Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827011101403X/sq3282sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827011101403X/sq3282Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827011101403X/sq3282IIsup3.hkl |
CCDC references: 829696; 829697
For related literature, see: Aslanov et al. (1977); Audrieth & Toy (1942); Bernstein et al. (1995); Collinson & Fenton (1996); Etter et al. (1990); Fu & Chivers (2007); Gholivand et al. (2010;) Gholivand & Shariatinia (2006); Gholivand et al. (2004); Gholivand, Shariatinia & Pourayoubi (2006); Hossain et al. (1996); Rheingold et al. (1984); Steiner (2002); Tarafder et al. (2002); Tursina et al. (1985); Tursina et al. (1987); Xie et al. (2007).
N,N',N''-Tricyclohexylphosphoric triamide (PTA) was prepared according to the procedure reported by Audrieth & Toy (1942). IR (KBr, cm-1): 3272 (NH), 2930, 2852, 2667, 1659, 1440, 1296, 1237, 1145, 1111, 1004, 926, 882. For the synthesis of [Sn(CH3)2Cl2(PTA)2], (I), a solution of dimethyltin(IV) dichloride (0.253 g, 1.15 mmol) in chloroform (5 ml) was added dropwise to a solution of PTA (0.787 g, 2.31 mmol) in chloroform (15 ml). The clear solution was stirred for 5 h. Colourless crystals were obtained after a few days in a refrigerator (at 278 K). An effort to prepare the trans complex under reflux conditions (24 h) in CH3OH was not successful and led to the cis complex, which was confirmed by X-ray crystallography (yield: approximately 80%). IR (KBr, cm-1): 3285 (NH), 2921, 2852, 1444, 1301, 1242, 1112, 1023, 936, 792. 31P{1H} NMR (202.45 MHz, DMSO-d6, 300.0 K, H3PO4 external): δ 12.83 (s). 1H NMR (500.13 MHz, DMSO-d6, 300.0 K, TMS): δ 1.02 (s, 6H, CH3), 1.13 (m, 30H), 1.49 (m, 6H), 1.63 (m, 12H), 1.79 (m, 12H), 2.80 (m, 6H, CH), 3.49 (b, 6H, NH). 13C NMR (125.75 MHz, DMSO-d6, 300.0 K, TMS): δ 22.95 (s, CH3), 25.01 (s), 25.23 (s), 35.48 [d, 3J(P,C) = 4.7 Hz], 49.48 (s).
For the synthesis of [Cu(PTA)2(H2O)2](NO3)2.PTA, (II), a solution of copper(II) nitrate trihydrate (0.547 g, 2.269 mmol) in CH3CN (5 ml) was added dropwise to a solution of PTA (1.423 g, 4.173 mmol) in ethanol (10 ml). The resulting clear solution was stirred for 2 h at room temperature. Single crystals were obtained from a mixture of dimethylformamide/ethanol after slow evaporation at room temperature (yield: approximately 30%). IR (KBr, cm-1): 3345, 3273, 2925, 2847, 1650, 1432, 1394, 1232, 1101, 1028, 950, 882, 828. 13C NMR (125.75 MHz, DMSO-d6, 300.0 K, TMS): δ 26.13 (s, CH3), 37.02 (s), 41.96 (b), 49.29 (s.
For (I), N-bonded H atoms were found in difference Fourier maps. C-bonded H-atom positions were calculated, and the C—H distances were normalized at standard values of 0.98–1.00 Å, depending on the hybridization. All the H atoms were treated as riding atoms with their Uiso(H) parameters equal to 1.5Ueq(C) for methyl H atoms and 1.2Ueq(Cj) otherwise. For (II), H atoms on N and O atoms were found in difference Fourier maps and were allowed to refine with DFIX restraints of 0.86 (0.01) for N—H, DFIX 0.84 (0.01) and DANG 1.20 (0.02) restraints for O—H, and isotropic displacement parameters fixed at 1.2Ueq of the parent atom. All other H atoms were placed in calculated positions and included as riding atoms with C—H = 1.00 (CH) or 0.99 Å (CH2) and Uiso(H) = 1.2Ueq(C).
For both compounds, data collection: APEX2 (Bruker, 2005). Cell refinement: APEX2 (Bruker, 2005) for (I); SAINT (Bruker, 2008) for (II). Data reduction: APEX2 (Bruker, 2005) for (I); SAINT (Bruker 2008) for (II). Program(s) used to solve structure: SHELXTL (Sheldrick, 2008) for (I); SHELXS97 (Sheldrick, 2008) for (II). Program(s) used to refine structure: SHELXTL (Sheldrick, 2008) for (I); SHELXL97 (Sheldrick, 2008) for (II). For both compounds, molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[Sn(CH3)2Cl2(C18H36N3OP)2] | F(000) = 1912 |
Mr = 902.59 | Dx = 1.318 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2689 reflections |
a = 12.0882 (6) Å | θ = 3–30° |
b = 25.1607 (13) Å | µ = 0.79 mm−1 |
c = 15.8103 (8) Å | T = 100 K |
β = 108.879 (1)° | Prism, colorless |
V = 4550.0 (4) Å3 | 0.35 × 0.25 × 0.25 mm |
Z = 4 |
Bruker SMART APEXII CCD area-detector diffractometer | 12101 independent reflections |
Radiation source: fine-focus sealed tube | 10758 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ϕ and ω scans | θmax = 29.0°, θmin = 1.6° |
Absorption correction: multi-scan (APEX2; Bruker, 2005) | h = −16→16 |
Tmin = 0.772, Tmax = 0.825 | k = −34→34 |
71686 measured reflections | l = −21→21 |
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)] = 0.024 | Hydrogen site location: mixed |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.057P)2 + 0.975P] where P = (Fo2 + 2Fc2)/3 |
12101 reflections | (Δ/σ)max = 0.002 |
462 parameters | Δρmax = 0.84 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
[Sn(CH3)2Cl2(C18H36N3OP)2] | V = 4550.0 (4) Å3 |
Mr = 902.59 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.0882 (6) Å | µ = 0.79 mm−1 |
b = 25.1607 (13) Å | T = 100 K |
c = 15.8103 (8) Å | 0.35 × 0.25 × 0.25 mm |
β = 108.879 (1)° |
Bruker SMART APEXII CCD area-detector diffractometer | 12101 independent reflections |
Absorption correction: multi-scan (APEX2; Bruker, 2005) | 10758 reflections with I > 2σ(I) |
Tmin = 0.772, Tmax = 0.825 | Rint = 0.030 |
71686 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | 0 restraints |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.84 e Å−3 |
12101 reflections | Δρmin = −0.48 e Å−3 |
462 parameters |
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 | ||
Sn1 | 0.957050 (8) | 0.170970 (4) | 0.484948 (6) | 0.01205 (4) | |
Cl1 | 1.09417 (3) | 0.130733 (14) | 0.62855 (2) | 0.01794 (8) | |
Cl2 | 0.99698 (3) | 0.267834 (14) | 0.54265 (2) | 0.02001 (8) | |
P1 | 0.89504 (3) | 0.058809 (15) | 0.34183 (3) | 0.01426 (8) | |
P2 | 0.74116 (3) | 0.243081 (14) | 0.31248 (2) | 0.01281 (7) | |
O1 | 0.92165 (10) | 0.08937 (4) | 0.42782 (7) | 0.0181 (2) | |
O2 | 0.83145 (9) | 0.20095 (4) | 0.35430 (7) | 0.0148 (2) | |
N1 | 1.01736 (12) | 0.04395 (5) | 0.32345 (9) | 0.0200 (3) | |
H1N | 1.0813 | 0.0597 | 0.3595 | 0.024* | |
N2 | 0.80391 (12) | 0.09493 (5) | 0.26441 (9) | 0.0179 (3) | |
H2N | 0.8007 | 0.1279 | 0.2781 | 0.021* | |
N3 | 0.83100 (11) | 0.00126 (5) | 0.33571 (9) | 0.0157 (2) | |
H3N | 0.8775 | −0.0280 | 0.3554 | 0.019* | |
N4 | 0.60732 (11) | 0.22405 (5) | 0.26440 (8) | 0.0170 (2) | |
H4N | 0.5796 | 0.2212 | 0.2055 | 0.020* | |
N5 | 0.73368 (12) | 0.28228 (5) | 0.39318 (9) | 0.0167 (2) | |
H5N | 0.7952 | 0.2848 | 0.4363 | 0.020* | |
N6 | 0.77483 (11) | 0.26937 (5) | 0.22959 (9) | 0.0166 (2) | |
H6N | 0.7288 | 0.2923 | 0.1938 | 0.020* | |
C1 | 1.03787 (13) | 0.00224 (6) | 0.26502 (10) | 0.0169 (3) | |
H1A | 0.9622 | −0.0168 | 0.2371 | 0.020* | |
C2 | 1.12652 (15) | −0.03836 (7) | 0.31941 (10) | 0.0210 (3) | |
H2A | 1.0980 | −0.0538 | 0.3661 | 0.025* | |
H2B | 1.2018 | −0.0204 | 0.3495 | 0.025* | |
C3 | 1.14549 (16) | −0.08276 (7) | 0.25947 (11) | 0.0252 (3) | |
H3A | 1.2072 | −0.1071 | 0.2955 | 0.030* | |
H3B | 1.0724 | −0.1035 | 0.2354 | 0.030* | |
C4 | 1.18104 (16) | −0.06083 (8) | 0.18220 (12) | 0.0265 (4) | |
H4A | 1.1861 | −0.0903 | 0.1422 | 0.032* | |
H4B | 1.2593 | −0.0442 | 0.2059 | 0.032* | |
C5 | 1.09300 (16) | −0.01960 (7) | 0.12890 (11) | 0.0235 (3) | |
H5A | 1.0169 | −0.0371 | 0.0995 | 0.028* | |
H5B | 1.1209 | −0.0043 | 0.0817 | 0.028* | |
C6 | 1.07677 (16) | 0.02497 (7) | 0.18973 (11) | 0.0229 (3) | |
H6A | 1.1514 | 0.0444 | 0.2154 | 0.027* | |
H6B | 1.0174 | 0.0504 | 0.1542 | 0.027* | |
C7 | 0.77644 (14) | 0.08442 (6) | 0.16817 (10) | 0.0177 (3) | |
H7A | 0.8228 | 0.0527 | 0.1614 | 0.021* | |
C8 | 0.81350 (17) | 0.13131 (7) | 0.12278 (11) | 0.0255 (4) | |
H8A | 0.8983 | 0.1377 | 0.1513 | 0.031* | |
H8B | 0.7712 | 0.1636 | 0.1310 | 0.031* | |
C9 | 0.78803 (18) | 0.12127 (8) | 0.02296 (12) | 0.0299 (4) | |
H9A | 0.8382 | 0.0920 | 0.0147 | 0.036* | |
