Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807062411/ng2382sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807062411/ng2382Isup2.hkl |
CCDC reference: 674073
The title complex was obtained by heating under reflux a 1:2 molar mixture of dibutyltin(IV) oxide (0.75 g, 3 mmol) and 4-(methylamino)benzoic acid (0.91 g, 6 mmol) in toluene-ethanol (4:1, v/v) (50 ml) for 4 h. A clear transparent solution was isolated by filtration and kept in a bottle. After 14 days, colourless crystals (0.54 g, 34% yield) were obtained. M.p. 427–428 K. Calculated for C24H34N2O4Sn: C 54.06, H 6.43, N 5.25 and Sn 22.61%; analysis found C 55.63, H 5.89, N 5.48 and Sn 22.61%.
H atoms attached to N atom except for N2A were located from the difference map and isotropically refined. The remainding H atoms were positioned geometrically and allowed to ride on their parent atoms, with N—H distance of 0.82 Å and C—H = 0.93 Å for aromatic rings and in the ranges 0.96–0.97 Å for CH2 and CH3. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak is located at 0.58 Å from Sn1C and the deepest hole is located at 0.74 Å from Sn1D. The crystal is a twin and the refined BASF value is 0.396(0.009).
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL (Sheldrick, 1998); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).
[Sn(C4H9)2(C8H8NO2)2] | F(000) = 2192 |
Mr = 533.22 | Dx = 1.456 Mg m−3 |
Monoclinic, P21 | Melting point = 427–428 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 15.4440 (3) Å | Cell parameters from 41599 reflections |
b = 11.7770 (2) Å | θ = 0.8–35.0° |
c = 27.2069 (5) Å | µ = 1.08 mm−1 |
β = 100.482 (1)° | T = 100 K |
V = 4865.92 (15) Å3 | Block, colourless |
Z = 8 | 0.57 × 0.50 × 0.35 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 41599 independent reflections |
Radiation source: medium-focus sealed tube | 37515 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 8.33 pixels mm-1 | θmax = 35.0°, θmin = 0.8° |
ϕ and ω scans | h = −24→24 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −19→19 |
Tmin = 0.577, Tmax = 0.701 | l = −43→43 |
106321 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.060 | w = 1/[σ2(Fo2) + (0.0187P)2 + 1.5089P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.005 |
41599 reflections | Δρmax = 0.55 e Å−3 |
1187 parameters | Δρmin = −0.78 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 19384 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.386 (9) |
[Sn(C4H9)2(C8H8NO2)2] | V = 4865.92 (15) Å3 |
Mr = 533.22 | Z = 8 |
Monoclinic, P21 | Mo Kα radiation |
a = 15.4440 (3) Å | µ = 1.08 mm−1 |
b = 11.7770 (2) Å | T = 100 K |
c = 27.2069 (5) Å | 0.57 × 0.50 × 0.35 mm |
β = 100.482 (1)° |
Bruker SMART APEXII CCD area-detector diffractometer | 41599 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 37515 reflections with I > 2σ(I) |
Tmin = 0.577, Tmax = 0.701 | Rint = 0.031 |
106321 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.060 | Δρmax = 0.55 e Å−3 |
S = 1.04 | Δρmin = −0.78 e Å−3 |
41599 reflections | Absolute structure: Flack (1983), 19384 Friedel pairs |
1187 parameters | Absolute structure parameter: 0.386 (9) |
1 restraint |
Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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) | |
Sn1A | 0.732628 (10) | 0.544969 (10) | 0.057900 (5) | 0.01736 (3) | |
N1A | 0.61588 (16) | 0.1306 (2) | −0.19094 (9) | 0.0326 (5) | |
H1AB | 0.5711 | 0.0859 | −0.1946 | 0.039* | |
N2A | 1.09439 (16) | 1.0706 (2) | 0.05754 (9) | 0.0293 (5) | |
H2AB | 1.1027 | 1.0876 | 0.0280 | 0.035* | |
O1A | 0.64204 (13) | 0.38967 (17) | 0.01865 (7) | 0.0251 (4) | |
O2A | 0.74456 (11) | 0.47719 (15) | −0.01322 (6) | 0.0215 (3) | |
O3A | 0.83615 (11) | 0.64668 (15) | 0.03912 (6) | 0.0212 (3) | |
O4A | 0.81181 (11) | 0.71292 (14) | 0.11119 (6) | 0.0201 (3) | |
C1A | 0.59769 (18) | 0.2520 (3) | −0.06929 (10) | 0.0303 (6) | |
H1AA | 0.5622 | 0.2443 | −0.0453 | 0.036* | |
C2A | 0.58154 (19) | 0.1864 (3) | −0.11199 (11) | 0.0344 (6) | |
H2AA | 0.5350 | 0.1352 | −0.1164 | 0.041* | |
C3A | 0.63355 (17) | 0.1954 (2) | −0.14870 (9) | 0.0257 (5) | |
C4A | 0.70370 (16) | 0.2726 (2) | −0.14095 (9) | 0.0227 (4) | |
H4AA | 0.7400 | 0.2792 | −0.1646 | 0.027* | |
C5A | 0.71934 (16) | 0.3392 (2) | −0.09807 (8) | 0.0210 (4) | |
H5AA | 0.7656 | 0.3910 | −0.0936 | 0.025* | |
C6A | 0.66712 (16) | 0.3297 (2) | −0.06191 (8) | 0.0205 (4) | |
C7A | 0.68368 (16) | 0.4004 (2) | −0.01667 (9) | 0.0207 (4) | |
C8A | 0.6677 (2) | 0.1329 (3) | −0.22946 (11) | 0.0370 (7) | |
H8AA | 0.6434 | 0.0810 | −0.2555 | 0.055* | |
H8AB | 0.7271 | 0.1109 | −0.2158 | 0.055* | |
H8AC | 0.6675 | 0.2082 | −0.2429 | 0.055* | |
C9A | 0.94627 (17) | 0.8284 (2) | 0.02603 (9) | 0.0203 (4) | |
H9AA | 0.9277 | 0.7804 | −0.0010 | 0.024* | |
C10A | 1.00510 (19) | 0.9144 (3) | 0.02192 (10) | 0.0243 (5) | |
H10A | 1.0247 | 0.9249 | −0.0081 | 0.029* | |
C11A | 1.03589 (17) | 0.9862 (2) | 0.06248 (10) | 0.0218 (5) | |
C12A | 1.00413 (16) | 0.9706 (2) | 0.10701 (9) | 0.0197 (4) | |
H12A | 1.0240 | 1.0171 | 0.1344 | 0.024* | |
C13A | 0.94305 (16) | 0.8858 (2) | 0.11050 (9) | 0.0199 (5) | |
H13A | 0.9210 | 0.8777 | 0.1399 | 0.024* | |
C14A | 0.91424 (15) | 0.8127 (2) | 0.07056 (8) | 0.0163 (4) | |
C15A | 0.85121 (14) | 0.7213 (2) | 0.07503 (8) | 0.0165 (4) | |
C16A | 1.14278 (17) | 1.1324 (2) | 0.09923 (11) | 0.0331 (6) | |
H16A | 1.1844 | 1.1817 | 0.0878 | 0.050* | |
H16B | 1.1735 | 1.0799 | 0.1233 | 0.050* | |
H16C | 1.1027 | 1.1767 | 0.1145 | 0.050* | |
C17A | 0.62339 (17) | 0.6552 (2) | 0.03600 (10) | 0.0242 (5) | |
H17A | 0.6020 | 0.6805 | 0.0651 | 0.029* | 0.663 (4) |
H17B | 0.5768 | 0.6145 | 0.0151 | 0.029* | 0.663 (4) |
H17I | 0.6354 | 0.7238 | 0.0551 | 0.029* | 0.337 (4) |
H17J | 0.5735 | 0.6201 | 0.0464 | 0.029* | 0.337 (4) |
C18A | 0.6501 (2) | 0.7609 (3) | 0.00678 (14) | 0.0213 (8) | 0.663 (4) |
H18A | 0.6966 | 0.8025 | 0.0281 | 0.026* | 0.663 (4) |
H18B | 0.6726 | 0.7352 | −0.0223 | 0.026* | 0.663 (4) |
C19A | 0.5725 (3) | 0.8386 (4) | −0.00959 (14) | 0.0237 (8) | 0.663 (4) |
H19A | 0.5478 | 0.8598 | 0.0194 | 0.028* | 0.663 (4) |
H19B | 0.5275 | 0.7976 | −0.0323 | 0.028* | 0.663 (4) |
C20A | 0.5961 (3) | 0.9464 (4) | −0.03543 (18) | 0.0348 (10) | 0.663 (4) |
H20A | 0.5446 | 0.9928 | −0.0443 | 0.052* | 0.663 (4) |
H20B | 0.6182 | 0.9263 | −0.0650 | 0.052* | 0.663 (4) |
H20C | 0.6404 | 0.9877 | −0.0131 | 0.052* | 0.663 (4) |
C18E | 0.5968 (4) | 0.6871 (6) | −0.0154 (2) | 0.0244 (13) | 0.337 (4) |
H18I | 0.5367 | 0.7149 | −0.0208 | 0.029* | 0.337 (4) |
H18J | 0.5982 | 0.6208 | −0.0364 | 0.029* | 0.337 (4) |
C19E | 0.6567 (5) | 0.7789 (6) | −0.0306 (2) | 0.0278 (14) | 0.337 (4) |
H19I | 0.7176 | 0.7557 | −0.0204 | 0.033* | 0.337 (4) |
H19J | 0.6451 | 0.7862 | −0.0667 | 0.033* | 0.337 (4) |
C20E | 0.6436 (9) | 0.8930 (8) | −0.0076 (4) | 0.063 (3) | 0.337 (4) |
H20M | 0.6816 | 0.9481 | −0.0188 | 0.095* | 0.337 (4) |
H20N | 0.6575 | 0.8872 | 0.0282 | 0.095* | 0.337 (4) |
H20O | 0.5834 | 0.9164 | −0.0176 | 0.095* | 0.337 (4) |
C21A | 0.80764 (17) | 0.4290 (2) | 0.10772 (8) | 0.0240 (4) | |
H21A | 0.8527 | 0.4703 | 0.1302 | 0.029* | |
H21B | 0.7696 | 0.3926 | 0.1277 | 0.029* | |
C22A | 0.85144 (17) | 0.3379 (2) | 0.08068 (9) | 0.0264 (5) | |
H22A | 0.8754 | 0.3733 | 0.0539 | 0.032* | |
H22B | 0.8071 | 0.2837 | 0.0657 | 0.032* | |
C23A | 0.92530 (18) | 0.2743 (2) | 0.11496 (11) | 0.0378 (6) | |
H23A | 0.9552 | 0.2257 | 0.0946 | 0.045* | |
H23B | 0.9678 | 0.3291 | 0.1314 | 0.045* | |
C24A | 0.8941 (2) | 0.2024 (3) | 0.15450 (10) | 0.0459 (8) | |
H24A | 0.9441 | 0.1759 | 0.1780 | 0.069* | |
H24B | 0.8615 | 0.1385 | 0.1389 | 0.069* | |
H24C | 0.8570 | 0.2472 | 0.1717 | 0.069* | |
Sn1B | 0.746804 (9) | 0.524665 (10) | 0.546591 (5) | 0.01482 (3) | |
N1B | 0.60700 (17) | 0.1085 (2) | 0.29977 (9) | 0.0271 (5) | |
H1NC | 0.5652 (19) | 0.062 (3) | 0.2985 (11) | 0.029 (8)* | |
N2B | 1.07919 (15) | 1.0864 (2) | 0.56370 (8) | 0.0217 (4) | |
H1ND | 1.0979 (17) | 1.099 (2) | 0.5372 (10) | 0.019 (7)* | |
O1B | 0.65559 (12) | 0.36903 (17) | 0.50943 (7) | 0.0205 (3) | |
O2B | 0.74945 (11) | 0.46310 (15) | 0.47291 (6) | 0.0187 (3) | |
O3B | 0.84344 (11) | 0.63817 (15) | 0.52590 (6) | 0.0162 (3) | |
O4B | 0.82446 (11) | 0.68014 (14) | 0.60184 (6) | 0.0164 (3) | |
C1B | 0.60340 (15) | 0.2303 (2) | 0.42298 (9) | 0.0195 (4) | |
