 mm
β = 109.413 (2)°
Data collection top
KappaCCD
diffractometer
1748 reflections with I > 2σ(I)
1977 measured reflectionsRint = 0.000
1977 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0363 restraints
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.26 e Å3
1977 reflectionsΔρmin = 0.28 e Å3
156 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C30.84601 (18)0.3900 (2)0.25660 (16)0.0410 (4)
H3A0.77970.46250.22880.049*
H3B0.92290.44240.29800.049*
C40.81610 (18)0.2857 (2)0.34458 (16)0.0417 (4)
C50.69751 (19)0.1990 (2)0.27789 (18)0.0473 (5)
H5A0.67770.13260.33350.057*
H5B0.62820.26710.24690.057*
C70.7899 (2)0.3789 (3)0.4417 (2)0.0660 (7)
H7A0.86270.43610.48330.099*
H7B0.76970.31520.49760.099*
H7C0.72090.44400.40500.099*
C80.9246 (2)0.1802 (3)0.40210 (18)0.0531 (5)
H8A0.94110.12290.34060.080*
H8B0.90300.11550.45660.080*
H8C0.99770.23600.44520.080*
C110.54109 (17)0.22268 (19)0.09812 (15)0.0353 (4)
C130.45742 (19)0.3183 (2)0.19981 (18)0.0476 (5)
N20.85984 (14)0.31238 (15)0.15204 (13)0.0346 (4)
H20.8913 (17)0.3663 (19)0.1113 (15)0.042*
N60.71308 (15)0.11290 (17)0.17773 (14)0.0439 (4)
H60.6623 (16)0.0419 (18)0.1551 (19)0.053*
N100.63981 (14)0.28988 (15)0.02049 (13)0.0346 (4)
H100.6454 (18)0.3836 (11)0.0234 (17)0.042*
O90.80507 (13)0.08740 (14)0.00389 (12)0.0488 (4)
O120.51616 (13)0.09177 (14)0.09905 (13)0.0502 (4)
F140.49766 (18)0.3089 (2)0.29274 (12)0.0964 (6)
F150.34028 (12)0.27180 (16)0.23594 (14)0.0791 (5)
F160.45729 (12)0.45963 (13)0.17218 (12)0.0661 (4)
P10.76025 (4)0.19006 (5)0.07696 (4)0.03353 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C30.0404 (10)0.0347 (10)0.0410 (10)0.0003 (8)0.0046 (8)0.0067 (8)
C40.0376 (10)0.0491 (11)0.0340 (9)0.0066 (8)0.0062 (8)0.0000 (8)
C50.0393 (10)0.0559 (12)0.0445 (11)0.0012 (9)0.0110 (9)0.0098 (9)
C70.0661 (15)0.0835 (18)0.0483 (12)0.0146 (13)0.0189 (11)0.0102 (12)
C80.0477 (12)0.0660 (14)0.0384 (11)0.0130 (10)0.0047 (9)0.0095 (9)
C110.0385 (10)0.0300 (9)0.0331 (9)0.0009 (7)0.0062 (8)0.0010 (7)
C130.0459 (11)0.0453 (11)0.0396 (10)0.0012 (9)0.0017 (9)0.0014 (9)
N20.0372 (8)0.0302 (8)0.0326 (8)0.0055 (6)0.0065 (6)0.0008 (6)
N60.0476 (9)0.0341 (9)0.0414 (9)0.0119 (7)0.0035 (7)0.0064 (7)
N100.0400 (8)0.0204 (7)0.0350 (8)0.0006 (6)0.0011 (7)0.0015 (6)
O90.0605 (9)0.0312 (7)0.0455 (7)0.0123 (6)0.0053 (6)0.0050 (6)
O120.0514 (8)0.0302 (7)0.0575 (8)0.0095 (6)0.0026 (7)0.0004 (6)
F140.1216 (14)0.1261 (15)0.0405 (7)0.0244 (11)0.0256 (8)0.0196 (8)
F150.0468 (8)0.0643 (9)0.0929 (11)0.0050 (6)0.0213 (7)0.0008 (8)
F160.0593 (8)0.0372 (7)0.0776 (9)0.0073 (6)0.0095 (6)0.0110 (6)
P10.0389 (3)0.0217 (2)0.0321 (3)0.00121 (17)0.0013 (2)0.00159 (16)
Geometric parameters (Å, º) top
C3—N21.473 (2)C8—H8C0.9600
C3—C41.523 (3)C11—O121.218 (2)
C3—H3A0.9700C11—N101.335 (2)
C3—H3B0.9700C11—C131.527 (2)
C4—C81.526 (3)C13—F161.321 (2)
C4—C51.530 (3)C13—F151.322 (2)
C4—C71.530 (3)C13—F141.323 (3)
C5—N61.475 (3)N2—P11.6194 (14)
C5—H5A0.9700N2—H20.844 (9)
C5—H5B0.9700N6—P11.6162 (16)
C7—H7A0.9600N6—H60.845 (9)
C7—H7B0.9600N10—P11.7209 (14)
C7—H7C0.9600N10—H100.853 (9)
C8—H8A0.9600O9—P11.4689 (13)
C8—H8B0.9600
N2—C3—C4112.64 (15)C4—C8—H8C109.5
N2—C3—H3A109.1H8A—C8—H8C109.5
C4—C3—H3A109.1H8B—C8—H8C109.5
N2—C3—H3B109.1O12—C11—N10126.10 (16)
C4—C3—H3B109.1O12—C11—C13117.56 (16)
H3A—C3—H3B107.8N10—C11—C13116.20 (15)
C3—C4—C8111.22 (16)F16—C13—F15107.73 (17)
C3—C4—C5108.93 (14)F16—C13—F14107.20 (18)
C8—C4—C5110.40 (17)F15—C13—F14107.38 (17)
C3—C4—C7108.11 (17)F16—C13—C11113.98 (16)
C8—C4—C7109.91 (16)F15—C13—C11111.62 (17)
C5—C4—C7108.19 (17)F14—C13—C11108.64 (17)
N6—C5—C4111.38 (15)C3—N2—P1122.38 (12)
N6—C5—H5A109.4C3—N2—H2112.6 (14)
C4—C5—H5A109.4P1—N2—H2115.7 (14)
N6—C5—H5B109.4C5—N6—P1121.24 (13)
C4—C5—H5B109.4C5—N6—H6113.9 (15)
H5A—C5—H5B108.0P1—N6—H6117.0 (15)
C4—C7—H7A109.5C11—N10—P1121.18 (12)
C4—C7—H7B109.5C11—N10—H10118.9 (13)
H7A—C7—H7B109.5P1—N10—H10119.8 (13)
C4—C7—H7C109.5O9—P1—N6114.98 (8)
H7A—C7—H7C109.5O9—P1—N2116.08 (8)
H7B—C7—H7C109.5N6—P1—N2103.55 (8)
C4—C8—H8A109.5O9—P1—N10107.02 (8)
C4—C8—H8B109.5N6—P1—N10109.61 (8)
H8A—C8—H8B109.5N2—P1—N10105.12 (7)
N2—C3—C4—C865.3 (2)C4—C5—N6—P152.8 (2)
N2—C3—C4—C556.6 (2)O12—C11—N10—P110.4 (3)
N2—C3—C4—C7173.95 (16)C13—C11—N10—P1165.17 (14)
C3—C4—C5—N659.3 (2)C5—N6—P1—O9163.49 (14)
C8—C4—C5—N663.1 (2)C5—N6—P1—N235.82 (16)
C7—C4—C5—N6176.57 (17)C5—N6—P1—N1075.93 (15)
O12—C11—C13—F16155.65 (19)C3—N2—P1—O9159.90 (13)
N10—C11—C13—F1628.4 (2)C3—N2—P1—N632.92 (15)
O12—C11—C13—F1533.3 (3)C3—N2—P1—N1082.08 (14)
N10—C11—C13—F15150.74 (17)C11—N10—P1—O955.09 (16)
O12—C11—C13—F1484.9 (2)C11—N10—P1—N670.21 (16)
N10—C11—C13—F1491.0 (2)C11—N10—P1—N2179.07 (14)
C4—C3—N2—P147.13 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O12i0.84 (1)2.32 (1)3.058 (2)146 (2)
N6—H6···O12ii0.85 (1)2.26 (1)3.074 (2)162 (2)
N10—H10···O9i0.85 (1)1.92 (1)2.7579 (18)167 (2)
Symmetry codes: (i) x+3/2, y+1/2, z; (ii) x+1, y, z.