H9B | 0.8072 | 0.1536 | −0.0053 | 0.036* | |
C10 | 0.65973 (17) | 0.10680 (8) | −0.02279 (11) | 0.0290 (4) | |
H10A | 0.6098 | 0.1377 | −0.0210 | 0.035* | |
H10B | 0.6470 | 0.0979 | −0.0862 | 0.035* | |
C11 | 0.62548 (16) | 0.05974 (8) | 0.02344 (12) | 0.0288 (4) | |
H11A | 0.6714 | 0.0282 | 0.0178 | 0.035* | |
H11B | 0.5416 | 0.0516 | −0.0058 | 0.035* | |
C12 | 0.64781 (15) | 0.07195 (8) | 0.12247 (11) | 0.0255 (3) | |
H12A | 0.5997 | 0.1027 | 0.1282 | 0.031* | |
H12B | 0.6251 | 0.0410 | 0.1518 | 0.031* | |
C13 | 0.71861 (13) | −0.00316 (6) | 0.35278 (10) | 0.0163 (3) | |
H13A | 0.6784 | 0.0321 | 0.3397 | 0.020* | |
C14 | 0.63946 (14) | −0.04458 (6) | 0.29203 (11) | 0.0185 (3) | |
H14A | 0.6786 | −0.0797 | 0.3025 | 0.022* | |
H14B | 0.6250 | −0.0347 | 0.2287 | 0.022* | |
C15 | 0.52328 (14) | −0.04814 (7) | 0.31045 (12) | 0.0234 (3) | |
H15A | 0.4817 | −0.0137 | 0.2958 | 0.028* | |
H15B | 0.4738 | −0.0758 | 0.2717 | 0.028* | |
C16 | 0.54231 (16) | −0.06172 (7) | 0.40814 (12) | 0.0263 (4) | |
H16A | 0.5772 | −0.0976 | 0.4214 | 0.032* | |
H16B | 0.4661 | −0.0622 | 0.4189 | 0.032* | |
C17 | 0.62317 (17) | −0.02111 (7) | 0.47047 (13) | 0.0277 (4) | |
H17A | 0.5841 | 0.0140 | 0.4623 | 0.033* | |
H17B | 0.6388 | −0.0322 | 0.5334 | 0.033* | |
C18 | 0.73878 (15) | −0.01645 (7) | 0.45099 (11) | 0.0215 (3) | |
H18A | 0.7873 | 0.0117 | 0.4892 | 0.026* | |
H18B | 0.7820 | −0.0504 | 0.4660 | 0.026* | |
C19 | 0.53166 (13) | 0.20113 (6) | 0.31108 (10) | 0.0170 (3) | |
H19A | 0.5575 | 0.2153 | 0.3735 | 0.020* | |
C20 | 0.54019 (18) | 0.14124 (7) | 0.31609 (16) | 0.0335 (4) | |
H20A | 0.6219 | 0.1308 | 0.3485 | 0.040* | |
H20B | 0.5187 | 0.1265 | 0.2548 | 0.040* | |
C21 | 0.45976 (19) | 0.11788 (8) | 0.36379 (18) | 0.0407 (5) | |
H21A | 0.4653 | 0.0786 | 0.3641 | 0.049* | |
H21B | 0.4854 | 0.1302 | 0.4266 | 0.049* | |
C22 | 0.33386 (18) | 0.13444 (9) | 0.31799 (16) | 0.0384 (5) | |
H22A | 0.3054 | 0.1187 | 0.2574 | 0.046* | |
H22B | 0.2844 | 0.1208 | 0.3523 | 0.046* | |
C23 | 0.32357 (19) | 0.19390 (10) | 0.3111 (2) | 0.0478 (6) | |
H23A | 0.3416 | 0.2091 | 0.3719 | 0.057* | |
H23B | 0.2420 | 0.2035 | 0.2767 | 0.057* | |
C24 | 0.40597 (17) | 0.21836 (9) | 0.26574 (16) | 0.0384 (5) | |
H24A | 0.3809 | 0.2074 | 0.2022 | 0.046* | |
H24B | 0.4011 | 0.2576 | 0.2677 | 0.046* | |
C25 | 0.65681 (15) | 0.32939 (6) | 0.37678 (11) | 0.0179 (3) | |
H25A | 0.5943 | 0.3245 | 0.3178 | 0.022* | |
C26 | 0.59773 (17) | 0.33411 (7) | 0.44852 (13) | 0.0273 (4) | |
H26A | 0.5358 | 0.3615 | 0.4303 | 0.033* | |
H26B | 0.5602 | 0.2998 | 0.4536 | 0.033* | |
C27 | 0.6838 (2) | 0.34878 (9) | 0.53889 (13) | 0.0375 (5) | |
H27A | 0.7414 | 0.3197 | 0.5602 | 0.045* | |
H27B | 0.6415 | 0.3531 | 0.5826 | 0.045* | |
C28 | 0.7476 (2) | 0.40024 (9) | 0.53322 (15) | 0.0414 (5) | |
H28A | 0.8065 | 0.4078 | 0.5921 | 0.050* | |
H28B | 0.6910 | 0.4300 | 0.5183 | 0.050* | |
C29 | 0.80812 (17) | 0.39618 (8) | 0.46232 (15) | 0.0351 (4) | |
H29A | 0.8440 | 0.4309 | 0.4569 | 0.042* | |
H29B | 0.8714 | 0.3694 | 0.4811 | 0.042* | |
C30 | 0.72256 (16) | 0.38058 (6) | 0.37215 (12) | 0.0253 (3) | |
H30A | 0.7657 | 0.3758 | 0.3291 | 0.030* | |
H30B | 0.6655 | 0.4097 | 0.3498 | 0.030* | |
C31 | 0.89225 (13) | 0.26720 (6) | 0.22196 (10) | 0.0157 (3) | |
H31A | 0.9245 | 0.2309 | 0.2411 | 0.019* | |
C32 | 0.97640 (14) | 0.30741 (6) | 0.28129 (11) | 0.0204 (3) | |
H32A | 0.9811 | 0.3017 | 0.3443 | 0.024* | |
H32B | 0.9466 | 0.3438 | 0.2640 | 0.024* | |
C33 | 1.09816 (15) | 0.30193 (8) | 0.27264 (13) | 0.0286 (4) | |
H33A | 1.1492 | 0.3303 | 0.3081 | 0.034* | |
H33B | 1.1319 | 0.2673 | 0.2979 | 0.034* | |
C34 | 1.09645 (16) | 0.30560 (7) | 0.17582 (14) | 0.0292 (4) | |
H34A | 1.0774 | 0.3425 | 0.1541 | 0.035* | |
H34B | 1.1751 | 0.2970 | 0.1730 | 0.035* | |
C35 | 1.00713 (18) | 0.26766 (8) | 0.11517 (13) | 0.0309 (4) | |
H35A | 1.0337 | 0.2306 | 0.1303 | 0.037* | |
H35B | 1.0021 | 0.2741 | 0.0523 | 0.037* | |
C36 | 0.88575 (16) | 0.27452 (7) | 0.12453 (11) | 0.0232 (3) | |
H36A | 0.8554 | 0.3104 | 0.1038 | 0.028* | |
H36B | 0.8313 | 0.2480 | 0.0867 | 0.028* | |
C37 | 1.09180 (15) | 0.17662 (7) | 0.42692 (12) | 0.0208 (3) | |
H37A | 1.0595 | 0.1695 | 0.3626 | 0.031* | |
H37B | 1.1529 | 0.1505 | 0.4548 | 0.031* | |
H37C | 1.1254 | 0.2124 | 0.4365 | 0.031* | |
C38 | 0.81486 (15) | 0.16500 (7) | 0.53441 (12) | 0.0208 (3) | |
H38A | 0.7790 | 0.1298 | 0.5203 | 0.031* | |
H38B | 0.7569 | 0.1924 | 0.5065 | 0.031* | |
H38C | 0.8428 | 0.1701 | 0.5994 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.01378 (6) | 0.01136 (6) | 0.01058 (6) | 0.00054 (3) | 0.00334 (4) | 0.00005 (3) |
Cl1 | 0.01958 (17) | 0.01477 (16) | 0.01538 (16) | 0.00142 (13) | 0.00001 (13) | 0.00133 (12) |
Cl2 | 0.02513 (19) | 0.01428 (16) | 0.01592 (16) | −0.00026 (13) | 0.00014 (14) | −0.00152 (12) |
P1 | 0.01785 (18) | 0.01163 (17) | 0.01397 (17) | −0.00104 (13) | 0.00608 (14) | −0.00172 (13) |
P2 | 0.01486 (17) | 0.01085 (16) | 0.01156 (16) | 0.00058 (13) | 0.00269 (13) | 0.00095 (12) |
O1 | 0.0243 (6) | 0.0148 (5) | 0.0152 (5) | −0.0003 (4) | 0.0064 (4) | −0.0028 (4) |
O2 | 0.0184 (5) | 0.0119 (5) | 0.0129 (5) | 0.0016 (4) | 0.0033 (4) | 0.0004 (4) |
N1 | 0.0177 (6) | 0.0192 (6) | 0.0241 (7) | −0.0042 (5) | 0.0080 (5) | −0.0081 (5) |
N2 | 0.0273 (7) | 0.0119 (6) | 0.0141 (6) | 0.0020 (5) | 0.0062 (5) | −0.0008 (5) |
N3 | 0.0165 (6) | 0.0133 (6) | 0.0185 (6) | 0.0003 (5) | 0.0074 (5) | 0.0000 (5) |
N4 | 0.0164 (6) | 0.0209 (6) | 0.0119 (6) | −0.0018 (5) | 0.0020 (5) | 0.0017 (5) |
N5 | 0.0191 (6) | 0.0141 (6) | 0.0144 (6) | 0.0026 (5) | 0.0019 (5) | −0.0010 (5) |
N6 | 0.0176 (6) | 0.0159 (6) | 0.0154 (6) | 0.0017 (5) | 0.0040 (5) | 0.0055 (5) |
C1 | 0.0172 (7) | 0.0169 (7) | 0.0178 (7) | −0.0018 (6) | 0.0071 (6) | −0.0030 (5) |
C2 | 0.0220 (8) | 0.0260 (8) | 0.0152 (7) | 0.0041 (6) | 0.0065 (6) | −0.0003 (6) |
C3 | 0.0288 (9) | 0.0267 (8) | 0.0213 (8) | 0.0098 (7) | 0.0097 (7) | 0.0021 (6) |
C4 | 0.0239 (8) | 0.0349 (10) | 0.0232 (8) | 0.0061 (7) | 0.0109 (7) | −0.0013 (7) |
C5 | 0.0269 (8) | 0.0275 (8) | 0.0181 (7) | −0.0005 (7) | 0.0101 (6) | 0.0006 (6) |
C6 | 0.0274 (8) | 0.0214 (8) | 0.0230 (8) | −0.0025 (6) | 0.0125 (7) | 0.0012 (6) |
C7 | 0.0223 (8) | 0.0158 (7) | 0.0148 (7) | 0.0016 (6) | 0.0055 (6) | −0.0012 (5) |
C8 | 0.0372 (10) | 0.0230 (8) | 0.0182 (8) | −0.0063 (7) | 0.0117 (7) | −0.0016 (6) |
C9 | 0.0420 (11) | 0.0325 (10) | 0.0188 (8) | −0.0032 (8) | 0.0150 (8) | −0.0002 (7) |
C10 | 0.0374 (10) | 0.0328 (9) | 0.0165 (7) | 0.0104 (8) | 0.0082 (7) | 0.0012 (7) |
C11 | 0.0261 (9) | 0.0338 (10) | 0.0213 (8) | −0.0002 (7) | 0.0005 (7) | −0.0013 (7) |
C12 | 0.0241 (8) | 0.0305 (9) | 0.0204 (8) | −0.0026 (7) | 0.0052 (6) | 0.0043 (7) |
C13 | 0.0170 (7) | 0.0142 (7) | 0.0191 (7) | −0.0007 (5) | 0.0077 (6) | −0.0019 (5) |
C14 | 0.0181 (7) | 0.0180 (7) | 0.0183 (7) | −0.0005 (6) | 0.0044 (6) | −0.0021 (6) |
C15 | 0.0176 (7) | 0.0190 (7) | 0.0338 (9) | −0.0003 (6) | 0.0086 (7) | −0.0052 (7) |
C16 | 0.0267 (9) | 0.0238 (8) | 0.0351 (9) | −0.0068 (7) | 0.0193 (8) | −0.0084 (7) |
C17 | 0.0340 (9) | 0.0269 (9) | 0.0303 (9) | −0.0098 (7) | 0.0216 (8) | −0.0102 (7) |
C18 | 0.0247 (8) | 0.0230 (8) | 0.0191 (7) | −0.0058 (6) | 0.0104 (6) | −0.0056 (6) |
C19 | 0.0155 (7) | 0.0176 (7) | 0.0181 (7) | −0.0003 (5) | 0.0057 (6) | −0.0002 (5) |
C20 | 0.0336 (10) | 0.0175 (8) | 0.0617 (13) | 0.0036 (7) | 0.0322 (10) | 0.0048 (8) |
C21 | 0.0406 (12) | 0.0246 (9) | 0.0710 (16) | 0.0035 (8) | 0.0378 (11) | 0.0126 (10) |
C22 | 0.0291 (10) | 0.0431 (12) | 0.0499 (12) | −0.0134 (9) | 0.0225 (9) | −0.0058 (10) |
C23 | 0.0257 (10) | 0.0455 (13) | 0.0809 (18) | 0.0092 (9) | 0.0293 (11) | 0.0142 (12) |
C24 | 0.0210 (9) | 0.0390 (11) | 0.0560 (13) | 0.0088 (8) | 0.0136 (9) | 0.0184 (10) |
C25 | 0.0214 (8) | 0.0132 (7) | 0.0193 (7) | 0.0037 (5) | 0.0065 (6) | 0.0010 (5) |
C26 | 0.0314 (10) | 0.0235 (8) | 0.0322 (10) | 0.0061 (7) | 0.0178 (8) | 0.0021 (7) |
