Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029138/at2070sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029138/at2070Isup2.hkl |
CCDC reference: 620526
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: APEX2; program(s) used to refine structure: APEX2; molecular graphics: APEX2; software used to prepare material for publication: APEX2.
[Sn(CH3)2(C15H12N4O2S)] | F(000) = 1840 |
Mr = 461.10 | Dx = 1.589 Mg m−3 |
Monoclinic, P21/c | Melting point: 441 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 14.2026 (8) Å | Cell parameters from 5092 reflections |
b = 10.5032 (6) Å | θ = 2.3–24.7° |
c = 26.3135 (14) Å | µ = 1.45 mm−1 |
β = 100.869 (1)° | T = 296 K |
V = 3854.8 (4) Å3 | Block, yellow |
Z = 8 | 0.39 × 0.18 × 0.16 mm |
Bruker APEX-II area-detector diffractometer | 7047 independent reflections |
Radiation source: fine-focus sealed tube | 5441 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 25.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −16→17 |
Tmin = 0.75, Tmax = 0.80 | k = −12→12 |
23464 measured reflections | l = −31→31 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.054P)2 + 1.068P] where P = (Fo2 + 2Fc2)/3 |
7047 reflections | (Δ/σ)max = 0.001 |
466 parameters | Δρmax = 0.82 e Å−3 |
18 restraints | Δρmin = −0.77 e Å−3 |
Experimental. IR (KBr, cm-1): 3435 ν(OH/NH); 1618, 1603 ν(C═N); 1581, 1547, 1491, 1471 ν(C═C); 1385 ν(C—S, C—N). 1H NMR (400 MHz, CDCl3): δ 0.82–1.20 (s, 6H, 2CH3), 6.73–7.36 (8H, Ar—H), 7.92(s, 1H, NH), 8.30 (s, 1H, CH═ N), 8.63 (s, 1H, CH═N), 11.02 (s, 1H, OH). |
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) | |
Sn1 | 0.21846 (2) | 0.14067 (3) | 0.161984 (8) | 0.05740 (10) | |
Sn2 | 0.311016 (18) | 0.76075 (2) | 0.340567 (9) | 0.05024 (9) | |
S1 | 0.41923 (7) | 0.70236 (11) | 0.42560 (4) | 0.0666 (3) | |
S2 | 0.09120 (8) | −0.00258 (10) | 0.10664 (4) | 0.0630 (3) | |
O1 | −0.0834 (2) | −0.2837 (3) | 0.06221 (12) | 0.0835 (9) | |
H1 | −0.0417 | −0.2318 | 0.0592 | 0.125* | |
O2A | 0.3426 (5) | 0.2544 (6) | 0.18105 (18) | 0.0623 (15) | 0.628 (13) |
O3 | 0.6117 (2) | 0.7123 (3) | 0.53564 (9) | 0.0762 (8) | |
H3 | 0.5570 | 0.6924 | 0.5217 | 0.114* | |
O4 | 0.1922 (2) | 0.7547 (3) | 0.27984 (11) | 0.0814 (9) | |
N1 | 0.4386 (2) | 0.6294 (3) | 0.53114 (10) | 0.0522 (7) | |
N2 | 0.3522 (2) | 0.5973 (3) | 0.50304 (11) | 0.0623 (8) | |
H2N | 0.3112 | 0.5569 | 0.5172 | 0.075* | |
