organic compounds
N,N-Bis(diphenylthiophosphinoyl)-4-ethylaniline
aDepartment of Chemistry, University of Fort Hare, Private Bag X1314, Alice 5700, South Africa, and bSchool of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
*Correspondence e-mail: owaga@ukzn.ac.za
The title compound, C32H29NP2S2, has two molecules in the with an r.m.s. difference of 0.218 Å in their best-fit overlay. Both molecules have a slightly distorted trigonal–planar N atom, bonded to two PV atoms and a C atom of the 4-ethylphenyl unit. The P—N—P angles of 126.34 (11) and 125.98 (11)° are larger than the four C—N—P bond angles. The two S atoms are trans to one another with respect to the P—N—P angle. The features C—H⋯π interactions. The methyl group in one of the molecules is disordered over two sets of sites, with occupancies of 0.518 (6) and 0.482 (6).
Related literature
For background to the chemistry of coordination compounds containing P—N bonds and for their applications, see: Hartley (1990); Greenwood & Earnshaw (1984); Balakrishna et al. (2000). For the ability of bis(diphenylphosphino)alkylaniline derivatives to form chelates with transition metal ions, see: Biricik et al. (2007); Fei & Dyson (2005). For the synthesis of the title and related compounds, see: Fernández et al. (2005); Gaw et al. (2002); Fei et al. (2004); Slawin et al. (2005).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
10.1107/S1600536812048416/fj2607sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812048416/fj2607Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812048416/fj2607Isup3.cml
N,N-Bis(diphenylphosphino)ethylaniline is prepared by the aminolysis reaction of H2NC6H4—C2H5(4-C2H5) with two equivalents of Ph2PCl according to the procedure given in the literature (Hartley, 1990). Solid N,N-bis(diphenylphosphino)ethylaniline (0.20 g, 0.420 mmol) and S8 (0.027 g, 0.840 mmol) were dissolved in 20 ml of tetrahydrofuran and refluxed for 6 h. The volume was concentrated in vacuo to about 2 ml follow by the addition of 20 ml n-hexane to give [(Ph2P(S)2N—C6H4(C2H5)] as a white solid. Recrystallization in chloroform hexane gave crystals suitable for X-ray analysis.
Data collection: APEX2 (Bruker, 2008); cell
SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. Overlay structure of the two molecules in the asymmetric unit. |
C32H29NP2S2 | Z = 4 |
Mr = 553.62 | F(000) = 1160 |
Triclinic, P1 | Dx = 1.33 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6305 (11) Å | Cell parameters from 56725 reflections |
b = 13.8027 (14) Å | θ = 1.0–28.2° |
c = 21.360 (2) Å | µ = 0.33 mm−1 |
α = 82.484 (2)° | T = 173 K |
β = 84.635 (2)° | Needle, colourless |
γ = 79.975 (2)° | 0.17 × 0.08 × 0.08 mm |
V = 2764.7 (5) Å3 |
Bruker X8 APEXII 4K KappaCCD diffractometer | 9271 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
ϕ and ω scans | θmax = 28.2°, θmin = 1.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −12→12 |
Tmin = 0.946, Tmax = 0.974 | k = −18→18 |
56725 measured reflections | l = −28→28 |
13522 independent reflections |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0442P)2 + 1.5667P] where P = (Fo2 + 2Fc2)/3 |
13522 reflections | (Δ/σ)max = 0.001 |
684 parameters | Δρmax = 0.82 e Å−3 |
9 restraints | Δρmin = −0.36 e Å−3 |
C32H29NP2S2 | γ = 79.975 (2)° |
Mr = 553.62 | V = 2764.7 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.6305 (11) Å | Mo Kα radiation |
b = 13.8027 (14) Å | µ = 0.33 mm−1 |
c = 21.360 (2) Å | T = 173 K |
α = 82.484 (2)° | 0.17 × 0.08 × 0.08 mm |
β = 84.635 (2)° |
Bruker X8 APEXII 4K KappaCCD diffractometer | 13522 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 9271 reflections with I > 2σ(I) |
Tmin = 0.946, Tmax = 0.974 | Rint = 0.054 |
56725 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 9 restraints |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.82 e Å−3 |
13522 reflections | Δρmin = −0.36 e Å−3 |
684 parameters |
Experimental. Carbon-bound H-atoms were placed in calculated positions [C—H = 0.98 Å for Me H atoms, 0.99 Å for Methylene H atoms and 0.95 for aromatic H atoms; Uiso(H) = 1.2Ueq(C) (1.5 for Me groups)] and were included in the refinement in the riding model approximation. Disorder: Disorder was found for one ethyl group in the p-ethylpyridyl moiety, which is not an uncommon situation. The disorder was modelled for C– and H– atoms using distance restraints and constraints, and PART instructions and the total occupancy was kept as 1 during the refinement. The carbon atom involved in disorder were modelled with anisotropic thermal parameters. The occupancy of the C atoms in the disordered ethyl moiety was fixed at 50:50 during the refinement. |
