A phosphoric triamide with the formula (4-CH
3—C
6H
4NH)P(O)(NC
4H
8O)
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 O
PH—N (O
P 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(O
P) → σ*(N—H), LP(O
P) being the lone pair of O
P, 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
CCDC reference: 292748
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).
Crystal data top
C15H24N3O3P | F(000) = 1392 |
Mr = 325.34 | Dx = 1.291 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2756 reflections |
a = 9.517 (3) Å | θ = 2.3–26.0° |
b = 10.723 (3) Å | µ = 0.18 mm−1 |
c = 32.993 (8) Å | T = 120 K |
β = 96.029 (6)° | Plate, colorless |
V = 3348.3 (16) Å3 | 0.50 × 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 tube | Rint = 0.068 |
Graphite monochromator | θmax = 26.0°, θmin = 2.0° |
ω scans | h = −11→11 |
16054 measured reflections | k = −12→12 |
6459 independent reflections | l = −40→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: mixed |
wR(F2) = 0.119 | H 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 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
Crystal data top
C15H24N3O3P | V = 3348.3 (16) Å3 |
Mr = 325.34 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.517 (3) Å | µ = 0.18 mm−1 |
b = 10.723 (3) Å | T = 120 K |
c = 32.993 (8) Å | 0.50 × 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 reflections | Rint = 0.068 |
6459 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.87 | Δρmax = 0.42 e Å−3 |
6459 reflections | Δρmin = −0.36 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
P1A | 0.12973 (8) | 0.17163 (7) | 0.11211 (2) | 0.0221 (2) | |
O1A | −0.0099 (2) | 0.18993 (18) | 0.12702 (5) | 0.0280 (5) | |
O2A | 0.2108 (2) | 0.4672 (2) | 0.02084 (6) | 0.0362 (6) | |
O3A | 0.0501 (2) | −0.2110 (2) | 0.07806 (7) | 0.0458 (6) | |
N1A | 0.2626 (3) | 0.1811 (3) | 0.14762 (7) | 0.0242 (6) | |
H1AA | 0.327 (3) | 0.224 (3) | 0.1429 (8) | 0.024 (9)* | |
N2A | 0.1556 (2) | 0.2759 (2) | 0.07677 (6) | 0.0214 (6) | |
N3A | 0.1455 (2) | 0.0386 (2) | 0.08912 (7) | 0.0264 (6) | |
C1A | 0.2682 (3) | 0.1409 (3) | 0.18865 (8) | 0.0242 (7) | |
C2A | 0.3779 (3) | 0.1840 (3) | 0.21643 (8) | 0.0306 (8) | |
H2AA | 0.4453 | 0.2408 | 0.2077 | 0.037* | |
C3A | 0.3893 (4) | 0.1447 (3) | 0.25646 (9) | 0.0373 (9) | |
H3AA | 0.4647 | 0.1751 | 0.2750 | 0.045* | |
C4A | 0.2929 (4) | 0.0615 (3) | 0.27040 (9) | 0.0358 (8) | |
C5A | 0.1844 (3) | 0.0194 (3) | 0.24244 (9) | 0.0333 (8) | |
H5AA | 0.1173 | −0.0378 | 0.2511 | 0.040* | |
C6A | 0.1715 (3) | 0.0588 (3) | 0.20222 (9) | 0.0307 (8) | |