H1BA | 0.5729 | 0.2208 | 0.4492 | 0.023* | |
C2B | 0.58297 (17) | 0.1630 (2) | 0.38097 (9) | 0.0216 (5) | |
H2BA | 0.5389 | 0.1085 | 0.3791 | 0.026* | |
C3B | 0.62832 (17) | 0.1762 (2) | 0.34081 (9) | 0.0203 (4) | |
C4B | 0.69498 (16) | 0.2586 (2) | 0.34474 (9) | 0.0213 (4) | |
H4BA | 0.7257 | 0.2686 | 0.3187 | 0.026* | |
C5B | 0.71514 (17) | 0.3253 (2) | 0.38746 (9) | 0.0202 (4) | |
H5BA | 0.7598 | 0.3790 | 0.3898 | 0.024* | |
C6B | 0.66974 (16) | 0.3128 (2) | 0.42658 (9) | 0.0175 (4) | |
C7B | 0.69170 (15) | 0.3837 (2) | 0.47170 (8) | 0.0164 (4) | |
C8B | 0.65333 (19) | 0.1111 (3) | 0.25801 (10) | 0.0311 (6) | |
H8BA | 0.6297 | 0.0540 | 0.2342 | 0.047* | |
H8BB | 0.7148 | 0.0967 | 0.2698 | 0.047* | |
H8BC | 0.6462 | 0.1845 | 0.2424 | 0.047* | |
C9B | 0.95150 (17) | 0.8320 (2) | 0.52154 (9) | 0.0171 (4) | |
H9BA | 0.9377 | 0.7879 | 0.4928 | 0.021* | |
C10B | 1.00553 (17) | 0.9246 (2) | 0.52179 (9) | 0.0183 (4) | |
H10B | 1.0281 | 0.9421 | 0.4933 | 0.022* | |
C11B | 1.02739 (15) | 0.9938 (2) | 0.56474 (8) | 0.0149 (4) | |
C12B | 0.99214 (16) | 0.9656 (2) | 0.60724 (9) | 0.0174 (4) | |
H12B | 1.0053 | 1.0102 | 0.6358 | 0.021* | |
C13B | 0.93774 (16) | 0.8717 (2) | 0.60676 (8) | 0.0165 (4) | |
H13B | 0.9149 | 0.8540 | 0.6352 | 0.020* | |
C14B | 0.91669 (15) | 0.8030 (2) | 0.56432 (8) | 0.0146 (4) | |
C15B | 0.85989 (14) | 0.7039 (2) | 0.56509 (8) | 0.0138 (4) | |
C16B | 1.11244 (16) | 1.1539 (2) | 0.60725 (9) | 0.0255 (5) | |
H16D | 1.1502 | 1.2124 | 0.5985 | 0.038* | |
H16E | 1.1452 | 1.1063 | 0.6327 | 0.038* | |
H16F | 1.0641 | 1.1879 | 0.6196 | 0.038* | |
C17B | 0.63445 (15) | 0.6327 (2) | 0.53074 (8) | 0.0162 (4) | |
H17C | 0.5883 | 0.5937 | 0.5080 | 0.019* | |
H17D | 0.6129 | 0.6468 | 0.5615 | 0.019* | |
C18B | 0.65272 (16) | 0.7465 (2) | 0.50767 (9) | 0.0174 (4) | |
H18C | 0.6999 | 0.7850 | 0.5299 | 0.021* | |
H18D | 0.6723 | 0.7329 | 0.4763 | 0.021* | |
C19B | 0.57196 (16) | 0.8227 (2) | 0.49833 (9) | 0.0188 (4) | |
H19C | 0.5536 | 0.8387 | 0.5299 | 0.023* | |
H19D | 0.5241 | 0.7833 | 0.4771 | 0.023* | |
C20B | 0.59014 (18) | 0.9349 (2) | 0.47347 (10) | 0.0235 (5) | |
H20D | 0.5390 | 0.9826 | 0.4701 | 0.035* | |
H20E | 0.6037 | 0.9198 | 0.4410 | 0.035* | |
H20F | 0.6391 | 0.9726 | 0.4937 | 0.035* | |
C21B | 0.83380 (15) | 0.4081 (2) | 0.58966 (9) | 0.0192 (4) | |
H21C | 0.8753 | 0.3824 | 0.5692 | 0.023* | |
H21H | 0.8673 | 0.4494 | 0.6177 | 0.023* | |
C22B | 0.79490 (14) | 0.30345 (17) | 0.61032 (8) | 0.0189 (4) | |
H22C | 0.7595 | 0.2620 | 0.5830 | 0.023* | |
H22D | 0.7567 | 0.3270 | 0.6330 | 0.023* | |
C23B | 0.86670 (15) | 0.2251 (2) | 0.63796 (8) | 0.0222 (4) | |
H23C | 0.9035 | 0.1995 | 0.6148 | 0.027* | |
H23D | 0.9036 | 0.2678 | 0.6643 | 0.027* | |
C24B | 0.82977 (18) | 0.1219 (2) | 0.66084 (9) | 0.0286 (5) | |
H24D | 0.8768 | 0.0820 | 0.6817 | 0.043* | |
H24E | 0.8016 | 0.0725 | 0.6347 | 0.043* | |
H24F | 0.7876 | 0.1463 | 0.6806 | 0.043* | |
Sn1C | 0.748868 (9) | 0.726987 (11) | 0.203718 (5) | 0.01618 (3) | |
N1C | 0.42110 (15) | 0.1625 (2) | 0.19635 (8) | 0.0220 (4) | |
H1NE | 0.399 (2) | 0.166 (3) | 0.2201 (11) | 0.037 (9)* | |
N2C | 0.88531 (16) | 1.1341 (2) | 0.45384 (8) | 0.0268 (5) | |
H1NF | 0.912 (2) | 1.187 (3) | 0.4497 (12) | 0.037 (9)* | |
O1C | 0.65017 (11) | 0.61520 (14) | 0.22304 (6) | 0.0178 (3) | |
O2C | 0.66822 (11) | 0.56898 (14) | 0.14741 (6) | 0.0178 (3) | |
O3C | 0.83795 (12) | 0.88120 (16) | 0.24196 (6) | 0.0207 (3) | |
O4C | 0.74354 (11) | 0.78666 (15) | 0.27766 (6) | 0.0214 (3) | |
C1C | 0.54797 (16) | 0.4209 (2) | 0.23189 (8) | 0.0178 (4) | |
H1CA | 0.5633 | 0.4669 | 0.2599 | 0.021* | |
C2C | 0.49653 (17) | 0.3268 (2) | 0.23438 (9) | 0.0188 (4) | |
H2CA | 0.4782 | 0.3095 | 0.2642 | 0.023* | |
C3C | 0.47103 (15) | 0.2559 (2) | 0.19256 (9) | 0.0175 (4) | |
C4C | 0.50187 (17) | 0.2833 (2) | 0.14830 (8) | 0.0190 (4) | |
H4CA | 0.4866 | 0.2375 | 0.1202 | 0.023* | |
C5C | 0.55423 (16) | 0.3769 (2) | 0.14622 (8) | 0.0166 (4) | |
H5CA | 0.5745 | 0.3930 | 0.1168 | 0.020* | |
C6C | 0.57769 (14) | 0.44852 (19) | 0.18754 (8) | 0.0145 (4) | |
C7C | 0.63436 (13) | 0.54798 (19) | 0.18478 (7) | 0.0146 (4) | |
C8C | 0.38471 (18) | 0.0912 (3) | 0.15440 (10) | 0.0310 (6) | |
H8CA | 0.3455 | 0.0367 | 0.1647 | 0.046* | |
H8CB | 0.4316 | 0.0524 | 0.1426 | 0.046* | |
H8CC | 0.3530 | 0.1374 | 0.1280 | 0.046* | |
C9C | 0.89113 (15) | 1.0156 (2) | 0.32983 (8) | 0.0198 (4) | |
H9CA | 0.9223 | 1.0254 | 0.3039 | 0.024* | |
C10C | 0.91152 (17) | 1.0807 (2) | 0.37248 (9) | 0.0229 (5) | |
H10C | 0.9568 | 1.1338 | 0.3752 | 0.027* | |
C11C | 0.86433 (16) | 1.0677 (2) | 0.41202 (8) | 0.0198 (4) | |
C12C | 0.79663 (16) | 0.9871 (2) | 0.40725 (8) | 0.0203 (4) | |
H12C | 0.7650 | 0.9770 | 0.4329 | 0.024* | |
C13C | 0.77690 (15) | 0.92229 (19) | 0.36388 (8) | 0.0177 (4) | |
H13C | 0.7314 | 0.8696 | 0.3607 | 0.021* | |
C14C | 0.82366 (15) | 0.93458 (19) | 0.32534 (8) | 0.0172 (4) | |
C15C | 0.80229 (15) | 0.86609 (19) | 0.27941 (8) | 0.0179 (4) | |
C16C | 0.83850 (19) | 1.1312 (3) | 0.49476 (9) | 0.0290 (5) | |
H16G | 0.8632 | 1.1863 | 0.5194 | 0.043* | |
H16H | 0.8434 | 1.0569 | 0.5095 | 0.043* | |
H16I | 0.7776 | 1.1485 | 0.4828 | 0.043* | |
C17C | 0.66119 (16) | 0.8437 (2) | 0.16031 (9) | 0.0224 (4) | |
H17E | 0.6273 | 0.8019 | 0.1326 | 0.027* | |
H17H | 0.6201 | 0.8699 | 0.1809 | 0.027* | |
C18C | 0.69914 (16) | 0.94783 (19) | 0.13884 (9) | 0.0238 (4) | |
H18E | 0.7354 | 0.9897 | 0.1657 | 0.029* | |
H18F | 0.7364 | 0.9238 | 0.1157 | 0.029* | |
C19C | 0.62719 (17) | 1.0251 (2) | 0.11196 (9) | 0.0275 (5) | |
H19E | 0.5916 | 1.0513 | 0.1356 | 0.033* | |
H19F | 0.5893 | 0.9817 | 0.0863 | 0.033* | |
C20C | 0.6624 (2) | 1.1279 (2) | 0.08780 (11) | 0.0391 (6) | |
H20G | 0.6141 | 1.1707 | 0.0697 | 0.059* | |
H20H | 0.6996 | 1.1028 | 0.0652 | 0.059* | |
H20I | 0.6959 | 1.1748 | 0.1133 | 0.059* | |
C21C | 0.85920 (15) | 0.6175 (2) | 0.22200 (8) | 0.0183 (4) | |
H21D | 0.8825 | 0.6020 | 0.1919 | 0.022* | |
H21E | 0.9047 | 0.6562 | 0.2453 | 0.022* | |
C22C | 0.83832 (16) | 0.5040 (2) | 0.24524 (9) | 0.0194 (4) | |
H22E | 0.8172 | 0.5189 | 0.2761 | 0.023* | |
H22F | 0.7916 | 0.4660 | 0.2225 | 0.023* | |
C23C | 0.91833 (16) | 0.4259 (2) | 0.25620 (9) | 0.0217 (5) | |
H23G | 0.9370 | 0.4069 | 0.2250 | 0.026* | |
H23H | 0.9663 | 0.4659 | 0.2770 | 0.026* | |
C24C | 0.89963 (18) | 0.3166 (2) | 0.28241 (10) | 0.0253 (5) | |
H24G | 0.9513 | 0.2697 | 0.2877 | 0.038* | |
H24H | 0.8521 | 0.2767 | 0.2620 | 0.038* | |
H24I | 0.8837 | 0.3347 | 0.3140 | 0.038* | |
Sn1D | 0.766802 (9) | 0.699798 (10) | 0.695916 (5) | 0.01476 (3) | |
N1D | 0.89640 (18) | 1.1199 (2) | 0.94227 (9) | 0.0292 (5) | |
H1NG | 0.921 (2) | 1.176 (3) | 0.9394 (12) | 0.036 (9)* | |
N2D | 0.40765 (14) | 0.16751 (19) | 0.68114 (8) | 0.0216 (4) | |
H1NH | 0.3815 (17) | 0.174 (2) | 0.7057 (9) | 0.017 (6)* | |
O1D | 0.76113 (11) | 0.76614 (15) | 0.76796 (6) | 0.0199 (3) | |
O2D | 0.85658 (12) | 0.85973 (17) | 0.73252 (6) | 0.0200 (3) | |
O3D | 0.69154 (10) | 0.53911 (14) | 0.64329 (6) | 0.0169 (3) | |
O4D | 0.66745 (11) | 0.59176 (15) | 0.71712 (6) | 0.0179 (3) | |
C1D | 0.79077 (17) | 0.9059 (2) | 0.85288 (9) | 0.0209 (4) | |
H1DA | 0.7463 | 0.8517 | 0.8500 | 0.025* | |
C2D | 0.80864 (17) | 0.9728 (2) | 0.89539 (9) | 0.0226 (5) | |
H2DA | 0.7760 | 0.9637 | 0.9207 | 0.027* | |
C3D | 0.87579 (17) | 1.0541 (2) | 0.90040 (9) | 0.0226 (5) | |
C4D | 0.92355 (17) | 1.0670 (2) | 0.86141 (9) | 0.0213 (4) | |
H4DA | 0.9686 | 1.1203 | 0.8644 | 0.026* | |
C5D | 0.90425 (16) | 1.0012 (2) | 0.81871 (9) | 0.0195 (4) | |
H5DA | 0.9352 | 1.0121 | 0.7928 | 0.023* | |
C6D | 0.83835 (15) | 0.9183 (2) | 0.81423 (8) | 0.0158 (4) | |
C7D | 0.81927 (15) | 0.8471 (2) | 0.76918 (8) | 0.0169 (4) | |
C8D | 0.8455 (2) | 1.1213 (3) | 0.98171 (10) | 0.0338 (6) | |
H8DA | 0.8700 | 1.1759 | 1.0066 | 0.051* | |
H8DB | 0.8469 | 1.0473 | 0.9967 | 0.051* | |
H8DC | 0.7857 | 1.1414 | 0.9681 | 0.051* | |
C9D | 0.55920 (16) | 0.3671 (2) | 0.63677 (8) | 0.0163 (4) | |
H9DA | 0.5813 | 0.3823 | 0.6078 | 0.020* | |
C10D | 0.49843 (16) | 0.2818 (2) | 0.63668 (8) | 0.0173 (4) | |
H10D | 0.4790 | 0.2414 | 0.6074 | 0.021* | |
C11D | 0.46515 (15) | 0.2546 (2) | 0.67969 (8) | 0.0166 (4) | |
C12D | 0.49460 (17) | 0.3191 (2) | 0.72343 (9) | 0.0196 (4) | |
H12D | 0.4734 | 0.3029 | 0.7525 | 0.024* | |