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) | |
C1 | 0.5587 (2) | 0.33146 (16) | 0.20639 (10) | 0.0147 (4) | |
C2 | 0.4212 (2) | 0.31222 (16) | 0.22027 (10) | 0.0158 (4) | |
H2 | 0.389 | 0.2643 | 0.1996 | 0.019* | |
C3 | 0.3308 (2) | 0.36277 (17) | 0.26418 (11) | 0.0180 (5) | |
H3 | 0.2371 | 0.3493 | 0.2733 | 0.022* | |
C4 | 0.3767 (2) | 0.43249 (17) | 0.29454 (11) | 0.0184 (5) | |
H4 | 0.3149 | 0.4666 | 0.3247 | 0.022* | |
C5 | 0.5134 (2) | 0.45267 (16) | 0.28089 (11) | 0.0178 (5) | |
H5 | 0.5449 | 0.5007 | 0.3018 | 0.021* | |
C6 | 0.6041 (2) | 0.40305 (16) | 0.23693 (11) | 0.0170 (5) | |
H6 | 0.6972 | 0.4176 | 0.2275 | 0.02* | |
C7 | 0.6830 (2) | 0.35878 (16) | 0.07850 (11) | 0.0163 (4) | |
C8 | 0.6379 (2) | 0.34382 (18) | 0.02078 (11) | 0.0202 (5) | |
H8 | 0.603 | 0.2848 | 0.0169 | 0.024* | |
C9 | 0.6443 (2) | 0.4158 (2) | −0.03108 (12) | 0.0258 (5) | |
H9 | 0.6149 | 0.4051 | −0.0705 | 0.031* | |
C10 | 0.6929 (2) | 0.50268 (19) | −0.02589 (12) | 0.0269 (6) | |
H10 | 0.6965 | 0.5515 | −0.0615 | 0.032* | |
C11 | 0.7366 (2) | 0.51829 (18) | 0.03159 (12) | 0.0241 (5) | |
H11 | 0.7694 | 0.5782 | 0.0354 | 0.029* | |
C12 | 0.7326 (2) | 0.44653 (17) | 0.08364 (11) | 0.0198 (5) | |
H12 | 0.7637 | 0.4572 | 0.1227 | 0.024* | |
C13 | 1.0769 (2) | 0.10323 (16) | 0.16047 (10) | 0.0138 (4) | |
C14 | 0.9979 (2) | 0.02726 (16) | 0.17924 (10) | 0.0152 (4) | |
H14 | 0.8976 | 0.0411 | 0.1801 | 0.018* | |
C15 | 1.0657 (2) | −0.06832 (17) | 0.19667 (11) | 0.0176 (5) | |
H15 | 1.0118 | −0.1195 | 0.2108 | 0.021* | |
C16 | 1.2126 (2) | −0.08925 (17) | 0.19343 (11) | 0.0199 (5) | |
H16 | 1.2589 | −0.155 | 0.2047 | 0.024* | |
C17 | 1.2917 (2) | −0.01454 (18) | 0.17376 (11) | 0.0193 (5) | |
H17 | 1.3921 | −0.0293 | 0.1712 | 0.023* | |
C18 | 1.2246 (2) | 0.08165 (17) | 0.15790 (10) | 0.0160 (4) | |
H18 | 1.2789 | 0.133 | 0.1452 | 0.019* | |
C19 | 0.9629 (2) | 0.22248 (17) | 0.05160 (10) | 0.0151 (4) | |
C20 | 0.9154 (2) | 0.14218 (17) | 0.03165 (11) | 0.0172 (5) | |
H20 | 0.8917 | 0.0895 | 0.0618 | 0.021* | |
C21 | 0.9029 (2) | 0.13954 (18) | −0.03239 (11) | 0.0212 (5) | |
H21 | 0.8696 | 0.0855 | −0.046 | 0.025* | |
C22 | 0.9392 (2) | 0.21577 (19) | −0.07646 (12) | 0.0253 (5) | |
H22 | 0.93 | 0.2139 | −0.1202 | 0.03* | |
C23 | 0.9888 (2) | 0.29476 (19) | −0.05695 (11) | 0.0233 (5) | |
H23 | 1.0149 | 0.3463 | −0.0874 | 0.028* | |
C24 | 1.0002 (2) | 0.29855 (17) | 0.00685 (11) | 0.0178 (5) | |
H24 | 1.0335 | 0.3529 | 0.0201 | 0.021* | |
C25 | 0.8366 (2) | 0.21872 (17) | 0.24500 (10) | 0.0159 (4) | |
C26 | 0.7654 (2) | 0.14545 (17) | 0.27729 (11) | 0.0212 (5) | |
H26 | 0.7177 | 0.1083 | 0.2544 | 0.025* | |
C27 | 0.7638 (3) | 0.12657 (19) | 0.34268 (12) | 0.0271 (6) | |
H27 | 0.7131 | 0.0773 | 0.3641 | 0.033* | |
C28 | 0.8352 (2) | 0.1784 (2) | 0.37793 (12) | 0.0280 (6) | |
C29 | 0.9056 (2) | 0.2508 (2) | 0.34481 (12) | 0.0268 (6) | |
H29 | 0.9549 | 0.2871 | 0.3676 | 0.032* | |
C30 | 0.9065 (2) | 0.27200 (18) | 0.27942 (11) | 0.0201 (5) | |
H30 | 0.9548 | 0.3227 | 0.2582 | 0.024* | |
C31A | 0.8203 (5) | 0.1365 (5) | 0.4457 (3) | 0.0251 (14) | 0.482 (6) |
H31A | 0.8463 | 0.0634 | 0.4503 | 0.03* | 0.482 (6) |
H31B | 0.722 | 0.1542 | 0.4637 | 0.03* | 0.482 (6) |
C32A | 0.9219 (6) | 0.1829 (4) | 0.4788 (3) | 0.0328 (16) | 0.482 (6) |
H32A | 1.0175 | 0.1681 | 0.4585 | 0.049* | 0.482 (6) |
H32B | 0.9217 | 0.1555 | 0.5235 | 0.049* | 0.482 (6) |
H32C | 0.8916 | 0.2548 | 0.4756 | 0.049* | 0.482 (6) |
C32B | 0.9574 (6) | 0.0888 (6) | 0.4745 (3) | 0.072 (3) | 0.518 (6) |
H32D | 0.9476 | 0.0255 | 0.4606 | 0.108* | 0.518 (6) |
H32E | 0.9522 | 0.0824 | 0.5209 | 0.108* | 0.518 (6) |
H32F | 1.0487 | 0.1068 | 0.4576 | 0.108* | 0.518 (6) |
C31B | 0.8439 (6) | 0.1653 (4) | 0.4514 (3) | 0.0204 (15)* | 0.518 (6) |
H31C | 0.8568 | 0.2292 | 0.4646 | 0.025* | 0.518 (6) |
H31D | 0.7528 | 0.1493 | 0.4719 | 0.025* | 0.518 (6) |
C33 | 0.0832 (2) | 0.32778 (16) | 0.71094 (10) | 0.0136 (4) | |
C34 | 0.1283 (2) | 0.39978 (16) | 0.74106 (11) | 0.0180 (5) | |
H34 | 0.2223 | 0.4129 | 0.7325 | 0.022* | |
C35 | 0.0356 (2) | 0.45200 (17) | 0.78348 (11) | 0.0182 (5) | |
H35 | 0.0668 | 0.5003 | 0.8042 | 0.022* | |
C36 | −0.1018 (2) | 0.43402 (17) | 0.79578 (11) | 0.0181 (5) | |
H36 | −0.1646 | 0.4698 | 0.8249 | 0.022* | |
C37 | −0.1477 (2) | 0.36362 (17) | 0.76552 (11) | 0.0179 (5) | |
H37 | −0.2424 | 0.3517 | 0.7736 | 0.022* | |
C38 | −0.0557 (2) | 0.31046 (16) | 0.72330 (10) | 0.0148 (4) | |
