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Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810021896/hg2693sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810021896/hg2693Isup2.hkl |
CCDC reference: 786448
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.007 Å
- R factor = 0.050
- wR factor = 0.101
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT919_ALERT_3_B Reflection(s) # Likely Affected by the Beamstop 1 PLAT923_ALERT_1_B S values in the CIF and FCF Differ by ....... 0.03
Alert level C PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 10 PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -1.86 eA-3 PLAT972_ALERT_2_C Large Calcd. Non-Metal Negative Residual Density -1.77 eA-3
Alert level G PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large. 27.19 PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c ....... P21/n
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The Schiff base ligand was prepared by the condensation reaction of 3-hydroxy-2-naphthoic hydrazide with 5-chloro-2-hydroxyacetophenone. The prepared Schiff base (0.74 g, 2.0 mmol), dibutyltin dichloride (0.61 g, 2 mmol) and triethylamine (0.6 ml) were refluxed in 50 ml of ethanol for 5 h. The solution was left for crystallizaton at room temperature during which yellow crystals were obtained.
Hydrogen atoms were placed at calculated positions (C–H 0.95 to 0.98 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times Ueq(C). The hydroxy-H was refined with a restraint of 0.84 ± 0.01 Å.
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
[Sn(C4H9)2(C19H13ClN2O3)] | F(000) = 2384 |
Mr = 585.67 | Dx = 1.544 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9440 reflections |
a = 24.8256 (13) Å | θ = 3.0–28.3° |
b = 7.1994 (4) Å | µ = 1.15 mm−1 |
c = 28.3649 (15) Å | T = 100 K |
β = 96.376 (1)° | Prism, yellow |
V = 5038.3 (5) Å3 | 0.25 × 0.25 × 0.15 mm |
Z = 8 |
Bruker APEXII CCD area-detector diffractometer | 8881 independent reflections |
Radiation source: fine-focus sealed tube | 8369 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω scans | θmax = 25.0°, θmin = 1.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −29→29 |
Tmin = 0.762, Tmax = 0.846 | k = −8→8 |
37459 measured reflections | l = −33→33 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.32 | w = 1/[σ2(Fo2) + (0.0158P)2 + 27.1939P] where P = (Fo2 + 2Fc2)/3 |
8881 reflections | (Δ/σ)max = 0.002 |
621 parameters | Δρmax = 0.82 e Å−3 |
0 restraints | Δρmin = −1.50 e Å−3 |
[Sn(C4H9)2(C19H13ClN2O3)] | V = 5038.3 (5) Å3 |
Mr = 585.67 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 24.8256 (13) Å | µ = 1.15 mm−1 |
b = 7.1994 (4) Å | T = 100 K |
c = 28.3649 (15) Å | 0.25 × 0.25 × 0.15 mm |
β = 96.376 (1)° |
