organic compounds
N,N′-Dibenzyl-N,N′-dimethyl-N′′-(p-tolyl)phosphoric triamide
aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran, and bDepartment of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com
The 23H28N3OP, contains two independent molecules with significant conformational differences. For example, the torsion angles N—C—C—C involving the N-benzyl moieties are 57.3 (7) and 11.6 (8)° in one molecule and 76.5 (7) and 97.4 (7)° in the other. In each molecule, the P atom exhibits a distorted tetrahedral conformation [the bond angles at P are in the ranges 104.7 (2)–115.2 (2) and 105.1 (2)–115.1 (2)° in the two molecules], and the phosphoryl group and the N—H group adopt an anti orientation with respect to one another. In the crystal, molecules are linked via N—H⋯O(P) hydrogen bonds, forming a chain parallel to the a axis.
of the title compound, CRelated literature
For background to the synthesis of related compounds, see: Toghraee et al., (2011). For related structures, see: Gholivand & Mahzouni (2011); Pourayoubi et al. (2011).
Experimental
Crystal data
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Refinement
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Data collection: COLLECT (Hooft, 1998); cell DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and enCIFer (Allen et al., 2004).
Supporting information
https://doi.org/10.1107/S1600536811046046/nc2247sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046046/nc2247Isup2.hkl
To a solution of 4-CH3—C6H4NHP(O)Cl2 in chloroform, a solution of N-methylbenzylamine in chloroform was added dropwise at 273 K. After stirring for 4 h, the solvent was evaporated at room temperature and the obtained solid was washed with distilled water to remove N-methylbenzylamine hydrochloride salt. Single crystals, suitable for X-ray crystallography, were obtained from a solution of title compound in chloroform after slow evaporation at room temperature.
The H-atoms were included at geometrically idealized positions with N—H distances 0.88 Å and C—H distances = 0.95, 0.98 and 0.99 Å for aryl, methyl and methylene type H-atoms, respectively. The methyl H-atoms at C1 were disordered over six sites with equal site occupancy factors. The H-atoms were assigned Uiso = 1.5 times Ueq C1 atom and 1.2 times Ueq of the rest of the parent atoms (C/N). The ADSYMM option in Platon suggests a pseudo-translation in the direction of the c-axis. Indeed the structure can also be refined in the
which leads to a strong disorder of the phenyl rings and practically no improvement of the reliability factors. This is in agreement with the results of the of the which shows that the torsion of the phenyl rings is different. Therefore, we decided to perform the in the In this context it is noted that the intensity of the super structure reflections is very low and therefore, only about 60% of all independent reflections are observed, which might also be responsible for the low reliability factors.In continuation of our investigations on the synthesis of new phosphoramidates (Toghraee et al., 2011; Pourayoubi et al., 2011) we now report the synthesis and
of the title phosphoric triamide.The ═O)(N)(N)2 environment with the bond angles in the range of 104.7 (2)° to 115.2 (2)° for P1 and 105.1 (2)° to 115.1 (2)° for P2. The P═O and P—N bond lengths and the P—N—C bond angles are within the expected values for analogous compounds reported in the literature (Gholivand et al., 2011). In both molecules, the P—N bond lengths of the P(O)[NHC6H4(4-CH3)] fragments (1.646 (5) Å and 1.653 (4) Å, respectively, for molecules labeled with P1 and P2) are between the values of the P—N bonds in the P(O)[N(CH3)(CH2C6H5)]2 moieties (P1: 1.639 (5) Å & 1.660 (5) Å and P2: 1.634 (5) Å & 1.661 (5) Å).