H38 | −0.0875 | 0.2622 | 0.7028 | 0.018* | |
C39 | 0.1969 (2) | 0.35422 (16) | 0.58254 (11) | 0.0162 (5) | |
C40 | 0.1467 (2) | 0.33689 (18) | 0.52653 (11) | 0.0197 (5) | |
H40 | 0.1147 | 0.2762 | 0.5242 | 0.024* | |
C41 | 0.1434 (2) | 0.4083 (2) | 0.47428 (12) | 0.0269 (6) | |
H41 | 0.1103 | 0.3959 | 0.436 | 0.032* | |
C42 | 0.1880 (2) | 0.4973 (2) | 0.47764 (13) | 0.0303 (6) | |
H42 | 0.1853 | 0.546 | 0.4417 | 0.036* | |
C43 | 0.2364 (2) | 0.51555 (18) | 0.53309 (13) | 0.0274 (6) | |
H43 | 0.2665 | 0.5769 | 0.5353 | 0.033* | |
C44 | 0.2412 (2) | 0.44471 (17) | 0.58575 (12) | 0.0215 (5) | |
H44 | 0.2745 | 0.4576 | 0.6238 | 0.026* | |
C45 | 0.6032 (2) | 0.10402 (16) | 0.65769 (10) | 0.0141 (4) | |
C46 | 0.5259 (2) | 0.02773 (16) | 0.67787 (10) | 0.0150 (4) | |
H46 | 0.4255 | 0.0414 | 0.6813 | 0.018* | |
C47 | 0.5958 (2) | −0.06828 (17) | 0.69293 (11) | 0.0180 (5) | |
H47 | 0.5433 | −0.1202 | 0.7074 | 0.022* | |
C48 | 0.7427 (2) | −0.08827 (17) | 0.68685 (11) | 0.0209 (5) | |
H48 | 0.7903 | −0.154 | 0.697 | 0.025* | |
C49 | 0.8201 (2) | −0.01322 (17) | 0.66622 (11) | 0.0203 (5) | |
H49 | 0.9204 | −0.0275 | 0.6618 | 0.024* | |
C50 | 0.7507 (2) | 0.08337 (17) | 0.65195 (11) | 0.0172 (5) | |
H50 | 0.8038 | 0.1352 | 0.6383 | 0.021* | |
C51 | 0.4775 (2) | 0.22518 (16) | 0.55163 (10) | 0.0145 (4) | |
C52 | 0.4342 (2) | 0.14306 (17) | 0.53204 (11) | 0.0172 (5) | |
H52 | 0.4193 | 0.0879 | 0.5619 | 0.021* | |
C53 | 0.4132 (2) | 0.14256 (18) | 0.46862 (11) | 0.0218 (5) | |
H53 | 0.3824 | 0.0873 | 0.4553 | 0.026* | |
C54 | 0.4369 (2) | 0.22218 (19) | 0.42477 (12) | 0.0245 (5) | |
H54 | 0.422 | 0.2214 | 0.3815 | 0.029* | |
C55 | 0.4823 (2) | 0.30330 (19) | 0.44380 (11) | 0.0225 (5) | |
H55 | 0.4996 | 0.3575 | 0.4135 | 0.027* | |
C56 | 0.5024 (2) | 0.30489 (17) | 0.50684 (11) | 0.0181 (5) | |
H56 | 0.5333 | 0.3604 | 0.5198 | 0.022* | |
C57 | 0.3692 (2) | 0.21982 (16) | 0.74692 (10) | 0.0137 (4) | |
C58 | 0.3021 (2) | 0.14614 (16) | 0.78082 (11) | 0.0164 (4) | |
H58 | 0.2532 | 0.108 | 0.7592 | 0.02* | |
C59 | 0.3063 (2) | 0.12780 (17) | 0.84639 (11) | 0.0172 (5) | |
H59 | 0.258 | 0.0782 | 0.8691 | 0.021* | |
C60 | 0.3801 (2) | 0.18089 (17) | 0.87935 (11) | 0.0182 (5) | |
C61 | 0.4467 (2) | 0.25418 (17) | 0.84421 (11) | 0.0197 (5) | |
H61 | 0.4977 | 0.2914 | 0.8655 | 0.024* | |
C62 | 0.4413 (2) | 0.27475 (17) | 0.77930 (11) | 0.0171 (5) | |
H62 | 0.4865 | 0.3261 | 0.7568 | 0.021* | |
C63 | 0.3924 (3) | 0.16013 (19) | 0.95017 (11) | 0.0247 (5) | |
H63A | 0.3512 | 0.2212 | 0.9694 | 0.03* | |
H63B | 0.4941 | 0.1456 | 0.958 | 0.03* | |
C64 | 0.3223 (3) | 0.0759 (2) | 0.98406 (12) | 0.0286 (6) | |
H64A | 0.2205 | 0.0907 | 0.9788 | 0.043* | |
H64B | 0.3382 | 0.0681 | 1.0292 | 0.043* | |
H64C | 0.3628 | 0.0145 | 0.9661 | 0.043* | |
N1 | 0.83303 (17) | 0.24265 (13) | 0.17644 (8) | 0.0141 (4) | |
N2 | 0.35942 (17) | 0.24277 (13) | 0.67843 (8) | 0.0128 (4) | |
P1 | 0.66983 (5) | 0.26622 (4) | 0.14637 (3) | 0.01357 (12) | |
P2 | 0.99377 (5) | 0.22740 (4) | 0.13353 (3) | 0.01236 (12) | |
P3 | 0.19389 (5) | 0.26192 (4) | 0.65115 (3) | 0.01247 (12) | |
P4 | 0.51696 (5) | 0.22863 (4) | 0.63272 (3) | 0.01222 (12) | |
S1 | 0.59676 (6) | 0.15083 (4) | 0.12805 (3) | 0.01966 (13) | |
S2 | 1.10868 (6) | 0.32748 (4) | 0.14140 (3) | 0.01785 (12) | |
S3 | 0.12578 (5) | 0.14324 (4) | 0.63558 (3) | 0.01649 (12) | |
S4 | 0.63275 (6) | 0.32894 (4) | 0.63852 (3) | 0.01812 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0126 (9) | 0.0130 (11) | 0.0178 (11) | 0.0006 (8) | −0.0011 (8) | −0.0030 (9) |
C2 | 0.0136 (9) | 0.0149 (11) | 0.0182 (11) | −0.0002 (8) | −0.0027 (8) | −0.0016 (9) |
C3 | 0.0124 (9) | 0.0201 (12) | 0.0205 (12) | −0.0009 (8) | −0.0005 (8) | −0.0017 (9) |
C4 | 0.0192 (10) | 0.0180 (12) | 0.0159 (11) | 0.0037 (8) | −0.0011 (8) | −0.0034 (9) |
C5 | 0.0210 (11) | 0.0125 (11) | 0.0197 (12) | 0.0007 (8) | −0.0052 (9) | −0.0029 (9) |
C6 | 0.0147 (10) | 0.0152 (11) | 0.0213 (12) | −0.0030 (8) | −0.0013 (8) | −0.0023 (9) |
C7 | 0.0122 (9) | 0.0148 (11) | 0.0215 (12) | −0.0013 (8) | −0.0004 (8) | −0.0026 (9) |
C8 | 0.0166 (10) | 0.0221 (13) | 0.0222 (12) | −0.0021 (9) | −0.0016 (9) | −0.0046 (10) |
C9 | 0.0216 (11) | 0.0340 (15) | 0.0202 (12) | −0.0021 (10) | −0.0024 (9) | −0.0003 (11) |
C10 | 0.0214 (11) | 0.0270 (14) | 0.0273 (14) | 0.0002 (10) | 0.0029 (10) | 0.0066 (11) |
C11 | 0.0214 (11) | 0.0167 (12) | 0.0330 (14) | −0.0052 (9) | 0.0041 (10) | 0.0006 (10) |
C12 | 0.0172 (10) | 0.0202 (12) | 0.0230 (12) | −0.0051 (9) | −0.0011 (9) | −0.0036 (10) |