H6AA | 0.0955 | 0.0290 | 0.1838 | 0.037* | |
C7A | 0.1391 (3) | 0.4087 (3) | 0.08661 (8) | 0.0254 (7) | |
H7AA | 0.2276 | 0.4401 | 0.1016 | 0.030* | |
H7AB | 0.0622 | 0.4185 | 0.1044 | 0.030* | |
C8A | 0.1054 (3) | 0.4834 (3) | 0.04846 (9) | 0.0325 (8) | |
H8AA | 0.0123 | 0.4573 | 0.0349 | 0.039* | |
H8AB | 0.0993 | 0.5728 | 0.0556 | 0.039* | |
C9A | 0.2186 (3) | 0.3391 (3) | 0.01067 (8) | 0.0337 (8) | |
H9AA | 0.2884 | 0.3281 | −0.0093 | 0.040* | |
H9AB | 0.1255 | 0.3113 | −0.0024 | 0.040* | |
C10A | 0.2604 (3) | 0.2584 (3) | 0.04742 (8) | 0.0268 (7) | |
H10A | 0.2632 | 0.1697 | 0.0392 | 0.032* | |
H10B | 0.3555 | 0.2824 | 0.0601 | 0.032* | |
C11A | 0.2397 (3) | −0.0649 (3) | 0.10124 (9) | 0.0330 (8) | |
H11A | 0.3039 | −0.0415 | 0.1256 | 0.040* | |
H11B | 0.2979 | −0.0851 | 0.0790 | 0.040* | |
C12A | 0.1522 (4) | −0.1782 (3) | 0.11074 (10) | 0.0423 (9) | |
H12A | 0.2162 | −0.2500 | 0.1171 | 0.051* | |
H12B | 0.1037 | −0.1605 | 0.1352 | 0.051* | |
C13A | −0.0420 (4) | −0.1082 (3) | 0.06783 (11) | 0.0445 (9) | |
H13A | −0.0924 | −0.0862 | 0.0916 | 0.053* | |
H13B | −0.1133 | −0.1322 | 0.0451 | 0.053* | |
C14A | 0.0394 (3) | 0.0024 (3) | 0.05551 (9) | 0.0354 (8) | |
H14A | 0.0868 | −0.0182 | 0.0311 | 0.043* | |
H14B | −0.0260 | 0.0729 | 0.0486 | 0.043* | |
C15A | 0.3072 (4) | 0.0149 (3) | 0.31375 (9) | 0.0497 (10) | |
H15A | 0.3605 | 0.0758 | 0.3314 | 0.075* | |
H15B | 0.3574 | −0.0650 | 0.3153 | 0.075* | |
H15C | 0.2131 | 0.0038 | 0.3227 | 0.075* | |
P1B | 0.37122 (8) | 0.64805 (7) | 0.88129 (2) | 0.0233 (2) | |
O1B | 0.5141 (2) | 0.66601 (18) | 0.86859 (5) | 0.0279 (5) | |
O2B | 0.2944 (2) | 0.8999 (2) | 0.98557 (6) | 0.0360 (6) | |
O3B | 0.3413 (3) | 0.2389 (2) | 0.89916 (7) | 0.0492 (7) | |
N1B | 0.2416 (3) | 0.6832 (2) | 0.84674 (7) | 0.0246 (6) | |
H1BA | 0.172 (3) | 0.722 (3) | 0.8549 (8) | 0.031 (9)* | |
N2B | 0.3490 (2) | 0.7356 (2) | 0.92136 (6) | 0.0234 (6) | |
N3B | 0.3472 (2) | 0.5017 (2) | 0.89366 (7) | 0.0259 (6) | |
C1B | 0.2223 (3) | 0.6413 (3) | 0.80566 (8) | 0.0241 (7) | |
C2B | 0.1041 (3) | 0.6827 (3) | 0.78086 (8) | 0.0318 (8) | |
H2BA | 0.0397 | 0.7386 | 0.7915 | 0.038* | |
C3B | 0.0800 (4) | 0.6431 (3) | 0.74091 (9) | 0.0388 (9) | |
H3BA | −0.0009 | 0.6727 | 0.7244 | 0.047* | |
C4B | 0.1716 (4) | 0.5607 (3) | 0.72420 (9) | 0.0353 (8) | |
C5B | 0.2891 (3) | 0.5208 (3) | 0.74934 (9) | 0.0366 (8) | |
H5BA | 0.3536 | 0.4648 | 0.7388 | 0.044* | |
C6B | 0.3151 (3) | 0.5605 (3) | 0.78948 (8) | 0.0306 (8) | |
H6BA | 0.3968 | 0.5320 | 0.8059 | 0.037* | |
C7B | 0.3619 (3) | 0.8719 (3) | 0.91702 (8) | 0.0281 (7) | |
H7BA | 0.2721 | 0.9062 | 0.9036 | 0.034* | |
