organic compounds
1,1-Bis(diphenylphosphoryl)hydrazine
aLeibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
*Correspondence e-mail: uwe.rosenthal@catalysis.de
The title compound, C24H22N2O2P2, contains a diphosphazane backbone, as well as a hydrazine entity. The P—N—P diphosphazane unit and the N-amine N atom are almost coplanar, and the O atoms of the Ph2P(O) units are oriented trans to each other with respect to the P⋯P axis. In the crystal, centrosymmetrically related molecules are linked into dimers by pairs of N—H⋯O hydrogen bonds, forming rings of graph-set motif R22(10).
Keywords: crystal structure; diphosphazane; hydrazine.
CCDC reference: 1841174
Structure description
The title compound (Fig. 1) contains a diphosphazane backbone, as well as a hydrazine entity. The P—N—P diphosphazane unit and the N-amine N atom are almost coplanar (r.m.s. deviation for P1/N1/P2/N2 = 0.045 Å). The N2 atom deviates from the P1/N1/P2 plane by 0.312 (4) Å. The geometry at atom N1 is nearly trigonal planar [Σ(∠N1) = 358.7°]. The O atoms of the Ph2P(O) units are oriented trans to each other with respect to the P⋯P axis, as was found in other Ph2P(O)—N(R)—(O)PPh2 compounds (Song et al., 2009; Slawin et al., 2001; Gümgüm et al., 2006; Copolovici et al., 2007). The P—N—P angle is 129.68 (6)°. The P—N bond lengths [P1—N1 = 1.6989 (10) Å and P2—N1 1.6769 (10) Å] are noticeably shortened compared to the calculated sum of the covalent radii by Pyykkö and show significant multiple-bond character [single: Σrcov(P—N) = 1.82 Å; double: Σrcov(P=N) = 1.62 Å] (Pyykkö, 2015). Nevertheless, these values are comparable to those observed in similar compounds with a Ph2P(O)—N(R)—(O)PPh2 skeleton (Song et al., 2009; Slawin et al., 2001; Gümgüm et al., 2006). The N—N distance within the hydrazine entity is 1.4391 (13) Å. In the crystal, centrosymmetrically related molecules are linked into dimers by pairs of N—H⋯O hydrogen bonds (Table 1), forming rings of graph-set motif R22(10).
Synthesis and crystallization
A solution of N,N-bis(diphenylphosphine)hydrazine, [Ph2P—N(NH2)—PPh2; 0.385 g, 0.965 mmol] and trimethylamine N-oxide (0.235 g, 2.115 mmol) in THF (10 ml) was stirred for 3 d at room temperature, followed by heating at 60°C for four weeks. Afterwards, the THF was removed in a vacuum and the product was recrystallized from mixed solvents of DCM/n-hexane (1:1 v/v). Yield 0.332 g (80%). 31P NMR (162 MHz, THF-d8, 298 K): δ 29.8. MS (ESI): m/z = 433 [M + H]+. Elemental analysis calculated (%) for C24H22N2O2P2: C 66.67, H 5.13, N 6.48, P 14.33; found: C 66.65, H 5.15, N 6.69, P 14.38. M.p. 211–212°C.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1841174