C13 | 0.0138 (9) | 0.0150 (11) | 0.0126 (10) | −0.0007 (8) | −0.0004 (8) | −0.0039 (8) |
C14 | 0.0125 (9) | 0.0181 (12) | 0.0150 (11) | −0.0016 (8) | 0.0002 (8) | −0.0045 (9) |
C15 | 0.0205 (11) | 0.0151 (12) | 0.0175 (11) | −0.0038 (8) | 0.0003 (8) | −0.0030 (9) |
C16 | 0.0207 (11) | 0.0175 (12) | 0.0196 (12) | 0.0044 (9) | −0.0023 (9) | −0.0044 (9) |
C17 | 0.0131 (10) | 0.0256 (13) | 0.0185 (12) | 0.0024 (9) | −0.0022 (8) | −0.0071 (10) |
C18 | 0.0128 (9) | 0.0202 (12) | 0.0159 (11) | −0.0024 (8) | −0.0002 (8) | −0.0059 (9) |
C19 | 0.0117 (9) | 0.0181 (12) | 0.0150 (11) | −0.0006 (8) | 0.0011 (8) | −0.0040 (9) |
C20 | 0.0162 (10) | 0.0160 (12) | 0.0194 (12) | −0.0014 (8) | −0.0011 (8) | −0.0040 (9) |
C21 | 0.0215 (11) | 0.0218 (13) | 0.0215 (12) | −0.0013 (9) | −0.0036 (9) | −0.0081 (10) |
C22 | 0.0278 (12) | 0.0303 (15) | 0.0173 (12) | 0.0001 (10) | −0.0025 (9) | −0.0069 (10) |
C23 | 0.0241 (11) | 0.0270 (14) | 0.0172 (12) | −0.0048 (10) | 0.0003 (9) | 0.0027 (10) |
C24 | 0.0161 (10) | 0.0172 (12) | 0.0203 (12) | −0.0041 (8) | −0.0005 (8) | −0.0022 (9) |
C25 | 0.0136 (9) | 0.0171 (11) | 0.0143 (11) | 0.0027 (8) | 0.0018 (8) | −0.0013 (9) |
C26 | 0.0204 (11) | 0.0146 (12) | 0.0249 (13) | 0.0016 (9) | 0.0076 (9) | −0.0014 (10) |
C27 | 0.0259 (12) | 0.0202 (13) | 0.0268 (14) | 0.0068 (10) | 0.0097 (10) | 0.0063 (11) |
C28 | 0.0203 (11) | 0.0355 (15) | 0.0198 (13) | 0.0110 (10) | 0.0020 (9) | 0.0050 (11) |
C29 | 0.0208 (11) | 0.0393 (16) | 0.0181 (12) | 0.0034 (10) | −0.0040 (9) | −0.0052 (11) |
C30 | 0.0165 (10) | 0.0236 (13) | 0.0189 (12) | −0.0005 (9) | 0.0010 (8) | −0.0025 (10) |
C31A | 0.020 (3) | 0.038 (4) | 0.022 (3) | −0.015 (3) | −0.005 (2) | −0.004 (3) |
C32A | 0.034 (3) | 0.034 (4) | 0.027 (3) | −0.001 (2) | −0.005 (2) | 0.004 (2) |
C32B | 0.088 (6) | 0.084 (6) | 0.021 (3) | 0.048 (5) | −0.006 (3) | −0.002 (3) |
C33 | 0.0125 (9) | 0.0105 (10) | 0.0167 (11) | 0.0010 (7) | −0.0007 (8) | −0.0015 (8) |
C34 | 0.0144 (10) | 0.0132 (11) | 0.0270 (13) | −0.0024 (8) | −0.0010 (9) | −0.0047 (9) |
C35 | 0.0198 (10) | 0.0145 (11) | 0.0205 (12) | −0.0012 (8) | −0.0032 (9) | −0.0042 (9) |
C36 | 0.0186 (10) | 0.0170 (12) | 0.0166 (11) | 0.0025 (8) | 0.0009 (8) | −0.0030 (9) |
C37 | 0.0123 (9) | 0.0182 (12) | 0.0221 (12) | −0.0005 (8) | −0.0001 (8) | −0.0015 (9) |
C38 | 0.0130 (9) | 0.0137 (11) | 0.0176 (11) | −0.0010 (8) | −0.0022 (8) | −0.0024 (9) |
C39 | 0.0101 (9) | 0.0139 (11) | 0.0235 (12) | −0.0007 (8) | 0.0015 (8) | −0.0010 (9) |
C40 | 0.0143 (10) | 0.0211 (12) | 0.0226 (12) | −0.0013 (8) | −0.0003 (8) | −0.0016 (10) |
C41 | 0.0185 (11) | 0.0339 (15) | 0.0250 (13) | −0.0011 (10) | 0.0009 (9) | 0.0025 (11) |
C42 | 0.0207 (12) | 0.0289 (15) | 0.0321 (15) | 0.0039 (10) | 0.0060 (10) | 0.0142 (12) |
C43 | 0.0208 (11) | 0.0155 (12) | 0.0423 (16) | −0.0027 (9) | 0.0073 (10) | 0.0034 (11) |
C44 | 0.0174 (10) | 0.0178 (12) | 0.0284 (13) | −0.0028 (9) | 0.0017 (9) | −0.0014 (10) |
C45 | 0.0153 (10) | 0.0147 (11) | 0.0121 (10) | 0.0002 (8) | −0.0002 (8) | −0.0049 (8) |
C46 | 0.0132 (9) | 0.0169 (11) | 0.0156 (11) | −0.0009 (8) | −0.0013 (8) | −0.0064 (9) |
C47 | 0.0207 (11) | 0.0158 (12) | 0.0177 (11) | −0.0026 (8) | −0.0005 (9) | −0.0042 (9) |
C48 | 0.0232 (11) | 0.0159 (12) | 0.0225 (12) | 0.0052 (9) | −0.0060 (9) | −0.0067 (10) |
C49 | 0.0139 (10) | 0.0221 (13) | 0.0245 (12) | 0.0029 (8) | −0.0025 (9) | −0.0083 (10) |
C50 | 0.0140 (10) | 0.0191 (12) | 0.0192 (11) | −0.0029 (8) | −0.0009 (8) | −0.0046 (9) |
C51 | 0.0110 (9) | 0.0158 (11) | 0.0160 (11) | −0.0003 (8) | 0.0013 (8) | −0.0039 (9) |
C52 | 0.0162 (10) | 0.0163 (12) | 0.0185 (12) | 0.0018 (8) | −0.0017 (8) | −0.0051 (9) |
C53 | 0.0214 (11) | 0.0222 (13) | 0.0227 (13) | 0.0019 (9) | −0.0044 (9) | −0.0110 (10) |
C54 | 0.0222 (11) | 0.0331 (15) | 0.0166 (12) | 0.0031 (10) | −0.0028 (9) | −0.0063 (11) |
C55 | 0.0191 (11) | 0.0278 (14) | 0.0179 (12) | −0.0007 (9) | 0.0015 (9) | 0.0014 (10) |
C56 | 0.0141 (10) | 0.0194 (12) | 0.0196 (12) | −0.0017 (8) | 0.0011 (8) | −0.0012 (9) |
C57 | 0.0121 (9) | 0.0132 (11) | 0.0153 (11) | 0.0001 (8) | −0.0001 (8) | −0.0032 (8) |
C58 | 0.0144 (10) | 0.0157 (11) | 0.0199 (12) | −0.0020 (8) | −0.0003 (8) | −0.0055 (9) |
C59 | 0.0169 (10) | 0.0152 (11) | 0.0184 (11) | −0.0021 (8) | 0.0015 (8) | −0.0011 (9) |
C60 | 0.0174 (10) | 0.0194 (12) | 0.0165 (11) | 0.0019 (8) | −0.0002 (8) | −0.0040 (9) |
C61 | 0.0196 (10) | 0.0209 (12) | 0.0204 (12) | −0.0051 (9) | −0.0012 (9) | −0.0073 (10) |
C62 | 0.0157 (10) | 0.0158 (11) | 0.0208 (12) | −0.0053 (8) | 0.0002 (8) | −0.0032 (9) |