N3 | 0.2437 (2) | 0.5987 (3) | 0.42885 (10) | 0.0528 (7) | |
N4 | 0.2209 (2) | 0.6269 (3) | 0.37572 (10) | 0.0472 (7) | |
N5 | 0.0430 (2) | −0.1695 (3) | 0.01616 (10) | 0.0492 (7) | |
N6 | 0.1131 (2) | −0.0829 (3) | 0.01326 (11) | 0.0568 (8) | |
H6N | 0.1367 | −0.0786 | −0.0145 | 0.068* | |
N7 | 0.2183 (2) | 0.0669 (3) | 0.04627 (10) | 0.0495 (7) | |
N8 | 0.2543 (2) | 0.1544 (3) | 0.08465 (10) | 0.0459 (6) | |
C1 | 0.1469 (2) | 0.5652 (3) | 0.35175 (13) | 0.0521 (8) | |
H1A | 0.1197 | 0.5073 | 0.3715 | 0.063* | |
C2 | 0.1019 (2) | 0.5754 (3) | 0.29815 (13) | 0.0519 (8) | |
C3 | 0.1268 (3) | 0.6678 (4) | 0.26459 (14) | 0.0575 (9) | |
C4 | 0.0750 (3) | 0.6702 (4) | 0.21344 (15) | 0.0684 (11) | |
H4 | 0.0907 | 0.7303 | 0.1904 | 0.082* | |
C5 | 0.0035 (3) | 0.5875 (4) | 0.19714 (16) | 0.0725 (12) | |
H5 | −0.0291 | 0.5911 | 0.1630 | 0.087* | |
C6 | −0.0224 (3) | 0.4971 (4) | 0.23013 (17) | 0.0748 (12) | |
H6 | −0.0725 | 0.4410 | 0.2186 | 0.090* | |
C7 | 0.0268 (3) | 0.4917 (4) | 0.28001 (15) | 0.0648 (10) | |
H7 | 0.0098 | 0.4308 | 0.3023 | 0.078* | |
C8 | 0.3306 (3) | 0.6297 (3) | 0.45173 (12) | 0.0494 (8) | |
C9 | 0.4585 (3) | 0.6042 (4) | 0.57982 (13) | 0.0570 (9) | |
H9 | 0.4134 | 0.5641 | 0.5958 | 0.068* | |
C10 | 0.5514 (3) | 0.6386 (3) | 0.60979 (12) | 0.0494 (8) | |
C11 | 0.6246 (3) | 0.6866 (3) | 0.58685 (13) | 0.0520 (8) | |
C12 | 0.7133 (3) | 0.7142 (4) | 0.61691 (15) | 0.0640 (10) | |
H12 | 0.7623 | 0.7444 | 0.6012 | 0.077* | |
C13 | 0.7294 (3) | 0.6977 (4) | 0.66905 (15) | 0.0663 (11) | |
H13 | 0.7892 | 0.7167 | 0.6889 | 0.080* | |
C14 | 0.6575 (3) | 0.6528 (4) | 0.69244 (15) | 0.0763 (13) | |
H14 | 0.6681 | 0.6431 | 0.7282 | 0.092* | |
C15 | 0.5702 (3) | 0.6224 (4) | 0.66333 (13) | 0.0664 (11) | |
H15 | 0.5224 | 0.5902 | 0.6795 | 0.080* | |
C16 | 0.3084 (3) | 0.2404 (3) | 0.06935 (13) | 0.0481 (8) | |
H16 | 0.3144 | 0.2356 | 0.0348 | 0.058* | |
C17 | 0.3598 (3) | 0.3411 (3) | 0.09852 (13) | 0.0504 (8) | |
C18 | 0.3666 (3) | 0.3558 (4) | 0.15171 (16) | 0.0740 (12) | |
C19 | 0.4182 (4) | 0.4602 (5) | 0.1759 (2) | 0.1060 (19) | |
H19 | 0.4242 | 0.4709 | 0.2115 | 0.127* | |
C20 | 0.4595 (4) | 0.5455 (5) | 0.1485 (2) | 0.0954 (16) | |
H20 | 0.4918 | 0.6151 | 0.1654 | 0.115* | |
C21 | 0.4547 (3) | 0.5316 (4) | 0.09630 (19) | 0.0817 (13) | |
H21 | 0.4843 | 0.5904 | 0.0780 | 0.098* | |
C22 | 0.4057 (3) | 0.4300 (4) | 0.07142 (16) | 0.0647 (10) | |