https://doi.org/10.1107/S241431461800679X/rz4023sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461800679X/rz4023Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S241431461800679X/rz4023Isup3.cml
Data collection: X-AREA (Stoe & Cie, 2005); cell
X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).C24H22N2O2P2 | Z = 2 |
Mr = 432.37 | F(000) = 452 |
Triclinic, P1 | Dx = 1.376 Mg m−3 |
a = 8.6901 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.1547 (5) Å | Cell parameters from 5988 reflections |
c = 12.6282 (7) Å | θ = 2.1–29.7° |
α = 71.352 (4)° | µ = 0.23 mm−1 |
β = 84.442 (4)° | T = 200 K |
γ = 81.817 (4)° | Prism, colourless |
V = 1043.56 (10) Å3 | 0.50 × 0.30 × 0.25 mm |
Stoe IPDS II diffractometer | 4301 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.014 |
Graphite monochromator | θmax = 28.0°, θmin = 2.1° |
ω scans | h = −11→11 |
15868 measured reflections | k = −13→13 |
5037 independent reflections | l = −16→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.081 | w = 1/[σ2(Fo2) + (0.0504P)2 + 0.1335P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
5037 reflections | Δρmax = 0.35 e Å−3 |
279 parameters | Δρmin = −0.28 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.89750 (13) | 0.48325 (12) | 0.26480 (10) | 0.0223 (2) | |
C2 | 0.77523 (15) | 0.55487 (13) | 0.19719 (11) | 0.0274 (2) | |
H2C | 0.7771 | 0.5531 | 0.1223 | 0.033* | |
C3 | 0.65113 (16) | 0.62857 (15) | 0.23907 (12) | 0.0331 (3) | |
H3 | 0.5681 | 0.6775 | 0.1928 | 0.040* | |
C4 | 0.64754 (17) | 0.63124 (15) | 0.34843 (13) | 0.0349 (3) | |
H4 | 0.5619 | 0.6814 | 0.3771 | 0.042* | |
C5 | 0.76835 (17) | 0.56106 (16) | 0.41553 (12) | 0.0360 (3) | |
H5 | 0.7660 | 0.5630 | 0.4904 | 0.043* | |
C6 | 0.89352 (16) | 0.48747 (14) | 0.37381 (11) | 0.0308 (3) | |
H6 | 0.9769 | 0.4398 | 0.4201 | 0.037* | |
C7 | 1.20749 (13) | 0.32186 (12) | 0.29927 (10) | 0.0209 (2) | |
C8 | 1.35584 (14) | 0.36535 (13) | 0.27120 (10) | 0.0258 (2) | |
H8 | 1.3740 | 0.4382 | 0.2037 | 0.031* | |
C9 | 1.47602 (14) | 0.30254 (14) | 0.34133 (12) | 0.0296 (3) | |
H9 | 1.5761 | 0.3337 | 0.3228 | 0.036* | |
C10 | 1.45090 (15) | 0.19430 (14) | 0.43856 (11) | 0.0296 (3) | |
H10 | 1.5346 | 0.1495 | 0.4854 | 0.036* | |
C11 | 1.30418 (16) | 0.15118 (14) | 0.46774 (11) | 0.0287 (3) | |
H11 | 1.2871 | 0.0776 | 0.5350 | 0.034* | |