C63 | 0.0323 (13) | 0.0279 (14) | 0.0137 (11) | −0.0035 (10) | −0.0032 (9) | −0.0034 (10) |
C64 | 0.0338 (14) | 0.0337 (15) | 0.0160 (12) | −0.0034 (11) | 0.0017 (10) | −0.0001 (11) |
N1 | 0.0125 (8) | 0.0149 (9) | 0.0145 (9) | −0.0013 (7) | 0.0010 (7) | −0.0025 (7) |
N2 | 0.0112 (8) | 0.0132 (9) | 0.0142 (9) | −0.0024 (6) | 0.0009 (6) | −0.0034 (7) |
P1 | 0.0114 (2) | 0.0116 (3) | 0.0184 (3) | −0.00273 (19) | 0.0005 (2) | −0.0043 (2) |
P2 | 0.0112 (2) | 0.0123 (3) | 0.0142 (3) | −0.00285 (19) | 0.00019 (19) | −0.0034 (2) |
P3 | 0.0108 (2) | 0.0107 (3) | 0.0163 (3) | −0.00226 (19) | −0.00034 (19) | −0.0027 (2) |
P4 | 0.0110 (2) | 0.0121 (3) | 0.0142 (3) | −0.00277 (19) | 0.00019 (19) | −0.0036 (2) |
S1 | 0.0173 (3) | 0.0155 (3) | 0.0286 (3) | −0.0069 (2) | 0.0029 (2) | −0.0094 (2) |
S2 | 0.0171 (2) | 0.0173 (3) | 0.0216 (3) | −0.0079 (2) | 0.0007 (2) | −0.0064 (2) |
S3 | 0.0162 (2) | 0.0135 (3) | 0.0214 (3) | −0.0049 (2) | −0.0010 (2) | −0.0049 (2) |
S4 | 0.0168 (2) | 0.0176 (3) | 0.0225 (3) | −0.0085 (2) | 0.0021 (2) | −0.0066 (2) |
C1—C2 | 1.393 (3) | C33—C34 | 1.400 (3) |
C1—C6 | 1.402 (3) | C33—P3 | 1.818 (2) |
C1—P1 | 1.819 (2) | C34—C35 | 1.390 (3) |
C2—C3 | 1.390 (3) | C34—H34 | 0.95 |
C2—H2 | 0.95 | C35—C36 | 1.384 (3) |
C3—C4 | 1.381 (3) | C35—H35 | 0.95 |
C3—H3 | 0.95 | C36—C37 | 1.387 (3) |
C4—C5 | 1.389 (3) | C36—H36 | 0.95 |
C4—H4 | 0.95 | C37—C38 | 1.391 (3) |
C5—C6 | 1.386 (3) | C37—H37 | 0.95 |
C5—H5 | 0.95 | C38—H38 | 0.95 |
C6—H6 | 0.95 | C39—C40 | 1.395 (3) |
C7—C8 | 1.396 (3) | C39—C44 | 1.400 (3) |
C7—C12 | 1.398 (3) | C39—P3 | 1.813 (2) |
C7—P1 | 1.813 (2) | C40—C41 | 1.388 (3) |
C8—C9 | 1.392 (3) | C40—H40 | 0.95 |
C8—H8 | 0.95 | C41—C42 | 1.383 (4) |
C9—C10 | 1.382 (4) | C41—H41 | 0.95 |
C9—H9 | 0.95 | C42—C43 | 1.381 (4) |
C10—C11 | 1.389 (4) | C42—H42 | 0.95 |
C10—H10 | 0.95 | C43—C44 | 1.389 (3) |
C11—C12 | 1.391 (3) | C43—H43 | 0.95 |
C11—H11 | 0.95 | C44—H44 | 0.95 |
C12—H12 | 0.95 | C45—C46 | 1.394 (3) |
C13—C14 | 1.397 (3) | C45—C50 | 1.397 (3) |
C13—C18 | 1.398 (3) | C45—P4 | 1.811 (2) |
C13—P2 | 1.806 (2) | C46—C47 | 1.390 (3) |
C14—C15 | 1.387 (3) | C46—H46 | 0.95 |
C14—H14 | 0.95 | C47—C48 | 1.391 (3) |
C15—C16 | 1.391 (3) | C47—H47 | 0.95 |
C15—H15 | 0.95 | C48—C49 | 1.382 (3) |
C16—C17 | 1.386 (3) | C48—H48 | 0.95 |
C16—H16 | 0.95 | C49—C50 | 1.392 (3) |
C17—C18 | 1.386 (3) | C49—H49 | 0.95 |
C17—H17 | 0.95 | C50—H50 | 0.95 |
C18—H18 | 0.95 | C51—C52 | 1.398 (3) |
C19—C24 | 1.396 (3) | C51—C56 | 1.399 (3) |
C19—C20 | 1.398 (3) | C51—P4 | 1.816 (2) |
C19—P2 | 1.814 (2) | C52—C53 | 1.389 (3) |
C20—C21 | 1.390 (3) | C52—H52 | 0.95 |
C20—H20 | 0.95 | C53—C54 | 1.384 (4) |
C21—C22 | 1.386 (3) | C53—H53 | 0.95 |
C21—H21 | 0.95 | C54—C55 | 1.391 (4) |
C22—C23 | 1.388 (4) | C54—H54 | 0.95 |
C22—H22 | 0.95 | C55—C56 | 1.382 (3) |
C23—C24 | 1.386 (3) | C55—H55 | 0.95 |
C23—H23 | 0.95 | C56—H56 | 0.95 |
C24—H24 | 0.95 | C57—C58 | 1.387 (3) |
C25—C26 | 1.392 (3) | C57—C62 | 1.395 (3) |
C25—C30 | 1.394 (3) | C57—N2 | 1.464 (3) |
C25—N1 | 1.461 (3) | C58—C59 | 1.393 (3) |
C26—C27 | 1.386 (3) | C58—H58 | 0.95 |
C26—H26 | 0.95 | C59—C60 | 1.396 (3) |
C27—C28 | 1.400 (4) | C59—H59 | 0.95 |
C27—H27 | 0.95 | C60—C61 | 1.391 (3) |
C28—C29 | 1.385 (4) | C60—C63 | 1.514 (3) |
C28—C31A | 1.491 (6) | C61—C62 | 1.382 (3) |
C28—C31B | 1.565 (7) | C61—H61 | 0.95 |
C29—C30 | 1.389 (3) | C62—H62 | 0.95 |
C29—H29 | 0.95 | C63—C64 | 1.514 (4) |
C30—H30 | 0.95 | C63—H63A | 0.99 |
C31A—C32A | 1.527 (2) | C63—H63B | 0.99 |
C31A—H31A | 0.99 | C64—H64A | 0.98 |
C31A—H31B | 0.99 | C64—H64B | 0.98 |
C32A—H32A | 0.98 | C64—H64C | 0.98 |
C32A—H32B | 0.98 | N1—P1 | 1.7160 (17) |
C32A—H32C | 0.98 | N1—P2 | 1.7183 (18) |
C32B—C31B | 1.455 (8) | N2—P3 | 1.7138 (17) |
C32B—H32D | 0.98 | N2—P4 | 1.7214 (17) |
C32B—H32E | 0.98 | P1—S1 | 1.9467 (8) |
C32B—H32F | 0.98 | P2—S2 | 1.9466 (8) |
C31B—H31C | 0.99 | P3—S3 | 1.9446 (8) |
C31B—H31D | 0.99 | P4—S4 | 1.9451 (8) |
C33—C38 | 1.394 (3) | ||
C2—C1—C6 | 119.05 (19) | C37—C36—H36 | 120.1 |
C2—C1—P1 | 118.31 (17) | C36—C37—C38 | 120.2 (2) |
C6—C1—P1 | 122.58 (16) | C36—C37—H37 | 119.9 |
C3—C2—C1 | 120.4 (2) | C38—C37—H37 | 119.9 |
C3—C2—H2 | 119.8 | C37—C38—C33 | 120.3 (2) |
C1—C2—H2 | 119.8 | C37—C38—H38 | 119.9 |
C4—C3—C2 | 120.2 (2) | C33—C38—H38 | 119.9 |
C4—C3—H3 | 119.9 | C40—C39—C44 | 119.4 (2) |
C2—C3—H3 | 119.9 | C40—C39—P3 | 119.23 (18) |
C3—C4—C5 | 120.0 (2) | C44—C39—P3 | 121.27 (18) |
C3—C4—H4 | 120 | C41—C40—C39 | 120.0 (2) |
C5—C4—H4 | 120 | C41—C40—H40 | 120 |
C6—C5—C4 | 120.3 (2) | C39—C40—H40 | 120 |
