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A phosphoric triamide with the formula (4-CH3—C6H4NH)P(O)(NC4H8O)2 has been synthesized and characterized. X-ray crystallography at 120 K reveals that the title compound is composed of two symmetrically independent molecules in the solid state. Density functional theory (DFT) calculations reveal that two conformers A and B are very close to each other from an energy point of view. Thus there is equal chance that the presence of two conformers in the lattice may lead to hydrogen-bonded chains with an ABABAB arrangement. Hydrogen bonds of the type OP...H—N (OP being the phosphoryl O atom) are established between the two conformers with binding energies of −18.8 and −20.3 kJ mol−1 (at B3LYP/6–31+G*). The electronic delocalization LP(OP) → σ*(N—H), LP(OP) being the lone pair of OP, leads to a decrease in the strength of the N—H bond during hydrogen bonding between the conformers. The charge density (ρ) at the bond critical point (b.c.p.) of N—H decreases by ∼ 0.012–0.014 e Å–3 when the molecule participates in hydrogen bonding. This may explain the red shift of the ν(N—H) stretching frequency from a single molecule in the gas phase to a hydrogen-bonded one in the solid state.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768111010470/so5046sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111010470/so5046Isup2.hkl
Contains datablock I

CCDC reference: 292748

Computing details top

Data collection: SMART (Bruker, 1998b); cell refinement: SAINTPlus (Bruker, 1998a); data reduction: SAINTPlus (Bruker, 1998a); program(s) used to solve structure: SHELXTL ver. 5.1 (Sheldrick, 1998a); program(s) used to refine structure: SHELXTL ver. 5.1 (Sheldrick, 1998a); molecular graphics: SHELXTL ver. 5.1 (Sheldrick, 1998a); software used to prepare material for publication: SHELXTL ver. 5.1 (Sheldrick, 1998a).

Figures top
[Figure 1]
[Figure 2]
(I) top
Crystal data top
C15H24N3O3PF(000) = 1392
Mr = 325.34Dx = 1.291 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2756 reflections
a = 9.517 (3) Åθ = 2.3–26.0°
b = 10.723 (3) ŵ = 0.18 mm1
c = 32.993 (8) ÅT = 120 K
β = 96.029 (6)°Plate, colorless
V = 3348.3 (16) Å30.50 × 0.15 × 0.05 mm
Z = 8
Data collection top
Bruker SMART 1000 CCD area detector