of the title compound (Fig. 1) contains two independent molecules with significant conformational differences. The torsion angles N1–C2–C3–C4 and N2–C10–C11–C16 involving the N-benzyl moiety in one molecule are: 57.3 (7) and 11.6 (8)°, respectively, compared to the corresponding angles in the second molecule with values 76.5 (7) and 97.4 (7)° (for torsion angles N5–C33–C34–C35 and N4–C25–C26–C31, respectively). In each molecule, the P atom adopts a distorted tetrahedral coordination P(In the crystal packing, the molecules are hydrogen bonded to each other resulting in a chain along to the a axis in an alternating sequence (Fig. 2).
For background to the synthesis of related compounds, see: Toghraee et al., (2011). For related structures, see: Gholivand & Mahzouni (2011); Pourayoubi et al. (2011).
Data collection: COLLECT (Hooft, 1998); cell
DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and enCIFer (Allen et al., 2004).C23H28N3OP | F(000) = 1680 |
Mr = 393.45 | Dx = 1.240 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 6919 reflections |
a = 9.9621 (3) Å | θ = 1.0–26.0° |
b = 14.8245 (5) Å | µ = 0.15 mm−1 |
c = 28.8407 (10) Å | T = 173 K |
β = 98.2682 (14)° | Prism, colorless |
V = 4215.0 (2) Å3 | 0.06 × 0.05 × 0.04 mm |
Z = 8 |
Nonius KappaCCD diffractometer with APEXII detector | 7788 independent reflections |
Radiation source: fine-focus sealed tube | 4450 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
ω and φ scans | θmax = 26.0°, θmin = 2.1° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −12→12 |
Tmin = 0.991, Tmax = 0.994 | k = −18→18 |
13508 measured reflections | l = −35→35 |
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)] = 0.104 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 1.15 | w = 1/[σ2(Fo2) + 17.8P] where P = (Fo2 + 2Fc2)/3 |
7788 reflections | (Δ/σ)max = 0.002 |
508 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C23H28N3OP | V = 4215.0 (2) Å3 |
Mr = 393.45 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.9621 (3) Å | µ = 0.15 mm−1 |
b = 14.8245 (5) Å | T = 173 K |
c = 28.8407 (10) Å | 0.06 × 0.05 × 0.04 mm |
β = 98.2682 (14)° |
Nonius KappaCCD diffractometer with APEXII detector | 7788 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 4450 reflections with I > 2σ(I) |
Tmin = 0.991, Tmax = 0.994 | Rint = 0.074 |
13508 measured reflections |
R[F2 > 2σ(F2)] = 0.104 | 0 restraints |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 1.15 | w = 1/[σ2(Fo2) + 17.8P] where P = (Fo2 + 2Fc2)/3 |
7788 reflections | Δρmax = 0.32 e Å−3 |
508 parameters | Δρmin = −0.33 e Å−3 |
Experimental. IR (KBr, cm-1): 3178, 3014, 2913, 1610, 1451, 1326, 1187, 1005, 942, 817. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
P1 | 0.79811 (14) | 0.81400 (11) | 0.52504 (5) | 0.0261 (3) | |
O1 | 0.9321 (4) | 0.7937 (3) | 0.51123 (14) | 0.0364 (10) | |
N1 | 0.7853 (4) | 0.9218 (3) | 0.53627 (16) | 0.0298 (11) | |
N2 | 0.7750 (4) | 0.7533 (3) | 0.57164 (15) | 0.0274 (11) | |
N3 | 0.6671 (4) | 0.7895 (3) | 0.48547 (15) | 0.0295 (11) | |
H3N | 0.6123 | 0.7464 | 0.4922 | 0.035* | |
C1 | 0.6567 (6) | 0.9707 (4) | 0.5311 (2) | 0.0381 (15) | |
H1A | 0.5820 | 0.9286 | 0.5215 | 0.057* | 0.50 |
H1B | 0.6571 | 1.0177 | 0.5072 | 0.057* | 0.50 |
H1C | 0.6449 | 0.9985 | 0.5610 | 0.057* | 0.50 |
H1D | 0.6740 | 1.0345 | 0.5383 | 0.057* | 0.50 |
H1E | 0.5989 | 0.9455 | 0.5526 | 0.057* | 0.50 |
H1F | 0.6111 | 0.9647 | 0.4988 | 0.057* | 0.50 |
C2 | 0.9044 (6) | 0.9791 (4) | 0.5503 (2) | 0.0349 (15) | |
H2A | 0.9046 | 1.0287 | 0.5273 | 0.042* | |
H2B | 0.9875 | 0.9429 | 0.5495 | 0.042* | |
C3 | 0.9086 (5) | 1.0190 (4) | 0.59821 (19) | 0.0270 (13) | |
C4 | 0.9063 (6) | 0.9621 (4) | 0.6366 (2) | 0.0386 (15) | |
H4 | 0.9031 | 0.8985 | 0.6324 | 0.046* | |
C5 | 0.9086 (7) | 0.9988 (4) | 0.6806 (2) | 0.0467 (17) | |
H5 | 0.9068 | 0.9599 | 0.7067 | 0.056* | |