H22 | 0.4028 | 0.4197 | 0.0361 | 0.078* | |
C23 | 0.1468 (3) | −0.0027 (3) | 0.05355 (12) | 0.0478 (8) | |
C24 | 0.0191 (3) | −0.2474 (3) | −0.02159 (14) | 0.0537 (9) | |
H24 | 0.0495 | −0.2420 | −0.0499 | 0.064* | |
C25 | −0.0534 (3) | −0.3429 (3) | −0.02140 (15) | 0.0561 (9) | |
C26 | −0.1014 (3) | −0.3590 (4) | 0.01961 (17) | 0.0663 (11) | |
C27 | −0.1686 (3) | −0.4551 (5) | 0.0178 (2) | 0.0883 (14) | |
H27 | −0.2009 | −0.4648 | 0.0452 | 0.106* | |
C28 | −0.1884 (4) | −0.5354 (5) | −0.0232 (3) | 0.0967 (18) | |
H28 | −0.2336 | −0.5996 | −0.0236 | 0.116* | |
C29 | −0.1422 (4) | −0.5223 (4) | −0.0640 (2) | 0.0890 (15) | |
H29 | −0.1560 | −0.5771 | −0.0922 | 0.107* | |
C30 | −0.0747 (3) | −0.4272 (4) | −0.06306 (16) | 0.0716 (11) | |
H30 | −0.0428 | −0.4190 | −0.0907 | 0.086* | |
C31 | 0.2976 (4) | −0.0047 (5) | 0.20611 (18) | 0.0968 (16) | |
H31A | 0.3211 | −0.0633 | 0.1834 | 0.145* | |
H31B | 0.2571 | −0.0491 | 0.2255 | 0.145* | |
H31C | 0.3508 | 0.0321 | 0.2295 | 0.145* | |
C32 | 0.1192 (4) | 0.2618 (4) | 0.18813 (18) | 0.0853 (14) | |
H32A | 0.1112 | 0.2355 | 0.2220 | 0.128* | |
H32B | 0.0586 | 0.2571 | 0.1647 | 0.128* | |
H32C | 0.1425 | 0.3477 | 0.1896 | 0.128* | |
C33 | 0.4030 (4) | 0.7017 (5) | 0.29079 (18) | 0.0872 (14) | |
H33A | 0.3848 | 0.6181 | 0.2778 | 0.131* | |
H33B | 0.4679 | 0.7000 | 0.3095 | 0.131* | |
H33C | 0.3981 | 0.7602 | 0.2624 | 0.131* | |
C34 | 0.2802 (3) | 0.9501 (4) | 0.35873 (18) | 0.0807 (13) | |
H34A | 0.2794 | 1.0032 | 0.3290 | 0.121* | |
H34B | 0.3285 | 0.9800 | 0.3867 | 0.121* | |
H34C | 0.2187 | 0.9532 | 0.3688 | 0.121* | |
O2 | 0.3058 (8) | 0.3018 (9) | 0.1768 (3) | 0.056 (2) | 0.372 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0721 (2) | 0.06783 (18) | 0.03486 (14) | −0.00788 (13) | 0.01675 (11) | −0.00158 (11) |
Sn2 | 0.05824 (17) | 0.04959 (15) | 0.04261 (15) | −0.00364 (11) | 0.00880 (11) | 0.00464 (10) |
S1 | 0.0571 (6) | 0.0926 (7) | 0.0475 (5) | −0.0190 (5) | 0.0032 (4) | 0.0167 (5) |
S2 | 0.0686 (6) | 0.0787 (6) | 0.0468 (5) | −0.0135 (5) | 0.0242 (4) | −0.0103 (5) |
O1 | 0.079 (2) | 0.106 (2) | 0.074 (2) | −0.0061 (18) | 0.0344 (17) | 0.0001 (18) |
O2A | 0.0627 (18) | 0.0647 (18) | 0.0595 (17) | −0.0011 (10) | 0.0116 (10) | −0.0006 (9) |
O3 | 0.0660 (18) | 0.123 (2) | 0.0411 (14) | −0.0109 (17) | 0.0151 (12) | 0.0148 (15) |
O4 | 0.091 (2) | 0.082 (2) | 0.0602 (17) | −0.0237 (17) | −0.0140 (16) | 0.0246 (14) |