diffractometer
3369 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tubeRint = 0.068
Graphite monochromatorθmax = 26.0°, θmin = 2.0°
ω scansh = 1111
16054 measured reflectionsk = 1212
6459 independent reflectionsl = 4017
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)] = 0.051Hydrogen site location: mixed
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 0.87 w = 1/[σ2(Fo2) + (0.0456P)2]
where P = (Fo2 + 2Fc2)/3
6459 reflections(Δ/σ)max = 0.001
407 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C15H24N3O3PV = 3348.3 (16) Å3
Mr = 325.34Z = 8
Monoclinic, P21/nMo Kα radiation
a = 9.517 (3) ŵ = 0.18 mm1
b = 10.723 (3) ÅT = 120 K
c = 32.993 (8) Å0.50 × 0.15 × 0.05 mm
β = 96.029 (6)°
Data collection top
Bruker SMART 1000 CCD area detector
diffractometer
3369 reflections with I > 2σ(I)
16054 measured reflectionsRint = 0.068
6459 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 0.87Δρmax = 0.42 e Å3
6459 reflectionsΔρmin = 0.36 e Å3
407 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
P1A0.12973 (8)0.17163 (7)0.11211 (2)0.0221 (2)
O1A0.0099 (2)0.18993 (18)0.12702 (5)0.0280 (5)
O2A0.2108 (2)0.4672 (2)0.02084 (6)0.0362 (6)
O3A0.0501 (2)0.2110 (2)0.07806 (7)0.0458 (6)
N1A0.2626 (3)0.1811 (3)0.14762 (7)0.0242 (6)
H1AA0.327 (3)0.224 (3)0.1429 (8)0.024 (9)*
N2A0.1556 (2)0.2759 (2)0.07677 (6)0.0214 (6)
N3A0.1455 (2)0.0386 (2)0.08912 (7)0.0264 (6)
C1A0.2682 (3)0.1409 (3)0.18865 (8)0.0242 (7)
C2A0.3779 (3)0.1840 (3)0.21643 (8)0.0306 (8)
H2AA0.44530.24080.20770.037*
C3A0.3893 (4)0.1447 (3)0.25646 (9)0.0373 (9)
H3AA0.46470.17510.27500.045*
C4A0.2929 (4)0.0615 (3)0.27040 (9)0.0358 (8)
C5A0.1844 (3)0.0194 (3)0.24244 (9)0.0333 (8)
H5AA0.11730.03780.25110.040*
C6A0.1715 (3)0.0588 (3)0.20222 (9)0.0307 (8)
H6AA0.09550.02900.18380.037*
C7A0.1391 (3)0.4087 (3)0.08661 (8)0.0254 (7)
H7AA0.22760.44010.10160.030*
H7AB0.06220.41850.10440.030*
C8A0.1054 (3)0.4834 (3)0.04846 (9)0.0325 (8)
H8AA0.01230.45730.03490.039*
H8AB0.09930.57280.05560.039*
C9A0.2186 (3)0.3391 (3)0.01067 (8)0.0337 (8)
H9AA0.28840.32810.00930.040*
H9AB0.12550.31130.00240.040*
C10A0.2604 (3)0.2584 (3)0.04742 (8)0.0268 (7)
H10A0.26320.16970.03920.032*
H10B0.35550.28240.06010.032*
C11A0.2397 (3)0.0649 (3)0.10124 (9)0.0330 (8)