C13D | 0.55475 (16) | 0.4059 (2) | 0.72311 (8) | 0.0176 (4) | |
H13D | 0.5732 | 0.4479 | 0.7520 | 0.021* | |
C14D | 0.58832 (15) | 0.4315 (2) | 0.67989 (8) | 0.0143 (4) | |
C15D | 0.65201 (14) | 0.5241 (2) | 0.67907 (8) | 0.0153 (4) | |
C16D | 0.35988 (16) | 0.1138 (2) | 0.63622 (10) | 0.0258 (5) | |
H16J | 0.3179 | 0.0610 | 0.6451 | 0.039* | |
H16K | 0.4005 | 0.0742 | 0.6195 | 0.039* | |
H16L | 0.3296 | 0.1707 | 0.6143 | 0.039* | |
C17D | 0.68483 (18) | 0.8130 (2) | 0.64780 (9) | 0.0243 (5) | |
H17F | 0.7176 | 0.8430 | 0.6235 | 0.029* | |
H17G | 0.6350 | 0.7711 | 0.6297 | 0.029* | |
C18D | 0.65087 (14) | 0.91159 (18) | 0.67494 (8) | 0.0184 (4) | |
H18G | 0.6981 | 0.9658 | 0.6847 | 0.022* | |
H18H | 0.6331 | 0.8836 | 0.7051 | 0.022* | |
C19D | 0.57253 (16) | 0.9719 (2) | 0.64257 (9) | 0.0277 (5) | |
H19G | 0.5281 | 0.9160 | 0.6297 | 0.033* | |
H19H | 0.5468 | 1.0244 | 0.6633 | 0.033* | |
C20D | 0.59772 (19) | 1.0368 (2) | 0.59901 (9) | 0.0354 (6) | |
H20J | 0.5453 | 1.0598 | 0.5766 | 0.053* | |
H20K | 0.6323 | 0.9888 | 0.5816 | 0.053* | |
H20L | 0.6314 | 1.1027 | 0.6113 | 0.053* | |
C21D | 0.87957 (15) | 0.5952 (2) | 0.71526 (9) | 0.0173 (4) | |
H21F | 0.9028 | 0.5781 | 0.6853 | 0.021* | |
H21G | 0.9245 | 0.6367 | 0.7378 | 0.021* | |
C22D | 0.86077 (16) | 0.4838 (2) | 0.74013 (9) | 0.0199 (4) | |
H22G | 0.8356 | 0.5007 | 0.7695 | 0.024* | |
H22H | 0.8175 | 0.4409 | 0.7171 | 0.024* | |
C23D | 0.94273 (16) | 0.4110 (2) | 0.75557 (9) | 0.0205 (4) | |
H23E | 0.9683 | 0.3943 | 0.7263 | 0.025* | |
H23F | 0.9859 | 0.4532 | 0.7789 | 0.025* | |
C24D | 0.92202 (19) | 0.3005 (2) | 0.77969 (10) | 0.0266 (5) | |
H24J | 0.9748 | 0.2561 | 0.7881 | 0.040* | |
H24K | 0.8790 | 0.2587 | 0.7567 | 0.040* | |
H24L | 0.8991 | 0.3166 | 0.8095 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1A | 0.01956 (6) | 0.01543 (6) | 0.01708 (6) | −0.00260 (5) | 0.00330 (5) | −0.00235 (5) |
N1A | 0.0289 (11) | 0.0323 (12) | 0.0341 (11) | −0.0020 (9) | −0.0013 (9) | −0.0172 (10) |
N2A | 0.0278 (10) | 0.0237 (10) | 0.0408 (12) | −0.0058 (8) | 0.0177 (9) | −0.0011 (9) |
O1A | 0.0294 (9) | 0.0232 (9) | 0.0237 (8) | −0.0080 (8) | 0.0074 (7) | −0.0035 (7) |
O2A | 0.0250 (8) | 0.0198 (7) | 0.0202 (7) | −0.0088 (6) | 0.0055 (6) | −0.0057 (6) |
O3A | 0.0211 (7) | 0.0194 (7) | 0.0237 (7) | −0.0052 (6) | 0.0057 (6) | −0.0061 (6) |
O4A | 0.0203 (7) | 0.0186 (8) | 0.0222 (7) | −0.0044 (6) | 0.0059 (5) | 0.0006 (6) |
C1A | 0.0287 (12) | 0.0328 (14) | 0.0307 (12) | −0.0101 (11) | 0.0084 (9) | −0.0098 (10) |
C2A | 0.0294 (12) | 0.0350 (14) | 0.0386 (13) | −0.0144 (12) | 0.0061 (10) | −0.0136 (12) |
C3A | 0.0259 (10) | 0.0222 (10) | 0.0263 (10) | 0.0036 (9) | −0.0029 (8) | −0.0092 (9) |
C4A | 0.0236 (10) | 0.0214 (10) | 0.0223 (9) | 0.0001 (8) | 0.0021 (8) | −0.0047 (8) |
C5A | 0.0203 (9) | 0.0196 (9) | 0.0216 (9) | −0.0031 (8) | 0.0001 (8) | −0.0034 (8) |
C6A | 0.0229 (10) | 0.0175 (9) | 0.0196 (9) | −0.0029 (8) | −0.0006 (8) | −0.0026 (8) |
C7A | 0.0228 (10) | 0.0174 (9) | 0.0208 (9) | −0.0030 (8) | 0.0014 (8) | −0.0025 (8) |
C8A | 0.0375 (14) | 0.0373 (15) | 0.0332 (13) | 0.0117 (12) | −0.0015 (11) | −0.0200 (11) |
C9A | 0.0215 (10) | 0.0186 (9) | 0.0223 (10) | 0.0008 (8) | 0.0079 (8) | −0.0021 (8) |
C10A | 0.0267 (12) | 0.0239 (11) | 0.0262 (10) | 0.0001 (9) | 0.0152 (9) | −0.0007 (8) |
C11A | 0.0188 (10) | 0.0155 (9) | 0.0335 (11) | 0.0012 (8) | 0.0107 (8) | 0.0015 (8) |
C12A | 0.0189 (10) | 0.0163 (9) | 0.0234 (9) | −0.0035 (8) | 0.0029 (8) | −0.0011 (8) |
C13A | 0.0190 (10) | 0.0223 (11) | 0.0185 (9) | −0.0016 (9) | 0.0037 (7) | 0.0003 (8) |
C14A | 0.0155 (9) | 0.0144 (9) | 0.0191 (9) | 0.0000 (8) | 0.0037 (7) | −0.0002 (8) |
C15A | 0.0165 (8) | 0.0152 (9) | 0.0170 (8) | 0.0009 (8) | 0.0005 (7) | 0.0006 (8) |
C16A | 0.0216 (11) | 0.0234 (11) | 0.0545 (16) | −0.0070 (9) | 0.0079 (11) | −0.0021 (11) |
C17A | 0.0224 (11) | 0.0202 (10) | 0.0277 (11) | −0.0006 (9) | −0.0015 (8) | −0.0002 (9) |
C18A | 0.0189 (14) | 0.0187 (15) | 0.0257 (16) | 0.0017 (12) | 0.0025 (12) | 0.0070 (12) |
C19A | 0.0214 (15) | 0.0255 (17) | 0.0225 (15) | 0.0005 (13) | −0.0007 (12) | 0.0013 (13) |
C20A | 0.034 (2) | 0.0236 (17) | 0.043 (2) | −0.0023 (16) | −0.0024 (17) | 0.0124 (16) |
C18E | 0.025 (3) | 0.029 (3) | 0.017 (2) | −0.005 (2) | −0.001 (2) | −0.004 (2) |
C19E | 0.031 (3) | 0.032 (3) | 0.021 (3) | 0.004 (3) | 0.006 (2) | 0.000 (2) |
C20E | 0.124 (10) | 0.034 (4) | 0.045 (5) | −0.011 (5) | 0.051 (6) | −0.007 (4) |
C21A | 0.0314 (12) | 0.0193 (10) | 0.0196 (9) | 0.0054 (9) | 0.0001 (8) | −0.0052 (8) |
C22A | 0.0301 (12) | 0.0229 (10) | 0.0280 (11) | 0.0026 (9) | 0.0097 (9) | −0.0026 (9) |
C23A | 0.0272 (12) | 0.0313 (13) | 0.0515 (16) | 0.0096 (10) | −0.0017 (11) | −0.0131 (12) |
C24A | 0.066 (2) | 0.0389 (16) | 0.0269 (11) | 0.0265 (15) | −0.0066 (12) | −0.0031 (13) |
Sn1B | 0.01493 (6) | 0.01194 (6) | 0.01787 (6) | −0.00171 (5) | 0.00371 (5) | −0.00083 (5) |
N1B | 0.0307 (11) | 0.0225 (10) | 0.0264 (10) | −0.0025 (9) | 0.0007 (9) | −0.0085 (9) |
N2B | 0.0256 (9) | 0.0184 (8) | 0.0234 (8) | −0.0076 (7) | 0.0109 (7) | −0.0009 (7) |
O1B | 0.0208 (8) | 0.0171 (8) | 0.0238 (8) | −0.0029 (6) | 0.0046 (6) | −0.0023 (7) |
O2B | 0.0223 (8) | 0.0139 (6) | 0.0205 (7) | −0.0052 (6) | 0.0055 (6) | −0.0051 (6) |
O3B | 0.0169 (7) | 0.0139 (6) | 0.0187 (7) | −0.0027 (6) | 0.0059 (5) | −0.0030 (5) |
O4B | 0.0163 (7) | 0.0145 (7) | 0.0192 (7) | −0.0008 (6) | 0.0050 (5) | 0.0024 (5) |
C1B | 0.0178 (9) | 0.0159 (9) | 0.0242 (9) | −0.0016 (9) | 0.0026 (7) | −0.0009 (9) |
C2B | 0.0211 (10) | 0.0158 (9) | 0.0263 (10) | −0.0035 (9) | −0.0002 (8) | −0.0016 (9) |
C3B | 0.0208 (10) | 0.0143 (9) | 0.0232 (10) | 0.0022 (8) | −0.0029 (8) | −0.0019 (8) |
C4B | 0.0206 (10) | 0.0204 (10) | 0.0230 (10) | 0.0009 (8) | 0.0037 (8) | −0.0019 (8) |
C5B | 0.0206 (10) | 0.0154 (9) | 0.0245 (10) | −0.0007 (8) | 0.0038 (8) | 0.0007 (8) |
C6B | 0.0169 (9) | 0.0115 (8) | 0.0229 (10) | 0.0002 (7) | 0.0010 (8) | −0.0016 (8) |
C7B | 0.0163 (9) | 0.0128 (8) | 0.0198 (9) | 0.0009 (7) | 0.0028 (7) | 0.0002 (7) |
C8B | 0.0326 (13) | 0.0311 (13) | 0.0265 (11) | 0.0091 (11) | −0.0026 (10) | −0.0104 (11) |
C9B | 0.0204 (10) | 0.0162 (9) | 0.0159 (8) | −0.0015 (8) | 0.0062 (8) | −0.0010 (8) |
C10B | 0.0216 (11) | 0.0161 (9) | 0.0197 (9) | −0.0021 (8) | 0.0103 (8) | 0.0009 (8) |
C11B | 0.0164 (9) | 0.0105 (8) | 0.0183 (8) | −0.0009 (7) | 0.0042 (7) | 0.0006 (7) |
C12B | 0.0194 (10) | 0.0169 (9) | 0.0164 (8) | −0.0040 (8) | 0.0048 (7) | −0.0006 (7) |
C13B | 0.0175 (9) | 0.0166 (9) | 0.0163 (8) | −0.0037 (8) | 0.0051 (7) | −0.0009 (8) |
C14B | 0.0140 (9) | 0.0123 (8) | 0.0181 (9) | 0.0000 (7) | 0.0040 (7) | 0.0010 (7) |
C15B | 0.0112 (7) | 0.0119 (8) | 0.0184 (8) | 0.0022 (7) | 0.0029 (6) | 0.0027 (7) |
C16B | 0.0223 (10) | 0.0234 (10) | 0.0311 (11) | −0.0095 (9) | 0.0058 (9) | −0.0054 (9) |
C17B | 0.0145 (9) | 0.0163 (9) | 0.0177 (9) | −0.0007 (7) | 0.0024 (7) | −0.0015 (7) |
C18B | 0.0171 (9) | 0.0181 (10) | 0.0174 (9) | −0.0006 (8) | 0.0043 (7) | 0.0019 (8) |
C19B | 0.0179 (9) | 0.0187 (9) | 0.0201 (9) | 0.0019 (8) | 0.0038 (7) | 0.0033 (8) |
C20B | 0.0238 (11) | 0.0212 (10) | 0.0261 (10) | 0.0028 (9) | 0.0061 (8) | 0.0046 (9) |
C21B | 0.0171 (9) | 0.0161 (9) | 0.0247 (10) | −0.0005 (8) | 0.0041 (8) | 0.0012 (8) |
C22B | 0.0190 (9) | 0.0153 (8) | 0.0231 (9) | 0.0010 (7) | 0.0060 (7) | 0.0004 (7) |
C23B | 0.0245 (10) | 0.0175 (9) | 0.0247 (9) | 0.0015 (9) | 0.0045 (8) | 0.0022 (8) |
C24B | 0.0372 (13) | 0.0206 (10) | 0.0293 (11) | 0.0019 (9) | 0.0090 (9) | 0.0061 (9) |
Sn1C | 0.01712 (6) | 0.01329 (6) | 0.01889 (5) | −0.00262 (5) | 0.00528 (5) | −0.00213 (5) |
N1C | 0.0252 (9) | 0.0181 (8) | 0.0246 (9) | −0.0066 (7) | 0.0094 (7) | 0.0007 (7) |
N2C | 0.0300 (11) | 0.0250 (10) | 0.0227 (9) | −0.0033 (9) | −0.0023 (8) | −0.0075 (8) |
O1C | 0.0193 (7) | 0.0169 (7) | 0.0183 (6) | −0.0036 (6) | 0.0060 (5) | −0.0042 (5) |
O2C | 0.0189 (7) | 0.0173 (7) | 0.0183 (7) | −0.0036 (6) | 0.0064 (5) | 0.0001 (6) |
O3C | 0.0211 (8) | 0.0206 (8) | 0.0209 (8) | −0.0048 (7) | 0.0053 (6) | −0.0034 (7) |
O4C | 0.0219 (8) | 0.0202 (7) | 0.0229 (7) | −0.0083 (6) | 0.0059 (6) | −0.0060 (6) |
C1C | 0.0218 (10) | 0.0144 (9) | 0.0189 (9) | 0.0016 (8) | 0.0079 (8) | −0.0017 (7) |
C2C | 0.0232 (11) | 0.0168 (9) | 0.0190 (9) | −0.0014 (8) | 0.0105 (8) | −0.0007 (7) |