C6—C5—H5 | 119.9 | C42—C41—C40 | 120.3 (2) |
C4—C5—H5 | 119.9 | C42—C41—H41 | 119.8 |
C5—C6—C1 | 120.1 (2) | C40—C41—H41 | 119.8 |
C5—C6—H6 | 119.9 | C43—C42—C41 | 120.1 (2) |
C1—C6—H6 | 119.9 | C43—C42—H42 | 120 |
C8—C7—C12 | 119.5 (2) | C41—C42—H42 | 120 |
C8—C7—P1 | 119.45 (18) | C42—C43—C44 | 120.4 (2) |
C12—C7—P1 | 121.05 (17) | C42—C43—H43 | 119.8 |
C9—C8—C7 | 119.7 (2) | C44—C43—H43 | 119.8 |
C9—C8—H8 | 120.1 | C43—C44—C39 | 119.8 (2) |
C7—C8—H8 | 120.1 | C43—C44—H44 | 120.1 |
C10—C9—C8 | 120.8 (2) | C39—C44—H44 | 120.1 |
C10—C9—H9 | 119.6 | C46—C45—C50 | 119.8 (2) |
C8—C9—H9 | 119.6 | C46—C45—P4 | 121.54 (15) |
C9—C10—C11 | 119.7 (2) | C50—C45—P4 | 118.51 (17) |
C9—C10—H10 | 120.2 | C47—C46—C45 | 119.97 (19) |
C11—C10—H10 | 120.2 | C47—C46—H46 | 120 |
C10—C11—C12 | 120.2 (2) | C45—C46—H46 | 120 |
C10—C11—H11 | 119.9 | C46—C47—C48 | 119.9 (2) |
C12—C11—H11 | 119.9 | C46—C47—H47 | 120.1 |
C11—C12—C7 | 120.1 (2) | C48—C47—H47 | 120.1 |
C11—C12—H12 | 119.9 | C49—C48—C47 | 120.5 (2) |
C7—C12—H12 | 119.9 | C49—C48—H48 | 119.8 |
C14—C13—C18 | 119.6 (2) | C47—C48—H48 | 119.8 |
C14—C13—P2 | 121.53 (15) | C48—C49—C50 | 119.9 (2) |
C18—C13—P2 | 118.75 (17) | C48—C49—H49 | 120.1 |
C15—C14—C13 | 120.00 (19) | C50—C49—H49 | 120.1 |
C15—C14—H14 | 120 | C49—C50—C45 | 120.0 (2) |
C13—C14—H14 | 120 | C49—C50—H50 | 120 |
C14—C15—C16 | 120.0 (2) | C45—C50—H50 | 120 |
C14—C15—H15 | 120 | C52—C51—C56 | 119.5 (2) |
C16—C15—H15 | 120 | C52—C51—P4 | 122.32 (17) |
C17—C16—C15 | 120.2 (2) | C56—C51—P4 | 117.95 (17) |
C17—C16—H16 | 119.9 | C53—C52—C51 | 119.7 (2) |
C15—C16—H16 | 119.9 | C53—C52—H52 | 120.2 |
C16—C17—C18 | 120.0 (2) | C51—C52—H52 | 120.2 |
C16—C17—H17 | 120 | C54—C53—C52 | 120.3 (2) |
C18—C17—H17 | 120 | C54—C53—H53 | 119.8 |
C17—C18—C13 | 120.1 (2) | C52—C53—H53 | 119.8 |
C17—C18—H18 | 119.9 | C53—C54—C55 | 120.2 (2) |
C13—C18—H18 | 119.9 | C53—C54—H54 | 119.9 |
C24—C19—C20 | 119.7 (2) | C55—C54—H54 | 119.9 |
C24—C19—P2 | 117.55 (17) | C56—C55—C54 | 119.9 (2) |
C20—C19—P2 | 122.52 (17) | C56—C55—H55 | 120.1 |
C21—C20—C19 | 119.9 (2) | C54—C55—H55 | 120.1 |
C21—C20—H20 | 120.1 | C55—C56—C51 | 120.3 (2) |
C19—C20—H20 | 120.1 | C55—C56—H56 | 119.8 |
C22—C21—C20 | 120.1 (2) | C51—C56—H56 | 119.8 |
C22—C21—H21 | 120 | C58—C57—C62 | 119.1 (2) |
C20—C21—H21 | 120 | C58—C57—N2 | 120.59 (19) |
C21—C22—C23 | 120.2 (2) | C62—C57—N2 | 120.23 (19) |
C21—C22—H22 | 119.9 | C57—C58—C59 | 120.3 (2) |
C23—C22—H22 | 119.9 | C57—C58—H58 | 119.8 |
C24—C23—C22 | 120.1 (2) | C59—C58—H58 | 119.8 |
C24—C23—H23 | 119.9 | C58—C59—C60 | 121.3 (2) |
C22—C23—H23 | 119.9 | C58—C59—H59 | 119.4 |
C23—C24—C19 | 120.0 (2) | C60—C59—H59 | 119.4 |
C23—C24—H24 | 120 | C61—C60—C59 | 117.3 (2) |
C19—C24—H24 | 120 | C61—C60—C63 | 119.9 (2) |
C26—C25—C30 | 119.0 (2) | C59—C60—C63 | 122.9 (2) |
C26—C25—N1 | 120.7 (2) | C62—C61—C60 | 122.2 (2) |
C30—C25—N1 | 120.3 (2) | C62—C61—H61 | 118.9 |
C27—C26—C25 | 120.3 (2) | C60—C61—H61 | 118.9 |
C27—C26—H26 | 119.9 | C61—C62—C57 | 119.8 (2) |
C25—C26—H26 | 119.9 | C61—C62—H62 | 120.1 |
C26—C27—C28 | 121.5 (2) | C57—C62—H62 | 120.1 |
C26—C27—H27 | 119.2 | C60—C63—C64 | 116.2 (2) |
C28—C27—H27 | 119.2 | C60—C63—H63A | 108.2 |
C29—C28—C27 | 117.2 (2) | C64—C63—H63A | 108.2 |
C29—C28—C31A | 134.5 (3) | C60—C63—H63B | 108.2 |
C27—C28—C31A | 108.2 (3) | C64—C63—H63B | 108.2 |
C29—C28—C31B | 115.3 (3) | H63A—C63—H63B | 107.4 |
C27—C28—C31B | 127.5 (3) | C63—C64—H64A | 109.5 |
C28—C29—C30 | 122.2 (2) | C63—C64—H64B | 109.5 |
C28—C29—H29 | 118.9 | H64A—C64—H64B | 109.5 |
C30—C29—H29 | 118.9 | C63—C64—H64C | 109.5 |
C29—C30—C25 | 119.8 (2) | H64A—C64—H64C | 109.5 |
C29—C30—H30 | 120.1 | H64B—C64—H64C | 109.5 |
C25—C30—H30 | 120.1 | C25—N1—P1 | 116.96 (13) |
C28—C31A—C32A | 105.0 (4) | C25—N1—P2 | 116.05 (13) |
C28—C31A—H31A | 110.8 | P1—N1—P2 | 126.34 (11) |
C32A—C31A—H31A | 110.8 | C57—N2—P3 | 117.07 (13) |
C28—C31A—H31B | 110.8 | C57—N2—P4 | 116.11 (13) |
C32A—C31A—H31B | 110.8 | P3—N2—P4 | 125.98 (11) |
H31A—C31A—H31B | 108.8 | N1—P1—C7 | 105.68 (9) |
C31B—C32B—H32D | 109.5 | N1—P1—C1 | 102.94 (9) |
C31B—C32B—H32E | 109.5 | C7—P1—C1 | 105.08 (10) |
H32D—C32B—H32E | 109.5 | N1—P1—S1 | 115.77 (7) |
C31B—C32B—H32F | 109.5 | C7—P1—S1 | 113.74 (8) |
H32D—C32B—H32F | 109.5 | C1—P1—S1 | 112.50 (8) |
H32E—C32B—H32F | 109.5 | N1—P2—C13 | 104.68 (9) |
C32B—C31B—C28 | 114.5 (5) | N1—P2—C19 | 108.30 (9) |
C32B—C31B—H31C | 108.6 | C13—P2—C19 | 104.31 (10) |
C28—C31B—H31C | 108.6 | N1—P2—S2 | 113.97 (7) |
C32B—C31B—H31D | 108.6 | C13—P2—S2 | 113.18 (7) |