C12 | 1.18228 (14) | 0.21521 (13) | 0.39899 (10) | 0.0245 (2) | |
H12 | 1.0814 | 0.1865 | 0.4197 | 0.029* | |
C13 | 1.01250 (14) | −0.02059 (12) | 0.25987 (10) | 0.0231 (2) | |
C14 | 1.08887 (15) | −0.08649 (13) | 0.35836 (10) | 0.0266 (2) | |
H14 | 1.0739 | −0.0463 | 0.4175 | 0.032* | |
C15 | 1.18663 (16) | −0.21031 (14) | 0.37088 (12) | 0.0341 (3) | |
H15 | 1.2391 | −0.2543 | 0.4381 | 0.041* | |
C16 | 1.20760 (17) | −0.26968 (15) | 0.28517 (14) | 0.0387 (3) | |
H16 | 1.2745 | −0.3545 | 0.2936 | 0.046* | |
C17 | 1.13138 (19) | −0.20583 (16) | 0.18727 (13) | 0.0388 (3) | |
H17 | 1.1457 | −0.2473 | 0.1289 | 0.047* | |
C18 | 1.03422 (17) | −0.08176 (14) | 0.17395 (11) | 0.0318 (3) | |
H18 | 0.9823 | −0.0382 | 0.1064 | 0.038* | |
C19 | 0.72636 (14) | 0.14265 (13) | 0.17142 (10) | 0.0247 (2) | |
C20 | 0.64662 (18) | 0.02528 (17) | 0.20351 (13) | 0.0375 (3) | |
H20 | 0.6832 | −0.0558 | 0.2616 | 0.045* | |
C21 | 0.51300 (19) | 0.0271 (2) | 0.15020 (16) | 0.0476 (4) | |
H21 | 0.4577 | −0.0525 | 0.1725 | 0.057* | |
C22 | 0.46105 (17) | 0.1442 (2) | 0.06523 (15) | 0.0462 (4) | |
H22 | 0.3717 | 0.1442 | 0.0275 | 0.055* | |
C23 | 0.53780 (18) | 0.26136 (19) | 0.03472 (13) | 0.0415 (3) | |
H23 | 0.4994 | 0.3428 | −0.0225 | 0.050* | |
C24 | 0.67102 (15) | 0.26122 (15) | 0.08710 (11) | 0.0305 (3) | |
H24 | 0.7243 | 0.3420 | 0.0653 | 0.037* | |
N1 | 0.98664 (11) | 0.27181 (10) | 0.16766 (8) | 0.02110 (19) | |
N2 | 1.03825 (14) | 0.24976 (12) | 0.06221 (9) | 0.0270 (2) | |
O1 | 1.12316 (11) | 0.49585 (9) | 0.09599 (7) | 0.02781 (19) | |
O2 | 0.84523 (10) | 0.16030 (9) | 0.36001 (7) | 0.02361 (17) | |
P1 | 1.05904 (3) | 0.39960 (3) | 0.20082 (2) | 0.02008 (8) | |
P2 | 0.88965 (3) | 0.14098 (3) | 0.24925 (2) | 0.01921 (8) | |
H2A | 1.0080 (19) | 0.3320 (18) | 0.0093 (14) | 0.031 (4)* | |
H2B | 1.146 (2) | 0.2365 (19) | 0.0615 (15) | 0.042 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0234 (5) | 0.0172 (5) | 0.0260 (6) | −0.0025 (4) | −0.0035 (4) | −0.0057 (4) |
C2 | 0.0285 (6) | 0.0265 (6) | 0.0254 (6) | −0.0006 (5) | −0.0057 (5) | −0.0055 (5) |
C3 | 0.0296 (6) | 0.0318 (7) | 0.0359 (7) | 0.0049 (5) | −0.0089 (5) | −0.0093 (6) |
C4 | 0.0321 (7) | 0.0331 (7) | 0.0418 (8) | 0.0063 (5) | −0.0050 (6) | −0.0183 (6) |
C5 | 0.0406 (7) | 0.0387 (8) | 0.0330 (7) | 0.0060 (6) | −0.0076 (6) | −0.0199 (6) |
C6 | 0.0320 (6) | 0.0309 (7) | 0.0312 (6) | 0.0053 (5) | −0.0106 (5) | −0.0132 (5) |
C7 | 0.0204 (5) | 0.0200 (5) | 0.0225 (5) | −0.0009 (4) | −0.0032 (4) | −0.0070 (4) |