C6 | 0.9135 (7) | 1.0905 (5) | 0.6874 (2) | 0.0464 (17) | |
H6 | 0.9155 | 1.1148 | 0.7180 | 0.056* | |
C7 | 0.9153 (6) | 1.1463 (5) | 0.6501 (2) | 0.0432 (17) | |
H7 | 0.9192 | 1.2098 | 0.6546 | 0.052* | |
C8 | 0.9116 (6) | 1.1112 (4) | 0.6054 (2) | 0.0340 (14) | |
H8 | 0.9111 | 1.1509 | 0.5795 | 0.041* | |
C9 | 0.7891 (6) | 0.6548 (4) | 0.5673 (2) | 0.0397 (16) | |
H9A | 0.8097 | 0.6280 | 0.5985 | 0.048* | |
H9B | 0.8628 | 0.6415 | 0.5492 | 0.048* | |
H9C | 0.7040 | 0.6295 | 0.5512 | 0.048* | |
C10 | 0.6726 (5) | 0.7793 (4) | 0.60118 (19) | 0.0323 (14) | |
H10A | 0.5884 | 0.7450 | 0.5908 | 0.039* | |
H10B | 0.6515 | 0.8441 | 0.5961 | 0.039* | |
C11 | 0.7145 (5) | 0.7634 (4) | 0.65308 (19) | 0.0278 (13) | |
C12 | 0.6183 (6) | 0.7749 (4) | 0.68242 (19) | 0.0328 (14) | |
H12 | 0.5273 | 0.7882 | 0.6695 | 0.039* | |
C13 | 0.6524 (6) | 0.7673 (4) | 0.7307 (2) | 0.0388 (15) | |
H13 | 0.5852 | 0.7760 | 0.7505 | 0.047* | |
C14 | 0.7856 (6) | 0.7468 (5) | 0.7501 (2) | 0.0447 (17) | |
H14 | 0.8099 | 0.7422 | 0.7831 | 0.054* | |
C15 | 0.8803 (6) | 0.7335 (4) | 0.7208 (2) | 0.0399 (16) | |
H15 | 0.9706 | 0.7180 | 0.7336 | 0.048* | |
C16 | 0.8458 (6) | 0.7424 (4) | 0.67252 (19) | 0.0308 (13) | |
H16 | 0.9132 | 0.7341 | 0.6527 | 0.037* | |
C17 | 0.6360 (5) | 0.8324 (4) | 0.44145 (19) | 0.0270 (13) | |
C18 | 0.7352 (6) | 0.8716 (4) | 0.4181 (2) | 0.0368 (15) | |
H18 | 0.8276 | 0.8695 | 0.4320 | 0.044* | |
C19 | 0.7010 (6) | 0.9127 (5) | 0.3758 (2) | 0.0420 (17) | |
H19 | 0.7706 | 0.9383 | 0.3606 | 0.050* | |
C20 | 0.5668 (6) | 0.9183 (4) | 0.3542 (2) | 0.0355 (15) | |
C21 | 0.4688 (6) | 0.8791 (4) | 0.3772 (2) | 0.0360 (15) | |
H21 | 0.3763 | 0.8818 | 0.3634 | 0.043* | |
C22 | 0.5024 (5) | 0.8364 (4) | 0.41954 (19) | 0.0277 (13) | |
H22 | 0.4330 | 0.8091 | 0.4341 | 0.033* | |
C23 | 0.5297 (7) | 0.9651 (5) | 0.3071 (2) | 0.0492 (18) | |
H23A | 0.4310 | 0.9646 | 0.2982 | 0.059* | |
H23B | 0.5723 | 0.9333 | 0.2832 | 0.059* | |
H23C | 0.5621 | 1.0276 | 0.3094 | 0.059* | |
P2 | 0.70017 (14) | 0.31166 (11) | 0.47176 (5) | 0.0258 (3) | |
O2 | 0.5670 (4) | 0.2915 (3) | 0.48617 (13) | 0.0315 (10) | |
N4 | 0.7215 (4) | 0.2499 (3) | 0.42532 (15) | 0.0286 (11) | |
N5 | 0.7131 (4) | 0.4189 (3) | 0.45992 (16) | 0.0286 (11) | |
N6 | 0.8327 (4) | 0.2883 (3) | 0.51137 (15) | 0.0277 (11) | |
H6N | 0.8884 | 0.2455 | 0.5050 | 0.033* | |
C24 | 0.6886 (6) | 0.1534 (4) | 0.4276 (2) | 0.0378 (15) | |
H24A | 0.6478 | 0.1324 | 0.3966 | 0.045* | |
H24B | 0.6244 | 0.1444 | 0.4500 | 0.045* | |
H24C | 0.7717 | 0.1192 | 0.4379 | 0.045* | |
C25 | 0.8327 (5) | 0.2691 (4) | 0.39825 (19) | 0.0323 (14) | |
H25A | 0.9089 | 0.2275 | 0.4085 | 0.039* | |
H25B | 0.8654 | 0.3314 | 0.4052 | 0.039* | |
C26 | 0.7919 (5) | 0.2594 (5) | 0.3457 (2) | 0.0330 (14) | |
C27 | 0.7932 (6) | 0.1764 (5) | 0.3239 (2) | 0.0428 (16) | |
H27 | 0.8191 | 0.1239 | 0.3418 | 0.051* | |
C28 | 0.7561 (7) | 0.1696 (6) | 0.2749 (2) | 0.058 (2) | |
H28 | 0.7560 | 0.1125 | 0.2600 | 0.070* | |
C29 | 0.7202 (7) | 0.2455 (8) | 0.2489 (3) | 0.067 (3) | |
H29 | 0.6954 | 0.2412 | 0.2160 | 0.080* | |
C30 | 0.7202 (7) | 0.3267 (7) | 0.2705 (2) | 0.064 (2) | |
H30 | 0.6956 | 0.3792 | 0.2524 | 0.076* | |
C31 | 0.7554 (6) | 0.3344 (5) | 0.3183 (2) | 0.0442 (17) | |
H31 | 0.7545 | 0.3920 | 0.3327 | 0.053* | |
C32 | 0.8413 (6) | 0.4676 (4) | 0.4625 (2) | 0.0408 (16) | |
H32A | 0.9169 | 0.4250 | 0.4691 | 0.061* | 0.50 |
H32B | 0.8471 | 0.5126 | 0.4876 | 0.061* | 0.50 |
H32C | 0.8461 | 0.4978 | 0.4326 | 0.061* | 0.50 |
H32D | 0.8232 | 0.5320 | 0.4571 | 0.061* | 0.50 |
H32E | 0.8929 | 0.4443 | 0.4386 | 0.061* | 0.50 |
H32F | 0.8940 | 0.4591 | 0.4936 | 0.061* | 0.50 |
C33 | 0.5917 (6) | 0.4758 (4) | 0.4501 (2) | 0.0359 (15) | |
H33A | 0.5993 | 0.5263 | 0.4728 | 0.043* | |
H33B | 0.5111 | 0.4397 | 0.4548 | 0.043* | |
C34 | 0.5701 (6) | 0.5140 (4) | 0.4010 (2) | 0.0313 (14) | |