N1 | 0.0550 (18) | 0.0599 (17) | 0.0408 (15) | −0.0050 (14) | 0.0066 (13) | 0.0047 (13) |
N2 | 0.0569 (19) | 0.084 (2) | 0.0436 (16) | −0.0176 (17) | 0.0034 (14) | 0.0136 (15) |
N3 | 0.0573 (19) | 0.0628 (17) | 0.0388 (15) | −0.0075 (15) | 0.0106 (13) | 0.0032 (13) |
N4 | 0.0480 (17) | 0.0544 (16) | 0.0389 (14) | −0.0035 (13) | 0.0076 (12) | 0.0037 (12) |
N5 | 0.0521 (18) | 0.0520 (16) | 0.0437 (16) | 0.0031 (14) | 0.0094 (13) | 0.0007 (13) |
N6 | 0.067 (2) | 0.0650 (19) | 0.0414 (15) | −0.0065 (16) | 0.0173 (14) | −0.0070 (14) |
N7 | 0.0582 (18) | 0.0559 (17) | 0.0363 (14) | 0.0021 (14) | 0.0136 (12) | −0.0063 (12) |
N8 | 0.0506 (17) | 0.0552 (16) | 0.0336 (13) | 0.0028 (14) | 0.0123 (12) | −0.0012 (12) |
C1 | 0.049 (2) | 0.057 (2) | 0.052 (2) | −0.0022 (17) | 0.0122 (16) | −0.0004 (16) |
C2 | 0.048 (2) | 0.058 (2) | 0.0486 (19) | 0.0039 (17) | 0.0057 (15) | −0.0048 (16) |
C3 | 0.056 (2) | 0.061 (2) | 0.053 (2) | 0.0034 (19) | 0.0032 (17) | −0.0018 (18) |
C4 | 0.077 (3) | 0.076 (3) | 0.047 (2) | 0.004 (2) | −0.0010 (19) | 0.0069 (19) |
C5 | 0.076 (3) | 0.080 (3) | 0.052 (2) | 0.010 (2) | −0.010 (2) | −0.013 (2) |
C6 | 0.067 (3) | 0.078 (3) | 0.072 (3) | −0.007 (2) | −0.004 (2) | −0.018 (2) |
C7 | 0.061 (2) | 0.068 (2) | 0.063 (2) | −0.010 (2) | 0.0071 (19) | −0.0074 (19) |
C8 | 0.055 (2) | 0.053 (2) | 0.0392 (17) | −0.0056 (16) | 0.0074 (15) | 0.0047 (15) |
C9 | 0.069 (2) | 0.064 (2) | 0.0391 (18) | −0.0082 (19) | 0.0132 (16) | 0.0071 (17) |
C10 | 0.061 (2) | 0.0515 (19) | 0.0357 (17) | 0.0011 (17) | 0.0087 (15) | 0.0020 (14) |
C11 | 0.059 (2) | 0.057 (2) | 0.0414 (18) | 0.0056 (17) | 0.0123 (16) | −0.0006 (16) |
C12 | 0.065 (3) | 0.073 (2) | 0.055 (2) | 0.001 (2) | 0.0132 (19) | 0.0056 (19) |
C13 | 0.072 (3) | 0.064 (2) | 0.056 (2) | −0.005 (2) | −0.004 (2) | −0.0006 (19) |
C14 | 0.094 (3) | 0.089 (3) | 0.040 (2) | −0.010 (3) | −0.003 (2) | 0.003 (2) |
C15 | 0.077 (3) | 0.084 (3) | 0.0384 (19) | −0.011 (2) | 0.0109 (18) | 0.0068 (18) |
C16 | 0.051 (2) | 0.058 (2) | 0.0384 (17) | 0.0083 (17) | 0.0159 (15) | 0.0006 (15) |
C17 | 0.050 (2) | 0.0542 (19) | 0.0483 (19) | 0.0047 (16) | 0.0141 (15) | −0.0030 (16) |
C18 | 0.079 (3) | 0.091 (3) | 0.055 (2) | −0.028 (2) | 0.023 (2) | −0.010 (2) |
C19 | 0.126 (5) | 0.120 (4) | 0.079 (3) | −0.056 (4) | 0.040 (3) | −0.045 (3) |
C20 | 0.102 (4) | 0.080 (3) | 0.106 (4) | −0.034 (3) | 0.026 (3) | −0.027 (3) |