H11A0.30390.04150.12560.040*
H11B0.29790.08510.07900.040*
C12A0.1522 (4)0.1782 (3)0.11074 (10)0.0423 (9)
H12A0.21620.25000.11710.051*
H12B0.10370.16050.13520.051*
C13A0.0420 (4)0.1082 (3)0.06783 (11)0.0445 (9)
H13A0.09240.08620.09160.053*
H13B0.11330.13220.04510.053*
C14A0.0394 (3)0.0024 (3)0.05551 (9)0.0354 (8)
H14A0.08680.01820.03110.043*
H14B0.02600.07290.04860.043*
C15A0.3072 (4)0.0149 (3)0.31375 (9)0.0497 (10)
H15A0.36050.07580.33140.075*
H15B0.35740.06500.31530.075*
H15C0.21310.00380.32270.075*
P1B0.37122 (8)0.64805 (7)0.88129 (2)0.0233 (2)
O1B0.5141 (2)0.66601 (18)0.86859 (5)0.0279 (5)
O2B0.2944 (2)0.8999 (2)0.98557 (6)0.0360 (6)
O3B0.3413 (3)0.2389 (2)0.89916 (7)0.0492 (7)
N1B0.2416 (3)0.6832 (2)0.84674 (7)0.0246 (6)
H1BA0.172 (3)0.722 (3)0.8549 (8)0.031 (9)*
N2B0.3490 (2)0.7356 (2)0.92136 (6)0.0234 (6)
N3B0.3472 (2)0.5017 (2)0.89366 (7)0.0259 (6)
C1B0.2223 (3)0.6413 (3)0.80566 (8)0.0241 (7)
C2B0.1041 (3)0.6827 (3)0.78086 (8)0.0318 (8)
H2BA0.03970.73860.79150.038*
C3B0.0800 (4)0.6431 (3)0.74091 (9)0.0388 (9)
H3BA0.00090.67270.72440.047*
C4B0.1716 (4)0.5607 (3)0.72420 (9)0.0353 (8)
C5B0.2891 (3)0.5208 (3)0.74934 (9)0.0366 (8)
H5BA0.35360.46480.73880.044*
C6B0.3151 (3)0.5605 (3)0.78948 (8)0.0306 (8)
H6BA0.39680.53200.80590.037*
C7B0.3619 (3)0.8719 (3)0.91702 (8)0.0281 (7)
H7BA0.27210.90620.90360.034*
H7BB0.43770.89110.89960.034*
C8B0.3956 (3)0.9321 (3)0.95827 (9)0.0370 (8)
H8BA0.49070.90530.97010.044*
H8BB0.39731.02390.95500.044*
C9B0.2883 (3)0.7674 (3)0.99015 (8)0.0356 (8)
H9BA0.21890.74651.00940.043*
H9BB0.38190.73641.00180.043*
C10B0.2472 (3)0.7032 (3)0.95036 (8)0.0279 (7)
H10C0.24630.61180.95450.033*
H10D0.15100.72960.93930.033*
C11B0.2147 (3)0.4322 (3)0.88771 (9)0.0310 (8)
H11C0.14650.47690.86810.037*
H11D0.17320.42540.91390.037*
C12B0.2423 (4)0.3039 (3)0.87168 (10)0.0431 (9)
H12C0.15260.25640.86790.052*
H12D0.27930.31110.84480.052*
C13B0.4719 (4)0.3034 (3)0.90311 (11)0.0426 (9)
H13C0.50830.30820.87610.051*
H13D0.54130.25620.92160.051*
C14B0.4582 (3)0.4335 (3)0.91956 (9)0.0350 (8)
H14C0.43320.42950.94790.042*
H14D0.54950.47790.91980.042*
C15B0.1447 (4)0.5134 (3)0.68097 (9)0.0477 (10)
H15D0.06530.55920.66660.072*
H15E0.12190.42430.68130.072*
H15F0.22940.52610.66690.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P1A0.0185 (4)0.0294 (5)0.0183 (4)0.0009 (4)0.0011 (3)0.0015 (3)