C35 | 0.5201 (6) | 0.4618 (4) | 0.3632 (2) | 0.0389 (15) | |
H35 | 0.5000 | 0.4001 | 0.3677 | 0.047* | |
C36 | 0.4983 (7) | 0.4981 (5) | 0.3182 (2) | 0.0494 (19) | |
H36 | 0.4652 | 0.4609 | 0.2923 | 0.059* | |
C37 | 0.5248 (7) | 0.5884 (5) | 0.3113 (3) | 0.055 (2) | |
H37 | 0.5090 | 0.6137 | 0.2807 | 0.066* | |
C38 | 0.5743 (7) | 0.6414 (5) | 0.3492 (2) | 0.0494 (18) | |
H38 | 0.5931 | 0.7034 | 0.3450 | 0.059* | |
C39 | 0.5964 (6) | 0.6037 (4) | 0.3934 (2) | 0.0369 (15) | |
H39 | 0.6307 | 0.6406 | 0.4193 | 0.044* | |
C40 | 0.8616 (5) | 0.3334 (4) | 0.55505 (18) | 0.0261 (13) | |
C41 | 0.9962 (5) | 0.3371 (4) | 0.57746 (19) | 0.0268 (13) | |
H41 | 1.0668 | 0.3104 | 0.5632 | 0.032* | |
C42 | 1.0257 (6) | 0.3798 (4) | 0.6203 (2) | 0.0322 (14) | |
H42 | 1.1172 | 0.3813 | 0.6351 | 0.039* | |
C43 | 0.9261 (6) | 0.4207 (4) | 0.6426 (2) | 0.0350 (15) | |
C44 | 0.7931 (6) | 0.4161 (4) | 0.6199 (2) | 0.0389 (16) | |
H44 | 0.7226 | 0.4436 | 0.6339 | 0.047* | |
C45 | 0.7613 (6) | 0.3722 (4) | 0.5770 (2) | 0.0335 (14) | |
H45 | 0.6694 | 0.3688 | 0.5627 | 0.040* | |
C46 | 0.9598 (7) | 0.4691 (5) | 0.6886 (2) | 0.0507 (19) | |
H46A | 0.8840 | 0.4632 | 0.7066 | 0.061* | |
H46B | 0.9759 | 0.5331 | 0.6828 | 0.061* | |
H46C | 1.0416 | 0.4426 | 0.7063 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0268 (8) | 0.0310 (9) | 0.0199 (7) | 0.0050 (7) | 0.0011 (6) | −0.0013 (6) |
O1 | 0.027 (2) | 0.050 (3) | 0.032 (2) | 0.011 (2) | 0.0028 (17) | −0.007 (2) |
N1 | 0.025 (2) | 0.035 (3) | 0.028 (3) | 0.009 (2) | 0.001 (2) | −0.006 (2) |
N2 | 0.035 (3) | 0.025 (3) | 0.021 (2) | 0.003 (2) | −0.001 (2) | −0.002 (2) |
N3 | 0.030 (3) | 0.032 (3) | 0.025 (3) | −0.003 (2) | 0.001 (2) | 0.005 (2) |
C1 | 0.041 (4) | 0.039 (4) | 0.034 (3) | 0.016 (3) | 0.003 (3) | 0.000 (3) |
C2 | 0.032 (3) | 0.035 (4) | 0.038 (4) | 0.000 (3) | 0.007 (3) | −0.001 (3) |
C3 | 0.020 (3) | 0.033 (3) | 0.029 (3) | −0.002 (2) | 0.006 (2) | 0.002 (3) |
C4 | 0.053 (4) | 0.027 (3) | 0.033 (3) | −0.002 (3) | −0.004 (3) | −0.001 (3) |
C5 | 0.069 (5) | 0.035 (4) | 0.032 (4) | −0.010 (3) | −0.004 (3) | 0.004 (3) |
C6 | 0.058 (4) | 0.048 (4) | 0.031 (4) | −0.008 (4) | 0.000 (3) | −0.006 (3) |
C7 | 0.051 (4) | 0.031 (4) | 0.046 (4) | 0.000 (3) | 0.002 (3) | −0.006 (3) |
C8 | 0.037 (3) | 0.031 (4) | 0.034 (4) | 0.002 (3) | 0.007 (3) | 0.009 (3) |
C9 | 0.047 (4) | 0.034 (4) | 0.038 (4) | 0.006 (3) | 0.005 (3) | −0.003 (3) |
C10 | 0.028 (3) | 0.040 (4) | 0.027 (3) | 0.001 (3) | 0.002 (2) | −0.001 (3) |
C11 | 0.031 (3) | 0.026 (3) | 0.026 (3) | −0.004 (3) | 0.003 (2) | 0.004 (3) |
C12 | 0.031 (3) | 0.038 (4) | 0.029 (3) | −0.003 (3) | 0.004 (2) | 0.003 (3) |
C13 | 0.044 (4) | 0.036 (4) | 0.039 (4) | 0.000 (3) | 0.012 (3) | −0.001 (3) |
C14 | 0.054 (4) | 0.056 (4) | 0.023 (3) | −0.010 (4) | 0.003 (3) | 0.006 (3) |
C15 | 0.033 (3) | 0.050 (4) | 0.033 (3) | −0.006 (3) | −0.007 (3) | 0.011 (3) |
C16 | 0.033 (3) | 0.026 (3) | 0.033 (3) | −0.003 (3) | 0.003 (2) | 0.005 (3) |
C17 | 0.026 (3) | 0.029 (3) | 0.025 (3) | 0.002 (3) | 0.001 (2) | −0.003 (3) |
C18 | 0.025 (3) | 0.048 (4) | 0.037 (4) | −0.003 (3) | 0.003 (3) | 0.000 (3) |
C19 | 0.046 (4) | 0.049 (4) | 0.031 (3) | −0.013 (3) | 0.003 (3) | 0.009 (3) |
C20 | 0.043 (4) | 0.039 (4) | 0.023 (3) | 0.003 (3) | 0.003 (3) | −0.002 (3) |
C21 | 0.036 (3) | 0.041 (4) | 0.027 (3) | 0.009 (3) | −0.007 (3) | −0.003 (3) |
C22 | 0.026 (3) | 0.034 (3) | 0.025 (3) | −0.002 (3) | 0.010 (2) | 0.001 (3) |
C23 | 0.064 (5) | 0.054 (5) | 0.028 (4) | −0.005 (4) | 0.001 (3) | 0.012 (3) |
P2 | 0.0239 (7) | 0.0327 (9) | 0.0204 (7) | −0.0018 (7) | 0.0021 (6) | 0.0029 (7) |
O2 | 0.026 (2) | 0.041 (3) | 0.027 (2) | −0.0002 (18) | 0.0027 (16) | 0.0055 (19) |
N4 | 0.029 (3) | 0.036 (3) | 0.021 (2) | −0.007 (2) | 0.005 (2) | −0.002 (2) |
N5 | 0.029 (3) | 0.031 (3) | 0.026 (3) | 0.000 (2) | 0.004 (2) | 0.004 (2) |