C3C | 0.0143 (9) | 0.0148 (9) | 0.0243 (9) | −0.0005 (7) | 0.0058 (7) | 0.0033 (8) |
C4C | 0.0219 (10) | 0.0177 (9) | 0.0174 (9) | −0.0033 (8) | 0.0035 (7) | −0.0026 (8) |
C5C | 0.0195 (9) | 0.0156 (9) | 0.0150 (8) | −0.0040 (8) | 0.0040 (7) | 0.0022 (7) |
C6C | 0.0131 (8) | 0.0135 (8) | 0.0169 (8) | 0.0001 (7) | 0.0027 (7) | −0.0002 (7) |
C7C | 0.0137 (8) | 0.0125 (9) | 0.0178 (8) | −0.0004 (7) | 0.0034 (6) | −0.0012 (7) |
C8C | 0.0279 (12) | 0.0300 (12) | 0.0334 (12) | −0.0146 (10) | 0.0013 (10) | 0.0034 (10) |
C9C | 0.0186 (9) | 0.0183 (10) | 0.0224 (9) | −0.0046 (8) | 0.0033 (7) | −0.0017 (8) |
C10C | 0.0226 (11) | 0.0199 (10) | 0.0244 (10) | −0.0057 (9) | −0.0003 (8) | −0.0044 (9) |
C11C | 0.0209 (10) | 0.0164 (9) | 0.0199 (9) | 0.0016 (8) | −0.0024 (8) | −0.0033 (8) |
C12C | 0.0228 (10) | 0.0183 (9) | 0.0195 (9) | 0.0014 (8) | 0.0032 (8) | −0.0034 (8) |
C13C | 0.0166 (9) | 0.0133 (8) | 0.0231 (9) | −0.0014 (7) | 0.0036 (7) | −0.0016 (7) |
C14C | 0.0182 (9) | 0.0131 (8) | 0.0194 (9) | −0.0014 (7) | 0.0006 (7) | −0.0016 (7) |
C15C | 0.0190 (9) | 0.0137 (8) | 0.0208 (9) | −0.0016 (8) | 0.0031 (7) | −0.0032 (7) |
C16C | 0.0327 (13) | 0.0298 (12) | 0.0221 (10) | 0.0061 (11) | −0.0012 (9) | −0.0077 (10) |
C17C | 0.0233 (10) | 0.0148 (9) | 0.0281 (11) | 0.0000 (8) | 0.0019 (8) | 0.0002 (8) |
C18C | 0.0275 (11) | 0.0177 (9) | 0.0275 (10) | −0.0006 (8) | 0.0084 (8) | 0.0007 (8) |
C19C | 0.0336 (12) | 0.0222 (10) | 0.0253 (10) | 0.0040 (10) | 0.0016 (9) | 0.0020 (9) |
C20C | 0.0494 (17) | 0.0286 (13) | 0.0408 (14) | 0.0065 (12) | 0.0121 (12) | 0.0118 (11) |
C21C | 0.0189 (10) | 0.0175 (9) | 0.0194 (9) | −0.0005 (8) | 0.0059 (7) | −0.0009 (8) |
C22C | 0.0189 (10) | 0.0194 (10) | 0.0208 (9) | −0.0020 (8) | 0.0056 (8) | 0.0000 (8) |
C23C | 0.0193 (10) | 0.0242 (11) | 0.0218 (9) | −0.0026 (9) | 0.0042 (8) | 0.0016 (8) |
C24C | 0.0260 (12) | 0.0237 (11) | 0.0256 (10) | 0.0014 (9) | 0.0031 (9) | 0.0056 (9) |
Sn1D | 0.01570 (6) | 0.01273 (6) | 0.01571 (5) | −0.00063 (5) | 0.00253 (5) | −0.00088 (5) |
N1D | 0.0342 (12) | 0.0244 (10) | 0.0276 (10) | −0.0052 (9) | 0.0020 (9) | −0.0126 (9) |
N2D | 0.0231 (9) | 0.0174 (8) | 0.0272 (9) | −0.0052 (7) | 0.0121 (7) | −0.0018 (7) |
O1D | 0.0227 (8) | 0.0168 (7) | 0.0200 (7) | −0.0043 (6) | 0.0034 (6) | −0.0048 (6) |
O2D | 0.0234 (8) | 0.0183 (8) | 0.0186 (7) | −0.0013 (7) | 0.0047 (6) | −0.0020 (6) |
O3D | 0.0178 (6) | 0.0150 (7) | 0.0184 (6) | −0.0019 (6) | 0.0047 (5) | 0.0000 (5) |
O4D | 0.0179 (7) | 0.0158 (7) | 0.0202 (7) | −0.0022 (6) | 0.0042 (6) | −0.0041 (6) |
C1D | 0.0212 (10) | 0.0202 (10) | 0.0200 (9) | −0.0033 (8) | 0.0004 (7) | −0.0003 (8) |
C2D | 0.0252 (11) | 0.0236 (11) | 0.0192 (9) | −0.0006 (9) | 0.0050 (8) | −0.0037 (8) |
C3D | 0.0244 (10) | 0.0188 (10) | 0.0222 (9) | 0.0028 (9) | −0.0019 (8) | −0.0058 (9) |
C4D | 0.0214 (10) | 0.0157 (9) | 0.0249 (10) | −0.0036 (8) | −0.0003 (8) | −0.0057 (8) |
C5D | 0.0189 (9) | 0.0167 (9) | 0.0224 (9) | −0.0015 (8) | 0.0028 (8) | −0.0019 (8) |
C6D | 0.0161 (9) | 0.0141 (9) | 0.0163 (8) | −0.0007 (7) | 0.0006 (7) | −0.0023 (7) |
C7D | 0.0169 (9) | 0.0146 (9) | 0.0182 (9) | 0.0011 (8) | 0.0004 (7) | −0.0011 (8) |
C8D | 0.0394 (15) | 0.0362 (14) | 0.0236 (11) | 0.0075 (12) | 0.0000 (10) | −0.0118 (11) |
C9D | 0.0181 (9) | 0.0157 (9) | 0.0155 (8) | 0.0000 (8) | 0.0040 (7) | 0.0001 (8) |
C10D | 0.0198 (9) | 0.0157 (9) | 0.0171 (8) | −0.0015 (8) | 0.0047 (7) | −0.0003 (7) |
C11D | 0.0162 (9) | 0.0125 (8) | 0.0214 (9) | 0.0015 (7) | 0.0046 (7) | −0.0001 (7) |
C12D | 0.0241 (11) | 0.0188 (10) | 0.0180 (9) | 0.0010 (9) | 0.0094 (8) | 0.0018 (8) |
C13D | 0.0194 (10) | 0.0167 (9) | 0.0165 (9) | 0.0014 (8) | 0.0031 (7) | −0.0014 (8) |
C14D | 0.0134 (9) | 0.0137 (9) | 0.0157 (8) | 0.0027 (7) | 0.0023 (7) | 0.0015 (7) |
C15D | 0.0139 (8) | 0.0125 (8) | 0.0191 (8) | 0.0016 (8) | 0.0017 (7) | −0.0004 (8) |
C16D | 0.0203 (10) | 0.0207 (10) | 0.0367 (12) | −0.0052 (8) | 0.0062 (9) | −0.0022 (9) |
C17D | 0.0342 (13) | 0.0194 (10) | 0.0174 (9) | 0.0078 (9) | −0.0002 (8) | −0.0017 (8) |
C18D | 0.0178 (9) | 0.0170 (8) | 0.0214 (9) | 0.0039 (7) | 0.0057 (7) | −0.0043 (7) |
C19D | 0.0235 (10) | 0.0272 (11) | 0.0299 (11) | 0.0095 (9) | −0.0021 (8) | −0.0087 (9) |
C20D | 0.0462 (15) | 0.0286 (13) | 0.0277 (11) | 0.0168 (12) | −0.0035 (10) | −0.0031 (11) |
C21D | 0.0164 (9) | 0.0182 (10) | 0.0178 (9) | 0.0002 (8) | 0.0045 (7) | 0.0010 (8) |
C22D | 0.0192 (10) | 0.0192 (10) | 0.0221 (10) | −0.0021 (8) | 0.0055 (8) | 0.0033 (8) |
C23D | 0.0190 (10) | 0.0195 (9) | 0.0229 (9) | 0.0032 (8) | 0.0033 (7) | 0.0008 (8) |
C24D | 0.0297 (12) | 0.0216 (10) | 0.0280 (11) | 0.0019 (9) | 0.0043 (9) | 0.0043 (9) |
Sn1A—C21A | 2.115 (2) | C23B—C24B | 1.522 (3) |
Sn1A—C17A | 2.126 (3) | C23B—H23C | 0.9700 |
Sn1A—O2A | 2.1320 (16) | C23B—H23D | 0.9700 |
Sn1A—O3A | 2.1329 (17) | C24B—H24D | 0.9600 |
Sn1A—O1A | 2.4288 (19) | C24B—H24E | 0.9600 |
N1A—C3A | 1.366 (3) | C24B—H24F | 0.9600 |
N1A—C8A | 1.430 (4) | Sn1C—C21C | 2.123 (2) |
N1A—H1AB | 0.8600 | Sn1C—C17C | 2.129 (2) |
N2A—C11A | 1.366 (3) | Sn1C—O4C | 2.1467 (16) |
N2A—C16A | 1.437 (4) | Sn1C—O1C | 2.1505 (16) |
N2A—H2AB | 0.8600 | Sn1C—O3C | 2.3986 (18) |
O1A—C7A | 1.256 (3) | N1C—C3C | 1.358 (3) |
O2A—C7A | 1.296 (3) | N1C—C8C | 1.446 (3) |
O3A—C15A | 1.303 (3) | N1C—H1NE | 0.79 (3) |
O4A—C15A | 1.251 (3) | N2C—C11C | 1.370 (3) |
C1A—C2A | 1.379 (4) | N2C—C16C | 1.434 (4) |
C1A—C6A | 1.397 (4) | N2C—H1NF | 0.77 (3) |
C1A—H1AA | 0.9300 | O1C—C7C | 1.295 (3) |
C2A—C3A | 1.395 (4) | O2C—C7C | 1.250 (2) |
C2A—H2AA | 0.9300 | O3C—C15C | 1.256 (3) |
C3A—C4A | 1.400 (4) | O4C—C15C | 1.298 (3) |
C4A—C5A | 1.391 (3) | C1C—C2C | 1.372 (3) |
C4A—H4AA | 0.9300 | C1C—C6C | 1.405 (3) |
C5A—C6A | 1.386 (3) | C1C—H1CA | 0.9300 |
C5A—H5AA | 0.9300 | C2C—C3C | 1.408 (3) |
C6A—C7A | 1.469 (3) | C2C—H2CA | 0.9300 |
C8A—H8AA | 0.9600 | C3C—C4C | 1.411 (3) |
C8A—H8AB | 0.9600 | C4C—C5C | 1.375 (3) |
C8A—H8AC | 0.9600 | C4C—H4CA | 0.9300 |
C9A—C10A | 1.378 (4) | C5C—C6C | 1.399 (3) |
C9A—C14A | 1.402 (3) | C5C—H5CA | 0.9300 |
C9A—H9AA | 0.9300 | C6C—C7C | 1.472 (3) |
C10A—C11A | 1.403 (4) | C8C—H8CA | 0.9600 |
C10A—H10A | 0.9300 | C8C—H8CB | 0.9600 |
C11A—C12A | 1.400 (3) | C8C—H8CC | 0.9600 |
C12A—C13A | 1.388 (4) | C9C—C10C | 1.379 (3) |
C12A—H12A | 0.9300 | C9C—C14C | 1.401 (3) |
C13A—C14A | 1.394 (3) | C9C—H9CA | 0.9300 |
C13A—H13A | 0.9300 | C10C—C11C | 1.413 (3) |
C14A—C15A | 1.472 (3) | C10C—H10C | 0.9300 |
C16A—H16A | 0.9600 | C11C—C12C | 1.401 (3) |
C16A—H16B | 0.9600 | C12C—C13C | 1.392 (3) |
C16A—H16C | 0.9600 | C12C—H12C | 0.9300 |
C17A—C18E | 1.435 (6) | C13C—C14C | 1.385 (3) |
C17A—C18A | 1.572 (5) | C13C—H13C | 0.9300 |
C17A—H17A | 0.9601 | C14C—C15C | 1.473 (3) |
C17A—H17B | 0.9600 | C16C—H16G | 0.9600 |
C17A—H17I | 0.9599 | C16C—H16H | 0.9600 |
C17A—H17J | 0.9599 | C16C—H16I | 0.9600 |
C18A—C19A | 1.510 (5) | C17C—C18C | 1.521 (3) |
C18A—H18A | 0.9700 | C17C—H17E | 0.9700 |
C18A—H18B | 0.9700 | C17C—H17H | 0.9700 |
C19A—C20A | 1.527 (6) | C18C—C19C | 1.517 (3) |
C19A—H19A | 0.9700 | C18C—H18E | 0.9700 |
C19A—H19B | 0.9700 | C18C—H18F | 0.9700 |
C20A—H20A | 0.9600 | C19C—C20C | 1.524 (4) |
C20A—H20B | 0.9600 | C19C—H19E | 0.9700 |
C20A—H20C | 0.9600 | C19C—H19F | 0.9700 |
C18E—C19E | 1.528 (9) | C20C—H20G | 0.9600 |
C18E—H17B | 1.2682 | C20C—H20H | 0.9600 |
C18E—H18I | 0.9700 | C20C—H20I | 0.9600 |
C18E—H18J | 0.9700 | C21C—C22C | 1.537 (3) |
C19E—C20E | 1.512 (11) | C21C—H21D | 0.9700 |
C19E—H19I | 0.9700 | C21C—H21E | 0.9700 |
C19E—H19J | 0.9700 | C22C—C23C | 1.526 (4) |
C20E—H20M | 0.9600 | C22C—H22E | 0.9700 |
C20E—H20N | 0.9600 | C22C—H22F | 0.9700 |
C20E—H20O | 0.9600 | C23C—C24C | 1.524 (4) |
C21A—C22A | 1.526 (4) | C23C—H23G | 0.9700 |
C21A—H21A | 0.9700 | C23C—H23H | 0.9700 |
C21A—H21B | 0.9700 | C24C—H24G | 0.9600 |
C22A—C23A | 1.532 (4) | C24C—H24H | 0.9600 |
C22A—H22A | 0.9700 | C24C—H24I | 0.9600 |
C22A—H22B | 0.9700 | Sn1D—C17D | 2.119 (2) |
C23A—C24A | 1.515 (4) | Sn1D—C21D | 2.120 (2) |
C23A—H23A | 0.9700 | Sn1D—O1D | 2.1266 (16) |
C23A—H23B | 0.9700 | Sn1D—O4D | 2.1514 (17) |
C24A—H24A | 0.9600 | Sn1D—O2D | 2.4412 (19) |
C24A—H24B | 0.9600 | Sn1D—O3D | 2.5252 (17) |
C24A—H24C | 0.9600 | N1D—C3D | 1.366 (3) |
Sn1B—C21B | 2.119 (2) | N1D—C8D | 1.441 (4) |