O1A0.0181 (12)0.0387 (13)0.0275 (10)0.0018 (9)0.0038 (9)0.0019 (10)
O2A0.0372 (15)0.0364 (15)0.0349 (12)0.0030 (11)0.0037 (10)0.0098 (11)
O3A0.0428 (16)0.0316 (14)0.0631 (15)0.0007 (11)0.0056 (13)0.0058 (12)
N1A0.0177 (16)0.0358 (17)0.0188 (12)0.0064 (13)0.0010 (11)0.0061 (12)
N2A0.0184 (14)0.0269 (15)0.0195 (11)0.0023 (11)0.0040 (10)0.0015 (11)
N3A0.0249 (15)0.0244 (15)0.0291 (13)0.0036 (11)0.0016 (11)0.0014 (11)
C1A0.0236 (18)0.0286 (18)0.0205 (14)0.0048 (14)0.0029 (12)0.0010 (14)
C2A0.032 (2)0.034 (2)0.0257 (15)0.0073 (15)0.0007 (14)0.0006 (14)
C3A0.043 (2)0.043 (2)0.0235 (16)0.0013 (17)0.0076 (15)0.0032 (16)
C4A0.049 (2)0.037 (2)0.0213 (16)0.0057 (17)0.0033 (15)0.0027 (15)
C5A0.034 (2)0.036 (2)0.0299 (16)0.0010 (16)0.0079 (14)0.0086 (15)
C6A0.027 (2)0.037 (2)0.0270 (16)0.0028 (15)0.0013 (14)0.0071 (15)
C7A0.0280 (19)0.0241 (18)0.0231 (15)0.0025 (14)0.0017 (13)0.0021 (13)
C8A0.031 (2)0.031 (2)0.0345 (17)0.0010 (15)0.0012 (15)0.0045 (15)
C9A0.032 (2)0.048 (2)0.0210 (15)0.0008 (16)0.0054 (13)0.0027 (16)
C10A0.0248 (18)0.0348 (19)0.0215 (14)0.0003 (14)0.0062 (12)0.0010 (14)
C11A0.032 (2)0.031 (2)0.0366 (18)0.0047 (15)0.0074 (15)0.0016 (15)
C12A0.047 (2)0.032 (2)0.049 (2)0.0091 (17)0.0113 (18)0.0089 (17)
C13A0.037 (2)0.034 (2)0.062 (2)0.0003 (17)0.0008 (18)0.0116 (18)
C14A0.035 (2)0.039 (2)0.0303 (17)0.0029 (16)0.0048 (15)0.0100 (16)
C15A0.068 (3)0.055 (3)0.0250 (17)0.002 (2)0.0030 (17)0.0112 (18)
P1B0.0187 (5)0.0311 (5)0.0199 (4)0.0016 (4)0.0019 (3)0.0002 (4)
O1B0.0176 (12)0.0384 (13)0.0280 (10)0.0051 (9)0.0031 (9)0.0022 (10)
O2B0.0291 (14)0.0507 (16)0.0289 (11)0.0001 (11)0.0063 (10)0.0096 (11)
O3B0.0555 (18)0.0375 (15)0.0550 (15)0.0029 (13)0.0083 (13)0.0053 (12)
N1B0.0216 (16)0.0331 (17)0.0192 (12)0.0054 (12)0.0023 (11)0.0024 (11)
N2B0.0219 (15)0.0298 (15)0.0187 (11)0.0043 (11)0.0025 (10)0.0012 (11)
N3B0.0136 (14)0.0323 (15)0.0318 (13)0.0026 (11)0.0018 (11)0.0025 (12)
C1B0.0251 (18)0.0237 (18)0.0227 (14)0.0033 (14)0.0008 (13)0.0007 (13)
C2B0.036 (2)0.031 (2)0.0271 (15)0.0035 (15)0.0013 (14)0.0039 (14)
C3B0.043 (2)0.042 (2)0.0283 (16)0.0033 (17)0.0113 (15)0.0033 (16)
C4B0.046 (2)0.035 (2)0.0246 (16)0.0082 (17)0.0004 (15)0.0006 (15)