C27 | 0.0558 (14) | 0.0368 (11) | 0.0219 (9) | 0.0133 (10) | 0.0152 (9) | 0.0003 (8) |
C28 | 0.0476 (13) | 0.0325 (11) | 0.0342 (11) | 0.0088 (9) | −0.0006 (9) | −0.0143 (9) |
C29 | 0.0280 (9) | 0.0187 (8) | 0.0514 (12) | 0.0005 (7) | 0.0030 (9) | −0.0075 (8) |
C30 | 0.0320 (9) | 0.0141 (7) | 0.0327 (9) | 0.0033 (6) | 0.0144 (7) | 0.0043 (6) |
C31 | 0.0177 (7) | 0.0132 (6) | 0.0168 (7) | 0.0006 (5) | 0.0066 (6) | 0.0008 (5) |
C32 | 0.0192 (7) | 0.0179 (7) | 0.0237 (8) | −0.0020 (6) | 0.0065 (6) | −0.0019 (6) |
C33 | 0.0195 (8) | 0.0295 (9) | 0.0365 (10) | −0.0012 (7) | 0.0088 (7) | 0.0020 (7) |
C34 | 0.0265 (9) | 0.0249 (9) | 0.0433 (11) | 0.0039 (7) | 0.0212 (8) | 0.0078 (8) |
C35 | 0.0414 (11) | 0.0292 (9) | 0.0309 (9) | 0.0025 (8) | 0.0238 (8) | 0.0008 (7) |
C36 | 0.0311 (9) | 0.0227 (8) | 0.0181 (7) | −0.0024 (7) | 0.0110 (7) | 0.0011 (6) |
C37 | 0.0179 (8) | 0.0239 (8) | 0.0217 (8) | −0.0002 (6) | 0.0081 (6) | 0.0015 (6) |
C38 | 0.0213 (8) | 0.0233 (8) | 0.0204 (8) | 0.0046 (6) | 0.0102 (6) | 0.0044 (6) |
Sn1—C38 | 2.1114 (16) | C15—H15A | 0.9900 |
Sn1—C37 | 2.1171 (16) | C15—H15B | 0.9900 |
Sn1—O1 | 2.2281 (11) | C16—C17 | 1.532 (2) |
Sn1—O2 | 2.2608 (10) | C16—H16A | 0.9900 |
Sn1—Cl1 | 2.5479 (4) | C16—H16B | 0.9900 |
Sn1—Cl2 | 2.5923 (4) | C17—C18 | 1.530 (2) |
P1—O1 | 1.5032 (11) | C17—H17A | 0.9900 |
P1—N3 | 1.6300 (13) | C17—H17B | 0.9900 |
P1—N2 | 1.6326 (14) | C18—H18A | 0.9900 |
P1—N1 | 1.6397 (14) | C18—H18B | 0.9900 |
P2—O2 | 1.5116 (11) | C19—C20 | 1.511 (2) |
P2—N4 | 1.6213 (13) | C19—C24 | 1.518 (2) |
P2—N6 | 1.6327 (13) | C19—H19A | 1.0000 |
P2—N5 | 1.6381 (13) | C20—C21 | 1.528 (3) |
N1—C1 | 1.4711 (19) | C20—H20A | 0.9900 |
N1—H1N | 0.8909 | C20—H20B | 0.9900 |
N2—C7 | 1.4725 (19) | C21—C22 | 1.517 (3) |
N2—H2N | 0.8612 | C21—H21A | 0.9900 |
N3—C13 | 1.4725 (19) | C21—H21B | 0.9900 |
N3—H3N | 0.9181 | C22—C23 | 1.502 (3) |
N4—C19 | 1.4665 (19) | C22—H22A | 0.9900 |
N4—H4N | 0.8840 | C22—H22B | 0.9900 |
N5—C25 | 1.4764 (19) | C23—C24 | 1.533 (3) |
N5—H5N | 0.8328 | C23—H23A | 0.9900 |
N6—C31 | 1.4640 (19) | C23—H23B | 0.9900 |
N6—H6N | 0.8713 | C24—H24A | 0.9900 |
C1—C6 | 1.526 (2) | C24—H24B | 0.9900 |
C1—C2 | 1.528 (2) | C25—C30 | 1.528 (2) |
C1—H1A | 1.0000 | C25—C26 | 1.528 (2) |
C2—C3 | 1.529 (2) | C25—H25A | 1.0000 |
C2—H2A | 0.9900 | C26—C27 | 1.516 (3) |
C2—H2B | 0.9900 | C26—H26A | 0.9900 |
C3—C4 | 1.524 (2) | C26—H26B | 0.9900 |
C3—H3A | 0.9900 | C27—C28 | 1.525 (3) |
C3—H3B | 0.9900 | C27—H27A | 0.9900 |
C4—C5 | 1.529 (2) | C27—H27B | 0.9900 |
C4—H4A | 0.9900 | C28—C29 | 1.527 (3) |
C4—H4B | 0.9900 | C28—H28A | 0.9900 |
C5—C6 | 1.531 (2) | C28—H28B | 0.9900 |
C5—H5A | 0.9900 | C29—C30 | 1.517 (3) |
C5—H5B | 0.9900 | C29—H29A | 0.9900 |
C6—H6A | 0.9900 | C29—H29B | 0.9900 |
C6—H6B | 0.9900 | C30—H30A | 0.9900 |
C7—C12 | 1.520 (2) | C30—H30B | 0.9900 |
C7—C8 | 1.522 (2) | C31—C32 | 1.523 (2) |
C7—H7A | 1.0000 | C31—C36 | 1.528 (2) |
C8—C9 | 1.528 (2) | C31—H31A | 1.0000 |
C8—H8A | 0.9900 | C32—C33 | 1.528 (2) |
C8—H8B | 0.9900 | C32—H32A | 0.9900 |
C9—C10 | 1.528 (3) | C32—H32B | 0.9900 |
C9—H9A | 0.9900 | C33—C34 | 1.527 (3) |
C9—H9B | 0.9900 | C33—H33A | 0.9900 |
C10—C11 | 1.518 (3) | C33—H33B | 0.9900 |
C10—H10A | 0.9900 | C34—C35 | 1.525 (3) |
C10—H10B | 0.9900 | C34—H34A | 0.9900 |
C11—C12 | 1.531 (2) | C34—H34B | 0.9900 |
C11—H11A | 0.9900 | C35—C36 | 1.531 (3) |
C11—H11B | 0.9900 | C35—H35A | 0.9900 |
C12—H12A | 0.9900 | C35—H35B | 0.9900 |
C12—H12B | 0.9900 | C36—H36A | 0.9900 |
C13—C14 | 1.526 (2) | C36—H36B | 0.9900 |
C13—C18 | 1.529 (2) | C37—H37A | 0.9800 |
C13—H13A | 1.0000 | C37—H37B | 0.9800 |
C14—C15 | 1.526 (2) | C37—H37C | 0.9800 |
C14—H14A | 0.9900 | C38—H38A | 0.9800 |
C14—H14B | 0.9900 | C38—H38B | 0.9800 |
C15—C16 | 1.525 (3) | C38—H38C | 0.9800 |
C38—Sn1—C37 | 176.31 (6) | C15—C16—H16A | 109.4 |
C38—Sn1—O1 | 90.69 (6) | C17—C16—H16A | 109.4 |
C37—Sn1—O1 | 87.70 (5) | C15—C16—H16B | 109.4 |
C38—Sn1—O2 | 88.60 (5) | C17—C16—H16B | 109.4 |
C37—Sn1—O2 | 88.00 (5) | H16A—C16—H16B | 108.0 |
O1—Sn1—O2 | 87.31 (4) | C18—C17—C16 | 110.85 (14) |
C38—Sn1—Cl1 | 90.83 (5) | C18—C17—H17A | 109.5 |
C37—Sn1—Cl1 | 92.46 (5) | C16—C17—H17A | 109.5 |
O1—Sn1—Cl1 | 88.82 (3) | C18—C17—H17B | 109.5 |
O2—Sn1—Cl1 | 176.07 (3) | C16—C17—H17B | 109.5 |
C38—Sn1—Cl2 | 91.01 (5) | H17A—C17—H17B | 108.1 |
C37—Sn1—Cl2 | 90.44 (5) | C13—C18—C17 | 111.43 (14) |
O1—Sn1—Cl2 | 176.84 (3) | C13—C18—H18A | 109.3 |
O2—Sn1—Cl2 | 90.08 (3) | C17—C18—H18A | 109.3 |
Cl1—Sn1—Cl2 | 93.818 (12) | C13—C18—H18B | 109.3 |
O1—P1—N3 | 117.82 (7) | C17—C18—H18B | 109.3 |
O1—P1—N2 | 106.76 (7) | H18A—C18—H18B | 108.0 |
N3—P1—N2 | 104.93 (7) | N4—C19—C20 | 112.06 (13) |
O1—P1—N1 | 109.61 (7) | N4—C19—C24 | 109.99 (14) |
N3—P1—N1 | 103.01 (7) | C20—C19—C24 | 110.51 (15) |
N2—P1—N1 | 114.98 (7) | N4—C19—H19A | 108.0 |
O2—P2—N4 | 117.89 (7) | C20—C19—H19A | 108.0 |
O2—P2—N6 | 107.63 (6) | C24—C19—H19A | 108.0 |
N4—P2—N6 | 102.32 (7) | C19—C20—C21 | 111.48 (15) |
O2—P2—N5 | 107.18 (6) | C19—C20—H20A | 109.3 |
N4—P2—N5 | 104.17 (7) | C21—C20—H20A | 109.3 |
N6—P2—N5 | 118.18 (7) | C19—C20—H20B | 109.3 |
P1—O1—Sn1 | 142.63 (7) | C21—C20—H20B | 109.3 |
P2—O2—Sn1 | 144.10 (6) | H20A—C20—H20B | 108.0 |
C1—N1—P1 | 128.23 (11) | C22—C21—C20 | 111.04 (19) |
C1—N1—H1N | 115.5 | C22—C21—H21A | 109.4 |
P1—N1—H1N | 115.5 | C20—C21—H21A | 109.4 |
C7—N2—P1 | 123.14 (10) | C22—C21—H21B | 109.4 |
C7—N2—H2N | 114.8 | C20—C21—H21B | 109.4 |
P1—N2—H2N | 114.9 | H21A—C21—H21B | 108.0 |
C13—N3—P1 | 120.32 (10) | C23—C22—C21 | 110.79 (17) |
C13—N3—H3N | 112.2 | C23—C22—H22A | 109.5 |
P1—N3—H3N | 117.8 | C21—C22—H22A | 109.5 |
C19—N4—P2 | 124.77 (10) | C23—C22—H22B | 109.5 |
C19—N4—H4N | 114.3 | C21—C22—H22B | 109.5 |
P2—N4—H4N | 119.9 | H22A—C22—H22B | 108.1 |
C25—N5—P2 | 122.46 (11) | C22—C23—C24 | 112.48 (18) |
C25—N5—H5N | 115.3 | C22—C23—H23A | 109.1 |
P2—N5—H5N | 115.1 | C24—C23—H23A | 109.1 |
C31—N6—P2 | 123.45 (10) | C22—C23—H23B | 109.1 |
C31—N6—H6N | 113.8 | C24—C23—H23B | 109.1 |
P2—N6—H6N | 121.2 | H23A—C23—H23B | 107.8 |
N1—C1—C6 | 112.32 (13) | C19—C24—C23 | 111.53 (17) |
N1—C1—C2 | 110.71 (13) | C19—C24—H24A | 109.3 |
C6—C1—C2 | 110.65 (13) | C23—C24—H24A | 109.3 |
N1—C1—H1A | 107.7 | C19—C24—H24B | 109.3 |
C6—C1—H1A | 107.7 | C23—C24—H24B | 109.3 |
C2—C1—H1A | 107.7 | H24A—C24—H24B | 108.0 |
C1—C2—C3 | 110.98 (13) | N5—C25—C30 | 112.18 (14) |
C1—C2—H2A | 109.4 | N5—C25—C26 | 110.54 (13) |
C3—C2—H2A | 109.4 | C30—C25—C26 | 110.20 (14) |
C1—C2—H2B | 109.4 | N5—C25—H25A | 107.9 |
C3—C2—H2B | 109.4 | C30—C25—H25A | 107.9 |
H2A—C2—H2B | 108.0 | C26—C25—H25A | 107.9 |
C4—C3—C2 | 111.72 (15) | C27—C26—C25 | 112.06 (16) |
C4—C3—H3A | 109.3 | C27—C26—H26A | 109.2 |
C2—C3—H3A | 109.3 | C25—C26—H26A | 109.2 |
C4—C3—H3B | 109.3 | C27—C26—H26B | 109.2 |
C2—C3—H3B | 109.3 | C25—C26—H26B | 109.2 |
H3A—C3—H3B | 107.9 | H26A—C26—H26B | 107.9 |
C3—C4—C5 | 111.16 (14) | C26—C27—C28 | 110.94 (17) |
C3—C4—H4A | 109.4 | C26—C27—H27A | 109.5 |
C5—C4—H4A | 109.4 | C28—C27—H27A | 109.5 |
C3—C4—H4B | 109.4 | C26—C27—H27B | 109.5 |
C5—C4—H4B | 109.4 | C28—C27—H27B | 109.5 |
H4A—C4—H4B | 108.0 | H27A—C27—H27B | 108.0 |
C4—C5—C6 | 111.01 (14) | C27—C28—C29 | 110.99 (16) |
C4—C5—H5A | 109.4 | C27—C28—H28A | 109.4 |
C6—C5—H5A | 109.4 | C29—C28—H28A | 109.4 |
C4—C5—H5B | 109.4 | C27—C28—H28B | 109.4 |
C6—C5—H5B | 109.4 | C29—C28—H28B | 109.4 |
H5A—C5—H5B | 108.0 | H28A—C28—H28B | 108.0 |
C1—C6—C5 | 110.50 (13) | C30—C29—C28 | 111.36 (17) |
C1—C6—H6A | 109.6 | C30—C29—H29A | 109.4 |
C5—C6—H6A | 109.6 | C28—C29—H29A | 109.4 |
C1—C6—H6B | 109.6 | C30—C29—H29B | 109.4 |
C5—C6—H6B | 109.6 | C28—C29—H29B | 109.4 |
H6A—C6—H6B | 108.1 | H29A—C29—H29B | 108.0 |
N2—C7—C12 | 112.47 (13) | C29—C30—C25 | 112.35 (15) |
N2—C7—C8 | 110.22 (13) | C29—C30—H30A | 109.1 |
C12—C7—C8 | 110.35 (14) | C25—C30—H30A | 109.1 |
N2—C7—H7A | 107.9 | C29—C30—H30B | 109.1 |
C12—C7—H7A | 107.9 | C25—C30—H30B | 109.1 |
C8—C7—H7A | 107.9 | H30A—C30—H30B | 107.9 |