N6 | 0.028 (3) | 0.029 (3) | 0.025 (2) | 0.004 (2) | 0.0017 (19) | −0.006 (2) |
C24 | 0.042 (4) | 0.036 (4) | 0.036 (4) | −0.005 (3) | 0.007 (3) | −0.001 (3) |
C25 | 0.025 (3) | 0.046 (4) | 0.026 (3) | −0.001 (3) | 0.001 (2) | −0.003 (3) |
C26 | 0.022 (3) | 0.050 (4) | 0.027 (3) | 0.001 (3) | 0.002 (2) | 0.006 (3) |
C27 | 0.037 (3) | 0.047 (4) | 0.047 (4) | −0.006 (3) | 0.015 (3) | −0.010 (3) |
C28 | 0.050 (4) | 0.084 (6) | 0.043 (4) | −0.020 (4) | 0.016 (3) | −0.023 (4) |
C29 | 0.047 (5) | 0.122 (8) | 0.032 (4) | −0.015 (5) | 0.006 (3) | −0.011 (5) |
C30 | 0.042 (4) | 0.118 (8) | 0.032 (4) | 0.011 (5) | 0.010 (3) | 0.030 (5) |
C31 | 0.031 (3) | 0.068 (5) | 0.039 (4) | 0.005 (3) | 0.022 (3) | 0.008 (3) |
C32 | 0.033 (3) | 0.039 (4) | 0.051 (4) | −0.008 (3) | 0.005 (3) | −0.004 (3) |
C33 | 0.039 (4) | 0.037 (4) | 0.032 (3) | 0.002 (3) | 0.009 (3) | 0.001 (3) |
C34 | 0.032 (3) | 0.034 (4) | 0.029 (3) | 0.007 (3) | 0.007 (3) | 0.003 (3) |
C35 | 0.048 (4) | 0.035 (4) | 0.032 (3) | 0.009 (3) | 0.001 (3) | −0.003 (3) |
C36 | 0.058 (4) | 0.064 (5) | 0.025 (3) | 0.026 (4) | 0.002 (3) | −0.011 (3) |
C37 | 0.060 (5) | 0.065 (5) | 0.041 (4) | 0.026 (4) | 0.016 (3) | 0.018 (4) |
C38 | 0.056 (4) | 0.049 (5) | 0.045 (4) | 0.017 (4) | 0.013 (3) | 0.018 (4) |
C39 | 0.037 (4) | 0.035 (4) | 0.037 (4) | 0.007 (3) | 0.004 (3) | 0.005 (3) |
C40 | 0.034 (3) | 0.023 (3) | 0.019 (3) | 0.001 (2) | −0.003 (2) | 0.001 (2) |
C41 | 0.027 (3) | 0.029 (3) | 0.025 (3) | 0.002 (3) | 0.006 (2) | 0.003 (3) |
C42 | 0.032 (3) | 0.032 (4) | 0.031 (3) | 0.001 (3) | −0.001 (3) | −0.001 (3) |
C43 | 0.046 (4) | 0.033 (4) | 0.025 (3) | 0.003 (3) | −0.001 (3) | 0.001 (3) |
C44 | 0.045 (4) | 0.040 (4) | 0.032 (3) | 0.011 (3) | 0.009 (3) | −0.009 (3) |
C45 | 0.031 (3) | 0.040 (4) | 0.029 (3) | 0.011 (3) | 0.005 (3) | −0.006 (3) |
C46 | 0.067 (5) | 0.044 (4) | 0.039 (4) | −0.005 (4) | 0.001 (3) | −0.008 (3) |
P1—O1 | 1.478 (4) | P2—O2 | 1.476 (4) |
P1—N1 | 1.639 (5) | P2—N5 | 1.634 (5) |
P1—N3 | 1.646 (5) | P2—N6 | 1.653 (4) |
P1—N2 | 1.660 (5) | P2—N4 | 1.661 (5) |
N1—C1 | 1.460 (7) | N4—C24 | 1.472 (7) |
N1—C2 | 1.469 (7) | N4—C25 | 1.472 (7) |
N2—C10 | 1.472 (7) | N5—C32 | 1.460 (7) |
N2—C9 | 1.474 (7) | N5—C33 | 1.469 (7) |
N3—C17 | 1.414 (7) | N6—C40 | 1.418 (7) |
N3—H3N | 0.8800 | N6—H6N | 0.8800 |
C1—H1A | 0.9800 | C24—H24A | 0.9800 |
C1—H1B | 0.9800 | C24—H24B | 0.9800 |
C1—H1C | 0.9800 | C24—H24C | 0.9800 |
C1—H1D | 0.9800 | C25—C26 | 1.518 (7) |
C1—H1E | 0.9800 | C25—H25A | 0.9900 |
C1—H1F | 0.9800 | C25—H25B | 0.9900 |
C2—C3 | 1.497 (8) | C26—C31 | 1.382 (9) |
C2—H2A | 0.9900 | C26—C27 | 1.383 (9) |
C2—H2B | 0.9900 | C27—C28 | 1.410 (9) |
C3—C8 | 1.383 (8) | C27—H27 | 0.9500 |
C3—C4 | 1.394 (8) | C28—C29 | 1.371 (11) |
C4—C5 | 1.379 (8) | C28—H28 | 0.9500 |
C4—H4 | 0.9500 | C29—C30 | 1.354 (12) |
C5—C6 | 1.374 (9) | C29—H29 | 0.9500 |
C5—H5 | 0.9500 | C30—C31 | 1.379 (9) |
C6—C7 | 1.360 (9) | C30—H30 | 0.9500 |
C6—H6 | 0.9500 | C31—H31 | 0.9500 |
C7—C8 | 1.385 (9) | C32—H32A | 0.9800 |
C7—H7 | 0.9500 | C32—H32B | 0.9800 |
C8—H8 | 0.9500 | C32—H32C | 0.9800 |
C9—H9A | 0.9800 | C32—H32D | 0.9800 |
C9—H9B | 0.9800 | C32—H32E | 0.9800 |
C9—H9C | 0.9800 | C32—H32F | 0.9800 |
C10—C11 | 1.513 (7) | C33—C34 | 1.510 (8) |
C10—H10A | 0.9900 | C33—H33A | 0.9900 |
C10—H10B | 0.9900 | C33—H33B | 0.9900 |
C11—C12 | 1.378 (7) | C34—C35 | 1.373 (8) |
C11—C16 | 1.382 (7) | C34—C39 | 1.379 (8) |
C12—C13 | 1.389 (8) | C35—C36 | 1.392 (8) |
C12—H12 | 0.9500 | C35—H35 | 0.9500 |
C13—C14 | 1.397 (8) | C36—C37 | 1.385 (10) |
C13—H13 | 0.9500 | C36—H36 | 0.9500 |
C14—C15 | 1.368 (8) | C37—C38 | 1.379 (10) |
C14—H14 | 0.9500 | C37—H37 | 0.9500 |
C15—C16 | 1.391 (7) | C38—C39 | 1.379 (8) |
C15—H15 | 0.9500 | C38—H38 | 0.9500 |
C16—H16 | 0.9500 | C39—H39 | 0.9500 |
C17—C22 | 1.390 (7) | C40—C45 | 1.384 (8) |