C5B0.039 (2)0.038 (2)0.0338 (17)0.0002 (16)0.0096 (16)0.0054 (16)
C6B0.027 (2)0.040 (2)0.0245 (16)0.0040 (15)0.0002 (14)0.0052 (15)
C7B0.0272 (19)0.032 (2)0.0249 (15)0.0022 (14)0.0023 (13)0.0014 (14)
C8B0.030 (2)0.045 (2)0.0355 (18)0.0084 (16)0.0039 (15)0.0126 (16)
C9B0.032 (2)0.050 (2)0.0247 (16)0.0035 (16)0.0028 (14)0.0013 (16)
C10B0.0263 (19)0.036 (2)0.0218 (14)0.0008 (14)0.0065 (13)0.0010 (14)
C11B0.0220 (19)0.034 (2)0.0376 (18)0.0060 (14)0.0059 (14)0.0032 (16)
C12B0.043 (2)0.039 (2)0.047 (2)0.0116 (17)0.0010 (17)0.0005 (18)
C13B0.035 (2)0.044 (2)0.050 (2)0.0146 (17)0.0091 (17)0.0123 (18)
C14B0.0250 (19)0.042 (2)0.0384 (18)0.0018 (15)0.0057 (15)0.0126 (16)
C15B0.069 (3)0.047 (2)0.0266 (17)0.004 (2)0.0008 (17)0.0068 (17)
Geometric parameters (Å, º) top
P1A—O1A1.478 (2)P1B—O1B1.477 (2)
P1A—N3A1.630 (2)P1B—N1B1.633 (2)
P1A—N1A1.634 (2)P1B—N3B1.643 (3)
P1A—N2A1.652 (2)P1B—N2B1.653 (2)
O2A—C9A1.418 (4)O2B—C8B1.428 (4)
O2A—C8A1.434 (4)O2B—C9B1.431 (4)
O3A—C12A1.418 (4)O3B—C13B1.417 (4)
O3A—C13A1.426 (4)O3B—C12B1.421 (4)
N1A—C1A1.416 (3)N1B—C1B1.421 (3)
N1A—H1AA0.79 (3)N1B—H1BA0.85 (3)
N2A—C10A1.473 (3)N2B—C10B1.474 (4)
N2A—C7A1.473 (3)N2B—C7B1.474 (4)
N3A—C11A1.456 (3)N3B—C11B1.460 (3)
N3A—C14A1.471 (3)N3B—C14B1.481 (3)
C1A—C6A1.382 (4)C1B—C6B1.384 (4)
C1A—C2A1.394 (4)C1B—C2B1.392 (4)
C2A—C3A1.380 (4)C2B—C3B1.381 (4)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.392 (4)C3B—C4B1.395 (5)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.386 (4)C4B—C5B1.388 (4)
C4A—C15A1.508 (4)C4B—C15B1.510 (4)
C5A—C6A1.385 (4)C5B—C6B1.388 (4)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—H6AA0.9500C6B—H6BA0.9500
C7A—C8A1.498 (4)C7B—C8B1.510 (4)
C7A—H7AA0.9900C7B—H7BA0.9900
C7A—H7AB0.9900C7B—H7BB0.9900
C8A—H8AA0.9900C8B—H8BA0.9900
C8A—H8AB0.9900C8B—H8BB0.9900
C9A—C10A1.508 (4)C9B—C10B1.497 (4)
C9A—H9AA0.9900C9B—H9BA0.9900
C9A—H9AB0.9900C9B—H9BB0.9900
C10A—H10A0.9900C10B—H10C0.9900
C10A—H10B0.9900C10B—H10D0.9900
C11A—C12A1.524 (4)C11B—C12B1.507 (4)
C11A—H11A0.9900C11B—H11C0.9900
C11A—H11B0.9900C11B—H11D0.9900
C12A—H12A0.9900C12B—H12C0.9900
C12A—H12B0.9900C12B—H12D0.9900
C13A—C14A1.497 (5)C13B—C14B1.507 (4)
C13A—H13A0.9900C13B—H13C0.9900
C13A—H13B0.9900C13B—H13D0.9900
C14A—H14A0.9900C14B—H14C0.9900
C14A—H14B0.9900C14B—H14D0.9900
C15A—H15A0.9800C15B—H15D0.9800