(IV) top
Crystal data top
C21H32Cl2N3O2PF(000) = 976
Mr = 460.37Dx = 1.261 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.1526 (4) ÅCell parameters from 4913 reflections
b = 12.9020 (6) Åθ = 3.2–29.0°
c = 18.5334 (9) ŵ = 0.36 mm1
β = 92.724 (4)°T = 295 K
V = 2424.9 (2) Å3Prism, colourless
Z = 40.27 × 0.19 × 0.12 mm
Data collection top
Xcalibur, Sapphire3, Gemini
diffractometer
4258 independent reflections
Radiation source: Enhance (Mo) X-ray Source3551 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 16.3280 pixels mm-1θmax = 25.0°, θmin = 3.2°
ω scansh = 1212
Absorption correction: multi-scan
CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 1515
Tmin = 0.943, Tmax = 1.000l = 2222
10444 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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0773P)2 + 1.3233P]
where P = (Fo2 + 2Fc2)/3
4258 reflections(Δ/σ)max = 0.001
267 parametersΔρmax = 0.52 e Å3
1 restraintΔρmin = 0.31 e Å3
Crystal data top
C21H32Cl2N3O2PV = 2424.9 (2) Å3
Mr = 460.37Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.1526 (4) ŵ = 0.36 mm1
b = 12.9020 (6) ÅT = 295 K
c = 18.5334 (9) Å0.27 × 0.19 × 0.12 mm
β = 92.724 (4)°
Data collection top
Xcalibur, Sapphire3, Gemini
diffractometer
4258 independent reflections
Absorption correction: multi-scan
CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
3551 reflections with I > 2σ(I)
Tmin = 0.943, Tmax = 1.000Rint = 0.022
10444 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0531 restraint
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.52 e Å3
4258 reflectionsΔρmin = 0.31 e Å3
267 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.45683 (6)0.17353 (5)0.02088 (3)0.03391 (19)
Cl10.08033 (9)0.02310 (8)0.07961 (5)0.0763 (3)
Cl20.47634 (10)0.13783 (9)0.22553 (5)0.0879 (3)
O40.54543 (17)0.09943 (13)0.05953 (10)0.0454 (5)
O50.23756 (19)0.21520 (15)0.10604 (10)0.0521 (5)
N60.53851 (19)0.27243 (16)0.00852 (11)0.0393 (5)
N70.33519 (19)0.22345 (17)0.06449 (11)0.0400 (5)
N80.3839 (2)0.10512 (15)0.04772 (11)0.0364 (5)
H80.410 (3)0.0427 (10)0.0516 (14)0.044*
C90.2955 (2)0.13328 (19)0.10175 (13)0.0364 (6)
C100.2751 (2)0.0501 (2)0.15838 (13)0.0399 (6)
C110.3698 (3)0.3034 (2)0.11981 (14)0.0454 (6)
H110.43750.34710.09920.055*
C120.4726 (3)0.3556 (2)0.04913 (18)0.0561 (8)
H12A0.50780.42110.03300.084*
H12B0.37980.35350.04150.084*
H12C0.48680.34710.09960.084*
C130.6848 (2)0.2719 (2)0.00371 (16)0.0466 (7)
H130.71120.21060.02460.056*
C140.3530 (3)0.0449 (3)0.21726 (15)0.0564 (8)
C150.1794 (3)0.0257 (2)0.15304 (15)0.0523 (7)
C160.7397 (3)0.3644 (3)0.0372 (2)0.0754 (11)
H16A0.70450.36600.08490.090*
H16B0.71260.42740.01210.090*
C170.2546 (3)0.3745 (3)0.13347 (17)0.0605 (8)
H17A0.22160.40440.08810.073*
H17B0.18390.33460.15330.073*
C180.2238 (3)0.1559 (3)0.07965 (19)0.0646 (9)
H18A0.24220.11970.12430.097*
H18B0.21050.10660.04120.097*
H18C0.14560.19700.08340.097*
C190.7449 (3)0.2607 (4)0.0749 (2)0.0828 (12)
H19A0.71610.31770.10590.099*
H19B0.71400.19680.09750.099*
C200.3590 (4)0.4195 (4)0.25527 (19)0.0855 (12)
H20A0.38930.47700.28540.103*
H20B0.29460.38070.28130.103*
C210.4301 (3)0.2616 (3)0.19037 (17)0.0711 (10)
H21A0.50570.21860.18080.085*
H21B0.36600.21900.21380.085*
C220.2402 (5)0.1066 (3)0.2603 (2)0.0858 (12)
H220.22880.15940.29410.103*
C230.2953 (4)0.4607 (3)0.1855 (2)0.0788 (11)
H23A0.21820.50110.19630.095*
H23B0.35680.50630.16260.095*
C240.3371 (4)0.0327 (3)0.26932 (18)0.0796 (11)
H240.39000.03470.30890.096*
C250.9485 (3)0.3522 (3)0.0278 (2)0.0843 (12)
H25A1.04360.34660.02170.101*
H25B0.92810.41460.05540.101*
C260.1614 (4)0.1035 (3)0.2030 (2)0.0740 (10)
H260.09650.15340.19770.089*
C270.8905 (3)0.3599 (4)0.0443 (2)0.0907 (13)
H27A0.92350.42180.06880.109*
H27B0.91740.30040.07330.109*
C280.8950 (4)0.2595 (4)0.0684 (3)0.1030 (15)
H28A0.92440.19690.04350.124*
H28B0.92950.25860.11630.124*
C290.4730 (4)0.3509 (4)0.24004 (19)0.0875 (13)
H29A0.51070.32330.28510.105*
H29B0.54050.39120.21750.105*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0348 (3)0.0276 (3)0.0385 (3)0.0022 (3)0.0063 (3)0.0014 (3)
Cl10.0702 (6)0.0792 (6)0.0801 (6)0.0321 (5)0.0103 (4)0.0001 (5)
Cl20.0767 (6)0.1077 (8)0.0819 (7)0.0069 (6)0.0325 (5)0.0095 (6)
O40.0498 (10)0.0335 (10)0.0508 (11)0.0007 (8)0.0191 (8)0.0007 (8)
O50.0572 (12)0.0405 (11)0.0570 (12)0.0125 (9)0.0140 (9)0.0014 (9)
N60.0353 (11)0.0309 (11)0.0516 (12)0.0005 (9)0.0008 (9)0.0025 (9)
N70.0366 (11)0.0413 (12)0.0419 (11)0.0083 (9)0.0003 (9)0.0018 (9)
N80.0415 (11)0.0267 (10)0.0399 (11)0.0018 (9)0.0101 (9)0.0008 (9)
C90.0343 (12)0.0353 (14)0.0394 (13)0.0023 (11)0.0025 (10)0.0064 (11)
C100.0427 (14)0.0398 (14)0.0358 (13)0.0069 (11)0.0133 (11)0.0035 (11)
C110.0421 (14)0.0534 (17)0.0407 (14)0.0083 (12)0.0004 (11)0.0044 (12)