C8 | 0.0244 (6) | 0.0244 (6) | 0.0273 (6) | −0.0036 (5) | 0.0010 (5) | −0.0065 (5) |
C9 | 0.0200 (5) | 0.0321 (7) | 0.0385 (7) | −0.0019 (5) | −0.0009 (5) | −0.0142 (5) |
C10 | 0.0268 (6) | 0.0292 (6) | 0.0340 (6) | 0.0061 (5) | −0.0110 (5) | −0.0128 (5) |
C11 | 0.0329 (6) | 0.0250 (6) | 0.0253 (6) | −0.0006 (5) | −0.0071 (5) | −0.0033 (5) |
C12 | 0.0247 (6) | 0.0239 (6) | 0.0239 (5) | −0.0044 (4) | −0.0032 (4) | −0.0047 (5) |
C13 | 0.0265 (6) | 0.0189 (5) | 0.0232 (5) | −0.0035 (4) | −0.0005 (4) | −0.0055 (4) |
C14 | 0.0312 (6) | 0.0221 (6) | 0.0248 (6) | −0.0037 (5) | −0.0026 (5) | −0.0045 (5) |
C15 | 0.0341 (7) | 0.0242 (6) | 0.0400 (7) | −0.0009 (5) | −0.0071 (6) | −0.0038 (5) |
C16 | 0.0355 (7) | 0.0236 (6) | 0.0560 (9) | 0.0010 (5) | 0.0013 (6) | −0.0141 (6) |
C17 | 0.0470 (8) | 0.0319 (7) | 0.0424 (8) | −0.0034 (6) | 0.0043 (6) | −0.0208 (6) |
C18 | 0.0417 (7) | 0.0283 (6) | 0.0274 (6) | −0.0043 (5) | −0.0019 (5) | −0.0116 (5) |
C19 | 0.0234 (5) | 0.0299 (6) | 0.0231 (5) | −0.0042 (5) | −0.0027 (4) | −0.0108 (5) |
C20 | 0.0374 (7) | 0.0380 (8) | 0.0402 (8) | −0.0138 (6) | −0.0055 (6) | −0.0113 (6) |
C21 | 0.0359 (8) | 0.0553 (10) | 0.0637 (11) | −0.0171 (7) | −0.0041 (7) | −0.0300 (9) |
C22 | 0.0263 (7) | 0.0692 (11) | 0.0568 (10) | 0.0029 (7) | −0.0128 (6) | −0.0395 (9) |
C23 | 0.0345 (7) | 0.0535 (9) | 0.0387 (8) | 0.0101 (7) | −0.0147 (6) | −0.0203 (7) |
C24 | 0.0294 (6) | 0.0346 (7) | 0.0279 (6) | 0.0004 (5) | −0.0057 (5) | −0.0108 (5) |
N1 | 0.0246 (5) | 0.0213 (5) | 0.0170 (4) | −0.0044 (4) | 0.0001 (4) | −0.0050 (4) |
N2 | 0.0331 (6) | 0.0269 (6) | 0.0195 (5) | −0.0014 (4) | 0.0033 (4) | −0.0073 (4) |
O1 | 0.0303 (4) | 0.0240 (4) | 0.0244 (4) | −0.0070 (3) | −0.0025 (3) | 0.0009 (3) |
O2 | 0.0250 (4) | 0.0263 (4) | 0.0199 (4) | −0.0039 (3) | −0.0005 (3) | −0.0076 (3) |
P1 | 0.02100 (14) | 0.01798 (14) | 0.01910 (14) | −0.00280 (10) | −0.00280 (10) | −0.00205 (11) |
P2 | 0.02125 (14) | 0.01898 (14) | 0.01705 (14) | −0.00319 (10) | −0.00204 (10) | −0.00449 (10) |
C1—C6 | 1.3879 (17) | C14—H14 | 0.9500 |
C1—C2 | 1.3948 (17) | C15—C16 | 1.384 (2) |
C1—P1 | 1.7957 (12) | C15—H15 | 0.9500 |
C2—C3 | 1.3841 (19) | C16—C17 | 1.383 (2) |
C2—H2C | 0.9500 | C16—H16 | 0.9500 |
C3—C4 | 1.387 (2) | C17—C18 | 1.385 (2) |
C3—H3 | 0.9500 | C17—H17 | 0.9500 |
C4—C5 | 1.379 (2) | C18—H18 | 0.9500 |
C4—H4 | 0.9500 | C19—C24 | 1.3890 (18) |
C5—C6 | 1.3887 (19) | C19—C20 | 1.3916 (18) |
C5—H5 | 0.9500 | C19—P2 | 1.7980 (12) |
C6—H6 | 0.9500 | C20—C21 | 1.393 (2) |