C15A—H15B0.9800C15B—H15E0.9800
C15A—H15C0.9800C15B—H15F0.9800
O1A—P1A—N3A113.64 (12)O1B—P1B—N1B115.00 (13)
O1A—P1A—N1A114.10 (12)O1B—P1B—N3B110.58 (12)
N3A—P1A—N1A106.59 (13)N1B—P1B—N3B106.18 (13)
O1A—P1A—N2A110.54 (11)O1B—P1B—N2B110.57 (12)
N3A—P1A—N2A103.66 (12)N1B—P1B—N2B106.05 (13)
N1A—P1A—N2A107.62 (13)N3B—P1B—N2B108.12 (12)
C9A—O2A—C8A109.0 (2)C8B—O2B—C9B110.1 (2)
C12A—O3A—C13A110.1 (2)C13B—O3B—C12B109.6 (2)
C1A—N1A—P1A128.0 (2)C1B—N1B—P1B127.2 (2)
C1A—N1A—H1AA114 (2)C1B—N1B—H1BA115.6 (19)
P1A—N1A—H1AA117 (2)P1B—N1B—H1BA116.5 (19)
C10A—N2A—C7A111.3 (2)C10B—N2B—C7B111.3 (2)
C10A—N2A—P1A122.62 (19)C10B—N2B—P1B122.21 (19)
C7A—N2A—P1A118.14 (18)C7B—N2B—P1B117.82 (18)
C11A—N3A—C14A111.1 (2)C11B—N3B—C14B112.3 (2)
C11A—N3A—P1A128.57 (19)C11B—N3B—P1B126.49 (19)
C14A—N3A—P1A119.4 (2)C14B—N3B—P1B120.36 (19)
C6A—C1A—C2A118.5 (3)C6B—C1B—C2B118.8 (3)
C6A—C1A—N1A123.0 (3)C6B—C1B—N1B122.8 (3)
C2A—C1A—N1A118.5 (3)C2B—C1B—N1B118.4 (3)
C3A—C2A—C1A120.4 (3)C3B—C2B—C1B120.4 (3)
C3A—C2A—H2AA119.8C3B—C2B—H2BA119.8
C1A—C2A—H2AA119.8C1B—C2B—H2BA119.8
C2A—C3A—C4A121.6 (3)C2B—C3B—C4B121.6 (3)
C2A—C3A—H3AA119.2C2B—C3B—H3BA119.2
C4A—C3A—H3AA119.2C4B—C3B—H3BA119.2
C5A—C4A—C3A117.4 (3)C5B—C4B—C3B117.2 (3)
C5A—C4A—C15A120.7 (3)C5B—C4B—C15B120.5 (3)
C3A—C4A—C15A121.9 (3)C3B—C4B—C15B122.3 (3)
C6A—C5A—C4A121.5 (3)C6B—C5B—C4B121.8 (3)
C6A—C5A—H5AA119.2C6B—C5B—H5BA119.1
C4A—C5A—H5AA119.2C4B—C5B—H5BA119.1
C1A—C6A—C5A120.6 (3)C1B—C6B—C5B120.2 (3)
C1A—C6A—H6AA119.7C1B—C6B—H6BA119.9
C5A—C6A—H6AA119.7C5B—C6B—H6BA119.9
N2A—C7A—C8A110.5 (2)N2B—C7B—C8B110.4 (2)
N2A—C7A—H7AA109.6N2B—C7B—H7BA109.6
C8A—C7A—H7AA109.6C8B—C7B—H7BA109.6
N2A—C7A—H7AB109.6N2B—C7B—H7BB109.6
C8A—C7A—H7AB109.6C8B—C7B—H7BB109.6
H7AA—C7A—H7AB108.1H7BA—C7B—H7BB108.1
O2A—C8A—C7A111.5 (2)O2B—C8B—C7B111.8 (2)
O2A—C8A—H8AA109.3O2B—C8B—H8BA109.3
C7A—C8A—H8AA109.3C7B—C8B—H8BA109.3
O2A—C8A—H8AB109.3O2B—C8B—H8BB109.3
C7A—C8A—H8AB109.3C7B—C8B—H8BB109.3
H8AA—C8A—H8AB108.0H8BA—C8B—H8BB107.9
O2A—C9A—C10A112.4 (2)O2B—C9B—C10B111.9 (2)
O2A—C9A—H9AA109.1O2B—C9B—H9BA109.2
C10A—C9A—H9AA109.1C10B—C9B—H9BA109.2
O2A—C9A—H9AB109.1O2B—C9B—H9BB109.2
C10A—C9A—H9AB109.1C10B—C9B—H9BB109.2
H9AA—C9A—H9AB107.9H9BA—C9B—H9BB107.9
N2A—C10A—C9A108.4 (2)N2B—C10B—C9B109.4 (2)
N2A—C10A—H10A110.0N2B—C10B—H10C109.8