Bruker APEXII CCD area-detector diffractometer | 8881 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 8369 reflections with I > 2σ(I) |
Tmin = 0.762, Tmax = 0.846 | Rint = 0.032 |
37459 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.32 | w = 1/[σ2(Fo2) + (0.0158P)2 + 27.1939P] where P = (Fo2 + 2Fc2)/3 |
8881 reflections | Δρmax = 0.82 e Å−3 |
621 parameters | Δρmin = −1.50 e Å−3 |
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 | 0.339899 (13) | 0.57545 (4) | 0.642199 (11) | 0.01339 (9) | |
Sn2 | 0.663321 (13) | 0.45272 (4) | 0.866500 (11) | 0.01362 (9) | |
Cl1 | 0.09889 (5) | 0.79045 (19) | 0.48251 (5) | 0.0265 (3) | |
Cl2 | 0.90500 (5) | 0.15766 (18) | 1.01382 (4) | 0.0222 (3) | |
N1 | 0.26021 (16) | 0.6163 (5) | 0.66655 (13) | 0.0155 (9) | |
N2 | 0.26107 (16) | 0.6250 (5) | 0.71576 (13) | 0.0156 (9) | |
N3 | 0.73912 (16) | 0.3783 (5) | 0.83779 (13) | 0.0143 (8) | |
N4 | 0.73331 (17) | 0.3608 (5) | 0.78836 (13) | 0.0154 (9) | |
O1 | 0.29315 (13) | 0.4587 (5) | 0.58494 (11) | 0.0181 (7) | |
O2 | 0.35201 (13) | 0.6827 (5) | 0.71334 (11) | 0.0169 (7) | |
O3 | 0.22477 (14) | 0.5987 (6) | 0.79810 (12) | 0.0249 (8) | |
H3A | 0.2236 | 0.5980 | 0.7684 | 0.037* | |
O4 | 0.71848 (14) | 0.5613 (5) | 0.91961 (11) | 0.0190 (7) | |
O5 | 0.64255 (13) | 0.3284 (5) | 0.79779 (11) | 0.0172 (7) | |
O6 | 0.76138 (14) | 0.3611 (6) | 0.70211 (12) | 0.0240 (8) | |
H6A | 0.7662 | 0.3611 | 0.7319 | 0.036* | |
C1 | 0.2097 (2) | 0.6282 (6) | 0.58896 (17) | 0.0161 (10) | |
C2 | 0.24893 (19) | 0.5410 (6) | 0.56375 (17) | 0.0158 (10) | |
C3 | 0.2405 (2) | 0.5362 (7) | 0.51393 (17) | 0.0180 (10) | |
H3 | 0.2668 | 0.4781 | 0.4970 | 0.022* | |
C4 | 0.1953 (2) | 0.6129 (7) | 0.48898 (17) | 0.0175 (10) | |
H4 | 0.1905 | 0.6096 | 0.4553 | 0.021* | |
C5 | 0.1570 (2) | 0.6953 (7) | 0.51414 (18) | 0.0191 (11) | |
C6 | 0.1634 (2) | 0.7064 (7) | 0.56248 (17) | 0.0185 (11) | |
H6 | 0.1367 | 0.7670 | 0.5785 | 0.022* | |
C7 | 0.2130 (2) | 0.6357 (6) | 0.64094 (17) | 0.0157 (10) | |
C8 | 0.3104 (2) | 0.6565 (6) | 0.73630 (16) | 0.0144 (10) | |
C9 | 0.3190 (2) | 0.6643 (6) | 0.78861 (17) | 0.0157 (10) | |
C10 | 0.27594 (19) | 0.6359 (7) | 0.81743 (17) | 0.0167 (10) | |
C11 | 0.2865 (2) | 0.6438 (7) | 0.86580 (17) | 0.0188 (11) | |
H11 | 0.2580 | 0.6214 | 0.8847 | 0.023* | |
C12 | 0.3386 (2) | 0.6845 (7) | 0.88818 (17) | 0.0174 (10) | |
C13 | 0.3501 (2) | 0.7017 (7) | 0.93840 (18) | 0.0221 (11) | |
H13 | 0.3221 | 0.6813 | 0.9581 | 0.027* | |
C14 | 0.4011 (2) | 0.7474 (7) | 0.95847 (18) | 0.0253 (12) | |
H14 | 0.4079 | 0.7604 | 0.9919 | 0.030* | |
C15 | 0.4434 (2) | 0.7753 (8) | 0.93039 (18) | 0.0258 (12) | |
H15 | 0.4786 | 0.8063 | 0.9450 | 0.031* | |
C16 | 0.4345 (2) | 0.7584 (7) | 0.88228 (18) | 0.0231 (11) | |