C7—C8—C9 | 111.54 (14) | N6—C31—C32 | 113.35 (12) |
C7—C8—H8A | 109.3 | N6—C31—C36 | 110.10 (13) |
C9—C8—H8A | 109.3 | C32—C31—C36 | 110.30 (13) |
C7—C8—H8B | 109.3 | N6—C31—H31A | 107.6 |
C9—C8—H8B | 109.3 | C32—C31—H31A | 107.6 |
H8A—C8—H8B | 108.0 | C36—C31—H31A | 107.6 |
C8—C9—C10 | 111.28 (15) | C31—C32—C33 | 110.82 (14) |
C8—C9—H9A | 109.4 | C31—C32—H32A | 109.5 |
C10—C9—H9A | 109.4 | C33—C32—H32A | 109.5 |
C8—C9—H9B | 109.4 | C31—C32—H32B | 109.5 |
C10—C9—H9B | 109.4 | C33—C32—H32B | 109.5 |
H9A—C9—H9B | 108.0 | H32A—C32—H32B | 108.1 |
C11—C10—C9 | 110.56 (15) | C34—C33—C32 | 112.54 (15) |
C11—C10—H10A | 109.5 | C34—C33—H33A | 109.1 |
C9—C10—H10A | 109.5 | C32—C33—H33A | 109.1 |
C11—C10—H10B | 109.5 | C34—C33—H33B | 109.1 |
C9—C10—H10B | 109.5 | C32—C33—H33B | 109.1 |
H10A—C10—H10B | 108.1 | H33A—C33—H33B | 107.8 |
C10—C11—C12 | 110.52 (15) | C35—C34—C33 | 111.69 (15) |
C10—C11—H11A | 109.5 | C35—C34—H34A | 109.3 |
C12—C11—H11A | 109.5 | C33—C34—H34A | 109.3 |
C10—C11—H11B | 109.5 | C35—C34—H34B | 109.3 |
C12—C11—H11B | 109.5 | C33—C34—H34B | 109.3 |
H11A—C11—H11B | 108.1 | H34A—C34—H34B | 107.9 |
C7—C12—C11 | 110.01 (14) | C34—C35—C36 | 111.97 (15) |
C7—C12—H12A | 109.7 | C34—C35—H35A | 109.2 |
C11—C12—H12A | 109.7 | C36—C35—H35A | 109.2 |
C7—C12—H12B | 109.7 | C34—C35—H35B | 109.2 |
C11—C12—H12B | 109.7 | C36—C35—H35B | 109.2 |
H12A—C12—H12B | 108.2 | H35A—C35—H35B | 107.9 |
N3—C13—C14 | 111.34 (12) | C31—C36—C35 | 110.21 (14) |
N3—C13—C18 | 110.44 (12) | C31—C36—H36A | 109.6 |
C14—C13—C18 | 110.56 (13) | C35—C36—H36A | 109.6 |
N3—C13—H13A | 108.1 | C31—C36—H36B | 109.6 |
C14—C13—H13A | 108.1 | C35—C36—H36B | 109.6 |
C18—C13—H13A | 108.1 | H36A—C36—H36B | 108.1 |
C13—C14—C15 | 110.37 (13) | Sn1—C37—H37A | 109.5 |
C13—C14—H14A | 109.6 | Sn1—C37—H37B | 109.5 |
C15—C14—H14A | 109.6 | H37A—C37—H37B | 109.5 |
C13—C14—H14B | 109.6 | Sn1—C37—H37C | 109.5 |
C15—C14—H14B | 109.6 | H37A—C37—H37C | 109.5 |
H14A—C14—H14B | 108.1 | H37B—C37—H37C | 109.5 |
C16—C15—C14 | 111.08 (14) | Sn1—C38—H38A | 109.5 |
C16—C15—H15A | 109.4 | Sn1—C38—H38B | 109.5 |
C14—C15—H15A | 109.4 | H38A—C38—H38B | 109.5 |
C16—C15—H15B | 109.4 | Sn1—C38—H38C | 109.5 |
C14—C15—H15B | 109.4 | H38A—C38—H38C | 109.5 |
H15A—C15—H15B | 108.0 | H38B—C38—H38C | 109.5 |
C15—C16—C17 | 110.96 (14) | ||
N3—P1—O1—Sn1 | −157.82 (10) | C7—C8—C9—C10 | 54.5 (2) |
N2—P1—O1—Sn1 | −40.22 (13) | C8—C9—C10—C11 | −55.0 (2) |
N1—P1—O1—Sn1 | 84.91 (12) | C9—C10—C11—C12 | 57.5 (2) |
C38—Sn1—O1—P1 | 122.65 (12) | N2—C7—C12—C11 | −178.26 (14) |
C37—Sn1—O1—P1 | −54.03 (12) | C8—C7—C12—C11 | 58.21 (19) |
O2—Sn1—O1—P1 | 34.08 (12) | C10—C11—C12—C7 | −59.4 (2) |
Cl1—Sn1—O1—P1 | −146.53 (11) | P1—N3—C13—C14 | 143.86 (11) |
N4—P2—O2—Sn1 | −115.63 (11) | P1—N3—C13—C18 | −92.91 (14) |
N6—P2—O2—Sn1 | 129.44 (11) | N3—C13—C14—C15 | −179.57 (13) |
N5—P2—O2—Sn1 | 1.35 (13) | C18—C13—C14—C15 | 57.26 (17) |
C38—Sn1—O2—P2 | 56.04 (12) | C13—C14—C15—C16 | −57.65 (17) |
C37—Sn1—O2—P2 | −125.41 (12) | C14—C15—C16—C17 | 56.57 (19) |
O1—Sn1—O2—P2 | 146.79 (11) | C15—C16—C17—C18 | −55.0 (2) |
Cl2—Sn1—O2—P2 | −34.97 (11) | N3—C13—C18—C17 | 179.85 (13) |
O1—P1—N1—C1 | 159.88 (13) | C14—C13—C18—C17 | −56.46 (17) |
N3—P1—N1—C1 | 33.66 (15) | C16—C17—C18—C13 | 55.2 (2) |
N2—P1—N1—C1 | −79.88 (15) | P2—N4—C19—C20 | −91.13 (17) |
O1—P1—N2—C7 | 166.42 (12) | P2—N4—C19—C24 | 145.53 (14) |
N3—P1—N2—C7 | −67.79 (14) | N4—C19—C20—C21 | −179.26 (17) |
N1—P1—N2—C7 | 44.62 (15) | C24—C19—C20—C21 | −56.2 (2) |
O1—P1—N3—C13 | 56.39 (13) | C19—C20—C21—C22 | 57.1 (3) |
N2—P1—N3—C13 | −62.17 (13) | C20—C21—C22—C23 | −55.4 (3) |
N1—P1—N3—C13 | 177.14 (11) | C21—C22—C23—C24 | 54.2 (3) |
O2—P2—N4—C19 | 67.05 (14) | N4—C19—C24—C23 | 178.41 (18) |
N6—P2—N4—C19 | −175.15 (13) | C20—C19—C24—C23 | 54.2 (2) |
N5—P2—N4—C19 | −51.53 (14) | C22—C23—C24—C19 | −54.0 (3) |
O2—P2—N5—C25 | 177.92 (12) | P2—N5—C25—C30 | −97.87 (15) |
N4—P2—N5—C25 | −56.41 (13) | P2—N5—C25—C26 | 138.69 (13) |
N6—P2—N5—C25 | 56.23 (14) | N5—C25—C26—C27 | 69.57 (18) |
O2—P2—N6—C31 | −21.62 (14) | C30—C25—C26—C27 | −55.00 (19) |
N4—P2—N6—C31 | −146.50 (12) | C25—C26—C27—C28 | 56.4 (2) |
N5—P2—N6—C31 | 99.84 (13) | C26—C27—C28—C29 | −55.8 (2) |
P1—N1—C1—C6 | 118.00 (15) | C27—C28—C29—C30 | 55.0 (2) |
P1—N1—C1—C2 | −117.76 (15) | C28—C29—C30—C25 | −54.7 (2) |
N1—C1—C2—C3 | 178.29 (13) | N5—C25—C30—C29 | −69.50 (18) |
C6—C1—C2—C3 | −56.52 (18) | C26—C25—C30—C29 | 54.13 (19) |
C1—C2—C3—C4 | 55.00 (19) | P2—N6—C31—C32 | −78.44 (16) |
C2—C3—C4—C5 | −54.4 (2) | P2—N6—C31—C36 | 157.47 (11) |
C3—C4—C5—C6 | 55.4 (2) | N6—C31—C32—C33 | 178.13 (13) |
N1—C1—C6—C5 | −178.06 (13) | C36—C31—C32—C33 | −57.89 (18) |
C2—C1—C6—C5 | 57.66 (18) | C31—C32—C33—C34 | 54.3 (2) |
C4—C5—C6—C1 | −57.14 (19) | C32—C33—C34—C35 | −51.4 (2) |
P1—N2—C7—C12 | 118.63 (14) | C33—C34—C35—C36 | 52.4 (2) |
P1—N2—C7—C8 | −117.77 (14) | N6—C31—C36—C35 | −175.31 (13) |
N2—C7—C8—C9 | 179.05 (14) | C32—C31—C36—C35 | 58.86 (18) |
C12—C7—C8—C9 | −56.1 (2) | C34—C35—C36—C31 | −56.32 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O2 | 0.86 | 2.16 | 2.9900 (16) | 161 |
N3—H3N···Cl1i | 0.92 | 2.61 | 3.4403 (13) | 151 |
N4—H4N···Cl2ii | 0.88 | 2.46 | 3.3296 (12) | 169 |
N5—H5N···Cl2 | 0.83 | 2.51 | 3.3135 (15) | 162 |
N6—H6N···Cl1ii | 0.87 | 2.53 | 3.3736 (14) | 165 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x−1/2, −y+1/2, z−1/2. |
[Cu(C18H36N3OP)2(H2O)2](NO3)2·2C18H36N3OP | F(000) = 1726 |
Mr = 1589.46 | Dx = 1.238 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9940 reflections |
a = 15.4495 (12) Å | θ = 2.4–27.7° |
b = 18.6924 (14) Å | µ = 0.39 mm−1 |
c = 16.5229 (12) Å | T = 100 K |
β = 116.656 (1)° | BLOCK, blue |
V = 4264.5 (6) Å3 | 0.24 × 0.20 × 0.18 mm |
Z = 2 |
Bruker APEXII CCD diffractometer | 9496 independent reflections |
Radiation source: fine-focus sealed tube | 7117 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
ϕ and ω scans | θmax = 28.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −20→19 |
Tmin = 0.911, Tmax = 0.932 | k = −20→24 |
32668 measured reflections | l = −21→21 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0396P)2 + 1.8998P] where P = (Fo2 + 2Fc2)/3 |
9496 reflections | (Δ/σ)max = 0.001 |
490 parameters | Δρmax = 0.47 e Å−3 |
9 restraints | Δρmin = −0.51 e Å−3 |
[Cu(C18H36N3OP)2(H2O)2](NO3)2·2C18H36N3OP | V = 4264.5 (6) Å3 |
Mr = 1589.46 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.4495 (12) Å | µ = 0.39 mm−1 |
b = 18.6924 (14) Å | T = 100 K |
c = 16.5229 (12) Å | 0.24 × 0.20 × 0.18 mm |
β = 116.656 (1)° |
Bruker APEXII CCD diffractometer | 9496 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 7117 reflections with I > 2σ(I) |
Tmin = 0.911, Tmax = 0.932 | Rint = 0.054 |
32668 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 9 restraints |
wR(F2) = 0.106 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.47 e Å−3 |
9496 reflections | Δρmin = −0.51 e Å−3 |
490 parameters |
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 > 2σ(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 | ||
P1 | 0.72928 (3) | 0.48314 (3) | 0.60731 (3) | 0.01544 (12) | |
Cu1 | 0.5000 | 0.5000 | 0.5000 | 0.01461 (9) | |
N1 | 0.72308 (13) | 0.48817 (10) | 0.70350 (12) | 0.0210 (4) | |
H1N | 0.7384 (15) | 0.4514 (8) | 0.7373 (13) | 0.025* | |
N2 | 0.80183 (11) | 0.54005 (10) | 0.59486 (12) | 0.0185 (4) | |
H2N | 0.7759 (14) | 0.5807 (7) | 0.5776 (14) | 0.022* | |
N3 | 0.77700 (11) | 0.40442 (10) | 0.61396 (11) | 0.0176 (4) | |
H3N | 0.7572 (15) | 0.3724 (9) | 0.6382 (13) | 0.021* | |
O1 | 0.63270 (9) | 0.49886 (8) | 0.52793 (9) | 0.0181 (3) | |
O2 | 0.49520 (10) | 0.39720 (8) | 0.49926 (10) | 0.0217 (3) | |
H2WA | 0.5343 (11) | 0.3717 (11) | 0.5399 (12) | 0.026* | |
H2WB | 0.4438 (9) | 0.3780 (11) | 0.4914 (14) | 0.026* | |
C1 | 0.67392 (14) | 0.54812 (12) | 0.72353 (14) | 0.0194 (4) | |
H1 | 0.6593 | 0.5853 | 0.6756 | 0.023* | |
C2 | 0.57806 (14) | 0.52547 (12) | 0.72194 (14) | 0.0226 (5) | |