C7—C12 | 1.3959 (16) | C20—H20 | 0.9500 |
C7—C8 | 1.3987 (16) | C21—C22 | 1.377 (3) |
C7—P1 | 1.7961 (12) | C21—H21 | 0.9500 |
C8—C9 | 1.3821 (18) | C22—C23 | 1.375 (3) |
C8—H8 | 0.9500 | C22—H22 | 0.9500 |
C9—C10 | 1.384 (2) | C23—C24 | 1.3875 (19) |
C9—H9 | 0.9500 | C23—H23 | 0.9500 |
C10—C11 | 1.3848 (19) | C24—H24 | 0.9500 |
C10—H10 | 0.9500 | N1—N2 | 1.4391 (13) |
C11—C12 | 1.3857 (17) | N1—P2 | 1.6769 (10) |
C11—H11 | 0.9500 | N1—P1 | 1.6989 (10) |
C12—H12 | 0.9500 | N2—H2A | 0.909 (17) |
C13—C14 | 1.3916 (17) | N2—H2B | 0.927 (19) |
C13—C18 | 1.3988 (17) | O1—P1 | 1.4843 (9) |
C13—P2 | 1.7994 (12) | O2—P2 | 1.4810 (8) |
C14—C15 | 1.3866 (19) | ||
C6—C1—C2 | 119.31 (11) | C17—C16—C15 | 120.17 (13) |
C6—C1—P1 | 123.61 (9) | C17—C16—H16 | 119.9 |
C2—C1—P1 | 116.94 (9) | C15—C16—H16 | 119.9 |
C3—C2—C1 | 120.08 (12) | C16—C17—C18 | 120.31 (13) |
C3—C2—H2C | 120.0 | C16—C17—H17 | 119.8 |
C1—C2—H2C | 120.0 | C18—C17—H17 | 119.8 |
C2—C3—C4 | 120.20 (12) | C17—C18—C13 | 120.02 (13) |
C2—C3—H3 | 119.9 | C17—C18—H18 | 120.0 |
C4—C3—H3 | 119.9 | C13—C18—H18 | 120.0 |
C5—C4—C3 | 119.98 (13) | C24—C19—C20 | 119.65 (12) |
C5—C4—H4 | 120.0 | C24—C19—P2 | 121.71 (10) |
C3—C4—H4 | 120.0 | C20—C19—P2 | 118.42 (10) |
C4—C5—C6 | 120.07 (13) | C19—C20—C21 | 119.81 (15) |
C4—C5—H5 | 120.0 | C19—C20—H20 | 120.1 |
C6—C5—H5 | 120.0 | C21—C20—H20 | 120.1 |
C1—C6—C5 | 120.35 (12) | C22—C21—C20 | 120.01 (15) |
C1—C6—H6 | 119.8 | C22—C21—H21 | 120.0 |
C5—C6—H6 | 119.8 | C20—C21—H21 | 120.0 |
C12—C7—C8 | 119.26 (11) | C23—C22—C21 | 120.35 (14) |
C12—C7—P1 | 122.47 (9) | C23—C22—H22 | 119.8 |
C8—C7—P1 | 118.17 (9) | C21—C22—H22 | 119.8 |
C9—C8—C7 | 120.17 (12) | C22—C23—C24 | 120.31 (15) |
C9—C8—H8 | 119.9 | C22—C23—H23 | 119.8 |
C7—C8—H8 | 119.9 | C24—C23—H23 | 119.8 |
C8—C9—C10 | 120.14 (12) | C23—C24—C19 | 119.85 (14) |
C8—C9—H9 | 119.9 | C23—C24—H24 | 120.1 |
C10—C9—H9 | 119.9 | C19—C24—H24 | 120.1 |
C9—C10—C11 | 120.20 (12) | N2—N1—P2 | 111.01 (7) |
C9—C10—H10 | 119.9 | N2—N1—P1 | 118.03 (8) |
C11—C10—H10 | 119.9 | P2—N1—P1 | 129.68 (6) |
C10—C11—C12 | 120.08 (12) | N1—N2—H2A | 105.2 (10) |
C10—C11—H11 | 120.0 | N1—N2—H2B | 105.7 (11) |
C12—C11—H11 | 120.0 | H2A—N2—H2B | 108.7 (15) |
C11—C12—C7 | 120.12 (11) | O1—P1—N1 | 107.98 (5) |
C11—C12—H12 | 119.9 | O1—P1—C1 | 112.80 (6) |
C7—C12—H12 | 119.9 | N1—P1—C1 | 105.50 (5) |
C14—C13—C18 | 119.11 (12) | O1—P1—C7 | 111.04 (5) |
C14—C13—P2 | 117.92 (9) | N1—P1—C7 | 109.40 (5) |
C18—C13—P2 | 122.96 (10) | C1—P1—C7 | 109.90 (5) |