C9A—C10A—H10A110.0C9B—C10B—H10C109.8
N2A—C10A—H10B110.0N2B—C10B—H10D109.8
C9A—C10A—H10B110.0C9B—C10B—H10D109.8
H10A—C10A—H10B108.4H10C—C10B—H10D108.3
N3A—C11A—C12A109.3 (3)N3B—C11B—C12B109.5 (3)
N3A—C11A—H11A109.8N3B—C11B—H11C109.8
C12A—C11A—H11A109.8C12B—C11B—H11C109.8
N3A—C11A—H11B109.8N3B—C11B—H11D109.8
C12A—C11A—H11B109.8C12B—C11B—H11D109.8
H11A—C11A—H11B108.3H11C—C11B—H11D108.2
O3A—C12A—C11A112.8 (3)O3B—C12B—C11B110.6 (3)
O3A—C12A—H12A109.0O3B—C12B—H12C109.5
C11A—C12A—H12A109.0C11B—C12B—H12C109.5
O3A—C12A—H12B109.0O3B—C12B—H12D109.5
C11A—C12A—H12B109.0C11B—C12B—H12D109.5
H12A—C12A—H12B107.8H12C—C12B—H12D108.1
O3A—C13A—C14A110.8 (3)O3B—C13B—C14B112.1 (3)
O3A—C13A—H13A109.5O3B—C13B—H13C109.2
C14A—C13A—H13A109.5C14B—C13B—H13C109.2
O3A—C13A—H13B109.5O3B—C13B—H13D109.2
C14A—C13A—H13B109.5C14B—C13B—H13D109.2
H13A—C13A—H13B108.1H13C—C13B—H13D107.9
N3A—C14A—C13A109.7 (3)N3B—C14B—C13B109.4 (2)
N3A—C14A—H14A109.7N3B—C14B—H14C109.8
C13A—C14A—H14A109.7C13B—C14B—H14C109.8
N3A—C14A—H14B109.7N3B—C14B—H14D109.8
C13A—C14A—H14B109.7C13B—C14B—H14D109.8
H14A—C14A—H14B108.2H14C—C14B—H14D108.2
C4A—C15A—H15A109.5C4B—C15B—H15D109.5
C4A—C15A—H15B109.5C4B—C15B—H15E109.5
H15A—C15A—H15B109.5H15D—C15B—H15E109.5
C4A—C15A—H15C109.5C4B—C15B—H15F109.5
H15A—C15A—H15C109.5H15D—C15B—H15F109.5
H15B—C15A—H15C109.5H15E—C15B—H15F109.5
O1A—P1A—N1A—C1A35.8 (3)O1B—P1B—N1B—C1B51.0 (3)
N3A—P1A—N1A—C1A90.5 (3)N3B—P1B—N1B—C1B71.7 (3)
N2A—P1A—N1A—C1A158.8 (3)N2B—P1B—N1B—C1B173.5 (3)
O1A—P1A—N2A—C10A160.0 (2)O1B—P1B—N2B—C10B154.6 (2)
N3A—P1A—N2A—C10A37.8 (2)N1B—P1B—N2B—C10B80.1 (2)
N1A—P1A—N2A—C10A74.8 (2)N3B—P1B—N2B—C10B33.5 (2)
O1A—P1A—N2A—C7A53.8 (2)O1B—P1B—N2B—C7B60.4 (2)
N3A—P1A—N2A—C7A175.95 (19)N1B—P1B—N2B—C7B64.9 (2)
N1A—P1A—N2A—C7A71.4 (2)N3B—P1B—N2B—C7B178.39 (19)
O1A—P1A—N3A—C11A115.6 (3)O1B—P1B—N3B—C11B146.5 (2)
N1A—P1A—N3A—C11A11.0 (3)N1B—P1B—N3B—C11B21.1 (3)
N2A—P1A—N3A—C11A124.4 (3)N2B—P1B—N3B—C11B92.4 (3)
O1A—P1A—N3A—C14A52.9 (3)O1B—P1B—N3B—C14B44.9 (2)
N1A—P1A—N3A—C14A179.4 (2)N1B—P1B—N3B—C14B170.3 (2)
N2A—P1A—N3A—C14A67.2 (2)N2B—P1B—N3B—C14B76.3 (2)
P1A—N1A—C1A—C6A16.8 (5)P1B—N1B—C1B—C6B0.9 (5)
P1A—N1A—C1A—C2A164.6 (2)P1B—N1B—C1B—C2B179.7 (2)
C6A—C1A—C2A—C3A0.3 (5)C6B—C1B—C2B—C3B0.3 (5)
N1A—C1A—C2A—C3A178.4 (3)N1B—C1B—C2B—C3B179.1 (3)