C120.0512 (16)0.0399 (16)0.077 (2)0.0046 (13)0.0031 (15)0.0156 (14)
C130.0364 (13)0.0392 (15)0.0643 (17)0.0041 (11)0.0043 (12)0.0005 (13)
C140.0611 (18)0.064 (2)0.0433 (15)0.0121 (15)0.0025 (13)0.0006 (14)
C150.0573 (17)0.0474 (16)0.0503 (16)0.0032 (14)0.0177 (13)0.0013 (13)
C160.0518 (18)0.091 (3)0.084 (2)0.0179 (18)0.0088 (17)0.036 (2)
C170.0639 (19)0.066 (2)0.0521 (17)0.0093 (16)0.0018 (15)0.0061 (15)
C180.0559 (18)0.069 (2)0.070 (2)0.0265 (16)0.0132 (16)0.0082 (17)
C190.0551 (19)0.109 (3)0.086 (3)0.011 (2)0.0175 (18)0.039 (2)
C200.084 (3)0.117 (3)0.056 (2)0.021 (2)0.0088 (18)0.035 (2)
C210.068 (2)0.093 (3)0.0504 (18)0.0130 (19)0.0132 (15)0.0043 (18)
C220.111 (3)0.073 (3)0.070 (2)0.011 (2)0.030 (2)0.028 (2)
C230.092 (3)0.069 (2)0.077 (2)0.003 (2)0.025 (2)0.020 (2)
C240.098 (3)0.096 (3)0.0443 (18)0.030 (2)0.0028 (18)0.0129 (19)
C250.0451 (18)0.088 (3)0.120 (3)0.0161 (18)0.010 (2)0.004 (2)
C260.085 (2)0.060 (2)0.074 (2)0.0086 (18)0.025 (2)0.0147 (18)
C270.052 (2)0.112 (3)0.108 (3)0.026 (2)0.005 (2)0.027 (3)
C280.053 (2)0.129 (4)0.130 (4)0.007 (2)0.031 (2)0.041 (3)
C290.076 (2)0.130 (4)0.055 (2)0.008 (2)0.0138 (18)0.024 (2)
Geometric parameters (Å, º) top
P1—O41.4748 (18)C17—H17B0.9700
P1—N61.630 (2)C18—H18A0.9600
P1—N71.640 (2)C18—H18B0.9600
P1—N81.689 (2)C18—H18C0.9600
Cl1—C151.730 (3)C19—C281.523 (5)
Cl2—C141.746 (4)C19—H19A0.9700
O5—C91.210 (3)C19—H19B0.9700
N6—C121.455 (3)C20—C291.495 (6)
N6—C131.483 (3)C20—C231.515 (6)
N7—C181.466 (3)C20—H20A0.9700
N7—C111.485 (3)C20—H20B0.9700
N8—C91.362 (3)C21—C291.525 (5)
N8—H80.854 (10)C21—H21A0.9700
C9—C101.508 (4)C21—H21B0.9700
C10—C141.380 (4)C22—C261.360 (6)
C10—C151.386 (4)C22—C241.386 (6)
C11—C171.518 (4)C22—H220.9300
C11—C211.516 (4)C23—H23A0.9700
C11—H110.9800C23—H23B0.9700
C12—H12A0.9600C24—H240.9300
C12—H12B0.9600C25—C271.489 (6)
C12—H12C0.9600C25—C281.501 (6)
C13—C191.487 (4)C25—H25A0.9700
C13—C161.506 (4)C25—H25B0.9700
C13—H130.9800C26—H260.9300
C14—C241.394 (5)C27—H27A0.9700
C15—C261.371 (4)C27—H27B0.9700
C16—C271.531 (5)C28—H28A0.9700
C16—H16A0.9700C28—H28B0.9700
C16—H16B0.9700C29—H29A0.9700
C17—C231.516 (5)C29—H29B0.9700
C17—H17A0.9700
O4—P1—N6111.20 (11)N7—C18—H18C109.5
O4—P1—N7118.14 (11)H18A—C18—H18C109.5
N6—P1—N7105.33 (11)H18B—C18—H18C109.5
O4—P1—N8105.20 (10)C13—C19—C28112.4 (3)
N6—P1—N8111.67 (11)C13—C19—H19A109.1
N7—P1—N8105.24 (11)C28—C19—H19A109.1
C12—N6—C13117.9 (2)C13—C19—H19B109.1
C12—N6—P1121.45 (17)C28—C19—H19B109.1
C13—N6—P1120.03 (17)H19A—C19—H19B107.8
C18—N7—C11116.1 (2)C29—C20—C23110.5 (3)
C18—N7—P1117.8 (2)C29—C20—H20A109.6
C11—N7—P1117.02 (16)C23—C20—H20A109.6
C9—N8—P1131.59 (18)C29—C20—H20B109.6
C9—N8—H8112.9 (19)C23—C20—H20B109.6
P1—N8—H8115.3 (19)H20A—C20—H20B108.1
O5—C9—N8125.6 (2)C11—C21—C29110.1 (3)
O5—C9—C10121.7 (2)C11—C21—H21A109.6
N8—C9—C10112.7 (2)C29—C21—H21A109.6
C14—C10—C15116.9 (3)C11—C21—H21B109.6
C14—C10—C9121.3 (2)C29—C21—H21B109.6
C15—C10—C9121.8 (2)H21A—C21—H21B108.2
N7—C11—C17112.1 (2)C26—C22—C24121.5 (3)
N7—C11—C21114.9 (3)C26—C22—H22119.3
C17—C11—C21110.7 (2)C24—C22—H22119.3
N7—C11—H11106.1C17—C23—C20112.2 (3)
C17—C11—H11106.1C17—C23—H23A109.2
C21—C11—H11106.1C20—C23—H23A109.2
N6—C12—H12A109.5C17—C23—H23B109.2
N6—C12—H12B109.5C20—C23—H23B109.2
H12A—C12—H12B109.5H23A—C23—H23B107.9
N6—C12—H12C109.5C22—C24—C14118.0 (3)
H12A—C12—H12C109.5C22—C24—H24121.0
H12B—C12—H12C109.5C14—C24—H24121.0
N6—C13—C19113.5 (2)C27—C25—C28110.7 (3)
N6—C13—C16111.9 (2)C27—C25—H25A109.5
C19—C13—C16111.5 (3)C28—C25—H25A109.5
N6—C13—H13106.5C27—C25—H25B109.5
C19—C13—H13106.5C28—C25—H25B109.5
C16—C13—H13106.5H25A—C25—H25B108.1
C10—C14—C24122.0 (3)C22—C26—C15118.9 (4)
C10—C14—Cl2118.5 (2)C22—C26—H26120.5
C24—C14—Cl2119.5 (3)C15—C26—H26120.5
C26—C15—C10122.7 (3)C25—C27—C16111.2 (3)
C26—C15—Cl1118.8 (3)C25—C27—H27A109.4
C10—C15—Cl1118.5 (2)C16—C27—H27A109.4
C13—C16—C27111.0 (3)C25—C27—H27B109.4
C13—C16—H16A109.4C16—C27—H27B109.4
C27—C16—H16A109.4H27A—C27—H27B108.0
C13—C16—H16B109.4C25—C28—C19111.6 (3)
C27—C16—H16B109.4C25—C28—H28A109.3
H16A—C16—H16B108.0C19—C28—H28A109.3
C23—C17—C11111.1 (3)C25—C28—H28B109.3
C23—C17—H17A109.4C19—C28—H28B109.3
C11—C17—H17A109.4H28A—C28—H28B108.0
C23—C17—H17B109.4C20—C29—C21111.1 (3)
C11—C17—H17B109.4C20—C29—H29A109.4
H17A—C17—H17B108.0C21—C29—H29A109.4
N7—C18—H18A109.5C20—C29—H29B109.4
N7—C18—H18B109.5C21—C29—H29B109.4
H18A—C18—H18B109.5H29A—C29—H29B108.0
O4—P1—N6—C12179.3 (2)C9—C10—C14—C24178.7 (3)
N7—P1—N6—C1251.6 (2)C15—C10—C14—Cl2179.1 (2)
N8—P1—N6—C1262.1 (2)C9—C10—C14—Cl20.5 (3)
O4—P1—N6—C138.3 (2)C14—C10—C15—C260.4 (4)
N7—P1—N6—C13137.45 (19)C9—C10—C15—C26178.3 (3)
N8—P1—N6—C13108.8 (2)C14—C10—C15—Cl1179.4 (2)
O4—P1—N7—C1872.0 (2)C9—C10—C15—Cl10.7 (3)
N6—P1—N7—C18163.1 (2)N6—C13—C16—C27177.6 (3)
N8—P1—N7—C1845.0 (2)C19—C13—C16—C2754.1 (4)