C28—C31B—H31D | 108.6 | C19—P2—S2 | 111.69 (8) |
H31C—C31B—H31D | 107.6 | N2—P3—C39 | 106.08 (9) |
C38—C33—C34 | 119.26 (19) | N2—P3—C33 | 103.69 (9) |
C38—C33—P3 | 117.85 (16) | C39—P3—C33 | 103.83 (10) |
C34—C33—P3 | 122.70 (16) | N2—P3—S3 | 115.40 (7) |
C35—C34—C33 | 120.0 (2) | C39—P3—S3 | 113.83 (8) |
C35—C34—H34 | 120 | C33—P3—S3 | 112.84 (8) |
C33—C34—H34 | 120 | N2—P4—C45 | 104.84 (9) |
C36—C35—C34 | 120.4 (2) | N2—P4—C51 | 107.95 (9) |
C36—C35—H35 | 119.8 | C45—P4—C51 | 104.40 (10) |
C34—C35—H35 | 119.8 | N2—P4—S4 | 114.04 (7) |
C35—C36—C37 | 119.9 (2) | C45—P4—S4 | 113.23 (7) |
C35—C36—H36 | 120.1 | C51—P4—S4 | 111.68 (8) |
C6—C1—C2—C3 | −0.5 (3) | C59—C60—C61—C62 | 0.0 (3) |
P1—C1—C2—C3 | −177.76 (16) | C63—C60—C61—C62 | 178.6 (2) |
C1—C2—C3—C4 | −0.1 (3) | C60—C61—C62—C57 | −1.2 (3) |
C2—C3—C4—C5 | 0.4 (3) | C58—C57—C62—C61 | 1.0 (3) |
C3—C4—C5—C6 | 0.0 (3) | N2—C57—C62—C61 | 178.31 (18) |
C4—C5—C6—C1 | −0.6 (3) | C61—C60—C63—C64 | −177.2 (2) |
C2—C1—C6—C5 | 0.9 (3) | C59—C60—C63—C64 | 1.3 (3) |
P1—C1—C6—C5 | 177.99 (17) | C26—C25—N1—P1 | 51.1 (2) |
C12—C7—C8—C9 | 0.7 (3) | C30—C25—N1—P1 | −126.23 (18) |
P1—C7—C8—C9 | 178.32 (17) | C26—C25—N1—P2 | −120.22 (19) |
C7—C8—C9—C10 | −1.0 (3) | C30—C25—N1—P2 | 62.5 (2) |
C8—C9—C10—C11 | 0.3 (4) | C58—C57—N2—P3 | 50.0 (2) |
C9—C10—C11—C12 | 0.5 (4) | C62—C57—N2—P3 | −127.31 (18) |
C10—C11—C12—C7 | −0.7 (3) | C58—C57—N2—P4 | −120.15 (18) |
C8—C7—C12—C11 | 0.1 (3) | C62—C57—N2—P4 | 62.5 (2) |
P1—C7—C12—C11 | −177.45 (17) | C25—N1—P1—C7 | 146.52 (16) |
C18—C13—C14—C15 | 1.6 (3) | P2—N1—P1—C7 | −43.21 (16) |
P2—C13—C14—C15 | 176.79 (17) | C25—N1—P1—C1 | 36.54 (18) |
C13—C14—C15—C16 | −2.2 (3) | P2—N1—P1—C1 | −153.19 (13) |
C14—C15—C16—C17 | 1.0 (3) | C25—N1—P1—S1 | −86.61 (16) |
C15—C16—C17—C18 | 0.7 (3) | P2—N1—P1—S1 | 83.65 (13) |
C16—C17—C18—C13 | −1.3 (3) | C8—C7—P1—N1 | 130.08 (17) |
C14—C13—C18—C17 | 0.1 (3) | C12—C7—P1—N1 | −52.36 (19) |
P2—C13—C18—C17 | −175.20 (17) | C8—C7—P1—C1 | −121.48 (18) |
C24—C19—C20—C21 | −1.3 (3) | C12—C7—P1—C1 | 56.09 (19) |
P2—C19—C20—C21 | −175.59 (16) | C8—C7—P1—S1 | 2.00 (19) |
C19—C20—C21—C22 | 0.8 (3) | C12—C7—P1—S1 | 179.56 (15) |
C20—C21—C22—C23 | 0.4 (3) | C2—C1—P1—N1 | −142.13 (17) |
C21—C22—C23—C24 | −1.0 (3) | C6—C1—P1—N1 | 40.7 (2) |
C22—C23—C24—C19 | 0.5 (3) | C2—C1—P1—C7 | 107.43 (18) |
C20—C19—C24—C23 | 0.7 (3) | C6—C1—P1—C7 | −69.7 (2) |
P2—C19—C24—C23 | 175.22 (17) | C2—C1—P1—S1 | −16.83 (19) |
C30—C25—C26—C27 | 0.4 (3) | C6—C1—P1—S1 | 166.03 (16) |
N1—C25—C26—C27 | −176.92 (19) | C25—N1—P2—C13 | 51.34 (17) |
C25—C26—C27—C28 | −1.3 (3) | P1—N1—P2—C13 | −119.00 (14) |
C26—C27—C28—C29 | 1.1 (3) | C25—N1—P2—C19 | 162.19 (16) |
C26—C27—C28—C31A | −176.5 (3) | P1—N1—P2—C19 | −8.16 (17) |
C26—C27—C28—C31B | −179.7 (3) | C25—N1—P2—S2 | −72.84 (16) |
C27—C28—C29—C30 | 0.0 (3) | P1—N1—P2—S2 | 116.82 (12) |
C31A—C28—C29—C30 | 176.8 (4) | C14—C13—P2—N1 | 33.0 (2) |
C31B—C28—C29—C30 | −179.3 (3) | C18—C13—P2—N1 | −151.82 (17) |
C28—C29—C30—C25 | −0.9 (3) | C14—C13—P2—C19 | −80.73 (19) |
C26—C25—C30—C29 | 0.7 (3) | C18—C13—P2—C19 | 94.49 (18) |
N1—C25—C30—C29 | 178.00 (19) | C14—C13—P2—S2 | 157.65 (16) |
C29—C28—C31A—C32A | −7.0 (6) | C18—C13—P2—S2 | −27.13 (19) |
C27—C28—C31A—C32A | 169.9 (3) | C24—C19—P2—N1 | 115.33 (17) |
C31B—C28—C31A—C32A | −17.6 (8) | C20—C19—P2—N1 | −70.27 (19) |
C29—C28—C31B—C32B | −94.2 (6) | C24—C19—P2—C13 | −133.58 (17) |
C27—C28—C31B—C32B | 86.6 (7) | C20—C19—P2—C13 | 40.82 (19) |
C31A—C28—C31B—C32B | 77.5 (10) | C24—C19—P2—S2 | −10.98 (18) |
C38—C33—C34—C35 | 1.0 (3) | C20—C19—P2—S2 | 163.42 (15) |
P3—C33—C34—C35 | 175.95 (17) | C57—N2—P3—C39 | 146.55 (16) |
C33—C34—C35—C36 | −0.6 (3) | P4—N2—P3—C39 | −44.39 (15) |
C34—C35—C36—C37 | −0.2 (3) | C57—N2—P3—C33 | 37.51 (17) |
C35—C36—C37—C38 | 0.6 (3) | P4—N2—P3—C33 | −153.44 (13) |
C36—C37—C38—C33 | −0.2 (3) | C57—N2—P3—S3 | −86.40 (15) |
C34—C33—C38—C37 | −0.5 (3) | P4—N2—P3—S3 | 82.65 (13) |
P3—C33—C38—C37 | −175.77 (16) | C40—C39—P3—N2 | 130.71 (17) |
C44—C39—C40—C41 | 1.2 (3) | C44—C39—P3—N2 | −52.92 (19) |
P3—C39—C40—C41 | 177.63 (17) | C40—C39—P3—C33 | −120.34 (17) |
C39—C40—C41—C42 | −0.9 (3) | C44—C39—P3—C33 | 56.03 (19) |
C40—C41—C42—C43 | 0.1 (4) | C40—C39—P3—S3 | 2.73 (19) |
C41—C42—C43—C44 | 0.3 (4) | C44—C39—P3—S3 | 179.10 (15) |
C42—C43—C44—C39 | 0.1 (3) | C38—C33—P3—N2 | −146.72 (16) |
C40—C39—C44—C43 | −0.8 (3) | C34—C33—P3—N2 | 38.2 (2) |
P3—C39—C44—C43 | −177.17 (17) | C38—C33—P3—C39 | 102.57 (18) |
C50—C45—C46—C47 | 0.8 (3) | C34—C33—P3—C39 | −72.49 (19) |