H7BB | 0.4377 | 0.8911 | 0.8996 | 0.034* | |
C8B | 0.3956 (3) | 0.9321 (3) | 0.95827 (9) | 0.0370 (8) | |
H8BA | 0.4907 | 0.9053 | 0.9701 | 0.044* | |
H8BB | 0.3973 | 1.0239 | 0.9550 | 0.044* | |
C9B | 0.2883 (3) | 0.7674 (3) | 0.99015 (8) | 0.0356 (8) | |
H9BA | 0.2189 | 0.7465 | 1.0094 | 0.043* | |
H9BB | 0.3819 | 0.7364 | 1.0018 | 0.043* | |
C10B | 0.2472 (3) | 0.7032 (3) | 0.95036 (8) | 0.0279 (7) | |
H10C | 0.2463 | 0.6118 | 0.9545 | 0.033* | |
H10D | 0.1510 | 0.7296 | 0.9393 | 0.033* | |
C11B | 0.2147 (3) | 0.4322 (3) | 0.88771 (9) | 0.0310 (8) | |
H11C | 0.1465 | 0.4769 | 0.8681 | 0.037* | |
H11D | 0.1732 | 0.4254 | 0.9139 | 0.037* | |
C12B | 0.2423 (4) | 0.3039 (3) | 0.87168 (10) | 0.0431 (9) | |
H12C | 0.1526 | 0.2564 | 0.8679 | 0.052* | |
H12D | 0.2793 | 0.3111 | 0.8448 | 0.052* | |
C13B | 0.4719 (4) | 0.3034 (3) | 0.90311 (11) | 0.0426 (9) | |
H13C | 0.5083 | 0.3082 | 0.8761 | 0.051* | |
H13D | 0.5413 | 0.2562 | 0.9216 | 0.051* | |
C14B | 0.4582 (3) | 0.4335 (3) | 0.91956 (9) | 0.0350 (8) | |
H14C | 0.4332 | 0.4295 | 0.9479 | 0.042* | |
H14D | 0.5495 | 0.4779 | 0.9198 | 0.042* | |
C15B | 0.1447 (4) | 0.5134 (3) | 0.68097 (9) | 0.0477 (10) | |
H15D | 0.0653 | 0.5592 | 0.6666 | 0.072* | |
H15E | 0.1219 | 0.4243 | 0.6813 | 0.072* | |
H15F | 0.2294 | 0.5261 | 0.6669 | 0.072* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1A | 0.0185 (4) | 0.0294 (5) | 0.0183 (4) | 0.0009 (4) | 0.0011 (3) | 0.0015 (3) |
O1A | 0.0181 (12) | 0.0387 (13) | 0.0275 (10) | 0.0018 (9) | 0.0038 (9) | 0.0019 (10) |
O2A | 0.0372 (15) | 0.0364 (15) | 0.0349 (12) | −0.0030 (11) | 0.0037 (10) | 0.0098 (11) |
O3A | 0.0428 (16) | 0.0316 (14) | 0.0631 (15) | −0.0007 (11) | 0.0056 (13) | −0.0058 (12) |
N1A | 0.0177 (16) | 0.0358 (17) | 0.0188 (12) | −0.0064 (13) | 0.0010 (11) | 0.0061 (12) |
N2A | 0.0184 (14) | 0.0269 (15) | 0.0195 (11) | 0.0023 (11) | 0.0040 (10) | 0.0015 (11) |
N3A | 0.0249 (15) | 0.0244 (15) | 0.0291 (13) | 0.0036 (11) | −0.0016 (11) | 0.0014 (11) |
C1A | 0.0236 (18) | 0.0286 (18) | 0.0205 (14) | 0.0048 (14) | 0.0029 (12) | 0.0010 (14) |
C2A | 0.032 (2) | 0.034 (2) | 0.0257 (15) | −0.0073 (15) | −0.0007 (14) | 0.0006 (14) |
C3A | 0.043 (2) | 0.043 (2) | 0.0235 (16) | −0.0013 (17) | −0.0076 (15) | 0.0032 (16) |
C4A | 0.049 (2) | 0.037 (2) | 0.0213 (16) | 0.0057 (17) | 0.0033 (15) | 0.0027 (15) |
C5A | 0.034 (2) | 0.036 (2) | 0.0299 (16) | 0.0010 (16) | 0.0079 (14) | 0.0086 (15) |
C6A | 0.027 (2) | 0.037 (2) | 0.0270 (16) | −0.0028 (15) | −0.0013 (14) | 0.0071 (15) |
C7A | 0.0280 (19) | 0.0241 (18) | 0.0231 (15) | 0.0025 (14) | −0.0017 (13) | −0.0021 (13) |