C21 | 0.091 (3) | 0.065 (3) | 0.090 (3) | −0.017 (2) | 0.020 (3) | 0.006 (2) |
C22 | 0.067 (3) | 0.065 (2) | 0.065 (2) | 0.001 (2) | 0.018 (2) | 0.0095 (19) |
C23 | 0.055 (2) | 0.0502 (19) | 0.0388 (17) | 0.0058 (17) | 0.0096 (15) | −0.0017 (15) |
C24 | 0.062 (2) | 0.056 (2) | 0.0441 (19) | 0.0097 (17) | 0.0112 (16) | 0.0004 (16) |
C25 | 0.049 (2) | 0.055 (2) | 0.061 (2) | 0.0072 (17) | 0.0022 (17) | 0.0044 (17) |
C26 | 0.054 (2) | 0.072 (3) | 0.072 (3) | 0.005 (2) | 0.010 (2) | 0.006 (2) |
C27 | 0.061 (3) | 0.086 (3) | 0.120 (4) | 0.002 (3) | 0.023 (3) | 0.019 (3) |
C28 | 0.059 (3) | 0.070 (3) | 0.149 (5) | −0.005 (2) | −0.010 (3) | 0.017 (3) |
C29 | 0.076 (3) | 0.066 (3) | 0.109 (4) | 0.002 (3) | −0.025 (3) | −0.008 (3) |
C30 | 0.076 (3) | 0.063 (2) | 0.067 (3) | 0.008 (2) | −0.009 (2) | −0.005 (2) |
C31 | 0.093 (4) | 0.123 (4) | 0.072 (3) | 0.014 (3) | 0.008 (3) | 0.031 (3) |
C32 | 0.113 (4) | 0.079 (3) | 0.067 (3) | 0.013 (3) | 0.026 (3) | −0.013 (2) |
C33 | 0.110 (4) | 0.087 (3) | 0.074 (3) | 0.020 (3) | 0.040 (3) | 0.012 (3) |
C34 | 0.094 (3) | 0.060 (2) | 0.085 (3) | 0.008 (2) | 0.011 (3) | −0.009 (2) |
O2 | 0.058 (3) | 0.057 (3) | 0.055 (2) | −0.0009 (10) | 0.0111 (11) | −0.0012 (10) |
Sn1—O2 | 2.091 (7) | C10—C15 | 1.394 (5) |
Sn1—C32 | 2.108 (4) | C11—C12 | 1.386 (5) |
Sn1—C31 | 2.110 (5) | C12—C13 | 1.359 (5) |
Sn1—N8 | 2.193 (3) | C12—H12 | 0.9300 |
Sn1—S2 | 2.5805 (10) | C13—C14 | 1.372 (6) |
Sn2—O4 | 2.095 (3) | C13—H13 | 0.9300 |
Sn2—C33 | 2.110 (4) | C14—C15 | 1.366 (6) |
Sn2—C34 | 2.110 (4) | C14—H14 | 0.9300 |
Sn2—N4 | 2.218 (3) | C15—H15 | 0.9300 |
Sn2—S1 | 2.5393 (10) | C16—C17 | 1.425 (5) |
S1—C8 | 1.722 (4) | C16—H16 | 0.9300 |
S2—C23 | 1.729 (3) | C17—C18 | 1.393 (5) |
O1—C26 | 1.356 (5) | C17—C22 | 1.407 (5) |
O1—H1 | 0.8200 | C18—O2 | 1.311 (8) |
O2A—C18 | 1.396 (7) | C18—C19 | 1.403 (6) |
O3—C11 | 1.353 (4) | C19—C20 | 1.352 (7) |
O3—H3 | 0.8200 | C19—H19 | 0.9300 |
O4—C3 | 1.310 (5) | C20—C21 | 1.369 (7) |
N1—C9 | 1.286 (4) | C20—H20 | 0.9300 |
N1—N2 | 1.350 (4) | C21—C22 | 1.371 (6) |
N2—C8 | 1.370 (4) | C21—H21 | 0.9300 |
N2—H2N | 0.8600 | C22—H22 | 0.9300 |
N3—C8 | 1.308 (4) | C24—C25 | 1.438 (5) |
N3—N4 | 1.406 (4) | C24—H24 | 0.9300 |
N4—C1 | 1.293 (4) | C25—C26 | 1.391 (6) |
N5—C24 | 1.282 (4) | C25—C30 | 1.397 (5) |
N5—N6 | 1.361 (4) | C26—C27 | 1.385 (6) |
N6—C23 | 1.368 (4) | C27—C28 | 1.356 (7) |