O4—P1—N7—C1173.9 (2)N7—C11—C17—C23175.4 (3)
N6—P1—N7—C1151.0 (2)C21—C11—C17—C2354.9 (4)
N8—P1—N7—C11169.12 (18)N6—C13—C19—C28179.5 (3)
O4—P1—N8—C9178.4 (2)C16—C13—C19—C2853.1 (5)
N6—P1—N8—C957.7 (3)N7—C11—C21—C29174.8 (3)
N7—P1—N8—C956.1 (2)C17—C11—C21—C2957.0 (4)
P1—N8—C9—O59.7 (4)C11—C17—C23—C2054.0 (4)
P1—N8—C9—C10170.26 (19)C29—C20—C23—C1755.0 (4)
O5—C9—C10—C1491.0 (3)C26—C22—C24—C140.8 (6)
N8—C9—C10—C1488.9 (3)C10—C14—C24—C220.6 (5)
O5—C9—C10—C1590.4 (3)Cl2—C14—C24—C22178.6 (3)
N8—C9—C10—C1589.7 (3)C24—C22—C26—C150.4 (6)
C18—N7—C11—C1757.6 (3)C10—C15—C26—C220.2 (5)
P1—N7—C11—C17155.9 (2)Cl1—C15—C26—C22179.2 (3)
C18—N7—C11—C2170.0 (3)C28—C25—C27—C1656.8 (5)
P1—N7—C11—C2176.5 (3)C13—C16—C27—C2556.4 (5)
C12—N6—C13—C1962.3 (4)C27—C25—C28—C1955.2 (5)
P1—N6—C13—C19108.9 (3)C13—C19—C28—C2553.7 (5)
C12—N6—C13—C1664.9 (4)C23—C20—C29—C2157.1 (5)
P1—N6—C13—C16123.8 (3)C11—C21—C29—C2058.6 (4)
C15—C10—C14—C240.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8—H8···O4i0.85 (1)1.90 (1)2.746 (3)175 (3)
Symmetry code: (i) x+1, y, z.
(V) top
Crystal data top
C23H24Cl2N3O2PF(000) = 992
Mr = 476.32Dx = 1.354 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.0375 (2) ÅCell parameters from 4008 reflections
b = 23.0525 (7) Åθ = 3.0–29.1°
c = 10.1700 (3) ŵ = 0.37 mm1
β = 96.809 (2)°T = 295 K
V = 2336.64 (11) Å3Prism, colourless
Z = 40.13 × 0.07 × 0.05 mm
Data collection top
Xcalibur, Sapphire3, Gemini
diffractometer
4092 independent reflections
Radiation source: Enhance (Mo) X-ray Source3324 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 16.3280 pixels mm-1θmax = 25.0°, θmin = 3.2°
ω scansh = 1111
Absorption correction: multi-scan
CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 2726
Tmin = 0.984, Tmax = 1.000l = 1112
9762 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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0523P)2 + 0.6582P]
where P = (Fo2 + 2Fc2)/3
4092 reflections(Δ/σ)max < 0.001
285 parametersΔρmax = 0.25 e Å3
1 restraintΔρmin = 0.24 e Å3
Crystal data top
C23H24Cl2N3O2PV = 2336.64 (11) Å3
Mr = 476.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.0375 (2) ŵ = 0.37 mm1
b = 23.0525 (7) ÅT = 295 K
c = 10.1700 (3) Å0.13 × 0.07 × 0.05 mm
β = 96.809 (2)°
Data collection top
Xcalibur, Sapphire3, Gemini
diffractometer
4092 independent reflections
Absorption correction: multi-scan
CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
3324 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 1.000Rint = 0.026
9762 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0501 restraint
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.25 e Å3
4092 reflectionsΔρmin = 0.24 e Å3
285 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.43467 (6)0.08429 (3)0.08652 (6)0.03369 (18)
Cl20.90330 (7)0.12598 (4)0.01365 (8)0.0695 (3)
Cl30.72870 (10)0.01484 (5)0.37835 (10)0.0928 (3)
O40.35699 (15)0.03297 (7)0.03733 (16)0.0436 (4)
O50.69200 (17)0.13148 (8)0.25482 (18)0.0534 (5)
N60.59806 (18)0.06507 (8)0.10605 (19)0.0352 (5)
H60.612 (2)0.0352 (7)0.061 (2)0.042*
N70.39038 (19)0.10519 (8)0.22853 (18)0.0365 (5)
N80.4212 (2)0.13849 (9)0.0157 (2)0.0445 (5)
C90.2768 (3)0.17871 (10)0.3502 (2)0.0409 (6)
C100.5869 (2)0.16937 (10)0.1675 (2)0.0396 (6)
C110.8284 (2)0.05323 (11)0.1990 (2)0.0402 (6)
C120.7001 (2)0.08741 (11)0.1907 (2)0.0382 (6)
C130.9299 (2)0.06862 (12)0.1239 (3)0.0489 (7)
C140.5291 (3)0.17822 (11)0.0377 (2)0.0454 (6)
H14A0.60080.17400.03440.055*
H14B0.49570.21760.03520.055*
C150.3967 (3)0.16483 (11)0.2787 (3)0.0463 (7)
H15A0.39950.19150.20540.056*
H15B0.47830.16990.33890.056*
C160.6563 (3)0.21474 (12)0.2178 (3)0.0512 (7)
H160.66280.25030.17420.061*
C170.6384 (3)0.11067 (13)0.3494 (3)0.0564 (7)
H170.63230.07530.39370.068*
C180.7066 (3)0.15561 (15)0.3981 (3)0.0620 (8)
H180.74640.15100.47550.074*
C190.5782 (3)0.11742 (12)0.2341 (2)0.0493 (7)
H190.53180.08660.20200.059*
C200.2920 (3)0.18696 (12)0.4856 (3)0.0558 (7)
H200.37650.18400.53360.067*
C210.1509 (3)0.18254 (13)0.2825 (3)0.0609 (8)
H210.13930.17680.19130.073*
C220.7157 (3)0.20736 (14)0.3323 (3)0.0616 (8)
H220.76250.23790.36490.074*
C230.3892 (3)0.06117 (11)0.3307 (3)0.0537 (7)
H23A0.46300.06760.39820.081*
H23B0.39730.02350.29240.081*
H23C0.30640.06340.36910.081*
C240.2914 (3)0.14904 (14)0.0955 (3)0.0653 (8)
H24A0.25890.18680.07530.098*
H24B0.22810.12010.07540.098*
H24C0.30260.14710.18780.098*
C251.0694 (3)0.00723 (16)0.2180 (4)0.0722 (10)
H251.15020.02740.22480.087*
C260.8531 (3)0.00651 (13)0.2834 (3)0.0550 (7)
C270.9720 (3)0.02410 (15)0.2935 (3)0.0713 (9)
H270.98580.05560.35050.086*
C280.0411 (3)0.19473 (17)0.3472 (4)0.0839 (11)
H280.04400.19680.30010.101*
C290.1816 (4)0.19968 (15)0.5499 (3)0.0776 (10)
H290.19220.20550.64100.093*
C301.0500 (3)0.03877 (15)0.1328 (3)0.0659 (9)