C8A | 0.031 (2) | 0.031 (2) | 0.0345 (17) | 0.0010 (15) | 0.0012 (15) | 0.0045 (15) |
C9A | 0.032 (2) | 0.048 (2) | 0.0210 (15) | −0.0008 (16) | 0.0054 (13) | 0.0027 (16) |
C10A | 0.0248 (18) | 0.0348 (19) | 0.0215 (14) | −0.0003 (14) | 0.0062 (12) | 0.0010 (14) |
C11A | 0.032 (2) | 0.031 (2) | 0.0366 (18) | 0.0047 (15) | 0.0074 (15) | 0.0016 (15) |
C12A | 0.047 (2) | 0.032 (2) | 0.049 (2) | 0.0091 (17) | 0.0113 (18) | 0.0089 (17) |
C13A | 0.037 (2) | 0.034 (2) | 0.062 (2) | 0.0003 (17) | 0.0008 (18) | −0.0116 (18) |
C14A | 0.035 (2) | 0.039 (2) | 0.0303 (17) | 0.0029 (16) | −0.0048 (15) | −0.0100 (16) |
C15A | 0.068 (3) | 0.055 (3) | 0.0250 (17) | 0.002 (2) | 0.0030 (17) | 0.0112 (18) |
P1B | 0.0187 (5) | 0.0311 (5) | 0.0199 (4) | −0.0016 (4) | 0.0019 (3) | −0.0002 (4) |
O1B | 0.0176 (12) | 0.0384 (13) | 0.0280 (10) | −0.0051 (9) | 0.0031 (9) | −0.0022 (10) |
O2B | 0.0291 (14) | 0.0507 (16) | 0.0289 (11) | 0.0001 (11) | 0.0063 (10) | −0.0096 (11) |
O3B | 0.0555 (18) | 0.0375 (15) | 0.0550 (15) | 0.0029 (13) | 0.0083 (13) | 0.0053 (12) |
N1B | 0.0216 (16) | 0.0331 (17) | 0.0192 (12) | 0.0054 (12) | 0.0023 (11) | −0.0024 (11) |
N2B | 0.0219 (15) | 0.0298 (15) | 0.0187 (11) | −0.0043 (11) | 0.0025 (10) | 0.0012 (11) |
N3B | 0.0136 (14) | 0.0323 (15) | 0.0318 (13) | 0.0026 (11) | 0.0018 (11) | 0.0025 (12) |
C1B | 0.0251 (18) | 0.0237 (18) | 0.0227 (14) | −0.0033 (14) | −0.0008 (13) | −0.0007 (13) |
C2B | 0.036 (2) | 0.031 (2) | 0.0271 (15) | 0.0035 (15) | −0.0013 (14) | −0.0039 (14) |
C3B | 0.043 (2) | 0.042 (2) | 0.0283 (16) | 0.0033 (17) | −0.0113 (15) | −0.0033 (16) |
C4B | 0.046 (2) | 0.035 (2) | 0.0246 (16) | −0.0082 (17) | 0.0004 (15) | −0.0006 (15) |
C5B | 0.039 (2) | 0.038 (2) | 0.0338 (17) | −0.0002 (16) | 0.0096 (16) | −0.0054 (16) |
C6B | 0.027 (2) | 0.040 (2) | 0.0245 (16) | 0.0040 (15) | −0.0002 (14) | −0.0052 (15) |
C7B | 0.0272 (19) | 0.032 (2) | 0.0249 (15) | −0.0022 (14) | 0.0023 (13) | 0.0014 (14) |
C8B | 0.030 (2) | 0.045 (2) | 0.0355 (18) | −0.0084 (16) | 0.0039 (15) | −0.0126 (16) |
C9B | 0.032 (2) | 0.050 (2) | 0.0247 (16) | 0.0035 (16) | 0.0028 (14) | 0.0013 (16) |
C10B | 0.0263 (19) | 0.036 (2) | 0.0218 (14) | 0.0008 (14) | 0.0065 (13) | 0.0010 (14) |
C11B | 0.0220 (19) | 0.034 (2) | 0.0376 (18) | −0.0060 (14) | 0.0059 (14) | 0.0032 (16) |
C12B | 0.043 (2) | 0.039 (2) | 0.047 (2) | −0.0116 (17) | 0.0010 (17) | 0.0005 (18) |
C13B | 0.035 (2) | 0.044 (2) | 0.050 (2) | 0.0146 (17) | 0.0091 (17) | 0.0123 (18) |
C14B | 0.0250 (19) | 0.042 (2) | 0.0384 (18) | 0.0018 (15) | 0.0057 (15) | 0.0126 (16) |