N6—H6N | 0.8600 | C27—H27 | 0.9300 |
N7—C23 | 1.295 (4) | C28—C29 | 1.367 (7) |
N7—N8 | 1.390 (4) | C28—H28 | 0.9300 |
N8—C16 | 1.298 (4) | C29—C30 | 1.382 (6) |
C1—C2 | 1.439 (5) | C29—H29 | 0.9300 |
C1—H1A | 0.9300 | C30—H30 | 0.9300 |
C2—C7 | 1.396 (5) | C31—H31A | 0.9600 |
C2—C3 | 1.401 (5) | C31—H31B | 0.9600 |
C3—C4 | 1.407 (5) | C31—H31C | 0.9600 |
C4—C5 | 1.344 (6) | C32—H32A | 0.9600 |
C4—H4 | 0.9300 | C32—H32B | 0.9600 |
C5—C6 | 1.382 (6) | C32—H32C | 0.9600 |
C5—H5 | 0.9300 | C33—H33A | 0.9600 |
C6—C7 | 1.367 (6) | C33—H33B | 0.9600 |
C6—H6 | 0.9300 | C33—H33C | 0.9600 |
C7—H7 | 0.9300 | C34—H34A | 0.9600 |
C9—C10 | 1.449 (5) | C34—H34B | 0.9600 |
C9—H9 | 0.9300 | C34—H34C | 0.9600 |
C10—C11 | 1.391 (5) | ||
Sn2—C34—H34C | 109.5 | C34—Sn2—S1 | 98.34 (13) |
Sn2—C34—H34B | 109.5 | C34—Sn2—N4 | 110.01 (16) |
Sn2—C34—H34A | 109.5 | C33—Sn2—S1 | 97.67 (14) |
Sn2—C33—H33C | 109.5 | C33—Sn2—N4 | 123.11 (16) |
Sn2—C33—H33B | 109.5 | C33—Sn2—C34 | 126.6 (2) |
Sn2—C33—H33A | 109.5 | C32—Sn1—S2 | 95.48 (15) |
Sn1—C32—H32C | 109.5 | C32—Sn1—N8 | 123.34 (15) |
Sn1—C32—H32B | 109.5 | C32—Sn1—C31 | 125.23 (19) |
Sn1—C32—H32A | 109.5 | C31—Sn1—S2 | 97.61 (16) |
Sn1—C31—H31C | 109.5 | C31—Sn1—N8 | 111.41 (16) |
Sn1—C31—H31B | 109.5 | C30—C29—H29 | 120.3 |
Sn1—C31—H31A | 109.5 | C30—C25—C24 | 119.3 (4) |
O4—Sn2—S1 | 158.67 (8) | C3—O4—Sn2 | 132.6 (2) |
O4—Sn2—N4 | 81.58 (10) | C3—C4—H4 | 119.3 |
O4—Sn2—C34 | 91.69 (16) | C3—C2—C1 | 123.4 (3) |
O4—Sn2—C33 | 91.24 (18) | C29—C30—H30 | 119.4 |
O4—C3—C4 | 119.5 (4) | C29—C30—C25 | 121.3 (5) |
O4—C3—C2 | 122.6 (3) | C29—C28—H28 | 119.8 |
O3—C11—C12 | 117.7 (3) | C28—C29—H29 | 120.3 |
O3—C11—C10 | 122.2 (3) | C28—C29—C30 | 119.5 (5) |
O2A—C18—C19 | 120.4 (4) | C28—C27—H27 | 119.4 |
O2—Sn1—S2 | 154.8 (2) | C28—C27—C26 | 121.2 (5) |
O2—Sn1—N8 | 83.5 (2) | C27—C28—H28 | 119.8 |
O2—Sn1—C32 | 82.0 (3) | C27—C28—C29 | 120.3 (5) |
O2—Sn1—C31 | 104.3 (4) | C27—C26—C25 | 119.9 (4) |
O2—C18—O2A | 30.4 (4) | C26—O1—H1 | 109.5 |
O2—C18—C19 | 116.6 (5) | C26—C27—H27 | 119.4 |
O2—C18—C17 | 122.0 (5) | C26—C25—C30 | 117.8 (4) |
O1—C26—C27 | 118.3 (4) | C26—C25—C24 | 122.9 (4) |
O1—C26—C25 | 121.8 (4) | C25—C30—H30 | 119.4 |
N8—Sn1—S2 | 76.99 (8) | C25—C24—H24 | 119.1 |
N8—C16—H16 | 115.7 | C24—N5—N6 | 118.2 (3) |
N8—C16—C17 | 128.5 (3) | C23—S2—Sn1 | 94.52 (12) |
N7—N8—Sn1 | 120.9 (2) | C23—N7—N8 | 117.2 (3) |