H301.11660.04980.08160.079*
C310.0578 (4)0.20374 (17)0.4805 (4)0.0863 (11)
H310.01580.21270.52410.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0275 (3)0.0383 (4)0.0368 (3)0.0013 (3)0.0102 (2)0.0040 (3)
Cl20.0517 (4)0.0844 (6)0.0756 (5)0.0053 (4)0.0212 (4)0.0144 (4)
Cl30.0885 (7)0.1081 (7)0.0875 (7)0.0118 (6)0.0345 (5)0.0428 (6)
O40.0308 (9)0.0467 (10)0.0544 (11)0.0009 (8)0.0094 (8)0.0149 (8)
O50.0406 (10)0.0580 (12)0.0615 (12)0.0037 (9)0.0061 (9)0.0247 (10)
N60.0293 (10)0.0380 (11)0.0392 (11)0.0011 (9)0.0078 (9)0.0088 (9)
N70.0394 (11)0.0350 (10)0.0380 (11)0.0005 (9)0.0160 (9)0.0028 (9)
N80.0377 (11)0.0549 (13)0.0424 (12)0.0038 (10)0.0111 (9)0.0066 (10)
C90.0436 (14)0.0362 (13)0.0457 (15)0.0009 (12)0.0167 (12)0.0045 (11)
C100.0386 (13)0.0418 (14)0.0390 (13)0.0056 (12)0.0073 (11)0.0071 (11)
C110.0291 (12)0.0491 (15)0.0418 (14)0.0011 (11)0.0018 (11)0.0114 (12)
C120.0341 (13)0.0443 (14)0.0375 (13)0.0052 (11)0.0100 (11)0.0050 (12)
C130.0323 (13)0.0594 (17)0.0548 (16)0.0008 (13)0.0041 (12)0.0085 (13)
C140.0540 (16)0.0407 (14)0.0435 (14)0.0016 (13)0.0136 (12)0.0022 (12)
C150.0459 (15)0.0432 (15)0.0540 (16)0.0057 (12)0.0234 (13)0.0104 (12)
C160.0508 (16)0.0476 (15)0.0568 (17)0.0018 (13)0.0140 (14)0.0063 (13)
C170.0656 (19)0.0616 (18)0.0430 (16)0.0077 (16)0.0107 (14)0.0061 (14)
C180.0583 (18)0.085 (2)0.0463 (16)0.0127 (17)0.0227 (14)0.0092 (16)
C190.0572 (17)0.0488 (16)0.0433 (15)0.0015 (14)0.0120 (13)0.0036 (13)
C200.0650 (18)0.0569 (17)0.0468 (16)0.0168 (15)0.0125 (14)0.0018 (13)
C210.0512 (17)0.079 (2)0.0534 (17)0.0081 (16)0.0082 (14)0.0119 (16)
C220.0567 (18)0.068 (2)0.0649 (19)0.0007 (16)0.0265 (15)0.0200 (16)
C230.0675 (18)0.0514 (16)0.0452 (15)0.0050 (15)0.0193 (14)0.0069 (13)
C240.0505 (17)0.081 (2)0.0636 (19)0.0125 (16)0.0041 (15)0.0191 (17)
C250.0376 (17)0.079 (2)0.096 (3)0.0156 (17)0.0068 (17)0.014 (2)
C260.0467 (16)0.0629 (18)0.0551 (17)0.0041 (15)0.0048 (13)0.0046 (15)
C270.060 (2)0.069 (2)0.081 (2)0.0161 (17)0.0104 (18)0.0063 (18)
C280.0429 (17)0.110 (3)0.100 (3)0.0142 (19)0.0121 (18)0.019 (2)
C290.107 (3)0.085 (2)0.0483 (18)0.028 (2)0.0387 (19)0.0024 (17)
C300.0278 (14)0.087 (2)0.084 (2)0.0004 (15)0.0102 (14)0.014 (2)
C310.072 (2)0.099 (3)0.098 (3)0.020 (2)0.053 (2)0.006 (2)
Geometric parameters (Å, º) top
P1—O41.4716 (17)C17—C181.366 (4)
P1—N81.621 (2)C17—C191.390 (4)
P1—N71.633 (2)C17—H170.9300
P1—N61.688 (2)C18—C221.366 (4)
Cl2—C131.734 (3)C18—H180.9300
Cl3—C261.737 (3)C19—H190.9300
O5—C121.215 (3)C20—C291.383 (4)
N6—C121.359 (3)C20—H200.9300
N6—H60.850 (10)C21—C281.378 (4)
N7—C231.454 (3)C21—H210.9300
N7—C151.465 (3)C22—H220.9300
N8—C141.456 (3)C23—H23A0.9600
N8—C241.471 (3)C23—H23B0.9600
C9—C211.368 (4)C23—H23C0.9600
C9—C201.380 (4)C24—H24A0.9600
C9—C151.512 (3)C24—H24B0.9600
C10—C191.374 (4)C24—H24C0.9600
C10—C161.388 (3)C25—C271.369 (5)
C10—C141.517 (3)C25—C301.369 (5)
C11—C261.381 (4)C25—H250.9300
C11—C131.390 (4)C26—C271.380 (4)
C11—C121.503 (3)C27—H270.9300
C13—C301.381 (4)C28—C311.361 (5)
C14—H14A0.9700C28—H280.9300
C14—H14B0.9700C29—C311.357 (5)
C15—H15A0.9700C29—H290.9300
C15—H15B0.9700C30—H300.9300
C16—C221.380 (4)C31—H310.9300
C16—H160.9300
O4—P1—N8113.66 (11)C17—C18—C22119.5 (3)
O4—P1—N7110.42 (10)C17—C18—H18120.3
N8—P1—N7109.20 (11)C22—C18—H18120.3
O4—P1—N6107.29 (10)C10—C19—C17120.4 (3)
N8—P1—N6106.49 (10)C10—C19—H19119.8
N7—P1—N6109.63 (10)C17—C19—H19119.8
C12—N6—P1128.61 (16)C9—C20—C29120.1 (3)
C12—N6—H6119.3 (17)C9—C20—H20120.0
P1—N6—H6111.8 (17)C29—C20—H20120.0
C23—N7—C15114.2 (2)C9—C21—C28121.1 (3)
C23—N7—P1116.91 (16)C9—C21—H21119.5
C15—N7—P1125.42 (16)C28—C21—H21119.5
C14—N8—C24115.9 (2)C18—C22—C16120.7 (3)
C14—N8—P1125.23 (17)C18—C22—H22119.6
C24—N8—P1118.83 (18)C16—C22—H22119.6
C21—C9—C20118.6 (2)N7—C23—H23A109.5
C21—C9—C15120.8 (2)N7—C23—H23B109.5
C20—C9—C15120.6 (2)H23A—C23—H23B109.5
C19—C10—C16118.7 (2)N7—C23—H23C109.5
C19—C10—C14122.6 (2)H23A—C23—H23C109.5
C16—C10—C14118.7 (2)H23B—C23—H23C109.5
C26—C11—C13116.8 (2)N8—C24—H24A109.5
C26—C11—C12122.2 (2)N8—C24—H24B109.5
C13—C11—C12120.9 (2)H24A—C24—H24B109.5
O5—C12—N6124.3 (2)N8—C24—H24C109.5
O5—C12—C11121.3 (2)H24A—C24—H24C109.5
N6—C12—C11114.4 (2)H24B—C24—H24C109.5
C30—C13—C11121.9 (3)C27—C25—C30121.2 (3)
C30—C13—Cl2119.2 (2)C27—C25—H25119.4
C11—C13—Cl2118.9 (2)C30—C25—H25119.4
N8—C14—C10114.7 (2)C11—C26—C27122.3 (3)
N8—C14—H14A108.6C11—C26—Cl3118.6 (2)
C10—C14—H14A108.6C27—C26—Cl3119.1 (2)
N8—C14—H14B108.6C25—C27—C26118.8 (3)
C10—C14—H14B108.6C25—C27—H27120.6
H14A—C14—H14B107.6C26—C27—H27120.6
N7—C15—C9111.21 (19)C31—C28—C21119.7 (3)
N7—C15—H15A109.4C31—C28—H28120.2
C9—C15—H15A109.4C21—C28—H28120.2
N7—C15—H15B109.4C31—C29—C20120.2 (3)
C9—C15—H15B109.4C31—C29—H29119.9
H15A—C15—H15B108.0C20—C29—H29119.9
C22—C16—C10120.3 (3)C25—C30—C13119.0 (3)
C22—C16—H16119.9C25—C30—H30120.5