C15B | 0.069 (3) | 0.047 (2) | 0.0266 (17) | −0.004 (2) | 0.0008 (17) | −0.0068 (17) |
Geometric parameters (Å, º) top
P1A—O1A | 1.478 (2) | P1B—O1B | 1.477 (2) |
P1A—N3A | 1.630 (2) | P1B—N1B | 1.633 (2) |
P1A—N1A | 1.634 (2) | P1B—N3B | 1.643 (3) |
P1A—N2A | 1.652 (2) | P1B—N2B | 1.653 (2) |
O2A—C9A | 1.418 (4) | O2B—C8B | 1.428 (4) |
O2A—C8A | 1.434 (4) | O2B—C9B | 1.431 (4) |
O3A—C12A | 1.418 (4) | O3B—C13B | 1.417 (4) |
O3A—C13A | 1.426 (4) | O3B—C12B | 1.421 (4) |
N1A—C1A | 1.416 (3) | N1B—C1B | 1.421 (3) |
N1A—H1AA | 0.79 (3) | N1B—H1BA | 0.85 (3) |
N2A—C10A | 1.473 (3) | N2B—C10B | 1.474 (4) |
N2A—C7A | 1.473 (3) | N2B—C7B | 1.474 (4) |
N3A—C11A | 1.456 (3) | N3B—C11B | 1.460 (3) |
N3A—C14A | 1.471 (3) | N3B—C14B | 1.481 (3) |
C1A—C6A | 1.382 (4) | C1B—C6B | 1.384 (4) |
C1A—C2A | 1.394 (4) | C1B—C2B | 1.392 (4) |
C2A—C3A | 1.380 (4) | C2B—C3B | 1.381 (4) |
C2A—H2AA | 0.9500 | C2B—H2BA | 0.9500 |
C3A—C4A | 1.392 (4) | C3B—C4B | 1.395 (5) |
C3A—H3AA | 0.9500 | C3B—H3BA | 0.9500 |
C4A—C5A | 1.386 (4) | C4B—C5B | 1.388 (4) |
C4A—C15A | 1.508 (4) | C4B—C15B | 1.510 (4) |
C5A—C6A | 1.385 (4) | C5B—C6B | 1.388 (4) |
C5A—H5AA | 0.9500 | C5B—H5BA | 0.9500 |
C6A—H6AA | 0.9500 | C6B—H6BA | 0.9500 |
C7A—C8A | 1.498 (4) | C7B—C8B | 1.510 (4) |
C7A—H7AA | 0.9900 | C7B—H7BA | 0.9900 |
C7A—H7AB | 0.9900 | C7B—H7BB | 0.9900 |
C8A—H8AA | 0.9900 | C8B—H8BA | 0.9900 |
C8A—H8AB | 0.9900 | C8B—H8BB | 0.9900 |
C9A—C10A | 1.508 (4) | C9B—C10B | 1.497 (4) |
C9A—H9AA | 0.9900 | C9B—H9BA | 0.9900 |
C9A—H9AB | 0.9900 | C9B—H9BB | 0.9900 |
C10A—H10A | 0.9900 | C10B—H10C | 0.9900 |
C10A—H10B | 0.9900 | C10B—H10D | 0.9900 |
C11A—C12A | 1.524 (4) | C11B—C12B | 1.507 (4) |
C11A—H11A | 0.9900 | C11B—H11C | 0.9900 |
C11A—H11B | 0.9900 | C11B—H11D | 0.9900 |
C12A—H12A | 0.9900 | C12B—H12C | 0.9900 |
C12A—H12B | 0.9900 | C12B—H12D | 0.9900 |
C13A—C14A | 1.497 (5) | C13B—C14B | 1.507 (4) |
C13A—H13A | 0.9900 | C13B—H13C | 0.9900 |
C13A—H13B | 0.9900 | C13B—H13D | 0.9900 |
C14A—H14A | 0.9900 | C14B—H14C | 0.9900 |
C14A—H14B | 0.9900 | C14B—H14D | 0.9900 |
C15A—H15A | 0.9800 | C15B—H15D | 0.9800 |
C15A—H15B | 0.9800 | C15B—H15E | 0.9800 |
C15A—H15C | 0.9800 | C15B—H15F | 0.9800 |
| | | |
O1A—P1A—N3A | 113.64 (12) | O1B—P1B—N1B | 115.00 (13) |
O1A—P1A—N1A | 114.10 (12) | O1B—P1B—N3B | 110.58 (12) |
N3A—P1A—N1A | 106.59 (13) | N1B—P1B—N3B | 106.18 (13) |
O1A—P1A—N2A | 110.54 (11) | O1B—P1B—N2B | 110.57 (12) |
N3A—P1A—N2A | 103.66 (12) | N1B—P1B—N2B | 106.05 (13) |
N1A—P1A—N2A | 107.62 (13) | N3B—P1B—N2B | 108.12 (12) |
C9A—O2A—C8A | 109.0 (2) | C8B—O2B—C9B | 110.1 (2) |