C17—C18 | 1.399 (8) | C40—C41 | 1.403 (7) |
C18—C19 | 1.364 (8) | C41—C42 | 1.381 (8) |
C18—H18 | 0.9500 | C41—H41 | 0.9500 |
C19—C20 | 1.394 (8) | C42—C43 | 1.397 (8) |
C19—H19 | 0.9500 | C42—H42 | 0.9500 |
C20—C21 | 1.386 (8) | C43—C44 | 1.393 (8) |
C20—C23 | 1.524 (8) | C43—C46 | 1.502 (8) |
C21—C22 | 1.373 (8) | C44—C45 | 1.393 (8) |
C21—H21 | 0.9500 | C44—H44 | 0.9500 |
C22—H22 | 0.9500 | C45—H45 | 0.9500 |
C23—H23A | 0.9800 | C46—H46A | 0.9800 |
C23—H23B | 0.9800 | C46—H46B | 0.9800 |
C23—H23C | 0.9800 | C46—H46C | 0.9800 |
O1—P1—N1 | 110.5 (3) | O2—P2—N5 | 110.9 (2) |
O1—P1—N3 | 115.2 (2) | O2—P2—N6 | 115.1 (2) |
N1—P1—N3 | 106.0 (2) | N5—P2—N6 | 105.6 (2) |
O1—P1—N2 | 110.1 (2) | O2—P2—N4 | 109.9 (2) |
N1—P1—N2 | 110.1 (2) | N5—P2—N4 | 110.1 (2) |
N3—P1—N2 | 104.7 (2) | N6—P2—N4 | 105.1 (2) |
C1—N1—C2 | 113.8 (5) | C24—N4—C25 | 113.7 (5) |
C1—N1—P1 | 123.7 (4) | C24—N4—P2 | 116.3 (4) |
C2—N1—P1 | 122.4 (4) | C25—N4—P2 | 121.0 (4) |
C10—N2—C9 | 113.0 (5) | C32—N5—C33 | 114.6 (5) |
C10—N2—P1 | 121.0 (4) | C32—N5—P2 | 124.4 (4) |
C9—N2—P1 | 116.2 (4) | C33—N5—P2 | 120.8 (4) |
C17—N3—P1 | 125.0 (4) | C40—N6—P2 | 123.7 (4) |
C17—N3—H3N | 117.5 | C40—N6—H6N | 118.1 |
P1—N3—H3N | 117.5 | P2—N6—H6N | 118.1 |
N1—C1—H1A | 109.5 | N4—C24—H24A | 109.5 |
N1—C1—H1B | 109.5 | N4—C24—H24B | 109.5 |
H1A—C1—H1B | 109.5 | H24A—C24—H24B | 109.5 |
N1—C1—H1C | 109.5 | N4—C24—H24C | 109.5 |
H1A—C1—H1C | 109.5 | H24A—C24—H24C | 109.5 |
H1B—C1—H1C | 109.5 | H24B—C24—H24C | 109.5 |
N1—C1—H1D | 109.5 | N4—C25—C26 | 113.4 (4) |
H1A—C1—H1D | 141.1 | N4—C25—H25A | 108.9 |
H1B—C1—H1D | 56.3 | C26—C25—H25A | 108.9 |
H1C—C1—H1D | 56.3 | N4—C25—H25B | 108.9 |
N1—C1—H1E | 109.5 | C26—C25—H25B | 108.9 |
H1A—C1—H1E | 56.3 | H25A—C25—H25B | 107.7 |
H1B—C1—H1E | 141.1 | C31—C26—C27 | 118.3 (6) |
H1C—C1—H1E | 56.3 | C31—C26—C25 | 120.3 (6) |
H1D—C1—H1E | 109.5 | C27—C26—C25 | 121.4 (6) |
N1—C1—H1F | 109.5 | C26—C27—C28 | 120.1 (7) |
H1A—C1—H1F | 56.3 | C26—C27—H27 | 119.9 |
H1B—C1—H1F | 56.3 | C28—C27—H27 | 119.9 |
H1C—C1—H1F | 141.1 | C29—C28—C27 | 119.9 (7) |
H1D—C1—H1F | 109.5 | C29—C28—H28 | 120.0 |
H1E—C1—H1F | 109.5 | C27—C28—H28 | 120.0 |
N1—C2—C3 | 113.4 (5) | C30—C29—C28 | 119.7 (7) |
N1—C2—H2A | 108.9 | C30—C29—H29 | 120.1 |
C3—C2—H2A | 108.9 | C28—C29—H29 | 120.1 |
N1—C2—H2B | 108.9 | C29—C30—C31 | 121.1 (8) |
C3—C2—H2B | 108.9 | C29—C30—H30 | 119.5 |
H2A—C2—H2B | 107.7 | C31—C30—H30 | 119.5 |
C8—C3—C4 | 118.8 (6) | C30—C31—C26 | 120.9 (7) |
C8—C3—C2 | 121.7 (5) | C30—C31—H31 | 119.5 |
C4—C3—C2 | 119.4 (5) | C26—C31—H31 | 119.5 |
C5—C4—C3 | 119.5 (6) | N5—C32—H32A | 109.5 |
C5—C4—H4 | 120.3 | N5—C32—H32B | 109.5 |
C3—C4—H4 | 120.3 | H32A—C32—H32B | 109.5 |
C6—C5—C4 | 121.2 (6) | N5—C32—H32C | 109.5 |
C6—C5—H5 | 119.4 | H32A—C32—H32C | 109.5 |
C4—C5—H5 | 119.4 | H32B—C32—H32C | 109.5 |
C7—C6—C5 | 119.5 (6) | N5—C32—H32D | 109.5 |
C7—C6—H6 | 120.2 | H32A—C32—H32D | 141.1 |
C5—C6—H6 | 120.2 | H32B—C32—H32D | 56.3 |
C6—C7—C8 | 120.5 (6) | H32C—C32—H32D | 56.3 |
C6—C7—H7 | 119.8 | N5—C32—H32E | 109.5 |
C8—C7—H7 | 119.8 | H32A—C32—H32E | 56.3 |
C3—C8—C7 | 120.5 (6) | H32B—C32—H32E | 141.1 |
C3—C8—H8 | 119.8 | H32C—C32—H32E | 56.3 |
C7—C8—H8 | 119.8 | H32D—C32—H32E | 109.5 |
N2—C9—H9A | 109.5 | N5—C32—H32F | 109.5 |
N2—C9—H9B | 109.5 | H32A—C32—H32F | 56.3 |
H9A—C9—H9B | 109.5 | H32B—C32—H32F | 56.3 |
N2—C9—H9C | 109.5 | H32C—C32—H32F | 141.1 |
H9A—C9—H9C | 109.5 | H32D—C32—H32F | 109.5 |
H9B—C9—H9C | 109.5 | H32E—C32—H32F | 109.5 |
N2—C10—C11 | 114.6 (4) | N5—C33—C34 | 113.5 (5) |
N2—C10—H10A | 108.6 | N5—C33—H33A | 108.9 |
C11—C10—H10A | 108.6 | C34—C33—H33A | 108.9 |
N2—C10—H10B | 108.6 | N5—C33—H33B | 108.9 |
C11—C10—H10B | 108.6 | C34—C33—H33B | 108.9 |
H10A—C10—H10B | 107.6 | H33A—C33—H33B | 107.7 |
C12—C11—C16 | 118.7 (5) | C35—C34—C39 | 118.1 (6) |
C12—C11—C10 | 118.1 (5) | C35—C34—C33 | 121.3 (6) |