C10—C16—H16119.9C13—C30—H30120.5
C18—C17—C19120.5 (3)C29—C31—C28120.3 (3)
C18—C17—H17119.8C29—C31—H31119.9
C19—C17—H17119.8C28—C31—H31119.9
O4—P1—N6—C12152.9 (2)P1—N7—C15—C9141.34 (19)
N8—P1—N6—C1285.1 (2)C21—C9—C15—N768.0 (3)
N7—P1—N6—C1232.9 (2)C20—C9—C15—N7111.0 (3)
O4—P1—N7—C2351.1 (2)C19—C10—C16—C220.3 (4)
N8—P1—N7—C23176.76 (18)C14—C10—C16—C22176.9 (2)
N6—P1—N7—C2366.9 (2)C19—C17—C18—C220.3 (4)
O4—P1—N7—C15151.30 (19)C16—C10—C19—C170.2 (4)
N8—P1—N7—C1525.6 (2)C14—C10—C19—C17176.9 (2)
N6—P1—N7—C1590.7 (2)C18—C17—C19—C100.2 (4)
O4—P1—N8—C14142.75 (18)C21—C9—C20—C291.0 (4)
N7—P1—N8—C1493.5 (2)C15—C9—C20—C29180.0 (3)
N6—P1—N8—C1424.8 (2)C20—C9—C21—C280.4 (5)
O4—P1—N8—C2436.2 (2)C15—C9—C21—C28179.5 (3)
N7—P1—N8—C2487.5 (2)C17—C18—C22—C160.4 (5)
N6—P1—N8—C24154.2 (2)C10—C16—C22—C180.4 (4)
P1—N6—C12—O510.9 (4)C13—C11—C26—C270.3 (4)
P1—N6—C12—C11169.76 (17)C12—C11—C26—C27178.5 (3)
C26—C11—C12—O594.8 (3)C13—C11—C26—Cl3179.4 (2)
C13—C11—C12—O583.3 (3)C12—C11—C26—Cl32.4 (4)
C26—C11—C12—N685.8 (3)C30—C25—C27—C260.6 (5)
C13—C11—C12—N696.1 (3)C11—C26—C27—C250.6 (5)
C26—C11—C13—C300.0 (4)Cl3—C26—C27—C25179.7 (3)
C12—C11—C13—C30178.2 (2)C9—C21—C28—C310.7 (6)
C26—C11—C13—Cl2178.7 (2)C9—C20—C29—C310.4 (5)
C12—C11—C13—Cl23.2 (3)C27—C25—C30—C130.3 (5)
C24—N8—C14—C1073.2 (3)C11—C13—C30—C250.0 (4)
P1—N8—C14—C10105.8 (2)Cl2—C13—C30—C25178.7 (2)
C19—C10—C14—N823.6 (3)C20—C29—C31—C280.7 (6)
C16—C10—C14—N8159.3 (2)C21—C28—C31—C291.2 (6)
C23—N7—C15—C960.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H6···O4i0.85 (1)1.91 (1)2.756 (2)178 (2)
Symmetry code: (i) x+1, y, z.
(III) top
Crystal data top
C15H24Cl2N3O2PZ = 2
Mr = 380.24F(000) = 400
Triclinic, P1Dx = 1.306 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7455 (2) ÅCell parameters from 11215 reflections
b = 10.0122 (3) Åθ = 2.0–29.0°
c = 11.7163 (3) ŵ = 0.43 mm1
α = 66.278 (3)°T = 150 K
β = 67.729 (2)°Long block, colourless
γ = 84.121 (2)°0.40 × 0.20 × 0.20 mm
V = 966.84 (5) Å3
Data collection top
Xcalibur, Sapphire3, Gemini
diffractometer
4853 independent reflections
Radiation source: Enhance (Mo) X-ray Source3805 reflections with I > 2.0σ(I)
Graphite monochromatorRint = 0.058
Detector resolution: 16.0143 pixels mm-1θmax = 29.1°, θmin = 2.0°
ω scansh = 1313
Absorption correction: multi-scan
CrysAlis PRO, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 1313
Tmin = 0.933, Tmax = 1.000l = 1515
43311 measured reflections
Refinement top
Refinement on F2Primary atom site location: other
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.067 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 0.119E + 04 0.124E + 04 666. 226. -17.0
S = 0.97(Δ/σ)max = 0.0002645
4853 reflectionsΔρmax = 0.55 e Å3
217 parametersΔρmin = 0.52 e Å3
3 restraints
Crystal data top
C15H24Cl2N3O2Pγ = 84.121 (2)°
Mr = 380.24V = 966.84 (5) Å3
Triclinic, P1Z = 2
a = 9.7455 (2) ÅMo Kα radiation
b = 10.0122 (3) ŵ = 0.43 mm1
c = 11.7163 (3) ÅT = 150 K
α = 66.278 (3)°0.40 × 0.20 × 0.20 mm
β = 67.729 (2)°
Data collection top
Xcalibur, Sapphire3, Gemini
diffractometer
4853 independent reflections
Absorption correction: multi-scan
CrysAlis PRO, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
3805 reflections with I > 2.0σ(I)
Tmin = 0.933, Tmax = 1.000Rint = 0.058
43311 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0553 restraints
wR(F2) = 0.067H atoms treated by a mixture of independent and constrained refinement
S = 0.97Δρmax = 0.55 e Å3
4853 reflectionsΔρmin = 0.52 e Å3
217 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K. Cosier, J. & Glazer, A·M., 1986. J. Appl. Cryst. 105–107.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.80505 (8)0.74524 (7)0.18215 (7)0.0419
C20.8154 (3)0.9139 (3)0.3122 (2)0.0294
C30.8387 (2)1.0394 (3)0.2991 (2)0.0246
C40.8489 (2)1.0312 (2)0.1703 (2)0.0242
O50.96792 (18)1.0226 (2)0.15579 (17)0.0340
N60.7162 (2)1.0318 (2)0.07689 (19)0.0239
P70.67903 (7)0.99785 (7)0.08665 (6)0.0233
O80.51546 (17)0.99268 (18)0.14913 (15)0.0284
N90.7660 (2)1.1237 (2)0.0924 (2)0.0274
C100.7171 (3)1.2717 (3)0.0818 (3)0.0316
C110.8518 (3)1.3613 (3)0.0548 (3)0.0485
H1130.82311.45820.04800.0727*
H1110.88931.31690.12550.0723*
H1120.93091.36750.03000.0726*
C120.6613 (3)1.3417 (3)0.0333 (3)0.0445
H1230.63601.44050.04280.0658*
H1210.73821.34450.11550.0657*
H1220.57351.28600.01190.0659*
C130.5940 (3)1.2628 (3)0.2131 (3)0.0444
H1330.56131.35940.20560.0662*
H1310.63041.22180.28380.0671*
H1320.51301.19960.23230.0668*
N140.7544 (2)0.8446 (2)0.1438 (2)0.0318
C150.6850 (3)0.7235 (3)0.2760 (2)0.0330
C160.5518 (4)0.6559 (3)0.2782 (4)0.0682
H1620.51180.57130.36110.1015*
H1610.47690.72520.26880.1019*
H1630.58300.62800.20300.1016*
C170.8006 (3)0.6103 (3)0.2905 (3)0.0498
H1720.76030.52870.37630.0743*