H2A | 0.5905 | 0.4885 | 0.7688 | 0.027* | |
H2B | 0.5354 | 0.5043 | 0.6622 | 0.027* | |
C3 | 0.52728 (15) | 0.58968 (13) | 0.73958 (15) | 0.0265 (5) | |
H3A | 0.5103 | 0.6249 | 0.6900 | 0.032* | |
H3B | 0.4665 | 0.5736 | 0.7400 | 0.032* | |
C4 | 0.59180 (15) | 0.62538 (13) | 0.82980 (15) | 0.0259 (5) | |
H4A | 0.6022 | 0.5921 | 0.8800 | 0.031* | |
H4B | 0.5592 | 0.6687 | 0.8372 | 0.031* | |
C5 | 0.68948 (15) | 0.64602 (13) | 0.83416 (15) | 0.0275 (5) | |
H5A | 0.7320 | 0.6651 | 0.8951 | 0.033* | |
H5B | 0.6797 | 0.6843 | 0.7895 | 0.033* | |
C6 | 0.73896 (14) | 0.58212 (13) | 0.81450 (14) | 0.0260 (5) | |
H6A | 0.8000 | 0.5981 | 0.8144 | 0.031* | |
H6B | 0.7554 | 0.5460 | 0.8630 | 0.031* | |
C7 | 0.90728 (13) | 0.54178 (11) | 0.64915 (13) | 0.0179 (4) | |
H7 | 0.9283 | 0.4937 | 0.6779 | 0.021* | |
C8 | 0.94072 (14) | 0.59728 (13) | 0.72434 (15) | 0.0274 (5) | |
H8A | 0.9112 | 0.5868 | 0.7653 | 0.033* | |
H8B | 0.9185 | 0.6452 | 0.6977 | 0.033* | |
C9 | 1.05097 (15) | 0.59758 (14) | 0.77882 (15) | 0.0301 (6) | |
H9A | 1.0706 | 0.6359 | 0.8251 | 0.036* | |
H9B | 1.0727 | 0.5513 | 0.8106 | 0.036* | |
C10 | 1.09981 (14) | 0.60982 (13) | 0.71756 (14) | 0.0248 (5) | |
H10A | 1.0838 | 0.6583 | 0.6908 | 0.030* | |
H10B | 1.1710 | 0.6067 | 0.7538 | 0.030* | |
C11 | 1.06614 (14) | 0.55434 (13) | 0.64249 (15) | 0.0270 (5) | |
H11A | 1.0877 | 0.5063 | 0.6692 | 0.032* | |
H11B | 1.0959 | 0.5644 | 0.6017 | 0.032* | |
C12 | 0.95604 (14) | 0.55489 (13) | 0.58800 (14) | 0.0252 (5) | |
H12A | 0.9359 | 0.5173 | 0.5409 | 0.030* | |
H12B | 0.9349 | 0.6017 | 0.5573 | 0.030* | |
C13 | 0.80362 (13) | 0.37606 (12) | 0.54470 (13) | 0.0176 (4) | |
H13 | 0.8191 | 0.4173 | 0.5148 | 0.021* | |
C14 | 0.89423 (14) | 0.32989 (12) | 0.59125 (14) | 0.0212 (5) | |
H14A | 0.8819 | 0.2918 | 0.6263 | 0.025* | |
H14B | 0.9481 | 0.3598 | 0.6343 | 0.025* | |
C15 | 0.92441 (16) | 0.29565 (13) | 0.52387 (15) | 0.0287 (5) | |
H15A | 0.9458 | 0.3334 | 0.4949 | 0.034* | |
H15B | 0.9798 | 0.2631 | 0.5566 | 0.034* | |
C16 | 0.84140 (17) | 0.25383 (14) | 0.45122 (16) | 0.0335 (6) | |
H16A | 0.8256 | 0.2122 | 0.4792 | 0.040* | |
H16B | 0.8616 | 0.2356 | 0.4060 | 0.040* | |
C17 | 0.75183 (17) | 0.30055 (13) | 0.40399 (15) | 0.0308 (5) | |
H17A | 0.6980 | 0.2714 | 0.3596 | 0.037* | |
H17B | 0.7656 | 0.3393 | 0.3706 | 0.037* | |
C18 | 0.72153 (14) | 0.33312 (13) | 0.47218 (14) | 0.0254 (5) | |
H18A | 0.6649 | 0.3648 | 0.4400 | 0.030* | |
H18B | 0.7019 | 0.2944 | 0.5014 | 0.030* | |
N7 | 0.64717 (11) | 0.30618 (10) | 0.71670 (11) | 0.0204 (4) | |
O4 | 0.72683 (11) | 0.33345 (9) | 0.76628 (10) | 0.0341 (4) | |
O5 | 0.62045 (10) | 0.30234 (8) | 0.63222 (9) | 0.0250 (3) | |
O6 | 0.59451 (11) | 0.28215 (10) | 0.74918 (11) | 0.0351 (4) | |
P2 | 0.34199 (3) | 0.26886 (3) | 0.51254 (3) | 0.01491 (12) | |
N4 | 0.43482 (11) | 0.21633 (10) | 0.53106 (11) | 0.0172 (4) | |
H4N | 0.4885 (10) | 0.2344 (11) | 0.5690 (11) | 0.021* | |
N5 | 0.24054 (11) | 0.22471 (9) | 0.46403 (11) | 0.0162 (4) | |
H5N | 0.2100 (13) | 0.2294 (12) | 0.4075 (7) | 0.019* | |
N6 | 0.36235 (11) | 0.28560 (10) | 0.61669 (11) | 0.0193 (4) | |
H6N | 0.4178 (9) | 0.2757 (12) | 0.6580 (11) | 0.023* | |
O3 | 0.33078 (9) | 0.33404 (8) | 0.45548 (9) | 0.0195 (3) | |
C19 | 0.44400 (13) | 0.17846 (11) | 0.45703 (13) | 0.0164 (4) | |
H19A | 0.3792 | 0.1584 | 0.4151 | 0.020* | |
C20 | 0.47768 (14) | 0.22722 (12) | 0.40244 (13) | 0.0208 (5) | |
H20A | 0.4289 | 0.2652 | 0.3731 | 0.025* | |
H20B | 0.5394 | 0.2505 | 0.4439 | 0.025* | |
C21 | 0.49226 (15) | 0.18565 (13) | 0.33017 (14) | 0.0250 (5) | |
H21A | 0.4292 | 0.1665 | 0.2852 | 0.030* | |
H21B | 0.5170 | 0.2184 | 0.2982 | 0.030* | |
C22 | 0.56321 (16) | 0.12408 (13) | 0.37111 (16) | 0.0289 (5) | |
H22A | 0.6282 | 0.1433 | 0.4113 | 0.035* | |
H22B | 0.5681 | 0.0965 | 0.3222 | 0.035* | |
C23 | 0.52963 (16) | 0.07478 (13) | 0.42536 (16) | 0.0305 (5) | |
H23A | 0.4681 | 0.0514 | 0.3838 | 0.037* | |
H23B | 0.5786 | 0.0369 | 0.4547 | 0.037* | |
C24 | 0.51466 (15) | 0.11640 (12) | 0.49758 (14) | 0.0236 (5) | |
H24A | 0.4895 | 0.0836 | 0.5292 | 0.028* | |
H24B | 0.5778 | 0.1352 | 0.5429 | 0.028* | |
C25 | 0.21519 (13) | 0.16361 (11) | 0.50416 (13) | 0.0175 (4) | |
H25A | 0.2539 | 0.1675 | 0.5714 | 0.021* | |
C26 | 0.23860 (14) | 0.09151 (11) | 0.47597 (14) | 0.0196 (4) | |
H26A | 0.3087 | 0.0891 | 0.4929 | 0.024* | |
H26B | 0.2024 | 0.0863 | 0.4094 | 0.024* | |
C27 | 0.21154 (14) | 0.03047 (12) | 0.52172 (15) | 0.0234 (5) | |
H27A | 0.2238 | −0.0158 | 0.4997 | 0.028* | |
H27B | 0.2529 | 0.0327 | 0.5879 | 0.028* | |
C28 | 0.10539 (15) | 0.03442 (13) | 0.50235 (17) | 0.0295 (5) | |
H28A | 0.0638 | 0.0260 | 0.4370 | 0.035* | |
H28B | 0.0916 | −0.0036 | 0.5366 | 0.035* | |
C29 | 0.08112 (17) | 0.10690 (13) | 0.52884 (19) | 0.0355 (6) | |
H29A | 0.1166 | 0.1127 | 0.5954 | 0.043* | |
H29B | 0.0109 | 0.1091 | 0.5113 | 0.043* | |
C30 | 0.10829 (15) | 0.16772 (12) | 0.48273 (17) | 0.0269 (5) | |
H30A | 0.0679 | 0.1648 | 0.4164 | 0.032* | |
H30B | 0.0952 | 0.2142 | 0.5037 | 0.032* | |
C31 | 0.30594 (14) | 0.33873 (11) | 0.63868 (14) | 0.0196 (4) | |
H31A | 0.2516 | 0.3552 | 0.5804 | 0.023* | |
C32 | 0.2617 (2) | 0.30433 (14) | 0.6949 (2) | 0.0436 (7) | |
H32A | 0.3139 | 0.2836 | 0.7505 | 0.052* | |
H32B | 0.2182 | 0.2649 | 0.6599 | 0.052* | |
C33 | 0.2043 (2) | 0.35869 (15) | 0.7210 (2) | 0.0459 (7) | |
H33A | 0.1484 | 0.3761 | 0.6657 | 0.055* | |
H33B | 0.1791 | 0.3351 | 0.7598 | 0.055* | |
C34 | 0.2663 (2) | 0.42037 (18) | 0.77038 (18) | 0.0536 (8) | |
H34A | 0.3196 | 0.4035 | 0.8280 | 0.064* | |
H34B | 0.2273 | 0.4553 | 0.7851 | 0.064* | |
C35 | 0.3080 (2) | 0.45635 (16) | 0.7139 (3) | 0.0701 (11) | |
H35A | 0.3512 | 0.4958 | 0.7492 | 0.084* | |
H35B | 0.2548 | 0.4772 | 0.6591 | 0.084* | |
C36 | 0.3656 (2) | 0.40315 (16) | 0.6853 (2) | 0.0586 (9) | |
H36A | 0.3868 | 0.4274 | 0.6439 | 0.070* | |
H36B | 0.4242 | 0.3876 | 0.7395 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0123 (2) | 0.0165 (3) | 0.0170 (3) | −0.00103 (19) | 0.0062 (2) | −0.0006 (2) |
Cu1 | 0.01126 (16) | 0.0145 (2) | 0.01600 (17) | −0.00115 (13) | 0.00427 (13) | 0.00030 (14) |
N1 | 0.0286 (9) | 0.0169 (11) | 0.0195 (9) | 0.0043 (7) | 0.0125 (8) | 0.0035 (8) |
N2 | 0.0132 (8) | 0.0152 (10) | 0.0234 (9) | 0.0007 (7) | 0.0049 (7) | 0.0041 (8) |
N3 | 0.0191 (8) | 0.0164 (10) | 0.0212 (9) | −0.0003 (7) | 0.0125 (7) | 0.0024 (8) |
O1 | 0.0133 (6) | 0.0197 (9) | 0.0200 (7) | −0.0008 (5) | 0.0062 (6) | −0.0008 (6) |
O2 | 0.0155 (7) | 0.0144 (9) | 0.0300 (9) | −0.0015 (6) | 0.0056 (6) | 0.0035 (6) |
C1 | 0.0226 (10) | 0.0186 (12) | 0.0184 (10) | 0.0009 (8) | 0.0105 (8) | 0.0008 (9) |
C2 | 0.0210 (10) | 0.0260 (13) | 0.0206 (11) | −0.0024 (9) | 0.0092 (9) | −0.0016 (9) |
C3 | 0.0197 (10) | 0.0329 (15) | 0.0273 (12) | 0.0012 (9) | 0.0108 (9) | 0.0016 (10) |
C4 | 0.0284 (11) | 0.0273 (14) | 0.0274 (12) | 0.0054 (9) | 0.0175 (10) | 0.0008 (10) |
C5 | 0.0272 (11) | 0.0294 (15) | 0.0263 (12) | −0.0040 (10) | 0.0122 (10) | −0.0097 (10) |
C6 | 0.0198 (10) | 0.0352 (15) | 0.0222 (11) | −0.0003 (9) | 0.0087 (9) | −0.0054 (10) |
C7 | 0.0120 (9) | 0.0179 (12) | 0.0201 (10) | −0.0005 (8) | 0.0040 (8) | 0.0022 (9) |
C8 | 0.0203 (10) | 0.0349 (15) | 0.0294 (12) | −0.0066 (9) | 0.0135 (9) | −0.0121 (11) |
C9 | 0.0221 (11) | 0.0444 (17) | 0.0229 (12) | −0.0099 (10) | 0.0092 (9) | −0.0091 (11) |
C10 | 0.0170 (10) | 0.0280 (14) | 0.0274 (12) | −0.0069 (9) | 0.0080 (9) | −0.0021 (10) |
C11 | 0.0187 (10) | 0.0356 (15) | 0.0290 (12) | −0.0042 (9) | 0.0128 (9) | −0.0044 (11) |
C12 | 0.0196 (10) | 0.0345 (15) | 0.0215 (11) | −0.0065 (9) | 0.0093 (9) | −0.0068 (10) |
C13 | 0.0178 (9) | 0.0194 (12) | 0.0171 (10) | −0.0011 (8) | 0.0092 (8) | 0.0001 (9) |
C14 | 0.0201 (10) | 0.0233 (13) | 0.0213 (11) | 0.0022 (8) | 0.0101 (9) | 0.0002 (9) |
C15 | 0.0320 (12) | 0.0316 (15) | 0.0293 (12) | 0.0078 (10) | 0.0199 (10) | 0.0017 (11) |