C12A—O3A—C13A | 110.1 (2) | C13B—O3B—C12B | 109.6 (2) |
C1A—N1A—P1A | 128.0 (2) | C1B—N1B—P1B | 127.2 (2) |
C1A—N1A—H1AA | 114 (2) | C1B—N1B—H1BA | 115.6 (19) |
P1A—N1A—H1AA | 117 (2) | P1B—N1B—H1BA | 116.5 (19) |
C10A—N2A—C7A | 111.3 (2) | C10B—N2B—C7B | 111.3 (2) |
C10A—N2A—P1A | 122.62 (19) | C10B—N2B—P1B | 122.21 (19) |
C7A—N2A—P1A | 118.14 (18) | C7B—N2B—P1B | 117.82 (18) |
C11A—N3A—C14A | 111.1 (2) | C11B—N3B—C14B | 112.3 (2) |
C11A—N3A—P1A | 128.57 (19) | C11B—N3B—P1B | 126.49 (19) |
C14A—N3A—P1A | 119.4 (2) | C14B—N3B—P1B | 120.36 (19) |
C6A—C1A—C2A | 118.5 (3) | C6B—C1B—C2B | 118.8 (3) |
C6A—C1A—N1A | 123.0 (3) | C6B—C1B—N1B | 122.8 (3) |
C2A—C1A—N1A | 118.5 (3) | C2B—C1B—N1B | 118.4 (3) |
C3A—C2A—C1A | 120.4 (3) | C3B—C2B—C1B | 120.4 (3) |
C3A—C2A—H2AA | 119.8 | C3B—C2B—H2BA | 119.8 |
C1A—C2A—H2AA | 119.8 | C1B—C2B—H2BA | 119.8 |
C2A—C3A—C4A | 121.6 (3) | C2B—C3B—C4B | 121.6 (3) |
C2A—C3A—H3AA | 119.2 | C2B—C3B—H3BA | 119.2 |
C4A—C3A—H3AA | 119.2 | C4B—C3B—H3BA | 119.2 |
C5A—C4A—C3A | 117.4 (3) | C5B—C4B—C3B | 117.2 (3) |
C5A—C4A—C15A | 120.7 (3) | C5B—C4B—C15B | 120.5 (3) |
C3A—C4A—C15A | 121.9 (3) | C3B—C4B—C15B | 122.3 (3) |
C6A—C5A—C4A | 121.5 (3) | C6B—C5B—C4B | 121.8 (3) |
C6A—C5A—H5AA | 119.2 | C6B—C5B—H5BA | 119.1 |
C4A—C5A—H5AA | 119.2 | C4B—C5B—H5BA | 119.1 |
C1A—C6A—C5A | 120.6 (3) | C1B—C6B—C5B | 120.2 (3) |
C1A—C6A—H6AA | 119.7 | C1B—C6B—H6BA | 119.9 |
C5A—C6A—H6AA | 119.7 | C5B—C6B—H6BA | 119.9 |
N2A—C7A—C8A | 110.5 (2) | N2B—C7B—C8B | 110.4 (2) |
N2A—C7A—H7AA | 109.6 | N2B—C7B—H7BA | 109.6 |
C8A—C7A—H7AA | 109.6 | C8B—C7B—H7BA | 109.6 |
N2A—C7A—H7AB | 109.6 | N2B—C7B—H7BB | 109.6 |
C8A—C7A—H7AB | 109.6 | C8B—C7B—H7BB | 109.6 |
H7AA—C7A—H7AB | 108.1 | H7BA—C7B—H7BB | 108.1 |
O2A—C8A—C7A | 111.5 (2) | O2B—C8B—C7B | 111.8 (2) |
O2A—C8A—H8AA | 109.3 | O2B—C8B—H8BA | 109.3 |
C7A—C8A—H8AA | 109.3 | C7B—C8B—H8BA | 109.3 |
O2A—C8A—H8AB | 109.3 | O2B—C8B—H8BB | 109.3 |
C7A—C8A—H8AB | 109.3 | C7B—C8B—H8BB | 109.3 |
H8AA—C8A—H8AB | 108.0 | H8BA—C8B—H8BB | 107.9 |
O2A—C9A—C10A | 112.4 (2) | O2B—C9B—C10B | 111.9 (2) |
O2A—C9A—H9AA | 109.1 | O2B—C9B—H9BA | 109.2 |
C10A—C9A—H9AA | 109.1 | C10B—C9B—H9BA | 109.2 |
O2A—C9A—H9AB | 109.1 | O2B—C9B—H9BB | 109.2 |
C10A—C9A—H9AB | 109.1 | C10B—C9B—H9BB | 109.2 |
H9AA—C9A—H9AB | 107.9 | H9BA—C9B—H9BB | 107.9 |
N2A—C10A—C9A | 108.4 (2) | N2B—C10B—C9B | 109.4 (2) |
N2A—C10A—H10A | 110.0 | N2B—C10B—H10C | 109.8 |
C9A—C10A—H10A | 110.0 | C9B—C10B—H10C | 109.8 |
N2A—C10A—H10B | 110.0 | N2B—C10B—H10D | 109.8 |
C9A—C10A—H10B | 110.0 | C9B—C10B—H10D | 109.8 |