P4—C45—C46—C47 | 175.98 (17) | C38—C33—P3—S3 | −21.15 (19) |
C45—C46—C47—C48 | −1.0 (3) | C34—C33—P3—S3 | 163.79 (16) |
C46—C47—C48—C49 | 0.3 (3) | C57—N2—P4—C45 | 52.68 (17) |
C47—C48—C49—C50 | 0.6 (4) | P3—N2—P4—C45 | −116.47 (13) |
C48—C49—C50—C45 | −0.8 (3) | C57—N2—P4—C51 | 163.55 (15) |
C46—C45—C50—C49 | 0.2 (3) | P3—N2—P4—C51 | −5.60 (16) |
P4—C45—C50—C49 | −175.19 (17) | C57—N2—P4—S4 | −71.72 (16) |
C56—C51—C52—C53 | −1.6 (3) | P3—N2—P4—S4 | 119.13 (11) |
P4—C51—C52—C53 | −176.41 (16) | C46—C45—P4—N2 | 32.5 (2) |
C51—C52—C53—C54 | 1.0 (3) | C50—C45—P4—N2 | −152.18 (17) |
C52—C53—C54—C55 | 0.2 (3) | C46—C45—P4—C51 | −80.85 (19) |
C53—C54—C55—C56 | −0.7 (3) | C50—C45—P4—C51 | 94.42 (18) |
C54—C55—C56—C51 | 0.1 (3) | C46—C45—P4—S4 | 157.47 (16) |
C52—C51—C56—C55 | 1.0 (3) | C50—C45—P4—S4 | −27.3 (2) |
P4—C51—C56—C55 | 176.08 (16) | C52—C51—P4—N2 | −73.50 (18) |
C62—C57—C58—C59 | 0.3 (3) | C56—C51—P4—N2 | 111.58 (17) |
N2—C57—C58—C59 | −176.99 (18) | C52—C51—P4—C45 | 37.67 (19) |
C57—C58—C59—C60 | −1.5 (3) | C56—C51—P4—C45 | −137.25 (16) |
C58—C59—C60—C61 | 1.3 (3) | C52—C51—P4—S4 | 160.37 (15) |
C58—C59—C60—C63 | −177.3 (2) | C56—C51—P4—S4 | −14.55 (18) |
Cg1 and Cg2 are the centroids of the C19–C24 and C57–C62 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···Cg2i | 0.95 | 2.97 | 3.759 (3) | 141 |
C64—H64A···Cg1ii | 0.98 | 2.88 | 3.767 (3) | 151 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x−1, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C32H29NP2S2 |
Mr | 553.62 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 9.6305 (11), 13.8027 (14), 21.360 (2) |
α, β, γ (°) | 82.484 (2), 84.635 (2), 79.975 (2) |
V (Å3) | 2764.7 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.17 × 0.08 × 0.08 |
Data collection | |
Diffractometer | Bruker X8 APEXII 4K KappaCCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.946, 0.974 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 56725, 13522, 9271 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.666 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.107, 1.00 |
No. of reflections | 13522 |
No. of parameters | 684 |
No. of restraints | 9 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.82, −0.36 |
Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SAINT-Plus and XPREP (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), WinGX (Farrugia, 2012).
Cg1 and Cg2 are the centroids of the C19–C24 and C57–C62 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···Cg2i | 0.95 | 2.97 | 3.759 (3) | 141 |
C64—H64A···Cg1ii | 0.98 | 2.88 | 3.767 (3) | 151 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x−1, y, z+1. |
Acknowledgements
The authors gratefully acknowledge the financial support of GMRDC, University of Fort Hare, South Africa.
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.
Compounds containing P—N bonds have been known for many years and their chemistry has been of considerable interest because of their applications in increasingly diverse fields (Hartley, 1990; Greenwood & Earnshaw, 1984) and in homogeneous catalysis as these ligands can be used for fine tuning the activity and selectivity of the catalyst (Balakrishna et al., 2000). Bis(diphenylphosphino)alkylaniline derivatives are of particular interest among amino phosphines due to their stability and ability to form chelates with transition metal ions (Biricik et al., 2007; Fei & Dyson, 2005). Synthesis of bis(diphenylphosphino)alkylaniline is through aminolysis of aniline (Fernández et al., 2005; Gaw et al., 2002) and incorporation of additional functional groups (Fei et al., 2004; Slawin et al., 2005).
The structure of (I) Fig. 1, has a slightly distorted trigonal planar N atom bound to two PV atoms and a C atom of the p-ethylphenyl moiety in which the P–N–P angle is larger, 126.01 (11) and 126.28 (11)°, than the four C–N–P bond angles in the two molecules (between 116.03(13 and 117.10 (13) Å). The two S atoms are trans to one another with respect to the trigonal plane. The P–N bond distances 1.7162 (18), 1.7192 (18), 1.7134 (17) and 1.7212 (18) Å and P–S bond distances 1.9469 (8), 1.9468 (8), 1.9446 (8) and 1.9449 (8) Å are similar in both molecules and compare well to those of similar molecules in literature (Slawin et al., 2005). The r.m.s. value of an overlay of the two molecules is 0.218 Å and shows major differences only between the ethyl moieties of the two molecules. The crystal lattice is stabilized by two C—H···π intermolecular interactions with Cg···H distances of 3.759 (3) and 3.767 (3) Å.