C15—C14—C13 | 120.55 (12) | O2—P2—N1 | 110.58 (5) |
C15—C14—H14 | 119.7 | O2—P2—C19 | 113.78 (5) |
C13—C14—H14 | 119.7 | N1—P2—C19 | 105.17 (5) |
C16—C15—C14 | 119.83 (13) | O2—P2—C13 | 112.32 (5) |
C16—C15—H15 | 120.1 | N1—P2—C13 | 107.58 (5) |
C14—C15—H15 | 120.1 | C19—P2—C13 | 106.97 (6) |
C6—C1—C2—C3 | −0.35 (19) | N2—N1—P1—C1 | 139.66 (9) |
P1—C1—C2—C3 | −176.26 (10) | P2—N1—P1—C1 | −54.55 (9) |
C1—C2—C3—C4 | −0.2 (2) | N2—N1—P1—C7 | −102.16 (9) |
C2—C3—C4—C5 | 0.4 (2) | P2—N1—P1—C7 | 63.63 (9) |
C3—C4—C5—C6 | −0.1 (2) | C6—C1—P1—O1 | −123.31 (11) |
C2—C1—C6—C5 | 0.6 (2) | C2—C1—P1—O1 | 52.41 (11) |
P1—C1—C6—C5 | 176.27 (11) | C6—C1—P1—N1 | 119.04 (11) |
C4—C5—C6—C1 | −0.4 (2) | C2—C1—P1—N1 | −65.25 (10) |
C12—C7—C8—C9 | 0.39 (18) | C6—C1—P1—C7 | 1.19 (12) |
P1—C7—C8—C9 | −176.16 (9) | C2—C1—P1—C7 | 176.91 (9) |
C7—C8—C9—C10 | 1.34 (19) | C12—C7—P1—O1 | −172.27 (9) |
C8—C9—C10—C11 | −1.92 (19) | C8—C7—P1—O1 | 4.17 (11) |
C9—C10—C11—C12 | 0.75 (19) | C12—C7—P1—N1 | −53.18 (11) |
C10—C11—C12—C7 | 0.99 (19) | C8—C7—P1—N1 | 123.26 (9) |
C8—C7—C12—C11 | −1.55 (18) | C12—C7—P1—C1 | 62.22 (11) |
P1—C7—C12—C11 | 174.85 (9) | C8—C7—P1—C1 | −121.35 (10) |
C18—C13—C14—C15 | 0.72 (19) | N2—N1—P2—O2 | 176.63 (8) |
P2—C13—C14—C15 | −179.18 (10) | P1—N1—P2—O2 | 10.06 (10) |
C13—C14—C15—C16 | −0.5 (2) | N2—N1—P2—C19 | −60.13 (9) |
C14—C15—C16—C17 | 0.0 (2) | P1—N1—P2—C19 | 133.29 (8) |
C15—C16—C17—C18 | 0.3 (2) | N2—N1—P2—C13 | 53.64 (9) |
C16—C17—C18—C13 | −0.2 (2) | P1—N1—P2—C13 | −112.94 (8) |
C14—C13—C18—C17 | −0.4 (2) | C24—C19—P2—O2 | 99.51 (11) |
P2—C13—C18—C17 | 179.52 (11) | C20—C19—P2—O2 | −75.13 (12) |
C24—C19—C20—C21 | 0.6 (2) | C24—C19—P2—N1 | −21.65 (12) |
P2—C19—C20—C21 | 175.37 (12) | C20—C19—P2—N1 | 163.71 (11) |
C19—C20—C21—C22 | 0.7 (2) | C24—C19—P2—C13 | −135.85 (10) |
C20—C21—C22—C23 | −1.9 (2) | C20—C19—P2—C13 | 49.51 (12) |
C21—C22—C23—C24 | 1.9 (2) | C14—C13—P2—O2 | −18.63 (11) |
C22—C23—C24—C19 | −0.6 (2) | C18—C13—P2—O2 | 161.48 (10) |
C20—C19—C24—C23 | −0.7 (2) | C14—C13—P2—N1 | 103.29 (10) |
P2—C19—C24—C23 | −175.25 (10) | C18—C13—P2—N1 | −76.60 (11) |
N2—N1—P1—O1 | 18.81 (10) | C14—C13—P2—C19 | −144.15 (10) |
P2—N1—P1—O1 | −175.40 (7) | C18—C13—P2—C19 | 35.95 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.909 (17) | 2.089 (18) | 2.9737 (15) | 164.0 (14) |
Symmetry code: (i) −x+2, −y+1, −z. |
Funding information
The publication of this article was funded by the Open Access Fund of the Leibniz Association.
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