H1710.89010.65260.28310.0749*
H1730.82980.57460.21870.0753*
C180.6419 (5)0.7781 (4)0.3876 (3)0.0793
H1820.59950.69640.47170.1182*
H1810.72720.82050.38350.1195*
H1830.56770.84950.37950.1186*
H1410.8463 (18)0.847 (3)0.111 (3)0.0394*
H610.642 (2)1.029 (3)0.097 (2)0.0307*
C190.8479 (3)1.1717 (3)0.4055 (2)0.0289
Cl200.88198 (8)1.33294 (7)0.39623 (7)0.0420
C210.8334 (3)1.1780 (3)0.5207 (2)0.0350
C220.8096 (3)1.0495 (3)0.5300 (3)0.0377
C230.8009 (3)0.9165 (3)0.4263 (3)0.0352
H2310.78890.82840.43270.0417*
H2210.80291.04990.60880.0446*
H2110.84001.27000.59220.0413*
H910.840 (2)1.097 (3)0.110 (2)0.0335*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0528 (4)0.0331 (4)0.0398 (4)0.0011 (3)0.0225 (3)0.0085 (3)
C20.0241 (12)0.0345 (13)0.0269 (12)0.0019 (10)0.0085 (10)0.0106 (11)
C30.0162 (10)0.0334 (12)0.0233 (11)0.0029 (9)0.0074 (9)0.0104 (10)
C40.0204 (11)0.0265 (12)0.0254 (12)0.0027 (9)0.0107 (10)0.0083 (10)
O50.0227 (9)0.0499 (11)0.0338 (10)0.0057 (8)0.0158 (8)0.0167 (9)
N60.0202 (10)0.0334 (11)0.0229 (10)0.0012 (8)0.0130 (8)0.0112 (8)
P70.0205 (3)0.0296 (3)0.0222 (3)0.0017 (2)0.0113 (2)0.0094 (3)
O80.0229 (8)0.0410 (10)0.0257 (8)0.0011 (7)0.0120 (7)0.0144 (8)
N90.0226 (10)0.0351 (11)0.0351 (11)0.0061 (9)0.0190 (9)0.0173 (10)
C100.0334 (14)0.0318 (13)0.0392 (14)0.0045 (11)0.0195 (12)0.0184 (12)
C110.0439 (17)0.0470 (17)0.067 (2)0.0022 (14)0.0228 (16)0.0314 (16)
C120.062 (2)0.0353 (15)0.0491 (17)0.0116 (14)0.0343 (16)0.0180 (13)
C130.0415 (17)0.0515 (18)0.0487 (18)0.0096 (14)0.0168 (14)0.0297 (15)
N140.0246 (11)0.0326 (11)0.0299 (11)0.0027 (10)0.0105 (10)0.0042 (9)
C150.0445 (16)0.0285 (13)0.0254 (12)0.0013 (11)0.0156 (12)0.0075 (11)
C160.054 (2)0.0401 (18)0.098 (3)0.0135 (16)0.034 (2)0.0051 (19)
C170.062 (2)0.0359 (16)0.0525 (18)0.0070 (14)0.0346 (17)0.0071 (14)
C180.149 (4)0.059 (2)0.0303 (17)0.023 (2)0.035 (2)0.0201 (16)
C190.0226 (12)0.0354 (14)0.0281 (12)0.0046 (10)0.0089 (10)0.0131 (11)
Cl200.0565 (4)0.0329 (3)0.0399 (4)0.0006 (3)0.0256 (3)0.0100 (3)
C210.0351 (14)0.0416 (15)0.0246 (12)0.0076 (12)0.0131 (11)0.0090 (11)
C220.0383 (15)0.0537 (17)0.0288 (13)0.0076 (13)0.0175 (12)0.0204 (13)
C230.0338 (14)0.0426 (15)0.0367 (14)0.0030 (12)0.0148 (12)0.0216 (13)
Geometric parameters (Å, º) top
Cl1—C21.741 (2)C13—H1310.949
C2—C31.377 (3)C13—H1320.962
C2—C231.386 (3)N14—C151.479 (3)
C3—C41.519 (3)N14—H1410.829 (16)
C3—C191.389 (3)C15—C161.512 (4)
C4—O51.224 (3)C15—C171.520 (4)
C4—N61.341 (3)C15—C181.517 (4)
N6—P71.7009 (19)C16—H1620.965
N6—H610.848 (15)C16—H1610.960
P7—O81.4770 (16)C16—H1630.961
P7—N91.625 (2)C17—H1720.968
P7—N141.631 (2)C17—H1710.968
N9—C101.480 (3)C17—H1730.978
N9—H910.815 (16)C18—H1820.961
C10—C111.526 (3)C18—H1810.949
C10—C121.524 (3)C18—H1830.966
C10—C131.525 (3)C19—Cl201.734 (3)
C11—H1130.961C19—C211.385 (3)
C11—H1110.958C21—C221.384 (4)
C11—H1120.982C21—H2110.951
C12—H1230.966C22—C231.378 (3)
C12—H1210.962C22—H2210.949
C12—H1220.963C23—H2310.937
C13—H1330.966
Cl1—C2—C3119.29 (18)C10—C13—H132108.8
Cl1—C2—C23118.4 (2)H133—C13—H132110.7
C3—C2—C23122.3 (2)H131—C13—H132108.4
C2—C3—C4120.3 (2)P7—N14—C15125.28 (17)
C2—C3—C19117.6 (2)P7—N14—H141115.9 (19)
C4—C3—C19122.1 (2)C15—N14—H141115.0 (19)
C3—C4—O5121.8 (2)N14—C15—C16109.4 (2)
C3—C4—N6113.22 (18)N14—C15—C17106.6 (2)
O5—C4—N6125.0 (2)C16—C15—C17109.0 (2)
C4—N6—P7127.02 (15)N14—C15—C18110.4 (2)
C4—N6—H61115.6 (16)C16—C15—C18111.3 (3)
P7—N6—H61115.8 (16)C17—C15—C18110.0 (2)
N6—P7—O8105.18 (9)C15—C16—H162109.6
N6—P7—N9108.68 (10)C15—C16—H161110.9
O8—P7—N9114.97 (10)H162—C16—H161110.1
N6—P7—N14105.41 (11)C15—C16—H163108.5
O8—P7—N14115.10 (10)H162—C16—H163110.2
N9—P7—N14106.94 (11)H161—C16—H163107.6
P7—N9—C10126.98 (15)C15—C17—H172109.7
P7—N9—H91113.7 (18)C15—C17—H171110.8
C10—N9—H91119.1 (18)H172—C17—H171110.0
N9—C10—C11107.0 (2)C15—C17—H173110.7
N9—C10—C12110.21 (19)H172—C17—H173109.1
C11—C10—C12110.0 (2)H171—C17—H173106.4
N9—C10—C13110.0 (2)C15—C18—H182108.0
C11—C10—C13109.8 (2)C15—C18—H181109.5
C12—C10—C13109.8 (2)H182—C18—H181110.8
C10—C11—H113108.9C15—C18—H183110.4
C10—C11—H111110.7H182—C18—H183108.2
H113—C11—H111109.7H181—C18—H183109.8
C10—C11—H112109.8C3—C19—Cl20119.51 (19)
H113—C11—H112109.1C3—C19—C21121.6 (2)
H111—C11—H112108.6Cl20—C19—C21118.92 (19)
C10—C12—H123109.3C19—C21—C22119.2 (2)
C10—C12—H121109.6C19—C21—H211119.9
H123—C12—H121108.9C22—C21—H211120.9
C10—C12—H122108.4C21—C22—C23120.6 (2)
H123—C12—H122109.0C21—C22—H221121.2
H121—C12—H122111.6C23—C22—H221118.2
C10—C13—H133109.9C2—C23—C22118.9 (2)
C10—C13—H131109.3C2—C23—H231119.7
H133—C13—H131109.7C22—C23—H231121.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H161···O80.9602.4623.137 (4)127.16 (8)
N6—H61···O8i0.8481.9142.758 (4)173 (2)
N9—H91···O5ii0.8152.2373.038 (4)168 (2)
Symmetry codes: (i) x+1, y+2, z; (ii) x+2, y+2, z.