C16 | 0.0506 (15) | 0.0284 (15) | 0.0296 (13) | 0.0008 (11) | 0.0251 (12) | −0.0059 (11) |
C17 | 0.0365 (13) | 0.0326 (15) | 0.0203 (11) | −0.0094 (10) | 0.0100 (10) | −0.0080 (10) |
C18 | 0.0205 (10) | 0.0297 (14) | 0.0231 (11) | −0.0038 (9) | 0.0071 (9) | −0.0036 (10) |
N7 | 0.0187 (8) | 0.0200 (11) | 0.0182 (9) | −0.0009 (7) | 0.0046 (7) | 0.0027 (8) |
O4 | 0.0251 (8) | 0.0372 (11) | 0.0243 (8) | −0.0130 (7) | −0.0028 (7) | 0.0033 (8) |
O5 | 0.0272 (8) | 0.0288 (10) | 0.0133 (7) | −0.0003 (6) | 0.0041 (6) | 0.0022 (7) |
O6 | 0.0310 (9) | 0.0470 (12) | 0.0315 (9) | −0.0087 (8) | 0.0177 (7) | 0.0045 (8) |
P2 | 0.0143 (2) | 0.0147 (3) | 0.0149 (3) | −0.00179 (19) | 0.0058 (2) | 0.0001 (2) |
N4 | 0.0131 (8) | 0.0213 (11) | 0.0147 (8) | −0.0010 (7) | 0.0041 (7) | 0.0001 (7) |
N5 | 0.0162 (8) | 0.0169 (10) | 0.0128 (8) | −0.0026 (7) | 0.0040 (7) | 0.0019 (7) |
N6 | 0.0165 (8) | 0.0221 (11) | 0.0152 (9) | 0.0020 (7) | 0.0036 (7) | −0.0026 (7) |
O3 | 0.0185 (7) | 0.0158 (8) | 0.0217 (7) | −0.0017 (6) | 0.0069 (6) | 0.0028 (6) |
C19 | 0.0140 (9) | 0.0184 (12) | 0.0160 (10) | −0.0007 (7) | 0.0062 (8) | −0.0008 (8) |
C20 | 0.0237 (10) | 0.0204 (13) | 0.0199 (10) | 0.0007 (8) | 0.0111 (9) | 0.0034 (9) |
C21 | 0.0278 (11) | 0.0316 (14) | 0.0205 (11) | −0.0039 (9) | 0.0152 (9) | 0.0005 (10) |
C22 | 0.0305 (12) | 0.0318 (15) | 0.0318 (13) | −0.0002 (10) | 0.0208 (10) | −0.0045 (11) |
C23 | 0.0320 (12) | 0.0254 (14) | 0.0409 (14) | 0.0059 (10) | 0.0224 (11) | 0.0029 (11) |
C24 | 0.0244 (11) | 0.0241 (14) | 0.0252 (12) | 0.0068 (9) | 0.0136 (9) | 0.0066 (10) |
C25 | 0.0168 (9) | 0.0174 (12) | 0.0188 (10) | −0.0043 (8) | 0.0085 (8) | −0.0011 (9) |
C26 | 0.0174 (9) | 0.0189 (12) | 0.0237 (11) | −0.0006 (8) | 0.0101 (8) | 0.0018 (9) |
C27 | 0.0223 (10) | 0.0183 (13) | 0.0297 (12) | −0.0034 (9) | 0.0118 (9) | 0.0001 (10) |
C28 | 0.0250 (11) | 0.0210 (14) | 0.0461 (15) | −0.0073 (9) | 0.0191 (11) | 0.0016 (11) |
C29 | 0.0300 (12) | 0.0290 (15) | 0.0606 (17) | −0.0073 (10) | 0.0321 (12) | −0.0031 (12) |
C30 | 0.0217 (11) | 0.0190 (13) | 0.0457 (14) | −0.0009 (9) | 0.0201 (10) | −0.0022 (11) |
C31 | 0.0204 (10) | 0.0193 (12) | 0.0176 (10) | 0.0010 (8) | 0.0072 (8) | −0.0016 (9) |
C32 | 0.0744 (19) | 0.0278 (16) | 0.0534 (17) | 0.0075 (13) | 0.0506 (16) | 0.0020 (13) |
C33 | 0.078 (2) | 0.0330 (17) | 0.0531 (17) | 0.0102 (14) | 0.0526 (16) | 0.0050 (14) |
C34 | 0.0477 (16) | 0.071 (2) | 0.0310 (15) | 0.0277 (15) | 0.0077 (13) | −0.0140 (15) |
C35 | 0.0551 (18) | 0.0311 (18) | 0.140 (3) | −0.0177 (14) | 0.058 (2) | −0.045 (2) |
C36 | 0.0428 (16) | 0.0385 (19) | 0.105 (3) | −0.0191 (13) | 0.0428 (17) | −0.0404 (18) |
P1—O1 | 1.5090 (14) | C18—H18B | 0.9900 |
P1—N2 | 1.6240 (17) | N7—O4 | 1.241 (2) |
P1—N3 | 1.6274 (18) | N7—O6 | 1.242 (2) |
P1—N1 | 1.6372 (17) | N7—O5 | 1.268 (2) |
Cu1—O1i | 1.8887 (12) | P2—O3 | 1.5024 (15) |
Cu1—O1 | 1.8888 (12) | P2—N5 | 1.6288 (16) |
Cu1—O2i | 1.9228 (15) | P2—N6 | 1.6348 (17) |
Cu1—O2 | 1.9229 (15) | P2—N4 | 1.6495 (17) |
N1—C1 | 1.472 (3) | N4—C19 | 1.474 (2) |
N1—H1N | 0.850 (9) | N4—H4N | 0.853 (9) |
N2—C7 | 1.466 (2) | N5—C25 | 1.460 (3) |
N2—H2N | 0.846 (9) | N5—H5N | 0.841 (9) |
N3—C13 | 1.477 (2) | N6—C31 | 1.470 (3) |
N3—H3N | 0.851 (9) | N6—H6N | 0.843 (9) |
O2—H2WA | 0.824 (9) | C19—C24 | 1.526 (3) |
O2—H2WB | 0.827 (9) | C19—C20 | 1.528 (3) |
C1—C6 | 1.522 (3) | C19—H19A | 1.0000 |
C1—C2 | 1.529 (3) | C20—C21 | 1.524 (3) |
C1—H1 | 1.0000 | C20—H20A | 0.9900 |
C2—C3 | 1.532 (3) | C20—H20B | 0.9900 |
C2—H2A | 0.9900 | C21—C22 | 1.523 (3) |
C2—H2B | 0.9900 | C21—H21A | 0.9900 |
C3—C4 | 1.526 (3) | C21—H21B | 0.9900 |
C3—H3A | 0.9900 | C22—C23 | 1.530 (3) |
C3—H3B | 0.9900 | C22—H22A | 0.9900 |
C4—C5 | 1.528 (3) | C22—H22B | 0.9900 |
C4—H4A | 0.9900 | C23—C24 | 1.526 (3) |
C4—H4B | 0.9900 | C23—H23A | 0.9900 |
C5—C6 | 1.530 (3) | C23—H23B | 0.9900 |
C5—H5A | 0.9900 | C24—H24A | 0.9900 |
C5—H5B | 0.9900 | C24—H24B | 0.9900 |
C6—H6A | 0.9900 | C25—C26 | 1.522 (3) |
C6—H6B | 0.9900 | C25—C30 | 1.528 (3) |
C7—C8 | 1.520 (3) | C25—H25A | 1.0000 |
C7—C12 | 1.527 (3) | C26—C27 | 1.527 (3) |
C7—H7 | 1.0000 | C26—H26A | 0.9900 |
C8—C9 | 1.528 (3) | C26—H26B | 0.9900 |
C8—H8A | 0.9900 | C27—C28 | 1.525 (3) |
C8—H8B | 0.9900 | C27—H27A | 0.9900 |
C9—C10 | 1.527 (3) | C27—H27B | 0.9900 |
C9—H9A | 0.9900 | C28—C29 | 1.521 (3) |
C9—H9B | 0.9900 | C28—H28A | 0.9900 |
C10—C11 | 1.518 (3) | C28—H28B | 0.9900 |
C10—H10A | 0.9900 | C29—C30 | 1.528 (3) |
C10—H10B | 0.9900 | C29—H29A | 0.9900 |
C11—C12 | 1.526 (3) | C29—H29B | 0.9900 |
C11—H11A | 0.9900 | C30—H30A | 0.9900 |
C11—H11B | 0.9900 | C30—H30B | 0.9900 |
C12—H12A | 0.9900 | C31—C36 | 1.502 (3) |
C12—H12B | 0.9900 | C31—C32 | 1.521 (3) |
C13—C18 | 1.525 (3) | C31—H31A | 1.0000 |
C13—C14 | 1.526 (3) | C32—C33 | 1.532 (3) |
C13—H13 | 1.0000 | C32—H32A | 0.9900 |
C14—C15 | 1.527 (3) | C32—H32B | 0.9900 |
C14—H14A | 0.9900 | C33—C34 | 1.486 (4) |
C14—H14B | 0.9900 | C33—H33A | 0.9900 |
C15—C16 | 1.522 (3) | C33—H33B | 0.9900 |
C15—H15A | 0.9900 | C34—C35 | 1.510 (5) |
C15—H15B | 0.9900 | C34—H34A | 0.9900 |
C16—C17 | 1.522 (3) | C34—H34B | 0.9900 |
C16—H16A | 0.9900 | C35—C36 | 1.544 (4) |
C16—H16B | 0.9900 | C35—H35A | 0.9900 |
C17—C18 | 1.527 (3) | C35—H35B | 0.9900 |
C17—H17A | 0.9900 | C36—H36A | 0.9900 |
C17—H17B | 0.9900 | C36—H36B | 0.9900 |
C18—H18A | 0.9900 | ||
O1—P1—N2 | 103.41 (8) | C13—C18—H18B | 109.3 |
O1—P1—N3 | 118.43 (9) | C17—C18—H18B | 109.3 |
N2—P1—N3 | 106.46 (9) | H18A—C18—H18B | 108.0 |
O1—P1—N1 | 111.53 (8) | O4—N7—O6 | 120.73 (17) |
N2—P1—N1 | 115.45 (9) | O4—N7—O5 | 119.12 (16) |
N3—P1—N1 | 102.03 (9) | O6—N7—O5 | 120.15 (16) |
O1i—Cu1—O1 | 180.0 | O3—P2—N5 | 106.71 (8) |
O1i—Cu1—O2i | 91.42 (6) | O3—P2—N6 | 114.77 (9) |
O1—Cu1—O2i | 88.58 (6) | N5—P2—N6 | 107.65 (8) |
O1i—Cu1—O2 | 88.58 (6) | O3—P2—N4 | 116.43 (8) |
O1—Cu1—O2 | 91.42 (6) | N5—P2—N4 | 110.75 (9) |
O2i—Cu1—O2 | 180.0 | N6—P2—N4 | 100.25 (8) |
C1—N1—P1 | 121.50 (14) | C19—N4—P2 | 122.08 (13) |
C1—N1—H1N | 119.2 (15) | C19—N4—H4N | 112.1 (14) |
P1—N1—H1N | 118.1 (15) | P2—N4—H4N | 112.2 (15) |
C7—N2—P1 | 125.28 (14) | C25—N5—P2 | 124.61 (13) |
C7—N2—H2N | 114.5 (15) | C25—N5—H5N | 117.1 (15) |
P1—N2—H2N | 112.4 (15) | P2—N5—H5N | 115.5 (15) |
C13—N3—P1 | 123.18 (14) | C31—N6—P2 | 122.27 (14) |
C13—N3—H3N | 113.4 (15) | C31—N6—H6N | 116.6 (15) |
P1—N3—H3N | 114.9 (15) | P2—N6—H6N | 117.2 (15) |
P1—O1—Cu1 | 139.13 (9) | N4—C19—C24 | 108.47 (16) |
Cu1—O2—H2WA | 124.1 (16) | N4—C19—C20 | 112.85 (17) |
Cu1—O2—H2WB | 117.8 (16) | C24—C19—C20 | 110.27 (15) |
H2WA—O2—H2WB | 100.2 (17) | N4—C19—H19A | 108.4 |
N1—C1—C6 | 111.17 (17) | C24—C19—H19A | 108.4 |
N1—C1—C2 | 112.25 (17) | C20—C19—H19A | 108.4 |
C6—C1—C2 | 109.73 (16) | C21—C20—C19 | 111.56 (18) |
N1—C1—H1 | 107.8 | C21—C20—H20A | 109.3 |
C6—C1—H1 | 107.8 | C19—C20—H20A | 109.3 |
C2—C1—H1 | 107.8 | C21—C20—H20B | 109.3 |
C1—C2—C3 | 110.77 (18) | C19—C20—H20B | 109.3 |
C1—C2—H2A | 109.5 | H20A—C20—H20B | 108.0 |
C3—C2—H2A | 109.5 | C22—C21—C20 | 111.56 (18) |
C1—C2—H2B | 109.5 | C22—C21—H21A | 109.3 |
C3—C2—H2B | 109.5 | C20—C21—H21A | 109.3 |
H2A—C2—H2B | 108.1 | C22—C21—H21B | 109.3 |
C4—C3—C2 | 111.27 (17) | C20—C21—H21B | 109.3 |
C4—C3—H3A | 109.4 | H21A—C21—H21B | 108.0 |
C2—C3—H3A | 109.4 | C21—C22—C23 | 110.48 (17) |
C4—C3—H3B | 109.4 | C21—C22—H22A | 109.6 |
C2—C3—H3B | 109.4 | C23—C22—H22A | 109.6 |
H3A—C3—H3B | 108.0 | C21—C22—H22B | 109.6 |
C3—C4—C5 | 110.80 (17) | C23—C22—H22B | 109.6 |
C3—C4—H4A | 109.5 | H22A—C22—H22B | 108.1 |
C5—C4—H4A | 109.5 | C24—C23—C22 | 111.2 (2) |
C3—C4—H4B | 109.5 | C24—C23—H23A | 109.4 |
C5—C4—H4B | 109.5 | C22—C23—H23A | 109.4 |
H4A—C4—H4B | 108.1 | C24—C23—H23B | 109.4 |
C4—C5—C6 | 111.71 (19) | C22—C23—H23B | 109.4 |
C4—C5—H5A | 109.3 | H23A—C23—H23B | 108.0 |
C6—C5—H5A | 109.3 | C19—C24—C23 | 111.94 (17) |
C4—C5—H5B | 109.3 | C19—C24—H24A | 109.2 |
C6—C5—H5B | 109.3 | C23—C24—H24A | 109.2 |
H5A—C5—H5B | 107.9 | C19—C24—H24B | 109.2 |