Sn1B—C17B | 2.131 (2) | N1D—H1NG | 0.77 (4) |
Sn1B—O2B | 2.1390 (16) | N2D—C11D | 1.362 (3) |
Sn1B—O3B | 2.1534 (16) | N2D—C16D | 1.453 (3) |
Sn1B—O1B | 2.4182 (19) | N2D—H1NH | 0.84 (3) |
Sn1B—O4B | 2.5288 (17) | O1D—C7D | 1.306 (3) |
N1B—C3B | 1.362 (3) | O2D—C7D | 1.248 (3) |
N1B—C8B | 1.449 (4) | O3D—C15D | 1.252 (3) |
N1B—H1NC | 0.84 (3) | O4D—C15D | 1.294 (3) |
N2B—C11B | 1.356 (3) | C1D—C2D | 1.386 (3) |
N2B—C16B | 1.441 (3) | C1D—C6D | 1.396 (3) |
N2B—H1ND | 0.84 (3) | C1D—H1DA | 0.9300 |
O1B—C7B | 1.266 (3) | C2D—C3D | 1.400 (4) |
O2B—C7B | 1.288 (3) | C2D—H2DA | 0.9300 |
O3B—C15B | 1.305 (3) | C3D—C4D | 1.406 (4) |
O4B—C15B | 1.256 (2) | C4D—C5D | 1.383 (3) |
C1B—C2B | 1.379 (3) | C4D—H4DA | 0.9300 |
C1B—C6B | 1.403 (3) | C5D—C6D | 1.400 (3) |
C1B—H1BA | 0.9300 | C5D—H5DA | 0.9300 |
C2B—C3B | 1.410 (4) | C6D—C7D | 1.470 (3) |
C2B—H2BA | 0.9300 | C8D—H8DA | 0.9600 |
C3B—C4B | 1.405 (4) | C8D—H8DB | 0.9600 |
C4B—C5B | 1.390 (3) | C8D—H8DC | 0.9600 |
C4B—H4BA | 0.9300 | C9D—C10D | 1.375 (3) |
C5B—C6B | 1.385 (3) | C9D—C14D | 1.400 (3) |
C5B—H5BA | 0.9300 | C9D—H9DA | 0.9300 |
C6B—C7B | 1.473 (3) | C10D—C11D | 1.398 (3) |
C8B—H8BA | 0.9600 | C10D—H10D | 0.9300 |
C8B—H8BB | 0.9600 | C11D—C12D | 1.415 (3) |
C8B—H8BC | 0.9600 | C12D—C13D | 1.382 (4) |
C9B—C10B | 1.372 (3) | C12D—H12D | 0.9300 |
C9B—C14B | 1.410 (3) | C13D—C14D | 1.401 (3) |
C9B—H9BA | 0.9300 | C13D—H13D | 0.9300 |
C10B—C11B | 1.414 (3) | C14D—C15D | 1.472 (3) |
C10B—H10B | 0.9300 | C16D—H16J | 0.9600 |
C11B—C12B | 1.404 (3) | C16D—H16K | 0.9600 |
C12B—C13B | 1.388 (3) | C16D—H16L | 0.9600 |
C12B—H12B | 0.9300 | C17D—C18D | 1.520 (3) |
C13B—C14B | 1.399 (3) | C17D—H17F | 0.9700 |
C13B—H13B | 0.9300 | C17D—H17G | 0.9700 |
C14B—C15B | 1.462 (3) | C18D—C19D | 1.535 (3) |
C16B—H16D | 0.9600 | C18D—H18G | 0.9700 |
C16B—H16E | 0.9600 | C18D—H18H | 0.9700 |
C16B—H16F | 0.9600 | C19D—C20D | 1.519 (4) |
C17B—C18B | 1.528 (4) | C19D—H19G | 0.9700 |
C17B—H17C | 0.9700 | C19D—H19H | 0.9700 |
C17B—H17D | 0.9700 | C20D—H20J | 0.9600 |
C18B—C19B | 1.520 (4) | C20D—H20K | 0.9600 |
C18B—H18C | 0.9700 | C20D—H20L | 0.9600 |
C18B—H18D | 0.9700 | C21D—C22D | 1.528 (3) |
C19B—C20B | 1.533 (4) | C21D—H21F | 0.9700 |
C19B—H19C | 0.9700 | C21D—H21G | 0.9700 |
C19B—H19D | 0.9700 | C22D—C23D | 1.523 (3) |
C20B—H20D | 0.9600 | C22D—H22G | 0.9700 |
C20B—H20E | 0.9600 | C22D—H22H | 0.9700 |
C20B—H20F | 0.9600 | C23D—C24D | 1.518 (4) |
C21B—C22B | 1.523 (3) | C23D—H23E | 0.9700 |
C21B—H21C | 0.9700 | C23D—H23F | 0.9700 |
C21B—H21H | 0.9700 | C24D—H24J | 0.9600 |
C22B—C23B | 1.531 (3) | C24D—H24K | 0.9600 |
C22B—H22C | 0.9700 | C24D—H24L | 0.9600 |
C22B—H22D | 0.9700 | ||
C21A—Sn1A—C17A | 152.63 (10) | C23B—C22B—H22C | 109.3 |
C21A—Sn1A—O2A | 102.24 (8) | C21B—C22B—H22D | 109.3 |
C17A—Sn1A—O2A | 99.76 (9) | C23B—C22B—H22D | 109.3 |
C21A—Sn1A—O3A | 99.74 (9) | H22C—C22B—H22D | 107.9 |
C17A—Sn1A—O3A | 100.45 (9) | C24B—C23B—C22B | 112.96 (19) |
O2A—Sn1A—O3A | 78.49 (6) | C24B—C23B—H23C | 109.0 |
C21A—Sn1A—O1A | 90.00 (8) | C22B—C23B—H23C | 109.0 |
C17A—Sn1A—O1A | 88.41 (9) | C24B—C23B—H23D | 109.0 |
O2A—Sn1A—O1A | 57.11 (6) | C22B—C23B—H23D | 109.0 |
O3A—Sn1A—O1A | 135.60 (6) | H23C—C23B—H23D | 107.8 |
C21A—Sn1A—C7A | 97.02 (8) | C23B—C24B—H24D | 109.5 |
C17A—Sn1A—C7A | 94.38 (9) | C23B—C24B—H24E | 109.5 |
O2A—Sn1A—C7A | 28.92 (7) | H24D—C24B—H24E | 109.5 |
O3A—Sn1A—C7A | 107.41 (7) | C23B—C24B—H24F | 109.5 |
O1A—Sn1A—C7A | 28.19 (7) | H24D—C24B—H24F | 109.5 |
C3A—N1A—C8A | 123.6 (3) | H24E—C24B—H24F | 109.5 |
C3A—N1A—H1AB | 118.2 | C21C—Sn1C—C17C | 157.58 (9) |
C8A—N1A—H1AB | 118.2 | C21C—Sn1C—O4C | 98.36 (8) |
C11A—N2A—C16A | 123.3 (2) | C17C—Sn1C—O4C | 100.35 (9) |
C11A—N2A—H2AB | 118.4 | C21C—Sn1C—O1C | 98.34 (8) |
C16A—N2A—H2AB | 118.4 | C17C—Sn1C—O1C | 97.07 (8) |
C7A—O1A—Sn1A | 85.80 (14) | O4C—Sn1C—O1C | 79.72 (6) |
C7A—O2A—Sn1A | 98.38 (14) | C21C—Sn1C—O3C | 89.19 (8) |
C15A—O3A—Sn1A | 103.79 (13) | C17C—Sn1C—O3C | 90.50 (8) |
C2A—C1A—C6A | 120.3 (2) | O4C—Sn1C—O3C | 57.47 (6) |
C2A—C1A—H1AA | 119.9 | O1C—Sn1C—O3C | 137.19 (6) |
C6A—C1A—H1AA | 119.9 | C21C—Sn1C—C15C | 94.05 (8) |
C1A—C2A—C3A | 121.4 (3) | C17C—Sn1C—C15C | 96.26 (8) |
C1A—C2A—H2AA | 119.3 | O4C—Sn1C—C15C | 29.16 (6) |
C3A—C2A—H2AA | 119.3 | O1C—Sn1C—C15C | 108.88 (6) |
N1A—C3A—C2A | 120.5 (3) | O3C—Sn1C—C15C | 28.32 (6) |
N1A—C3A—C4A | 121.3 (2) | C3C—N1C—C8C | 123.7 (2) |
C2A—C3A—C4A | 118.2 (2) | C3C—N1C—H1NE | 111 (2) |
C5A—C4A—C3A | 120.3 (2) | C8C—N1C—H1NE | 121 (2) |
C5A—C4A—H4AA | 119.9 | C11C—N2C—C16C | 123.7 (2) |
C3A—C4A—H4AA | 119.9 | C11C—N2C—H1NF | 113 (2) |
C6A—C5A—C4A | 121.0 (2) | C16C—N2C—H1NF | 120 (2) |
C6A—C5A—H5AA | 119.5 | C7C—O1C—Sn1C | 102.48 (12) |
C4A—C5A—H5AA | 119.5 | C15C—O3C—Sn1C | 86.73 (13) |
C5A—C6A—C1A | 118.8 (2) | C15C—O4C—Sn1C | 97.16 (13) |
C5A—C6A—C7A | 120.9 (2) | C2C—C1C—C6C | 120.8 (2) |
C1A—C6A—C7A | 120.3 (2) | C2C—C1C—H1CA | 119.6 |
O1A—C7A—O2A | 118.7 (2) | C6C—C1C—H1CA | 119.6 |
O1A—C7A—C6A | 123.3 (2) | C1C—C2C—C3C | 121.2 (2) |
O2A—C7A—C6A | 118.0 (2) | C1C—C2C—H2CA | 119.4 |
O1A—C7A—Sn1A | 66.00 (13) | C3C—C2C—H2CA | 119.4 |
O2A—C7A—Sn1A | 52.70 (11) | N1C—C3C—C2C | 119.9 (2) |
C6A—C7A—Sn1A | 170.69 (17) | N1C—C3C—C4C | 122.3 (2) |
N1A—C8A—H8AA | 109.5 | C2C—C3C—C4C | 117.8 (2) |
N1A—C8A—H8AB | 109.5 | C5C—C4C—C3C | 120.7 (2) |
H8AA—C8A—H8AB | 109.5 | C5C—C4C—H4CA | 119.6 |
N1A—C8A—H8AC | 109.5 | C3C—C4C—H4CA | 119.6 |
H8AA—C8A—H8AC | 109.5 | C4C—C5C—C6C | 121.2 (2) |
H8AB—C8A—H8AC | 109.5 | C4C—C5C—H5CA | 119.4 |
C10A—C9A—C14A | 120.5 (2) | C6C—C5C—H5CA | 119.4 |
C10A—C9A—H9AA | 119.7 | C5C—C6C—C1C | 118.2 (2) |
C14A—C9A—H9AA | 119.7 | C5C—C6C—C7C | 120.53 (19) |
C9A—C10A—C11A | 120.9 (2) | C1C—C6C—C7C | 121.2 (2) |
C9A—C10A—H10A | 119.6 | O2C—C7C—O1C | 119.2 (2) |
C11A—C10A—H10A | 119.6 | O2C—C7C—C6C | 122.65 (19) |
N2A—C11A—C12A | 121.6 (2) | O1C—C7C—C6C | 118.18 (18) |
N2A—C11A—C10A | 119.8 (2) | N1C—C8C—H8CA | 109.5 |
C12A—C11A—C10A | 118.6 (2) | N1C—C8C—H8CB | 109.5 |
C13A—C12A—C11A | 120.2 (2) | H8CA—C8C—H8CB | 109.5 |
C13A—C12A—H12A | 119.9 | N1C—C8C—H8CC | 109.5 |
C11A—C12A—H12A | 119.9 | H8CA—C8C—H8CC | 109.5 |
C12A—C13A—C14A | 121.0 (2) | H8CB—C8C—H8CC | 109.5 |
C12A—C13A—H13A | 119.5 | C10C—C9C—C14C | 120.3 (2) |
C14A—C13A—H13A | 119.5 | C10C—C9C—H9CA | 119.8 |
C13A—C14A—C9A | 118.7 (2) | C14C—C9C—H9CA | 119.8 |
C13A—C14A—C15A | 120.6 (2) | C9C—C10C—C11C | 120.6 (2) |
C9A—C14A—C15A | 120.7 (2) | C9C—C10C—H10C | 119.7 |
O4A—C15A—O3A | 119.4 (2) | C11C—C10C—H10C | 119.7 |
O4A—C15A—C14A | 123.1 (2) | N2C—C11C—C12C | 121.6 (2) |
O3A—C15A—C14A | 117.52 (19) | N2C—C11C—C10C | 119.6 (2) |
N2A—C16A—H16A | 109.5 | C12C—C11C—C10C | 118.8 (2) |
N2A—C16A—H16B | 109.5 | C13C—C12C—C11C | 119.7 (2) |
H16A—C16A—H16B | 109.5 | C13C—C12C—H12C | 120.2 |
N2A—C16A—H16C | 109.5 | C11C—C12C—H12C | 120.2 |
H16A—C16A—H16C | 109.5 | C14C—C13C—C12C | 121.4 (2) |
H16B—C16A—H16C | 109.5 | C14C—C13C—H13C | 119.3 |
C18E—C17A—C18A | 49.8 (3) | C12C—C13C—H13C | 119.3 |
C18E—C17A—Sn1A | 120.3 (3) | C13C—C14C—C9C | 119.1 (2) |
C18A—C17A—Sn1A | 110.95 (19) | C13C—C14C—C15C | 121.2 (2) |
C18E—C17A—H17A | 130.1 | C9C—C14C—C15C | 119.7 (2) |
C18A—C17A—H17A | 109.5 | O3C—C15C—O4C | 118.6 (2) |
Sn1A—C17A—H17A | 109.4 | O3C—C15C—C14C | 123.1 (2) |
C18E—C17A—H17B | 60.1 | O4C—C15C—C14C | 118.2 (2) |
C18A—C17A—H17B | 109.4 | O3C—C15C—Sn1C | 64.95 (12) |
Sn1A—C17A—H17B | 109.4 | O4C—C15C—Sn1C | 53.69 (11) |
H17A—C17A—H17B | 108.1 | C14C—C15C—Sn1C | 171.90 (16) |
C18E—C17A—H17I | 107.4 | N2C—C16C—H16G | 109.5 |
C18A—C17A—H17I | 64.1 | N2C—C16C—H16H | 109.5 |
Sn1A—C17A—H17I | 107.3 | H16G—C16C—H16H | 109.5 |
H17A—C17A—H17I | 49.8 | N2C—C16C—H16I | 109.5 |
H17B—C17A—H17I | 142.2 | H16G—C16C—H16I | 109.5 |
C18E—C17A—H17J | 107.2 | H16H—C16C—H16I | 109.5 |
C18A—C17A—H17J | 141.9 | C18C—C17C—Sn1C | 118.86 (16) |
Sn1A—C17A—H17J | 107.1 | C18C—C17C—H17E | 107.6 |
H17A—C17A—H17J | 58.4 | Sn1C—C17C—H17E | 107.6 |
H17B—C17A—H17J | 53.5 | C18C—C17C—H17H | 107.6 |
H17I—C17A—H17J | 106.9 | Sn1C—C17C—H17H | 107.6 |
C19A—C18A—C17A | 111.2 (3) | H17E—C17C—H17H | 107.0 |
C19A—C18A—H17I | 101.8 | C19C—C18C—C17C | 111.7 (2) |
C19A—C18A—H18A | 109.4 | C19C—C18C—H18E | 109.3 |
C17A—C18A—H18A | 109.4 | C17C—C18C—H18E | 109.3 |
H17I—C18A—H18A | 80.2 | C19C—C18C—H18F | 109.3 |
C19A—C18A—H18B | 109.4 | C17C—C18C—H18F | 109.3 |