H10A—C10A—H10B | 108.4 | H10C—C10B—H10D | 108.3 |
N3A—C11A—C12A | 109.3 (3) | N3B—C11B—C12B | 109.5 (3) |
N3A—C11A—H11A | 109.8 | N3B—C11B—H11C | 109.8 |
C12A—C11A—H11A | 109.8 | C12B—C11B—H11C | 109.8 |
N3A—C11A—H11B | 109.8 | N3B—C11B—H11D | 109.8 |
C12A—C11A—H11B | 109.8 | C12B—C11B—H11D | 109.8 |
H11A—C11A—H11B | 108.3 | H11C—C11B—H11D | 108.2 |
O3A—C12A—C11A | 112.8 (3) | O3B—C12B—C11B | 110.6 (3) |
O3A—C12A—H12A | 109.0 | O3B—C12B—H12C | 109.5 |
C11A—C12A—H12A | 109.0 | C11B—C12B—H12C | 109.5 |
O3A—C12A—H12B | 109.0 | O3B—C12B—H12D | 109.5 |
C11A—C12A—H12B | 109.0 | C11B—C12B—H12D | 109.5 |
H12A—C12A—H12B | 107.8 | H12C—C12B—H12D | 108.1 |
O3A—C13A—C14A | 110.8 (3) | O3B—C13B—C14B | 112.1 (3) |
O3A—C13A—H13A | 109.5 | O3B—C13B—H13C | 109.2 |
C14A—C13A—H13A | 109.5 | C14B—C13B—H13C | 109.2 |
O3A—C13A—H13B | 109.5 | O3B—C13B—H13D | 109.2 |
C14A—C13A—H13B | 109.5 | C14B—C13B—H13D | 109.2 |
H13A—C13A—H13B | 108.1 | H13C—C13B—H13D | 107.9 |
N3A—C14A—C13A | 109.7 (3) | N3B—C14B—C13B | 109.4 (2) |
N3A—C14A—H14A | 109.7 | N3B—C14B—H14C | 109.8 |
C13A—C14A—H14A | 109.7 | C13B—C14B—H14C | 109.8 |
N3A—C14A—H14B | 109.7 | N3B—C14B—H14D | 109.8 |
C13A—C14A—H14B | 109.7 | C13B—C14B—H14D | 109.8 |
H14A—C14A—H14B | 108.2 | H14C—C14B—H14D | 108.2 |
C4A—C15A—H15A | 109.5 | C4B—C15B—H15D | 109.5 |
C4A—C15A—H15B | 109.5 | C4B—C15B—H15E | 109.5 |
H15A—C15A—H15B | 109.5 | H15D—C15B—H15E | 109.5 |
C4A—C15A—H15C | 109.5 | C4B—C15B—H15F | 109.5 |
H15A—C15A—H15C | 109.5 | H15D—C15B—H15F | 109.5 |
H15B—C15A—H15C | 109.5 | H15E—C15B—H15F | 109.5 |
| | | |
O1A—P1A—N1A—C1A | 35.8 (3) | O1B—P1B—N1B—C1B | 51.0 (3) |
N3A—P1A—N1A—C1A | −90.5 (3) | N3B—P1B—N1B—C1B | −71.7 (3) |
N2A—P1A—N1A—C1A | 158.8 (3) | N2B—P1B—N1B—C1B | 173.5 (3) |
O1A—P1A—N2A—C10A | −160.0 (2) | O1B—P1B—N2B—C10B | −154.6 (2) |
N3A—P1A—N2A—C10A | −37.8 (2) | N1B—P1B—N2B—C10B | 80.1 (2) |
N1A—P1A—N2A—C10A | 74.8 (2) | N3B—P1B—N2B—C10B | −33.5 (2) |
O1A—P1A—N2A—C7A | 53.8 (2) | O1B—P1B—N2B—C7B | 60.4 (2) |
N3A—P1A—N2A—C7A | 175.95 (19) | N1B—P1B—N2B—C7B | −64.9 (2) |
N1A—P1A—N2A—C7A | −71.4 (2) | N3B—P1B—N2B—C7B | −178.39 (19) |
O1A—P1A—N3A—C11A | −115.6 (3) | O1B—P1B—N3B—C11B | −146.5 (2) |
N1A—P1A—N3A—C11A | 11.0 (3) | N1B—P1B—N3B—C11B | −21.1 (3) |
N2A—P1A—N3A—C11A | 124.4 (3) | N2B—P1B—N3B—C11B | 92.4 (3) |
O1A—P1A—N3A—C14A | 52.9 (3) | O1B—P1B—N3B—C14B | 44.9 (2) |
N1A—P1A—N3A—C14A | 179.4 (2) | N1B—P1B—N3B—C14B | 170.3 (2) |
N2A—P1A—N3A—C14A | −67.2 (2) | N2B—P1B—N3B—C14B | −76.3 (2) |
P1A—N1A—C1A—C6A | 16.8 (5) | P1B—N1B—C1B—C6B | 0.9 (5) |
P1A—N1A—C1A—C2A | −164.6 (2) | P1B—N1B—C1B—C2B | −179.7 (2) |