C1—C6—C5 | 111.37 (17) | C23—C24—H24B | 109.2 |
C1—C6—H6A | 109.4 | H24A—C24—H24B | 107.9 |
C5—C6—H6A | 109.4 | N5—C25—C26 | 113.89 (15) |
C1—C6—H6B | 109.4 | N5—C25—C30 | 109.74 (17) |
C5—C6—H6B | 109.4 | C26—C25—C30 | 110.75 (16) |
H6A—C6—H6B | 108.0 | N5—C25—H25A | 107.4 |
N2—C7—C8 | 113.08 (16) | C26—C25—H25A | 107.4 |
N2—C7—C12 | 109.96 (16) | C30—C25—H25A | 107.4 |
C8—C7—C12 | 110.10 (17) | C25—C26—C27 | 110.78 (16) |
N2—C7—H7 | 107.8 | C25—C26—H26A | 109.5 |
C8—C7—H7 | 107.8 | C27—C26—H26A | 109.5 |
C12—C7—H7 | 107.8 | C25—C26—H26B | 109.5 |
C7—C8—C9 | 111.36 (17) | C27—C26—H26B | 109.5 |
C7—C8—H8A | 109.4 | H26A—C26—H26B | 108.1 |
C9—C8—H8A | 109.4 | C28—C27—C26 | 111.55 (18) |
C7—C8—H8B | 109.4 | C28—C27—H27A | 109.3 |
C9—C8—H8B | 109.4 | C26—C27—H27A | 109.3 |
H8A—C8—H8B | 108.0 | C28—C27—H27B | 109.3 |
C10—C9—C8 | 111.21 (18) | C26—C27—H27B | 109.3 |
C10—C9—H9A | 109.4 | H27A—C27—H27B | 108.0 |
C8—C9—H9A | 109.4 | C29—C28—C27 | 111.30 (18) |
C10—C9—H9B | 109.4 | C29—C28—H28A | 109.4 |
C8—C9—H9B | 109.4 | C27—C28—H28A | 109.4 |
H9A—C9—H9B | 108.0 | C29—C28—H28B | 109.4 |
C11—C10—C9 | 110.44 (17) | C27—C28—H28B | 109.4 |
C11—C10—H10A | 109.6 | H28A—C28—H28B | 108.0 |
C9—C10—H10A | 109.6 | C28—C29—C30 | 111.15 (18) |
C11—C10—H10B | 109.6 | C28—C29—H29A | 109.4 |
C9—C10—H10B | 109.6 | C30—C29—H29A | 109.4 |
H10A—C10—H10B | 108.1 | C28—C29—H29B | 109.4 |
C10—C11—C12 | 111.10 (18) | C30—C29—H29B | 109.4 |
C10—C11—H11A | 109.4 | H29A—C29—H29B | 108.0 |
C12—C11—H11A | 109.4 | C25—C30—C29 | 110.92 (19) |
C10—C11—H11B | 109.4 | C25—C30—H30A | 109.5 |
C12—C11—H11B | 109.4 | C29—C30—H30A | 109.5 |
H11A—C11—H11B | 108.0 | C25—C30—H30B | 109.5 |
C11—C12—C7 | 111.02 (17) | C29—C30—H30B | 109.5 |
C11—C12—H12A | 109.4 | H30A—C30—H30B | 108.0 |
C7—C12—H12A | 109.4 | N6—C31—C36 | 111.88 (17) |
C11—C12—H12B | 109.4 | N6—C31—C32 | 110.11 (18) |
C7—C12—H12B | 109.4 | C36—C31—C32 | 111.5 (2) |
H12A—C12—H12B | 108.0 | N6—C31—H31A | 107.7 |
N3—C13—C18 | 112.03 (15) | C36—C31—H31A | 107.7 |
N3—C13—C14 | 108.88 (16) | C32—C31—H31A | 107.7 |
C18—C13—C14 | 110.48 (18) | C31—C32—C33 | 111.5 (2) |
N3—C13—H13 | 108.5 | C31—C32—H32A | 109.3 |
C18—C13—H13 | 108.5 | C33—C32—H32A | 109.3 |
C14—C13—H13 | 108.5 | C31—C32—H32B | 109.3 |
C13—C14—C15 | 112.37 (17) | C33—C32—H32B | 109.3 |
C13—C14—H14A | 109.1 | H32A—C32—H32B | 108.0 |
C15—C14—H14A | 109.1 | C34—C33—C32 | 111.0 (2) |
C13—C14—H14B | 109.1 | C34—C33—H33A | 109.4 |
C15—C14—H14B | 109.1 | C32—C33—H33A | 109.4 |
H14A—C14—H14B | 107.9 | C34—C33—H33B | 109.4 |
C16—C15—C14 | 111.44 (17) | C32—C33—H33B | 109.4 |
C16—C15—H15A | 109.3 | H33A—C33—H33B | 108.0 |
C14—C15—H15A | 109.3 | C33—C34—C35 | 110.8 (2) |
C16—C15—H15B | 109.3 | C33—C34—H34A | 109.5 |
C14—C15—H15B | 109.3 | C35—C34—H34A | 109.5 |
H15A—C15—H15B | 108.0 | C33—C34—H34B | 109.5 |
C15—C16—C17 | 111.1 (2) | C35—C34—H34B | 109.5 |
C15—C16—H16A | 109.4 | H34A—C34—H34B | 108.1 |
C17—C16—H16A | 109.4 | C34—C35—C36 | 111.6 (3) |
C15—C16—H16B | 109.4 | C34—C35—H35A | 109.3 |
C17—C16—H16B | 109.4 | C36—C35—H35A | 109.3 |
H16A—C16—H16B | 108.0 | C34—C35—H35B | 109.3 |
C16—C17—C18 | 111.07 (18) | C36—C35—H35B | 109.3 |
C16—C17—H17A | 109.4 | H35A—C35—H35B | 108.0 |
C18—C17—H17A | 109.4 | C31—C36—C35 | 111.6 (2) |
C16—C17—H17B | 109.4 | C31—C36—H36A | 109.3 |
C18—C17—H17B | 109.4 | C35—C36—H36A | 109.3 |
H17A—C17—H17B | 108.0 | C31—C36—H36B | 109.3 |
C13—C18—C17 | 111.55 (16) | C35—C36—H36B | 109.3 |
C13—C18—H18A | 109.3 | H36A—C36—H36B | 108.0 |
C17—C18—H18A | 109.3 | ||
O1—P1—N1—C1 | −45.78 (18) | C14—C13—C18—C17 | −55.2 (2) |
N2—P1—N1—C1 | 71.86 (18) | C16—C17—C18—C13 | 56.6 (3) |
N3—P1—N1—C1 | −173.17 (16) | O3—P2—N4—C19 | −63.31 (17) |
O1—P1—N2—C7 | −172.83 (16) | N5—P2—N4—C19 | 58.81 (17) |
N3—P1—N2—C7 | −47.33 (19) | N6—P2—N4—C19 | 172.27 (15) |
N1—P1—N2—C7 | 65.08 (19) | O3—P2—N5—C25 | −170.52 (15) |
O1—P1—N3—C13 | 61.28 (17) | N6—P2—N5—C25 | −46.84 (18) |
N2—P1—N3—C13 | −54.50 (17) | N4—P2—N5—C25 | 61.85 (17) |
N1—P1—N3—C13 | −175.90 (15) | O3—P2—N6—C31 | 46.27 (18) |
N2—P1—O1—Cu1 | −145.01 (13) | N5—P2—N6—C31 | −72.36 (18) |
N3—P1—O1—Cu1 | 97.58 (14) | N4—P2—N6—C31 | 171.83 (16) |
N1—P1—O1—Cu1 | −20.34 (17) | P2—N4—C19—C24 | −160.31 (14) |
O2i—Cu1—O1—P1 | 106.65 (14) | P2—N4—C19—C20 | 77.21 (19) |
O2—Cu1—O1—P1 | −73.35 (14) | N4—C19—C20—C21 | 176.59 (16) |
P1—N1—C1—C6 | −128.38 (17) | C24—C19—C20—C21 | 55.1 (2) |
P1—N1—C1—C2 | 108.29 (18) | C19—C20—C21—C22 | −56.3 (2) |
N1—C1—C2—C3 | −177.91 (17) | C20—C21—C22—C23 | 55.9 (2) |
C6—C1—C2—C3 | 57.9 (2) | C21—C22—C23—C24 | −55.4 (2) |
C1—C2—C3—C4 | −57.4 (2) | N4—C19—C24—C23 | −179.14 (17) |
C2—C3—C4—C5 | 54.9 (3) | C20—C19—C24—C23 | −55.1 (2) |
C3—C4—C5—C6 | −54.0 (3) | C22—C23—C24—C19 | 55.8 (2) |
N1—C1—C6—C5 | 178.09 (17) | P2—N5—C25—C26 | −94.65 (19) |
C2—C1—C6—C5 | −57.1 (2) | P2—N5—C25—C30 | 140.55 (16) |
C4—C5—C6—C1 | 55.7 (2) | N5—C25—C26—C27 | 179.12 (16) |
P1—N2—C7—C8 | −99.0 (2) | C30—C25—C26—C27 | −56.6 (2) |
P1—N2—C7—C12 | 137.46 (17) | C25—C26—C27—C28 | 55.7 (2) |
N2—C7—C8—C9 | −179.66 (18) | C26—C27—C28—C29 | −54.9 (3) |
C12—C7—C8—C9 | −56.2 (2) | C27—C28—C29—C30 | 54.8 (3) |
C7—C8—C9—C10 | 56.2 (3) | N5—C25—C30—C29 | −176.49 (18) |
C8—C9—C10—C11 | −55.7 (3) | C26—C25—C30—C29 | 56.9 (2) |
C9—C10—C11—C12 | 56.3 (3) | C28—C29—C30—C25 | −56.0 (3) |
C10—C11—C12—C7 | −57.3 (3) | P2—N6—C31—C36 | −110.7 (2) |
N2—C7—C12—C11 | −178.02 (18) | P2—N6—C31—C32 | 124.65 (19) |
C8—C7—C12—C11 | 56.7 (2) | N6—C31—C32—C33 | 178.6 (2) |
P1—N3—C13—C18 | −91.9 (2) | C36—C31—C32—C33 | 53.8 (3) |
P1—N3—C13—C14 | 145.60 (15) | C31—C32—C33—C34 | −56.5 (3) |
N3—C13—C14—C15 | 177.51 (17) | C32—C33—C34—C35 | 57.7 (3) |
C18—C13—C14—C15 | 54.1 (2) | C33—C34—C35—C36 | −56.5 (3) |
C13—C14—C15—C16 | −54.2 (3) | N6—C31—C36—C35 | −176.1 (3) |
C14—C15—C16—C17 | 54.6 (3) | C32—C31—C36—C35 | −52.3 (4) |
C15—C16—C17—C18 | −55.9 (3) | C34—C35—C36—C31 | 53.9 (4) |
N3—C13—C18—C17 | −176.77 (18) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O4 | 0.85 (1) | 2.28 (1) | 3.064 (2) | 154 (2) |
N3—H3N···O5 | 0.85 (1) | 2.45 (1) | 3.199 (2) | 148 (2) |
N3—H3N···O4 | 0.85 (1) | 2.47 (1) | 3.232 (2) | 149 (2) |
O2—H2WA···O5 | 0.82 (1) | 1.99 (1) | 2.811 (2) | 175 (2) |
O2—H2WB···O3 | 0.83 (1) | 1.77 (1) | 2.5926 (19) | 170 (2) |
N2—H2N···O3i | 0.85 (1) | 2.18 (1) | 2.983 (2) | 159 (2) |
N4—H4N···O5 | 0.85 (1) | 2.23 (1) | 3.050 (2) | 163 (2) |
N5—H5N···O6ii | 0.84 (1) | 2.43 (1) | 3.244 (2) | 164 (2) |
N5—H5N···O4ii | 0.84 (1) | 2.73 (2) | 3.359 (2) | 133 (2) |
N6—H6N···O6 | 0.84 (1) | 2.46 (1) | 3.258 (2) | 159 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1/2, −y+1/2, z−1/2. |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | [Sn(CH3)2Cl2(C18H36N3OP)2] | [Cu(C18H36N3OP)2(H2O)2](NO3)2·2C18H36N3OP |
Mr | 902.59 | 1589.46 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 100 | 100 |
a, b, c (Å) | 12.0882 (6), 25.1607 (13), 15.8103 (8) | 15.4495 (12), 18.6924 (14), 16.5229 (12) |
β (°) | 108.879 (1) | 116.656 (1) |
V (Å3) | 4550.0 (4) | 4264.5 (6) |
Z | 4 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.79 | 0.39 |
Crystal size (mm) | 0.35 × 0.25 × 0.25 | 0.24 × 0.20 × 0.18 |
Data collection | ||
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (APEX2; Bruker, 2005) | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.772, 0.825 | 0.911, 0.932 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 71686, 12101, 10758 | 32668, 9496, 7117 |
Rint | 0.030 | 0.054 |
(sin θ/λ)max (Å−1) | 0.682 | 0.661 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.080, 1.00 | 0.043, 0.106, 1.04 |
No. of reflections | 12101 | 9496 |
No. of parameters | 462 | 490 |
No. of restraints | 0 | 9 |
H-atom treatment | H-atom parameters constrained | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.84, −0.48 | 0.47, −0.51 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2008), SAINT (Bruker 2008), SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).