C17A—C18A—H18B | 109.4 | H18E—C18C—H18F | 107.9 |
H17I—C18A—H18B | 142.1 | C18C—C19C—C20C | 113.4 (2) |
H18A—C18A—H18B | 108.0 | C18C—C19C—H19E | 108.9 |
C18A—C19A—C20A | 113.3 (3) | C20C—C19C—H19E | 108.9 |
C18A—C19A—H19A | 108.9 | C18C—C19C—H19F | 108.9 |
C20A—C19A—H19A | 108.9 | C20C—C19C—H19F | 108.9 |
C18A—C19A—H19B | 108.9 | H19E—C19C—H19F | 107.7 |
C20A—C19A—H19B | 108.9 | C19C—C20C—H20G | 109.5 |
H19A—C19A—H19B | 107.7 | C19C—C20C—H20H | 109.5 |
C17A—C18E—C19E | 111.6 (4) | H20G—C20C—H20H | 109.5 |
C19E—C18E—H17B | 152.2 | C19C—C20C—H20I | 109.5 |
C17A—C18E—H18I | 109.3 | H20G—C20C—H20I | 109.5 |
C19E—C18E—H18I | 109.3 | H20H—C20C—H20I | 109.5 |
H17B—C18E—H18I | 89.2 | C22C—C21C—Sn1C | 113.89 (15) |
C17A—C18E—H18J | 109.3 | C22C—C21C—H21D | 108.8 |
C19E—C18E—H18J | 109.3 | Sn1C—C21C—H21D | 108.8 |
H17B—C18E—H18J | 83.0 | C22C—C21C—H21E | 108.8 |
H18I—C18E—H18J | 108.0 | Sn1C—C21C—H21E | 108.8 |
C20E—C19E—C18E | 112.6 (6) | H21D—C21C—H21E | 107.7 |
C20E—C19E—H19I | 109.1 | C23C—C22C—C21C | 112.4 (2) |
C18E—C19E—H19I | 109.1 | C23C—C22C—H22E | 109.1 |
C20E—C19E—H19J | 109.1 | C21C—C22C—H22E | 109.1 |
C18E—C19E—H19J | 109.1 | C23C—C22C—H22F | 109.1 |
H19I—C19E—H19J | 107.8 | C21C—C22C—H22F | 109.1 |
C19E—C20E—H20M | 109.5 | H22E—C22C—H22F | 107.8 |
C19E—C20E—H20N | 109.5 | C24C—C23C—C22C | 112.6 (2) |
H20M—C20E—H20N | 109.5 | C24C—C23C—H23G | 109.1 |
C19E—C20E—H20O | 109.5 | C22C—C23C—H23G | 109.1 |
H20M—C20E—H20O | 109.5 | C24C—C23C—H23H | 109.1 |
H20N—C20E—H20O | 109.5 | C22C—C23C—H23H | 109.1 |
C22A—C21A—Sn1A | 112.58 (15) | H23G—C23C—H23H | 107.8 |
C22A—C21A—H21A | 109.1 | C23C—C24C—H24G | 109.5 |
Sn1A—C21A—H21A | 109.1 | C23C—C24C—H24H | 109.5 |
C22A—C21A—H21B | 109.1 | H24G—C24C—H24H | 109.5 |
Sn1A—C21A—H21B | 109.1 | C23C—C24C—H24I | 109.5 |
H21A—C21A—H21B | 107.8 | H24G—C24C—H24I | 109.5 |
C21A—C22A—C23A | 113.4 (2) | H24H—C24C—H24I | 109.5 |
C21A—C22A—H22A | 108.9 | C17D—Sn1D—C21D | 152.92 (10) |
C23A—C22A—H22A | 108.9 | C17D—Sn1D—O1D | 102.60 (8) |
C21A—C22A—H22B | 108.9 | C21D—Sn1D—O1D | 98.89 (8) |
C23A—C22A—H22B | 108.9 | C17D—Sn1D—O4D | 99.36 (9) |
H22A—C22A—H22B | 107.7 | C21D—Sn1D—O4D | 100.57 (8) |
C24A—C23A—C22A | 114.1 (2) | O1D—Sn1D—O4D | 79.58 (6) |
C24A—C23A—H23A | 108.7 | C17D—Sn1D—O2D | 89.87 (8) |
C22A—C23A—H23A | 108.7 | C21D—Sn1D—O2D | 88.12 (8) |
C24A—C23A—H23B | 108.7 | O1D—Sn1D—O2D | 57.05 (6) |
C22A—C23A—H23B | 108.7 | O4D—Sn1D—O2D | 136.62 (6) |
H23A—C23A—H23B | 107.6 | C17D—Sn1D—O3D | 87.68 (8) |
C23A—C24A—H24A | 109.5 | C21D—Sn1D—O3D | 88.73 (8) |
C23A—C24A—H24B | 109.5 | O1D—Sn1D—O3D | 134.91 (6) |
H24A—C24A—H24B | 109.5 | O4D—Sn1D—O3D | 55.36 (5) |
C23A—C24A—H24C | 109.5 | O2D—Sn1D—O3D | 168.02 (5) |
H24A—C24A—H24C | 109.5 | C17D—Sn1D—C7D | 96.85 (8) |
H24B—C24A—H24C | 109.5 | C21D—Sn1D—C7D | 93.93 (8) |
C21B—Sn1B—C17B | 155.44 (9) | O1D—Sn1D—C7D | 29.10 (7) |
C21B—Sn1B—O2B | 100.39 (8) | O4D—Sn1D—C7D | 108.67 (7) |
C17B—Sn1B—O2B | 99.57 (8) | O2D—Sn1D—C7D | 27.95 (6) |
C21B—Sn1B—O3B | 98.44 (8) | O3D—Sn1D—C7D | 164.00 (6) |
C17B—Sn1B—O3B | 98.86 (8) | C3D—N1D—C8D | 123.5 (3) |
O2B—Sn1B—O3B | 80.39 (6) | C3D—N1D—H1NG | 116 (2) |
C21B—Sn1B—O1B | 90.16 (8) | C8D—N1D—H1NG | 114 (2) |
C17B—Sn1B—O1B | 88.68 (8) | C11D—N2D—C16D | 122.5 (2) |
O2B—Sn1B—O1B | 57.34 (6) | C11D—N2D—H1NH | 111.3 (19) |
O3B—Sn1B—O1B | 137.72 (6) | C16D—N2D—H1NH | 117.5 (18) |
C21B—Sn1B—O4B | 87.47 (8) | C7D—O1D—Sn1D | 98.52 (13) |
C17B—Sn1B—O4B | 88.21 (7) | C7D—O2D—Sn1D | 85.60 (15) |
O2B—Sn1B—O4B | 135.61 (6) | C15D—O3D—Sn1D | 84.50 (14) |
O3B—Sn1B—O4B | 55.22 (6) | C15D—O4D—Sn1D | 100.73 (13) |
O1B—Sn1B—O4B | 167.04 (5) | C2D—C1D—C6D | 121.2 (2) |
C21B—Sn1B—C7B | 95.87 (8) | C2D—C1D—H1DA | 119.4 |
C17B—Sn1B—C7B | 94.74 (8) | C6D—C1D—H1DA | 119.4 |
O2B—Sn1B—C7B | 28.83 (6) | C1D—C2D—C3D | 120.1 (2) |
O3B—Sn1B—C7B | 109.22 (7) | C1D—C2D—H2DA | 119.9 |
O1B—Sn1B—C7B | 28.51 (6) | C3D—C2D—H2DA | 119.9 |
O4B—Sn1B—C7B | 164.44 (6) | N1D—C3D—C2D | 121.7 (2) |
C3B—N1B—C8B | 123.4 (3) | N1D—C3D—C4D | 119.6 (2) |
C3B—N1B—H1NC | 119 (2) | C2D—C3D—C4D | 118.8 (2) |
C8B—N1B—H1NC | 118 (2) | C5D—C4D—C3D | 120.7 (2) |
C11B—N2B—C16B | 123.3 (2) | C5D—C4D—H4DA | 119.6 |
C11B—N2B—H1ND | 117.0 (19) | C3D—C4D—H4DA | 119.6 |
C16B—N2B—H1ND | 119.1 (19) | C4D—C5D—C6D | 120.4 (2) |
C7B—O1B—Sn1B | 85.78 (14) | C4D—C5D—H5DA | 119.8 |
C7B—O2B—Sn1B | 97.98 (13) | C6D—C5D—H5DA | 119.8 |
C15B—O3B—Sn1B | 101.30 (13) | C1D—C6D—C5D | 118.8 (2) |
C15B—O4B—Sn1B | 85.21 (14) | C1D—C6D—C7D | 121.0 (2) |
C2B—C1B—C6B | 120.7 (2) | C5D—C6D—C7D | 120.2 (2) |
C2B—C1B—H1BA | 119.7 | O2D—C7D—O1D | 118.8 (2) |
C6B—C1B—H1BA | 119.7 | O2D—C7D—C6D | 123.1 (2) |
C1B—C2B—C3B | 120.5 (2) | O1D—C7D—C6D | 118.0 (2) |
C1B—C2B—H2BA | 119.7 | O2D—C7D—Sn1D | 66.45 (13) |
C3B—C2B—H2BA | 119.7 | O1D—C7D—Sn1D | 52.38 (11) |
N1B—C3B—C4B | 122.1 (2) | C6D—C7D—Sn1D | 170.42 (17) |
N1B—C3B—C2B | 119.4 (2) | N1D—C8D—H8DA | 109.5 |
C4B—C3B—C2B | 118.5 (2) | N1D—C8D—H8DB | 109.5 |
C5B—C4B—C3B | 120.2 (2) | H8DA—C8D—H8DB | 109.5 |
C5B—C4B—H4BA | 119.9 | N1D—C8D—H8DC | 109.5 |
C3B—C4B—H4BA | 119.9 | H8DA—C8D—H8DC | 109.5 |
C6B—C5B—C4B | 121.0 (2) | H8DB—C8D—H8DC | 109.5 |
C6B—C5B—H5BA | 119.5 | C10D—C9D—C14D | 120.8 (2) |
C4B—C5B—H5BA | 119.5 | C10D—C9D—H9DA | 119.6 |
C5B—C6B—C1B | 119.0 (2) | C14D—C9D—H9DA | 119.6 |
C5B—C6B—C7B | 120.6 (2) | C9D—C10D—C11D | 121.4 (2) |
C1B—C6B—C7B | 120.4 (2) | C9D—C10D—H10D | 119.3 |
O1B—C7B—O2B | 118.9 (2) | C11D—C10D—H10D | 119.3 |
O1B—C7B—C6B | 122.0 (2) | N2D—C11D—C10D | 122.5 (2) |
O2B—C7B—C6B | 119.1 (2) | N2D—C11D—C12D | 119.4 (2) |
O1B—C7B—Sn1B | 65.72 (13) | C10D—C11D—C12D | 118.0 (2) |
O2B—C7B—Sn1B | 53.19 (11) | C13D—C12D—C11D | 120.3 (2) |
C6B—C7B—Sn1B | 172.28 (17) | C13D—C12D—H12D | 119.8 |
N1B—C8B—H8BA | 109.5 | C11D—C12D—H12D | 119.8 |
N1B—C8B—H8BB | 109.5 | C12D—C13D—C14D | 121.1 (2) |
H8BA—C8B—H8BB | 109.5 | C12D—C13D—H13D | 119.5 |
N1B—C8B—H8BC | 109.5 | C14D—C13D—H13D | 119.5 |
H8BA—C8B—H8BC | 109.5 | C9D—C14D—C13D | 118.4 (2) |
H8BB—C8B—H8BC | 109.5 | C9D—C14D—C15D | 120.1 (2) |
C10B—C9B—C14B | 120.7 (2) | C13D—C14D—C15D | 121.5 (2) |
C10B—C9B—H9BA | 119.6 | O3D—C15D—O4D | 119.4 (2) |
C14B—C9B—H9BA | 119.6 | O3D—C15D—C14D | 122.6 (2) |
C9B—C10B—C11B | 121.0 (2) | O4D—C15D—C14D | 118.07 (19) |
C9B—C10B—H10B | 119.5 | N2D—C16D—H16J | 109.5 |
C11B—C10B—H10B | 119.5 | N2D—C16D—H16K | 109.5 |
N2B—C11B—C12B | 121.7 (2) | H16J—C16D—H16K | 109.5 |
N2B—C11B—C10B | 120.0 (2) | N2D—C16D—H16L | 109.5 |
C12B—C11B—C10B | 118.3 (2) | H16J—C16D—H16L | 109.5 |
C13B—C12B—C11B | 120.4 (2) | H16K—C16D—H16L | 109.5 |
C13B—C12B—H12B | 119.8 | C18D—C17D—Sn1D | 113.62 (15) |
C11B—C12B—H12B | 119.8 | C18D—C17D—H17F | 108.8 |
C12B—C13B—C14B | 121.2 (2) | Sn1D—C17D—H17F | 108.8 |
C12B—C13B—H13B | 119.4 | C18D—C17D—H17G | 108.8 |
C14B—C13B—H13B | 119.4 | Sn1D—C17D—H17G | 108.8 |
C13B—C14B—C9B | 118.4 (2) | H17F—C17D—H17G | 107.7 |
C13B—C14B—C15B | 120.0 (2) | C17D—C18D—C19D | 112.37 (19) |
C9B—C14B—C15B | 121.7 (2) | C17D—C18D—H18G | 109.1 |
O4B—C15B—O3B | 118.0 (2) | C19D—C18D—H18G | 109.1 |
O4B—C15B—C14B | 122.6 (2) | C17D—C18D—H18H | 109.1 |
O3B—C15B—C14B | 119.34 (18) | C19D—C18D—H18H | 109.1 |
N2B—C16B—H16D | 109.5 | H18G—C18D—H18H | 107.9 |
N2B—C16B—H16E | 109.5 | C20D—C19D—C18D | 113.2 (2) |
H16D—C16B—H16E | 109.5 | C20D—C19D—H19G | 108.9 |
N2B—C16B—H16F | 109.5 | C18D—C19D—H19G | 108.9 |
H16D—C16B—H16F | 109.5 | C20D—C19D—H19H | 108.9 |
H16E—C16B—H16F | 109.5 | C18D—C19D—H19H | 108.9 |
C18B—C17B—Sn1B | 113.72 (15) | H19G—C19D—H19H | 107.8 |
C18B—C17B—H17C | 108.8 | C19D—C20D—H20J | 109.5 |
Sn1B—C17B—H17C | 108.8 | C19D—C20D—H20K | 109.5 |
C18B—C17B—H17D | 108.8 | H20J—C20D—H20K | 109.5 |
Sn1B—C17B—H17D | 108.8 | C19D—C20D—H20L | 109.5 |
H17C—C17B—H17D | 107.7 | H20J—C20D—H20L | 109.5 |
C19B—C18B—C17B | 112.31 (19) | H20K—C20D—H20L | 109.5 |
C19B—C18B—H18C | 109.1 | C22D—C21D—Sn1D | 113.27 (15) |
C17B—C18B—H18C | 109.1 | C22D—C21D—H21F | 108.9 |
C19B—C18B—H18D | 109.1 | Sn1D—C21D—H21F | 108.9 |
C17B—C18B—H18D | 109.1 | C22D—C21D—H21G | 108.9 |
H18C—C18B—H18D | 107.9 | Sn1D—C21D—H21G | 108.9 |
C18B—C19B—C20B | 111.9 (2) | H21F—C21D—H21G | 107.7 |
C18B—C19B—H19C | 109.2 | C23D—C22D—C21D | 112.9 (2) |
C20B—C19B—H19C | 109.2 | C23D—C22D—H22G | 109.0 |
C18B—C19B—H19D | 109.2 | C21D—C22D—H22G | 109.0 |