Experimental details

(I)(IV)(V)(III)
Crystal data
Chemical formulaC7H13F3N3O2PC21H32Cl2N3O2PC23H24Cl2N3O2PC15H24Cl2N3O2P
Mr259.17460.37476.32380.24
Crystal system, space groupMonoclinic, P21/aMonoclinic, P21/nMonoclinic, P21/cTriclinic, P1
Temperature (K)295295295150
a, b, c (Å)11.3416 (3), 9.0552 (3), 11.8030 (4)10.1526 (4), 12.9020 (6), 18.5334 (9)10.0375 (2), 23.0525 (7), 10.1700 (3)9.7455 (2), 10.0122 (3), 11.7163 (3)
α, β, γ (°)90, 109.413 (2), 9090, 92.724 (4), 9090, 96.809 (2), 9066.278 (3), 67.729 (2), 84.121 (2)
V3)1143.26 (6)2424.9 (2)2336.64 (11)966.84 (5)
Z4442
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.270.360.370.43
Crystal size (mm)0.41 × 0.35 × 0.240.27 × 0.19 × 0.120.13 × 0.07 × 0.050.40 × 0.20 × 0.20
Data collection
DiffractometerKappaCCD
diffractometer
Xcalibur, Sapphire3, Gemini
diffractometer
Xcalibur, Sapphire3, Gemini
diffractometer
Xcalibur, Sapphire3, Gemini
diffractometer
Absorption correctionMulti-scan
CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Multi-scan
CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Multi-scan
CrysAlis PRO, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Tmin, Tmax0.943, 1.0000.984, 1.0000.933, 1.000
No. of measured, independent and
observed reflections
1977, 1977, 1748 [I > 2σ(I)]10444, 4258, 3551 [I > 2σ(I)]9762, 4092, 3324 [I > 2σ(I)]43311, 4853, 3805 [I > 2.0σ(I)]
Rint0.0000.0220.0260.058
(sin θ/λ)max1)0.5950.5950.5950.683
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.094, 1.03 0.053, 0.146, 1.02 0.050, 0.114, 1.04 0.055, 0.067, 0.97
No. of reflections1977425840924853
No. of parameters156267285217
No. of restraints3113
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
Δρmax, Δρmin (e Å3)0.26, 0.280.52, 0.310.25, 0.240.55, 0.52

Computer programs: Collect (Bruker AXS BV, 1997-2004), CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58), CrysAlis PRO, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39), HKL SCALEPACK (Otwinowski & Minor 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor 1997), SIR2002 (Giacovazzo et al., 2003), SIR92 (Altomare et al., 1993), Superflip (Palatinus & Chapuis, 2007), SHELXL97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 2008), CRYSTALS (Betteridge et al., 2003), ORTEP-3 for Windows (Farrugia, 1997), Mercury (Macrae et al., 2008), CAMERON (Watkin et al., 1996), WinGX publication routines (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O12i0.844 (9)2.322 (14)3.058 (2)146.1 (18)
N6—H6···O12ii0.845 (9)2.260 (11)3.074 (2)162 (2)
N10—H10···O9i0.853 (9)1.920 (11)2.7579 (18)167.0 (19)
Symmetry codes: (i) x+3/2, y+1/2, z; (ii) x+1, y, z.
Hydrogen-bond geometry (Å, º) for (IV) top
D—H···AD—HH···AD···AD—H···A
N8—H8···O4i0.854 (10)1.895 (11)2.746 (3)175 (3)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) for (V) top
D—H···AD—HH···AD···AD—H···A
N6—H6···O4i0.850 (10)1.906 (10)2.756 (2)178 (2)
Symmetry code: (i) x+1, y, z.
Selected geometric parameters (Å, º) for (III) top
Cl1—C21.741 (2)C10—C111.526 (3)
C2—C31.377 (3)C10—C121.524 (3)
C2—C231.386 (3)C10—C131.525 (3)
C3—C41.519 (3)N14—C151.479 (3)
C3—C191.389 (3)C15—C161.512 (4)
C4—O51.224 (3)C15—C171.520 (4)
C4—N61.341 (3)C15—C181.517 (4)
N6—P71.7009 (19)C19—Cl201.734 (3)
P7—O81.4770 (16)C19—C211.385 (3)
P7—N91.625 (2)C21—C221.384 (4)
P7—N141.631 (2)C22—C231.378 (3)
N9—C101.480 (3)
Cl1—C2—C3119.29 (18)N9—C10—C12110.21 (19)
Cl1—C2—C23118.4 (2)C11—C10—C12110.0 (2)
C3—C2—C23122.3 (2)N9—C10—C13110.0 (2)
C2—C3—C4120.3 (2)C11—C10—C13109.8 (2)
C2—C3—C19117.6 (2)C12—C10—C13109.8 (2)
C4—C3—C19122.1 (2)P7—N14—C15125.28 (17)
C3—C4—O5121.8 (2)N14—C15—C16109.4 (2)
C3—C4—N6113.22 (18)N14—C15—C17106.6 (2)
O5—C4—N6125.0 (2)C16—C15—C17109.0 (2)
C4—N6—P7127.02 (15)N14—C15—C18110.4 (2)
N6—P7—O8105.18 (9)C16—C15—C18111.3 (3)
N6—P7—N9108.68 (10)C17—C15—C18110.0 (2)
O8—P7—N9114.97 (10)C3—C19—Cl20119.51 (19)
N6—P7—N14105.41 (11)C3—C19—C21121.6 (2)
O8—P7—N14115.10 (10)Cl20—C19—C21118.92 (19)
N9—P7—N14106.94 (11)C19—C21—C22119.2 (2)
P7—N9—C10126.98 (15)C21—C22—C23120.6 (2)
N9—C10—C11107.0 (2)C2—C23—C22118.9 (2)
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
C16—H161···O80.9602.4623.137 (4)127.16 (8)
N6—H61···O8i0.8481.9142.758 (4)173 (2)
N9—H91···O5ii0.8152.2373.038 (4)168 (2)
Symmetry codes: (i) x+1, y+2, z; (ii) x+2, y+2, z.
 

Subscribe to Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

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