Sn1—C38 | 2.1114 (16) | P1—O1 | 1.5032 (11) |
Sn1—O1 | 2.2281 (11) | P1—N1 | 1.6397 (14) |
Sn1—Cl1 | 2.5479 (4) | P2—O2 | 1.5116 (11) |
C38—Sn1—C37 | 176.31 (6) | O2—P2—N6 | 107.63 (6) |
C38—Sn1—O1 | 90.69 (6) | P1—O1—Sn1 | 142.63 (7) |
O1—Sn1—O2 | 87.31 (4) | P2—O2—Sn1 | 144.10 (6) |
C38—Sn1—Cl1 | 90.83 (5) | C1—N1—P1 | 128.23 (11) |
O2—Sn1—Cl1 | 176.07 (3) | C7—N2—P1 | 123.14 (10) |
O1—P1—N3 | 117.82 (7) | C13—N3—P1 | 120.32 (10) |
O1—P1—N2 | 106.76 (7) | C19—N4—P2 | 124.77 (10) |
O2—P2—N4 | 117.89 (7) | C25—N5—P2 | 122.46 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O2 | 0.86 | 2.16 | 2.9900 (16) | 161 |
N3—H3N···Cl1i | 0.92 | 2.61 | 3.4403 (13) | 151 |
N4—H4N···Cl2ii | 0.88 | 2.46 | 3.3296 (12) | 169 |
N5—H5N···Cl2 | 0.83 | 2.51 | 3.3135 (15) | 162 |
N6—H6N···Cl1ii | 0.87 | 2.53 | 3.3736 (14) | 165 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x−1/2, −y+1/2, z−1/2. |
P1—O1 | 1.5090 (14) | Cu1—O2 | 1.9229 (15) |
P1—N2 | 1.6240 (17) | P2—O3 | 1.5024 (15) |
P1—N3 | 1.6274 (18) | P2—N5 | 1.6288 (16) |
P1—N1 | 1.6372 (17) | P2—N6 | 1.6348 (17) |
Cu1—O1 | 1.8888 (12) | P2—N4 | 1.6495 (17) |
O1—P1—N2 | 103.41 (8) | P1—O1—Cu1 | 139.13 (9) |
O1—P1—N3 | 118.43 (9) | O3—P2—N5 | 106.71 (8) |
N2—P1—N3 | 106.46 (9) | O3—P2—N6 | 114.77 (9) |
O1—P1—N1 | 111.53 (8) | N5—P2—N6 | 107.65 (8) |
N2—P1—N1 | 115.45 (9) | O3—P2—N4 | 116.43 (8) |
N3—P1—N1 | 102.03 (9) | N5—P2—N4 | 110.75 (9) |
O1—Cu1—O2 | 91.42 (6) | N6—P2—N4 | 100.25 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O4 | 0.850 (9) | 2.280 (14) | 3.064 (2) | 154 (2) |
N3—H3N···O5 | 0.851 (9) | 2.449 (14) | 3.199 (2) | 147.6 (19) |
N3—H3N···O4 | 0.851 (9) | 2.473 (14) | 3.232 (2) | 149.0 (19) |
O2—H2WA···O5 | 0.824 (9) | 1.989 (10) | 2.811 (2) | 175 (2) |
O2—H2WB···O3 | 0.827 (9) | 1.774 (10) | 2.5926 (19) | 170 (2) |
N2—H2N···O3i | 0.846 (9) | 2.178 (12) | 2.983 (2) | 159 (2) |
N4—H4N···O5 | 0.853 (9) | 2.225 (11) | 3.050 (2) | 163 (2) |
N5—H5N···O6ii | 0.841 (9) | 2.426 (11) | 3.244 (2) | 164 (2) |
N5—H5N···O4ii | 0.841 (9) | 2.727 (17) | 3.359 (2) | 133.2 (18) |
N6—H6N···O6 | 0.843 (9) | 2.458 (12) | 3.258 (2) | 159 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1/2, −y+1/2, z−1/2. |
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The P═O···H—N hydrogen bond exists in the structures of phosphoramide compounds containing the P(O)NH moiety. In the process of coordination to a metal cation (M), one would anticipate that this interaction would be replaced with a P═O···M bond (Gholivand et al., 2006). Here we discuss two cases where this type of hydrogen bond remains in a coordinated phosphoric triamide ligand in two new complexes and its possible role in the coordination manner of the ligand.
Organotin(IV) complexes, particularly those with organophosphorus ligands, have attracted attention because of their versatile biological properties (Gholivand et al., 2010). Similar to the organophosphorus ligands, the phosphoramides are suitable for reacting with organotin(IV) compounds. In this series, a few organotin(IV)–phosphoramide compounds have been reported with some phosphoramide ligands. A search of the Cambridge Structural Database (CSD, Version 5.32, November 2010 update; Allen, 2002) shows that in all reported dialkyltin(IV) dihalide tris(alkylamido)phosphate compounds, the phosphoramide ligands adopt a trans arrangement. We present here the first structure of an organotin(IV) tris(alkylamido)phosphate complex with two phosphoric triamide ligands in cis positions (Fig. 1). The Sn coordination geometry in cis-dichlorido-trans-dimethyl-cis-βis(N,N',N''-tricyclohexylphosphoric triamide-κO)tin(IV), (I), is octahedral with the N,N',N''-tricyclohexylphosphoric triamide (PTA) and chloride ligands cis, but the methyl groups trans (Fig. 1, Table 1). The P atoms in the PTA ligands adopt a slightly distorted tetrahedral environment. The Sn—O—P angles are both a little greater than 140°. These geometric parameters are consistent with those observed in related structures: [(Me2N)3PO]2X2Me2Sn, with X = Br (CSD refcode BDMSAP; Aslanov et al., 1977), Cl (CDMSAP01; Rheingold et al., 1984); [(Me2N)3PO]2X2Et2Sn, with X = I (DUCJAM; Tursina et al., 1985), Br (FILCIM and FILCIM01; Tursina et al., 1987); [(R)2(PhC(O)NH)PO]2Cl2Me2Sn (Gholivand & Shariatinia, 2006), with R = t-BuNH (YERGEI), C4H8N (YERGIM), C5H10N (YERGOS) and (Me)(Cy)N (YERGUY); {(C5H10N)2[(p-F–Ph)C(O)NH]PO}2Cl2Me2Sn (LEHWIF; Gholivand et al., 2006).
The two symmetry-independent PTA ligands in (I) are involved in an intramolecular N2—H2N···O2—P2 hydrogen bond (Table 2) in which the amide group of one ligand (P1) interacts with the phosphoryl O atom of the other ligand. This hydrogen bond may be considered as a factor helping to stabilize the previously unobserved cis geometry. The P2—O2 bond length is a little longer than the P1—O1 bond length, the latter O atom not serving as a hydrogen-bond acceptor. An intramolecular N5—H5N···Cl2 hydrogen bond is also found in the structure. The environment of each N atom in the PTA ligands is almost planar and it does not form any hydrogen bonds as an acceptor, showing its low Lewis-base character. In previously reported phosphoramide compounds and their dialkyl dichloride tin(IV)–phosphoramide complexes (Gholivand et al., 2004, 2006; Gholivand & Shariatinia, 2006), the N—H···O hydrogen bonds which appear in the structures of the free phosphoramide molecules are replaced by N—H···Cl hydrogen bonds in the complexes, as the phosphoryl O atoms are involved in Sn—O covalent bonds in the latter. This fact may be supported by IR spectroscopy in which the N—H stretching frequencies in the tin complexes are higher than in the free molecules as they are involved in weaker N—H···Cl hydrogen bonds.
The two-dimensional hydrogen-bonded network in (I) is produced via some different weak N—H···Cl hydrogen bonds between the complex and three neighbouring complexes in the crystal (Fig. 2). In this case, the Cl1 and Cl2 atoms are, respectively, involved in N6—H6N···Cl1ii and N4—H4N···Cl2ii interactions [symmetry code: (ii) x - 1/2, -y + 1/2, z - 1/2] to build an R22(8) ring (Etter et al., 1990; Bernstein et al., 1995). The Cl2 atom is also involved in an intramolecular N—H···Cl hydrogen bond, which has been noted earlier, while the Cl1 atom co-operates in another intermolecular N3—H3N···Cl1i hydrogen bond [symmetry code: (i) -x + 2, -y, -z + 1] (Table 2).
Copper complexes have been of interest as the interface between biochemistry and coordination chemistry (Collinson & Fenton, 1996; Hossain et al., 1996; Tarafder et al., 2002). The PTA ligand was also used to prepare a new copper(II) phosphoramidate complex, namely trans-diaquabis(N,N',N''-tricyclohexylphosphoric triamide-κO)copper(II) dinitrate–\<i>N,N',N''-tricyclohexylphosphoric triamide (1/2), (II) (Fig. 3). The asymmetric unit contains one half of a [Cu2(PTA)(H2O)2]2+ dication, one nitrate anion and one free PTA molecule. The CuII ion is located on a crystallographic inversion centre. The complex thus adopts a square-planar trans-[CuO2O2] coordination geometry, with the CuII ion coordinated by two PTA ligands and two water molecules. The phosphoryl O atom makes a shorter Cu—O bond than the water O atom (Table 3). The P atoms in the PTA ligands adopt a slightly distorted tetrahedral environment and the Cu—O—P angle is similarly a little under 140°. These geometric parameters are consistent with those in related structures: [Cu4OCl6{(O)P(NHtBu)3}4] (LIDNIW; Fu & Chivers, 2007); [Cu(ONO2)2{(O)P(NHtBu)3}2] (LIDPAQ; Fu & Chivers, 2007) and [CuCl2(NHC4H6O){(O)P[NMe2]3} (YIBZEP; Xie et al., 2007).
Each of the noncoordinated PTA molecules is hydrogen bonded to a neighbouring coordinated PTA via an N2—H2N···O3i hydrogen bond [Table 4; symmetry code: (i) -x + 1, -y + 1, -z + 1] and to an adjacent water molecule via an O2—H2WB···O3 hydrogen bond. The noncoordinated PTA phosphoryl O atom thus acts as a double-H-atom acceptor (Steiner, 2002). Atom O5 of the nitrate anion co-operates in O2—H2WA···O5, N3—H3N···O5 and N4—H4N···O5 hydrogen bonds, respectively, with neighbouring coordinated water, and coordinated and uncoordinated PTA molecules (Fig. 4, Table 4). Moreover, atom O4 of the nitrate anion co-operates in hydrogen-bonding interactions with N1—H1N and N3—H3N groups of the adjacent coordinated PTA. These interactions make a centrosymmetric hydrogen-bonded pentamer containing one dication, two PTA molecules and two nitrate anions. The N5—H5N group of free PTA molecules is involved in two weak hydrogen bonds, viz. N5—H5N···O4ii and N5—H5N···O6ii [symmetry code: (ii) x - 1/2, -y + 1/2, z - 1/2] (Fig. 4). These hydrogen bonds assemble the centrosymmetric pentamers in a two-dimensional arrangement along the (101) plane (Fig. 5).