C16—C11—C10 | 123.2 (5) | C39—C34—C33 | 120.5 (6) |
C11—C12—C13 | 120.9 (5) | C34—C35—C36 | 120.9 (6) |
C11—C12—H12 | 119.6 | C34—C35—H35 | 119.6 |
C13—C12—H12 | 119.6 | C36—C35—H35 | 119.6 |
C12—C13—C14 | 120.0 (6) | C37—C36—C35 | 120.1 (6) |
C12—C13—H13 | 120.0 | C37—C36—H36 | 120.0 |
C14—C13—H13 | 120.0 | C35—C36—H36 | 120.0 |
C15—C14—C13 | 118.9 (6) | C38—C37—C36 | 119.3 (7) |
C15—C14—H14 | 120.5 | C38—C37—H37 | 120.3 |
C13—C14—H14 | 120.5 | C36—C37—H37 | 120.3 |
C14—C15—C16 | 120.7 (6) | C39—C38—C37 | 119.6 (7) |
C14—C15—H15 | 119.7 | C39—C38—H38 | 120.2 |
C16—C15—H15 | 119.7 | C37—C38—H38 | 120.2 |
C11—C16—C15 | 120.7 (6) | C38—C39—C34 | 122.0 (7) |
C11—C16—H16 | 119.6 | C38—C39—H39 | 119.0 |
C15—C16—H16 | 119.6 | C34—C39—H39 | 119.0 |
C22—C17—C18 | 117.4 (5) | C45—C40—C41 | 118.6 (5) |
C22—C17—N3 | 120.0 (5) | C45—C40—N6 | 122.3 (5) |
C18—C17—N3 | 122.7 (5) | C41—C40—N6 | 119.1 (5) |
C19—C18—C17 | 120.9 (6) | C42—C41—C40 | 119.7 (5) |
C19—C18—H18 | 119.5 | C42—C41—H41 | 120.1 |
C17—C18—H18 | 119.5 | C40—C41—H41 | 120.1 |
C18—C19—C20 | 121.8 (6) | C41—C42—C43 | 122.5 (5) |
C18—C19—H19 | 119.1 | C41—C42—H42 | 118.7 |
C20—C19—H19 | 119.1 | C43—C42—H42 | 118.7 |
C21—C20—C19 | 117.3 (6) | C44—C43—C42 | 116.9 (5) |
C21—C20—C23 | 121.4 (6) | C44—C43—C46 | 121.0 (6) |
C19—C20—C23 | 121.3 (6) | C42—C43—C46 | 122.1 (6) |
C22—C21—C20 | 121.4 (5) | C45—C44—C43 | 121.3 (6) |
C22—C21—H21 | 119.3 | C45—C44—H44 | 119.3 |
C20—C21—H21 | 119.3 | C43—C44—H44 | 119.3 |
C21—C22—C17 | 121.3 (5) | C40—C45—C44 | 120.9 (5) |
C21—C22—H22 | 119.4 | C40—C45—H45 | 119.5 |
C17—C22—H22 | 119.4 | C44—C45—H45 | 119.5 |
C20—C23—H23A | 109.5 | C43—C46—H46A | 109.5 |
C20—C23—H23B | 109.5 | C43—C46—H46B | 109.5 |
H23A—C23—H23B | 109.5 | H46A—C46—H46B | 109.5 |
C20—C23—H23C | 109.5 | C43—C46—H46C | 109.5 |
H23A—C23—H23C | 109.5 | H46A—C46—H46C | 109.5 |
H23B—C23—H23C | 109.5 | H46B—C46—H46C | 109.5 |
O1—P1—N1—C1 | 152.6 (4) | O2—P2—N4—C24 | −47.0 (5) |
N3—P1—N1—C1 | 27.2 (5) | N5—P2—N4—C24 | −169.4 (4) |
N2—P1—N1—C1 | −85.5 (5) | N6—P2—N4—C24 | 77.3 (4) |
O1—P1—N1—C2 | −24.2 (5) | O2—P2—N4—C25 | 168.0 (4) |
N3—P1—N1—C2 | −149.6 (4) | N5—P2—N4—C25 | 45.6 (5) |
N2—P1—N1—C2 | 97.7 (5) | N6—P2—N4—C25 | −67.7 (5) |
O1—P1—N2—C10 | 160.9 (4) | O2—P2—N5—C32 | 155.0 (4) |
N1—P1—N2—C10 | 38.8 (5) | N6—P2—N5—C32 | 29.8 (5) |
N3—P1—N2—C10 | −74.8 (4) | N4—P2—N5—C32 | −83.2 (5) |
O1—P1—N2—C9 | −55.5 (5) | O2—P2—N5—C33 | −18.8 (5) |
N1—P1—N2—C9 | −177.7 (4) | N6—P2—N5—C33 | −144.0 (4) |
N3—P1—N2—C9 | 68.8 (4) | N4—P2—N5—C33 | 103.0 (4) |
O1—P1—N3—C17 | −65.8 (5) | O2—P2—N6—C40 | −65.4 (5) |
N1—P1—N3—C17 | 56.7 (5) | N5—P2—N6—C40 | 57.2 (5) |
N2—P1—N3—C17 | 173.2 (4) | N4—P2—N6—C40 | 173.7 (4) |
C1—N1—C2—C3 | 65.1 (6) | C24—N4—C25—C26 | 73.7 (6) |
P1—N1—C2—C3 | −117.8 (5) | P2—N4—C25—C26 | −140.4 (5) |
N1—C2—C3—C8 | −121.2 (6) | N4—C25—C26—C31 | 97.4 (7) |
N1—C2—C3—C4 | 57.3 (7) | N4—C25—C26—C27 | −84.2 (7) |
C8—C3—C4—C5 | −0.7 (9) | C31—C26—C27—C28 | −0.9 (9) |
C2—C3—C4—C5 | −179.3 (6) | C25—C26—C27—C28 | −179.3 (5) |
C3—C4—C5—C6 | −0.2 (10) | C26—C27—C28—C29 | 0.7 (10) |
C4—C5—C6—C7 | 0.4 (11) | C27—C28—C29—C30 | −0.2 (11) |
C5—C6—C7—C8 | 0.4 (11) | C28—C29—C30—C31 | −0.2 (11) |
C4—C3—C8—C7 | 1.4 (9) | C29—C30—C31—C26 | 0.1 (10) |
C2—C3—C8—C7 | 179.9 (5) | C27—C26—C31—C30 | 0.5 (9) |
C6—C7—C8—C3 | −1.3 (10) | C25—C26—C31—C30 | 178.9 (5) |
C9—N2—C10—C11 | 72.7 (6) | C32—N5—C33—C34 | 69.1 (7) |
P1—N2—C10—C11 | −142.7 (4) | P2—N5—C33—C34 | −116.5 (5) |
N2—C10—C11—C12 | −171.8 (5) | N5—C33—C34—C35 | 76.5 (7) |
N2—C10—C11—C16 | 11.6 (8) | N5—C33—C34—C39 | −105.6 (6) |
C16—C11—C12—C13 | 1.1 (9) | C39—C34—C35—C36 | 0.9 (9) |
C10—C11—C12—C13 | −175.7 (6) | C33—C34—C35—C36 | 178.8 (6) |
C11—C12—C13—C14 | −0.6 (9) | C34—C35—C36—C37 | −1.2 (10) |
C12—C13—C14—C15 | −0.7 (10) | C35—C36—C37—C38 | 0.8 (10) |