C1A—C2A—C3A—C4A0.0 (5)C1B—C2B—C3B—C4B0.3 (5)
C2A—C3A—C4A—C5A0.0 (5)C2B—C3B—C4B—C5B0.6 (5)
C2A—C3A—C4A—C15A178.0 (3)C2B—C3B—C4B—C15B178.1 (3)
C3A—C4A—C5A—C6A0.3 (5)C3B—C4B—C5B—C6B0.2 (5)
C15A—C4A—C5A—C6A178.4 (3)C15B—C4B—C5B—C6B178.6 (3)
C2A—C1A—C6A—C5A0.6 (5)C2B—C1B—C6B—C5B0.7 (5)
N1A—C1A—C6A—C5A178.0 (3)N1B—C1B—C6B—C5B178.7 (3)
C4A—C5A—C6A—C1A0.7 (5)C4B—C5B—C6B—C1B0.5 (5)
C10A—N2A—C7A—C8A54.1 (3)C10B—N2B—C7B—C8B53.6 (3)
P1A—N2A—C7A—C8A156.1 (2)P1B—N2B—C7B—C8B157.9 (2)
C9A—O2A—C8A—C7A59.2 (3)C9B—O2B—C8B—C7B57.8 (3)
N2A—C7A—C8A—O2A56.3 (3)N2B—C7B—C8B—O2B55.1 (3)
C8A—O2A—C9A—C10A61.1 (3)C8B—O2B—C9B—C10B59.7 (3)
C7A—N2A—C10A—C9A54.2 (3)C7B—N2B—C10B—C9B54.8 (3)
P1A—N2A—C10A—C9A157.56 (19)P1B—N2B—C10B—C9B158.3 (2)
O2A—C9A—C10A—N2A58.7 (3)O2B—C9B—C10B—N2B58.0 (3)
C14A—N3A—C11A—C12A53.8 (3)C14B—N3B—C11B—C12B53.8 (3)
P1A—N3A—C11A—C12A115.5 (3)P1B—N3B—C11B—C12B136.8 (2)
C13A—O3A—C12A—C11A57.7 (4)C13B—O3B—C12B—C11B62.0 (3)
N3A—C11A—C12A—O3A54.9 (4)N3B—C11B—C12B—O3B58.7 (3)
C12A—O3A—C13A—C14A59.6 (4)C12B—O3B—C13B—C14B60.6 (3)
C11A—N3A—C14A—C13A56.9 (3)C11B—N3B—C14B—C13B51.7 (3)
P1A—N3A—C14A—C13A113.5 (3)P1B—N3B—C14B—C13B138.1 (2)
O3A—C13A—C14A—N3A59.2 (4)O3B—C13B—C14B—N3B54.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···O1Bi0.79 (3)1.99 (3)2.780 (4)179 (2)
N1B—H1BA···O1Aii0.85 (3)1.95 (3)2.804 (3)179 (4)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC15H24N3O3P
Mr325.34
Crystal system, space groupMonoclinic, P21/n
Temperature (K)120
a, b, c (Å)9.517 (3), 10.723 (3), 32.993 (8)
β (°) 96.029 (6)
V3)3348.3 (16)
Z8
Radiation typeMo Kα
µ (mm1)0.18
Crystal size (mm)0.50 × 0.15 × 0.05
Data collection
DiffractometerBruker SMART 1000 CCD area detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
16054, 6459, 3369
Rint0.068
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.119, 0.87
No. of reflections6459
No. of parameters407
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.42, 0.36

Computer programs: SMART (Bruker, 1998b), SAINTPlus (Bruker, 1998a), SHELXTL ver. 5.1 (Sheldrick, 1998a).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···O1Bi0.79 (3)1.99 (3)2.780 (4)179 (2)
N1B—H1BA···O1Aii0.85 (3)1.95 (3)2.804 (3)179 (4)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1.
 

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