C6A—C1A—C2A—C3A | 0.3 (5) | C6B—C1B—C2B—C3B | 0.3 (5) |
N1A—C1A—C2A—C3A | −178.4 (3) | N1B—C1B—C2B—C3B | −179.1 (3) |
C1A—C2A—C3A—C4A | 0.0 (5) | C1B—C2B—C3B—C4B | 0.3 (5) |
C2A—C3A—C4A—C5A | 0.0 (5) | C2B—C3B—C4B—C5B | −0.6 (5) |
C2A—C3A—C4A—C15A | 178.0 (3) | C2B—C3B—C4B—C15B | 178.1 (3) |
C3A—C4A—C5A—C6A | −0.3 (5) | C3B—C4B—C5B—C6B | 0.2 (5) |
C15A—C4A—C5A—C6A | −178.4 (3) | C15B—C4B—C5B—C6B | −178.6 (3) |
C2A—C1A—C6A—C5A | −0.6 (5) | C2B—C1B—C6B—C5B | −0.7 (5) |
N1A—C1A—C6A—C5A | 178.0 (3) | N1B—C1B—C6B—C5B | 178.7 (3) |
C4A—C5A—C6A—C1A | 0.7 (5) | C4B—C5B—C6B—C1B | 0.5 (5) |
C10A—N2A—C7A—C8A | 54.1 (3) | C10B—N2B—C7B—C8B | 53.6 (3) |
P1A—N2A—C7A—C8A | −156.1 (2) | P1B—N2B—C7B—C8B | −157.9 (2) |
C9A—O2A—C8A—C7A | 59.2 (3) | C9B—O2B—C8B—C7B | 57.8 (3) |
N2A—C7A—C8A—O2A | −56.3 (3) | N2B—C7B—C8B—O2B | −55.1 (3) |
C8A—O2A—C9A—C10A | −61.1 (3) | C8B—O2B—C9B—C10B | −59.7 (3) |
C7A—N2A—C10A—C9A | −54.2 (3) | C7B—N2B—C10B—C9B | −54.8 (3) |
P1A—N2A—C10A—C9A | 157.56 (19) | P1B—N2B—C10B—C9B | 158.3 (2) |
O2A—C9A—C10A—N2A | 58.7 (3) | O2B—C9B—C10B—N2B | 58.0 (3) |
C14A—N3A—C11A—C12A | −53.8 (3) | C14B—N3B—C11B—C12B | −53.8 (3) |
P1A—N3A—C11A—C12A | 115.5 (3) | P1B—N3B—C11B—C12B | 136.8 (2) |
C13A—O3A—C12A—C11A | −57.7 (4) | C13B—O3B—C12B—C11B | −62.0 (3) |
N3A—C11A—C12A—O3A | 54.9 (4) | N3B—C11B—C12B—O3B | 58.7 (3) |
C12A—O3A—C13A—C14A | 59.6 (4) | C12B—O3B—C13B—C14B | 60.6 (3) |
C11A—N3A—C14A—C13A | 56.9 (3) | C11B—N3B—C14B—C13B | 51.7 (3) |
P1A—N3A—C14A—C13A | −113.5 (3) | P1B—N3B—C14B—C13B | −138.1 (2) |
O3A—C13A—C14A—N3A | −59.2 (4) | O3B—C13B—C14B—N3B | −54.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1AA···O1Bi | 0.79 (3) | 1.99 (3) | 2.780 (4) | 179 (2) |
N1B—H1BA···O1Aii | 0.85 (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 formula | C15H24N3O3P |
Mr | 325.34 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 120 |
a, b, c (Å) | 9.517 (3), 10.723 (3), 32.993 (8) |
β (°) | 96.029 (6) |
V (Å3) | 3348.3 (16) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.50 × 0.15 × 0.05 |
|
Data collection |
Diffractometer | Bruker SMART 1000 CCD area detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16054, 6459, 3369 |
Rint | 0.068 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.119, 0.87 |
No. of reflections | 6459 |
No. of parameters | 407 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.42, −0.36 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1AA···O1Bi | 0.79 (3) | 1.99 (3) | 2.780 (4) | 179 (2) |
N1B—H1BA···O1Aii | 0.85 (3) | 1.95 (3) | 2.804 (3) | 179 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1. |