C13—C14—C15—C16 | 1.6 (10) | C36—C37—C38—C39 | −0.1 (10) |
C12—C11—C16—C15 | −0.3 (9) | C37—C38—C39—C34 | −0.1 (10) |
C10—C11—C16—C15 | 176.4 (6) | C35—C34—C39—C38 | −0.3 (9) |
C14—C15—C16—C11 | −1.1 (9) | C33—C34—C39—C38 | −178.2 (6) |
P1—N3—C17—C22 | −152.8 (5) | P2—N6—C40—C45 | 27.2 (8) |
P1—N3—C17—C18 | 27.5 (8) | P2—N6—C40—C41 | −154.3 (4) |
C22—C17—C18—C19 | 0.6 (9) | C45—C40—C41—C42 | −0.6 (8) |
N3—C17—C18—C19 | −179.7 (6) | N6—C40—C41—C42 | −179.2 (5) |
C17—C18—C19—C20 | 0.6 (10) | C40—C41—C42—C43 | −0.5 (9) |
C18—C19—C20—C21 | −0.9 (10) | C41—C42—C43—C44 | 0.6 (9) |
C18—C19—C20—C23 | 179.4 (6) | C41—C42—C43—C46 | −178.3 (6) |
C19—C20—C21—C22 | −0.1 (9) | C42—C43—C44—C45 | 0.4 (9) |
C23—C20—C21—C22 | 179.6 (6) | C46—C43—C44—C45 | 179.3 (6) |
C20—C21—C22—C17 | 1.3 (9) | C41—C40—C45—C44 | 1.6 (9) |
C18—C17—C22—C21 | −1.5 (9) | N6—C40—C45—C44 | −179.8 (6) |
N3—C17—C22—C21 | 178.8 (5) | C43—C44—C45—C40 | −1.6 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O2i | 0.88 | 2.05 | 2.846 (6) | 149 |
N6—H6N···O1ii | 0.88 | 2.00 | 2.799 (6) | 151 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C23H28N3OP |
Mr | 393.45 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 9.9621 (3), 14.8245 (5), 28.8407 (10) |
β (°) | 98.2682 (14) |
V (Å3) | 4215.0 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.15 |
Crystal size (mm) | 0.06 × 0.05 × 0.04 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer with APEXII detector |
Absorption correction | Multi-scan (SORTAV; Blessing, 1997) |
Tmin, Tmax | 0.991, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13508, 7788, 4450 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.104, 0.199, 1.15 |
No. of reflections | 7788 |
No. of parameters | 508 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + 17.8P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.32, −0.33 |
Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1993), Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and enCIFer (Allen et al., 2004).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O2i | 0.88 | 2.05 | 2.846 (6) | 149.4 |
N6—H6N···O1ii | 0.88 | 2.00 | 2.799 (6) | 150.6 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1. |
Acknowledgements
Support of this investigation by the Ferdowsi University of Mashhad is gratefully acknowledged.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
In continuation of our investigations on the synthesis of new phosphoramidates (Toghraee et al., 2011; Pourayoubi et al., 2011) we now report the synthesis and crystal structure of the title phosphoric triamide.
The asymmetric unit of the title compound (Fig. 1) contains two independent molecules with significant conformational differences. The torsion angles N1–C2–C3–C4 and N2–C10–C11–C16 involving the N-benzyl moiety in one molecule are: 57.3 (7) and 11.6 (8)°, respectively, compared to the corresponding angles in the second molecule with values 76.5 (7) and 97.4 (7)° (for torsion angles N5–C33–C34–C35 and N4–C25–C26–C31, respectively). In each molecule, the P atom adopts a distorted tetrahedral coordination P(═O)(N)(N)2 environment with the bond angles in the range of 104.7 (2)° to 115.2 (2)° for P1 and 105.1 (2)° to 115.1 (2)° for P2. The P═O and P—N bond lengths and the P—N—C bond angles are within the expected values for analogous compounds reported in the literature (Gholivand et al., 2011). In both molecules, the P—N bond lengths of the P(O)[NHC6H4(4-CH3)] fragments (1.646 (5) Å and 1.653 (4) Å, respectively, for molecules labeled with P1 and P2) are between the values of the P—N bonds in the P(O)[N(CH3)(CH2C6H5)]2 moieties (P1: 1.639 (5) Å & 1.660 (5) Å and P2: 1.634 (5) Å & 1.661 (5) Å).
In the crystal packing, the molecules are hydrogen bonded to each other resulting in a chain along to the a axis in an alternating sequence (Fig. 2).