C20B—C19B—H19D | 109.2 | C23D—C22D—H22H | 109.0 |
H19C—C19B—H19D | 107.9 | C21D—C22D—H22H | 109.0 |
C19B—C20B—H20D | 109.5 | H22G—C22D—H22H | 107.8 |
C19B—C20B—H20E | 109.5 | C24D—C23D—C22D | 111.8 (2) |
H20D—C20B—H20E | 109.5 | C24D—C23D—H23E | 109.2 |
C19B—C20B—H20F | 109.5 | C22D—C23D—H23E | 109.2 |
H20D—C20B—H20F | 109.5 | C24D—C23D—H23F | 109.2 |
H20E—C20B—H20F | 109.5 | C22D—C23D—H23F | 109.2 |
C22B—C21B—Sn1B | 118.39 (15) | H23E—C23D—H23F | 107.9 |
C22B—C21B—H21C | 107.7 | C23D—C24D—H24J | 109.5 |
Sn1B—C21B—H21C | 107.7 | C23D—C24D—H24K | 109.5 |
C22B—C21B—H21H | 107.7 | H24J—C24D—H24K | 109.5 |
Sn1B—C21B—H21H | 107.7 | C23D—C24D—H24L | 109.5 |
H21C—C21B—H21H | 107.1 | H24J—C24D—H24L | 109.5 |
C21B—C22B—C23B | 111.73 (17) | H24K—C24D—H24L | 109.5 |
C21B—C22B—H22C | 109.3 | ||
C21A—Sn1A—O1A—C7A | −104.99 (16) | O4B—Sn1B—C21B—C22B | 129.92 (18) |
C17A—Sn1A—O1A—C7A | 102.34 (16) | C7B—Sn1B—C21B—C22B | −65.32 (18) |
O2A—Sn1A—O1A—C7A | −0.36 (14) | Sn1B—C21B—C22B—C23B | 176.83 (15) |
O3A—Sn1A—O1A—C7A | −1.01 (19) | C21B—C22B—C23B—C24B | 177.7 (2) |
C21A—Sn1A—O2A—C7A | 82.29 (16) | C21C—Sn1C—O1C—C7C | −78.75 (14) |
C17A—Sn1A—O2A—C7A | −81.32 (16) | C17C—Sn1C—O1C—C7C | 84.92 (14) |
O3A—Sn1A—O2A—C7A | 179.89 (16) | O4C—Sn1C—O1C—C7C | −175.79 (14) |
O1A—Sn1A—O2A—C7A | 0.35 (14) | O3C—Sn1C—O1C—C7C | −176.64 (12) |
C21A—Sn1A—O3A—C15A | −84.75 (15) | C15C—Sn1C—O1C—C7C | −175.96 (13) |
C17A—Sn1A—O3A—C15A | 76.66 (16) | C21C—Sn1C—O3C—C15C | −100.08 (15) |
O2A—Sn1A—O3A—C15A | 174.61 (15) | C17C—Sn1C—O3C—C15C | 102.34 (15) |
O1A—Sn1A—O3A—C15A | 175.16 (13) | O4C—Sn1C—O3C—C15C | 0.37 (13) |
C7A—Sn1A—O3A—C15A | 174.66 (14) | O1C—Sn1C—O3C—C15C | 1.35 (18) |
C6A—C1A—C2A—C3A | 0.1 (5) | C21C—Sn1C—O4C—C15C | 83.29 (15) |
C8A—N1A—C3A—C2A | −178.2 (3) | C17C—Sn1C—O4C—C15C | −84.28 (15) |
C8A—N1A—C3A—C4A | 2.0 (4) | O1C—Sn1C—O4C—C15C | −179.68 (15) |
C1A—C2A—C3A—N1A | −179.3 (3) | O3C—Sn1C—O4C—C15C | −0.36 (13) |
C1A—C2A—C3A—C4A | 0.5 (5) | C6C—C1C—C2C—C3C | −0.8 (4) |
N1A—C3A—C4A—C5A | 178.8 (2) | C8C—N1C—C3C—C2C | 173.8 (3) |
C2A—C3A—C4A—C5A | −1.1 (4) | C8C—N1C—C3C—C4C | −8.8 (4) |
C3A—C4A—C5A—C6A | 1.0 (4) | C1C—C2C—C3C—N1C | 179.1 (2) |
C4A—C5A—C6A—C1A | −0.3 (4) | C1C—C2C—C3C—C4C | 1.5 (4) |
C4A—C5A—C6A—C7A | −179.9 (2) | N1C—C3C—C4C—C5C | −178.3 (2) |
C2A—C1A—C6A—C5A | −0.3 (4) | C2C—C3C—C4C—C5C | −0.7 (4) |
C2A—C1A—C6A—C7A | 179.3 (3) | C3C—C4C—C5C—C6C | −0.8 (4) |
Sn1A—O1A—C7A—O2A | 0.6 (2) | C4C—C5C—C6C—C1C | 1.5 (4) |
Sn1A—O1A—C7A—C6A | −179.6 (2) | C4C—C5C—C6C—C7C | 179.6 (2) |
Sn1A—O2A—C7A—O1A | −0.7 (3) | C2C—C1C—C6C—C5C | −0.7 (4) |
Sn1A—O2A—C7A—C6A | 179.52 (19) | C2C—C1C—C6C—C7C | −178.8 (2) |
C5A—C6A—C7A—O1A | −175.1 (2) | Sn1C—O1C—C7C—O2C | −7.4 (2) |
C1A—C6A—C7A—O1A | 5.3 (4) | Sn1C—O1C—C7C—C6C | 171.81 (16) |
C5A—C6A—C7A—O2A | 4.7 (4) | C5C—C6C—C7C—O2C | −4.6 (3) |
C1A—C6A—C7A—O2A | −174.9 (2) | C1C—C6C—C7C—O2C | 173.4 (2) |
C21A—Sn1A—C7A—O1A | 76.72 (16) | C5C—C6C—C7C—O1C | 176.2 (2) |
C17A—Sn1A—C7A—O1A | −78.35 (16) | C1C—C6C—C7C—O1C | −5.8 (3) |
O2A—Sn1A—C7A—O1A | 179.4 (2) | C14C—C9C—C10C—C11C | −0.6 (4) |
O3A—Sn1A—C7A—O1A | 179.26 (14) | C16C—N2C—C11C—C12C | −2.9 (4) |
C21A—Sn1A—C7A—O2A | −102.65 (16) | C16C—N2C—C11C—C10C | 176.8 (2) |
C17A—Sn1A—C7A—O2A | 102.28 (16) | C9C—C10C—C11C—N2C | −179.4 (2) |
O3A—Sn1A—C7A—O2A | −0.11 (16) | C9C—C10C—C11C—C12C | 0.2 (4) |
O1A—Sn1A—C7A—O2A | −179.4 (2) | N2C—C11C—C12C—C13C | 179.3 (2) |
C14A—C9A—C10A—C11A | 1.6 (4) | C10C—C11C—C12C—C13C | −0.4 (3) |
C16A—N2A—C11A—C12A | 14.4 (4) | C11C—C12C—C13C—C14C | 0.9 (3) |
C16A—N2A—C11A—C10A | −166.8 (3) | C12C—C13C—C14C—C9C | −1.2 (3) |
C9A—C10A—C11A—N2A | 179.8 (3) | C12C—C13C—C14C—C15C | −179.7 (2) |
C9A—C10A—C11A—C12A | −1.4 (4) | C10C—C9C—C14C—C13C | 1.1 (4) |
N2A—C11A—C12A—C13A | 178.4 (3) | C10C—C9C—C14C—C15C | 179.6 (2) |
C10A—C11A—C12A—C13A | −0.4 (4) | Sn1C—O3C—C15C—O4C | −0.6 (2) |
C11A—C12A—C13A—C14A | 2.0 (4) | Sn1C—O3C—C15C—C14C | 179.7 (2) |
C12A—C13A—C14A—C9A | −1.8 (4) | Sn1C—O4C—C15C—O3C | 0.7 (2) |
C12A—C13A—C14A—C15A | 178.4 (2) | Sn1C—O4C—C15C—C14C | −179.57 (17) |
C10A—C9A—C14A—C13A | 0.0 (4) | C13C—C14C—C15C—O3C | 173.8 (2) |
C10A—C9A—C14A—C15A | 179.8 (2) | C9C—C14C—C15C—O3C | −4.7 (4) |
Sn1A—O3A—C15A—O4A | 5.5 (2) | C13C—C14C—C15C—O4C | −6.0 (3) |
Sn1A—O3A—C15A—C14A | −174.05 (17) | C9C—C14C—C15C—O4C | 175.5 (2) |
C13A—C14A—C15A—O4A | 9.6 (4) | C21C—Sn1C—C15C—O3C | 80.72 (15) |
C9A—C14A—C15A—O4A | −170.2 (2) | C17C—Sn1C—C15C—O3C | −79.33 (15) |
C13A—C14A—C15A—O3A | −170.9 (2) | O4C—Sn1C—C15C—O3C | −179.4 (2) |
C9A—C14A—C15A—O3A | 9.4 (3) | O1C—Sn1C—C15C—O3C | −179.03 (13) |
C21A—Sn1A—C17A—C18E | −159.5 (3) | C21C—Sn1C—C15C—O4C | −99.91 (15) |
O2A—Sn1A—C17A—C18E | −16.4 (3) | C17C—Sn1C—C15C—O4C | 100.03 (15) |
O3A—Sn1A—C17A—C18E | 63.6 (3) | O1C—Sn1C—C15C—O4C | 0.34 (15) |
O1A—Sn1A—C17A—C18E | −72.6 (3) | O3C—Sn1C—C15C—O4C | 179.4 (2) |
C7A—Sn1A—C17A—C18E | −45.1 (3) | C21C—Sn1C—C17C—C18C | −49.9 (3) |
C21A—Sn1A—C17A—C18A | 145.7 (2) | O4C—Sn1C—C17C—C18C | 96.15 (19) |
O2A—Sn1A—C17A—C18A | −71.2 (2) | O1C—Sn1C—C17C—C18C | 176.93 (18) |
O3A—Sn1A—C17A—C18A | 8.8 (2) | O3C—Sn1C—C17C—C18C | 39.17 (19) |
O1A—Sn1A—C17A—C18A | −127.4 (2) | C15C—Sn1C—C17C—C18C | 66.96 (19) |
C7A—Sn1A—C17A—C18A | −99.8 (2) | Sn1C—C17C—C18C—C19C | −176.28 (17) |
C18E—C17A—C18A—C19A | 66.5 (4) | C17C—C18C—C19C—C20C | −177.3 (2) |
Sn1A—C17A—C18A—C19A | 179.1 (2) | C17C—Sn1C—C21C—C22C | −136.9 (2) |
C17A—C18A—C19A—C20A | 176.5 (3) | O4C—Sn1C—C21C—C22C | 76.80 (17) |
C18A—C17A—C18E—C19E | 14.8 (4) | O1C—Sn1C—C21C—C22C | −3.95 (17) |
Sn1A—C17A—C18E—C19E | −78.0 (5) | O3C—Sn1C—C21C—C22C | 133.74 (16) |
C17A—C18E—C19E—C20E | −71.2 (8) | C15C—Sn1C—C21C—C22C | 105.82 (16) |
C17A—Sn1A—C21A—C22A | 145.9 (2) | Sn1C—C21C—C22C—C23C | 177.99 (16) |
O2A—Sn1A—C21A—C22A | 3.11 (19) | C21C—C22C—C23C—C24C | 176.2 (2) |
O3A—Sn1A—C21A—C22A | −77.10 (18) | C17D—Sn1D—O1D—C7D | −81.36 (16) |
O1A—Sn1A—C21A—C22A | 59.36 (18) | C21D—Sn1D—O1D—C7D | 82.05 (15) |
C7A—Sn1A—C21A—C22A | 31.98 (19) | O4D—Sn1D—O1D—C7D | −178.74 (15) |
Sn1A—C21A—C22A—C23A | 163.91 (18) | O2D—Sn1D—O1D—C7D | 0.15 (13) |
C21A—C22A—C23A—C24A | 66.3 (3) | O3D—Sn1D—O1D—C7D | 179.18 (12) |
C21B—Sn1B—O1B—C7B | −102.08 (15) | C17D—Sn1D—O2D—C7D | 104.99 (15) |
C17B—Sn1B—O1B—C7B | 102.45 (15) | C21D—Sn1D—O2D—C7D | −102.02 (15) |
O2B—Sn1B—O1B—C7B | 0.19 (13) | O1D—Sn1D—O2D—C7D | −0.16 (13) |
O3B—Sn1B—O1B—C7B | 0.70 (19) | O4D—Sn1D—O2D—C7D | 1.42 (18) |
O4B—Sn1B—O1B—C7B | 178.6 (2) | O3D—Sn1D—O2D—C7D | −176.8 (2) |
C21B—Sn1B—O2B—C7B | 83.26 (15) | C17D—Sn1D—O3D—C15D | −104.21 (15) |
C17B—Sn1B—O2B—C7B | −82.38 (15) | C21D—Sn1D—O3D—C15D | 102.63 (14) |
O3B—Sn1B—O2B—C7B | −179.84 (15) | O1D—Sn1D—O3D—C15D | 1.32 (17) |
O1B—Sn1B—O2B—C7B | −0.19 (13) | O4D—Sn1D—O3D—C15D | −1.16 (13) |
O4B—Sn1B—O2B—C7B | −179.67 (12) | O2D—Sn1D—O3D—C15D | 177.4 (3) |
C21B—Sn1B—O3B—C15B | −83.73 (15) | C7D—Sn1D—O3D—C15D | 2.8 (3) |
C17B—Sn1B—O3B—C15B | 78.77 (14) | C17D—Sn1D—O4D—C15D | 81.72 (15) |
O2B—Sn1B—O3B—C15B | 177.07 (14) | C21D—Sn1D—O4D—C15D | −79.87 (15) |
O1B—Sn1B—O3B—C15B | 176.63 (12) | O1D—Sn1D—O4D—C15D | −177.08 (15) |
O4B—Sn1B—O3B—C15B | −2.79 (12) | O2D—Sn1D—O4D—C15D | −178.43 (13) |
C7B—Sn1B—O3B—C15B | 176.98 (13) | O3D—Sn1D—O4D—C15D | 1.14 (12) |
C21B—Sn1B—O4B—C15B | 104.95 (14) | C7D—Sn1D—O4D—C15D | −177.72 (13) |
C17B—Sn1B—O4B—C15B | −99.23 (14) | C6D—C1D—C2D—C3D | −0.5 (4) |
O2B—Sn1B—O4B—C15B | 2.66 (17) | C8D—N1D—C3D—C2D | −7.4 (4) |
O3B—Sn1B—O4B—C15B | 2.86 (12) | C8D—N1D—C3D—C4D | 173.3 (3) |
O1B—Sn1B—O4B—C15B | −175.4 (2) | C1D—C2D—C3D—N1D | −178.6 (3) |
C7B—Sn1B—O4B—C15B | 2.1 (3) | C1D—C2D—C3D—C4D | 0.7 (4) |
C6B—C1B—C2B—C3B | −0.1 (4) | N1D—C3D—C4D—C5D | 179.7 (3) |
C8B—N1B—C3B—C4B | 3.2 (4) | C2D—C3D—C4D—C5D | 0.4 (4) |
C8B—N1B—C3B—C2B | −176.2 (3) | C3D—C4D—C5D—C6D | −1.8 (4) |
C1B—C2B—C3B—N1B | 179.9 (2) | C2D—C1D—C6D—C5D | −0.9 (4) |
C1B—C2B—C3B—C4B | 0.4 (4) | C2D—C1D—C6D—C7D | 180.0 (2) |
N1B—C3B—C4B—C5B | −179.5 (2) | C4D—C5D—C6D—C1D | 2.0 (4) |
C2B—C3B—C4B—C5B | 0.0 (4) | C4D—C5D—C6D—C7D | −178.8 (2) |
C3B—C4B—C5B—C6B | −0.7 (4) | Sn1D—O2D—C7D—O1D | 0.2 (2) |
C4B—C5B—C6B—C1B | 1.0 (4) | Sn1D—O2D—C7D—C6D | 179.5 (2) |
C4B—C5B—C6B—C7B | 179.9 (2) | Sn1D—O1D—C7D—O2D | −0.3 (2) |
C2B—C1B—C6B—C5B | −0.6 (4) | Sn1D—O1D—C7D—C6D | −179.58 (17) |
C2B—C1B—C6B—C7B | −179.5 (2) | C1D—C6D—C7D—O2D | 175.7 (2) |