N7—C23—S2 | 127.5 (3) | C23—N6—H6N | 119.3 |
N7—C23—N6 | 113.7 (3) | C22—C21—H21 | 120.5 |
N6—C23—S2 | 118.7 (3) | C22—C17—C16 | 117.3 (3) |
N5—N6—H6N | 119.3 | C21—C22—H22 | 119.5 |
N5—N6—C23 | 121.4 (3) | C21—C22—C17 | 121.1 (4) |
N5—C24—H24 | 119.1 | C21—C20—H20 | 119.3 |
N5—C24—C25 | 121.8 (3) | C20—C21—H21 | 120.5 |
N4—Sn2—S1 | 77.32 (7) | C20—C21—C22 | 119.1 (4) |
N4—C1—H1A | 116.2 | C20—C19—H19 | 119.4 |
N4—C1—C2 | 127.7 (3) | C20—C19—C18 | 121.1 (5) |
N3—N4—Sn2 | 120.3 (2) | C2—C7—H7 | 119.3 |
N3—C8—S1 | 128.6 (3) | C2—C3—C4 | 117.8 (4) |
N3—C8—N2 | 114.1 (3) | C2—C1—H1A | 116.2 |
N2—C8—S1 | 117.3 (3) | C19—C20—H20 | 119.3 |
N1—N2—H2N | 120.4 | C19—C20—C21 | 121.4 (4) |
N1—N2—C8 | 119.3 (3) | C18—O2—Sn1 | 132.9 (6) |
N1—C9—H9 | 120.1 | C18—C19—H19 | 119.4 |
N1—C9—C10 | 119.9 (3) | C18—C17—C22 | 119.0 (4) |
H34B—C34—H34C | 109.5 | C18—C17—C16 | 123.7 (3) |
H34A—C34—H34C | 109.5 | C17—C22—H22 | 119.5 |
H34A—C34—H34B | 109.5 | C17—C18—O2A | 119.5 (4) |
H33B—C33—H33C | 109.5 | C17—C18—C19 | 118.3 (4) |
H33A—C33—H33C | 109.5 | C17—C16—H16 | 115.7 |
H33A—C33—H33B | 109.5 | C16—N8—Sn1 | 126.0 (2) |
H32B—C32—H32C | 109.5 | C16—N8—N7 | 113.1 (3) |
H32A—C32—H32C | 109.5 | C15—C14—H14 | 119.9 |
H32A—C32—H32B | 109.5 | C15—C14—C13 | 120.2 (4) |
H31B—C31—H31C | 109.5 | C15—C10—C9 | 120.0 (3) |
H31A—C31—H31C | 109.5 | C14—C15—H15 | 119.4 |
H31A—C31—H31B | 109.5 | C14—C15—C10 | 121.2 (4) |
C9—N1—N2 | 120.1 (3) | C14—C13—H13 | 120.1 |
C8—S1—Sn2 | 95.30 (12) | C13—C14—H14 | 119.9 |
C8—N3—N4 | 115.2 (3) | C13—C12—H12 | 119.6 |
C8—N2—H2N | 120.4 | C13—C12—C11 | 120.8 (4) |
C7—C6—H6 | 120.5 | C12—C13—H13 | 120.1 |
C7—C6—C5 | 118.9 (4) | C12—C13—C14 | 119.9 (4) |
C7—C2—C3 | 119.2 (3) | C12—C11—C10 | 120.1 (3) |
C7—C2—C1 | 117.3 (3) | C11—O3—H3 | 109.5 |
C6—C7—H7 | 119.3 | C11—C12—H12 | 119.6 |
C6—C7—C2 | 121.4 (4) | C11—C10—C9 | 122.1 (3) |
C6—C5—H5 | 119.4 | C11—C10—C15 | 117.8 (3) |
C5—C6—H6 | 120.5 | C10—C9—H9 | 120.1 |
C5—C4—H4 | 119.3 | C10—C15—H15 | 119.4 |
C5—C4—C3 | 121.4 (4) | C1—N4—Sn2 | 126.4 (2) |
C4—C5—H5 | 119.4 | C1—N4—N3 | 113.2 (3) |
C4—C5—C6 | 121.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···N1 | 0.82 | 1.87 | 2.589 (4) | 146 |
O1—H1···N5 | 0.82 | 1.92 | 2.636 (4) | 146 |
N2—H2N···N7i | 0.86 | 2.10 | 2.949 (4) | 171 |
N6—H6N···N3ii | 0.86 | 2.33 | 3.155 (4) | 161 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2. |