Sn1B—O1B—C7B—O2B | −0.3 (2) | C5D—C6D—C7D—O2D | −3.5 (4) |
Sn1B—O1B—C7B—C6B | 179.6 (2) | C1D—C6D—C7D—O1D | −5.1 (3) |
Sn1B—O2B—C7B—O1B | 0.3 (2) | C5D—C6D—C7D—O1D | 175.8 (2) |
Sn1B—O2B—C7B—C6B | −179.57 (18) | C17D—Sn1D—C7D—O2D | −76.64 (16) |
C5B—C6B—C7B—O1B | −175.0 (2) | C21D—Sn1D—C7D—O2D | 78.48 (15) |
C1B—C6B—C7B—O1B | 3.9 (4) | O1D—Sn1D—C7D—O2D | 179.7 (2) |
C5B—C6B—C7B—O2B | 4.9 (3) | O4D—Sn1D—C7D—O2D | −178.97 (13) |
C1B—C6B—C7B—O2B | −176.2 (2) | O3D—Sn1D—C7D—O2D | 177.63 (19) |
C21B—Sn1B—C7B—O1B | 79.43 (15) | C17D—Sn1D—C7D—O1D | 103.64 (15) |
C17B—Sn1B—C7B—O1B | −78.40 (15) | C21D—Sn1D—C7D—O1D | −101.24 (15) |
O2B—Sn1B—C7B—O1B | −179.7 (2) | O4D—Sn1D—C7D—O1D | 1.31 (16) |
O3B—Sn1B—C7B—O1B | −179.50 (13) | O2D—Sn1D—C7D—O1D | −179.7 (2) |
O4B—Sn1B—C7B—O1B | −178.81 (19) | O3D—Sn1D—C7D—O1D | −2.1 (3) |
C21B—Sn1B—C7B—O2B | −100.91 (15) | C14D—C9D—C10D—C11D | −1.5 (4) |
C17B—Sn1B—C7B—O2B | 101.27 (15) | C16D—N2D—C11D—C10D | −15.3 (4) |
O3B—Sn1B—C7B—O2B | 0.17 (16) | C16D—N2D—C11D—C12D | 166.3 (2) |
O1B—Sn1B—C7B—O2B | 179.7 (2) | C9D—C10D—C11D—N2D | −177.2 (2) |
O4B—Sn1B—C7B—O2B | 0.9 (3) | C9D—C10D—C11D—C12D | 1.2 (4) |
C14B—C9B—C10B—C11B | −0.4 (4) | N2D—C11D—C12D—C13D | 178.3 (2) |
C16B—N2B—C11B—C12B | 9.0 (4) | C10D—C11D—C12D—C13D | −0.2 (4) |
C16B—N2B—C11B—C10B | −172.9 (2) | C11D—C12D—C13D—C14D | −0.5 (4) |
C9B—C10B—C11B—N2B | −178.4 (2) | C10D—C9D—C14D—C13D | 0.8 (4) |
C9B—C10B—C11B—C12B | −0.2 (4) | C10D—C9D—C14D—C15D | −178.7 (2) |
N2B—C11B—C12B—C13B | 178.6 (2) | C12D—C13D—C14D—C9D | 0.2 (4) |
C10B—C11B—C12B—C13B | 0.4 (4) | C12D—C13D—C14D—C15D | 179.7 (2) |
C11B—C12B—C13B—C14B | 0.0 (4) | Sn1D—O3D—C15D—O4D | 1.8 (2) |
C12B—C13B—C14B—C9B | −0.6 (4) | Sn1D—O3D—C15D—C14D | −177.9 (2) |
C12B—C13B—C14B—C15B | 179.4 (2) | Sn1D—O4D—C15D—O3D | −2.2 (2) |
C10B—C9B—C14B—C13B | 0.8 (4) | Sn1D—O4D—C15D—C14D | 177.53 (17) |
C10B—C9B—C14B—C15B | −179.2 (2) | C9D—C14D—C15D—O3D | −10.2 (3) |
Sn1B—O4B—C15B—O3B | −4.39 (19) | C13D—C14D—C15D—O3D | 170.4 (2) |
Sn1B—O4B—C15B—C14B | 174.2 (2) | C9D—C14D—C15D—O4D | 170.1 (2) |
Sn1B—O3B—C15B—O4B | 5.2 (2) | C13D—C14D—C15D—O4D | −9.3 (3) |
Sn1B—O3B—C15B—C14B | −173.44 (17) | C21D—Sn1D—C17D—C18D | −137.4 (2) |
C13B—C14B—C15B—O4B | 3.9 (3) | O1D—Sn1D—C17D—C18D | 4.26 (19) |
C9B—C14B—C15B—O4B | −176.1 (2) | O4D—Sn1D—C17D—C18D | 85.58 (18) |
C13B—C14B—C15B—O3B | −177.5 (2) | O2D—Sn1D—C17D—C18D | −51.83 (18) |
C9B—C14B—C15B—O3B | 2.5 (3) | O3D—Sn1D—C17D—C18D | 139.90 (18) |
C21B—Sn1B—C17B—C18B | 138.2 (2) | C7D—Sn1D—C17D—C18D | −24.70 (19) |
O2B—Sn1B—C17B—C18B | −77.79 (17) | Sn1D—C17D—C18D—C19D | −163.65 (16) |
O3B—Sn1B—C17B—C18B | 3.87 (17) | C17D—C18D—C19D—C20D | −69.0 (3) |
O1B—Sn1B—C17B—C18B | −134.32 (16) | C17D—Sn1D—C21D—C22D | −140.3 (2) |
O4B—Sn1B—C17B—C18B | 58.25 (16) | O1D—Sn1D—C21D—C22D | 77.46 (17) |
C7B—Sn1B—C17B—C18B | −106.44 (16) | O4D—Sn1D—C21D—C22D | −3.50 (18) |
Sn1B—C17B—C18B—C19B | −178.24 (16) | O2D—Sn1D—C21D—C22D | 133.69 (16) |
C17B—C18B—C19B—C20B | −178.0 (2) | O3D—Sn1D—C21D—C22D | −57.88 (17) |
C17B—Sn1B—C21B—C22B | 49.8 (3) | C7D—Sn1D—C21D—C22D | 106.33 (17) |
O2B—Sn1B—C21B—C22B | −94.09 (18) | Sn1D—C21D—C22D—C23D | −177.97 (16) |
O3B—Sn1B—C21B—C22B | −175.79 (17) | C21D—C22D—C23D—C24D | −179.4 (2) |
O1B—Sn1B—C21B—C22B | −37.34 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2AB···O3Ai | 0.86 | 2.31 | 3.146 (3) | 164 |
N2B—H1ND···O3Bii | 0.84 (3) | 2.13 (3) | 2.967 (3) | 174 (2) |
N1C—H1NE···O4Diii | 0.78 (3) | 2.32 (3) | 3.046 (3) | 155 (3) |
N2D—H1NH···O1Ciii | 0.84 (3) | 2.20 (2) | 2.970 (3) | 152 (2) |
N2D—H1NH···O4Ciii | 0.84 (3) | 2.45 (3) | 3.103 (3) | 134 (2) |
C8B—H8BC···Cg1 | 0.96 | 2.91 | 3.750 (3) | 147 |
Symmetry codes: (i) −x+2, y+1/2, −z; (ii) −x+2, y+1/2, −z+1; (iii) −x+1, y−1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Sn(C4H9)2(C8H8NO2)2] |
Mr | 533.22 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 100 |
a, b, c (Å) | 15.4440 (3), 11.7770 (2), 27.2069 (5) |
β (°) | 100.482 (1) |
V (Å3) | 4865.92 (15) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.08 |
Crystal size (mm) | 0.57 × 0.50 × 0.35 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.577, 0.701 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 106321, 41599, 37515 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.807 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.060, 1.04 |
No. of reflections | 41599 |
No. of parameters | 1187 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.55, −0.78 |
Absolute structure | Flack (1983), 19384 Friedel pairs |
Absolute structure parameter | 0.386 (9) |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2AB···O3Ai | 0.86 | 2.3105 | 3.146 (3) | 164 |
N2B—H1ND···O3Bii | 0.84 (3) | 2.13 (3) | 2.967 (3) | 174 (2) |
N1C—H1NE···O4Diii | 0.78 (3) | 2.32 (3) | 3.046 (3) | 155 (3) |
N2D—H1NH···O1Ciii | 0.84 (3) | 2.20 (2) | 2.970 (3) | 152 (2) |
N2D—H1NH···O4Ciii | 0.84 (3) | 2.45 (3) | 3.103 (3) | 134 (2) |
C8B—H8BC···Cg1 | 0.96 | 2.9078 | 3.750 (3) | 147 |
Symmetry codes: (i) −x+2, y+1/2, −z; (ii) −x+2, y+1/2, −z+1; (iii) −x+1, y−1/2, −z+1. |
The coordination number of organotin(IV) atom vary from four to seven resulting in various kinds of geometric formations (Szorcsik et al., 2004; Yin et al., 2006; Win et al., 2006; Win et al., 2007). In addition, it is well known that organotin(IV) complexes are extensively studied due to their industrial applications as well as biocidal properties (Molloy et al., 1984; Willem et al., 1997; Gielen et al., 2000). Moreover, recent in vitro studies of organotin(IV) complexes on cancer cell lines, bacterial and fungal growths have revealed their inhibitory properties (Teoh et al., 1997; Novelli et al., 1999; Gielen et al., 2000; Tian et al., 2005). Generally the complexes obtained from the reaction of dibutyltin(IV) oxide with carboxylic acid in 1:1 ratio are distannoxane-dimer type whereas in 1:2 ratio will produce monomer type (Yin et al., 2005; Win et al., 2006). In this study, the title compound obtained exhibit a normal monomer type from the 1:2 ratio reaction of dibutyltin(IV) oxide with 4-(methylamino)benzoic acid. In addition, the title complex obtained is similar to that found in the dibutylbis[3-(dimethylamino)benzoato]tin(IV) (Win et al., 2007). The only striking difference is that the methylamine group is substituted at para position in the titled compound whereas the dimethylamine group is substituted at meta position in dibutylbis[3-(dimethylamino)benzoato]tin(IV).
The asymmetric unit of the title complex contains four molecules, A, B, C and D of SnIV complex (Fig. 1). In each molecule, the SnIV is in a six-coordinated skew-trapezoidal environment and coordinates with the two bidentate 4-methylaminobenzoate ligands through O atoms in the equatorial plane (O1, O2, O3 and O4) and the two butyl ligands in the axial positions. There is a disorder of one butyl ligand in molecule A (Fig. 2). In the coordination sphere of SnIV, two Sn—O bond distances lie in the ranges of 2.1320 (16)–2.1467 (16) Å which are shorter than the other two Sn—O distances [in the ranges of 2.3986 (18)–2.5288 (17) Å]. The Sn—O bond distances observed in the title complex are longer than a typical Sn—O bond distance [Yearwood et al., 2002]. The Sn—C distances, in the ranges of 2.115 (2)–2.13192) Å, are similar to the other six similar coordination SnIV complexes (Yearwood et al., 2002). The dihedral angles between the two benzene rings (C1–C6) and (C9–C14) are 13.43 (13) °, 11.34 (12) °, 14.92 (11) ° and 11.10 (12) ° in molecules A, B, C and D, respectively. In each molecule, the methylamino groups are slightly twisted from the mean planes of the attached benzene rings, as indicated by the torsion angles C8–N1–C3–C4 and C16–N2–C11–C12 of 2.0 (4) ° and 14.4 (4) ° in molecule A [3.2 (4) ° and 9.0 (4) ° in molecule B; -8.8 (4) ° and -2.9 (4) ° in molecule C; -7.4 (4) ° and -15.3 (4) ° in molecule D]. Bond lengths and angles observed in the structure are normal.
In the crystal packing (Fig. 3), the molecules are arranged into chains along the [0 1 0] direction. The neighbouring chains are arranged in a T-shape manner (Fig. 3). The crystal is stabilized by N—H···O hydrogen bonds and C—H···π interaction [C8B–H8BC···Cg1 (Table 1); Cg1 is the centroid of C1C–C6C benzene ring].