H16 | 0.4636 | 0.7767 | 0.8636 | 0.028* | |
C17 | 0.3820 (2) | 0.7133 (6) | 0.85986 (17) | 0.0164 (10) | |
C18 | 0.3703 (2) | 0.7002 (6) | 0.81034 (17) | 0.0164 (10) | |
H18 | 0.3989 | 0.7169 | 0.7911 | 0.020* | |
C19 | 0.1629 (2) | 0.6682 (7) | 0.66458 (18) | 0.0198 (11) | |
H19A | 0.1657 | 0.6011 | 0.6948 | 0.030* | |
H19B | 0.1313 | 0.6234 | 0.6440 | 0.030* | |
H19C | 0.1589 | 0.8014 | 0.6704 | 0.030* | |
C20 | 0.3635 (2) | 0.8241 (7) | 0.60966 (17) | 0.0181 (10) | |
H20A | 0.3316 | 0.8751 | 0.5898 | 0.022* | |
H20B | 0.3745 | 0.9162 | 0.6348 | 0.022* | |
C21 | 0.4097 (2) | 0.8011 (7) | 0.57894 (17) | 0.0196 (11) | |
H21A | 0.3985 | 0.7128 | 0.5529 | 0.024* | |
H21B | 0.4172 | 0.9222 | 0.5645 | 0.024* | |
C22 | 0.4611 (2) | 0.7306 (8) | 0.60696 (19) | 0.0261 (12) | |
H22A | 0.4533 | 0.6115 | 0.6222 | 0.031* | |
H22B | 0.4729 | 0.8208 | 0.6324 | 0.031* | |
C23 | 0.5069 (2) | 0.7017 (8) | 0.5766 (2) | 0.0341 (14) | |
H23A | 0.5391 | 0.6569 | 0.5965 | 0.051* | |
H23B | 0.5153 | 0.8196 | 0.5618 | 0.051* | |
H23C | 0.4960 | 0.6098 | 0.5519 | 0.051* | |
C24 | 0.3781 (2) | 0.3161 (6) | 0.66053 (16) | 0.0158 (10) | |
H24A | 0.3497 | 0.2197 | 0.6606 | 0.019* | |
H24B | 0.4013 | 0.2827 | 0.6356 | 0.019* | |
C25 | 0.4127 (2) | 0.3118 (7) | 0.70831 (18) | 0.0218 (11) | |
H25A | 0.3916 | 0.3649 | 0.7327 | 0.026* | |
H25B | 0.4449 | 0.3916 | 0.7066 | 0.026* | |
C26 | 0.4315 (2) | 0.1172 (7) | 0.72372 (18) | 0.0233 (12) | |
H26A | 0.4526 | 0.0628 | 0.6995 | 0.028* | |
H26B | 0.3996 | 0.0371 | 0.7263 | 0.028* | |
C27 | 0.4666 (2) | 0.1227 (9) | 0.7715 (2) | 0.0330 (14) | |
H27A | 0.4744 | −0.0044 | 0.7826 | 0.050* | |
H27B | 0.4472 | 0.1888 | 0.7947 | 0.050* | |
H27C | 0.5007 | 0.1873 | 0.7679 | 0.050* | |
C28 | 0.79522 (19) | 0.3650 (6) | 0.91222 (16) | 0.0143 (10) | |
C29 | 0.76097 (18) | 0.4648 (6) | 0.93933 (16) | 0.0133 (9) | |
C30 | 0.7725 (2) | 0.4687 (7) | 0.98883 (17) | 0.0168 (10) | |
H30 | 0.7496 | 0.5376 | 1.0071 | 0.020* | |
C31 | 0.8163 (2) | 0.3747 (7) | 1.01155 (17) | 0.0167 (10) | |
H31 | 0.8234 | 0.3775 | 1.0451 | 0.020* | |
C32 | 0.84958 (19) | 0.2763 (6) | 0.98459 (17) | 0.0150 (10) | |
C33 | 0.84028 (19) | 0.2696 (6) | 0.93631 (17) | 0.0138 (10) | |
H33 | 0.8640 | 0.2010 | 0.9188 | 0.017* | |
C34 | 0.7875 (2) | 0.3568 (6) | 0.86017 (17) | 0.0156 (10) | |
C35 | 0.68199 (19) | 0.3368 (6) | 0.77180 (17) | 0.0153 (10) | |
C36 | 0.66883 (19) | 0.3165 (6) | 0.71995 (16) | 0.0148 (10) | |
C37 | 0.70804 (19) | 0.3304 (7) | 0.68733 (17) | 0.0165 (10) | |
C38 | 0.69298 (19) | 0.3140 (7) | 0.63940 (17) | 0.0172 (10) | |
H38 | 0.7196 | 0.3257 | 0.6180 | 0.021* | |
C39 | 0.6383 (2) | 0.2799 (6) | 0.62151 (17) | 0.0159 (10) | |
C40 | 0.6216 (2) | 0.2574 (7) | 0.57239 (18) | 0.0221 (11) | |
H40 | 0.6475 | 0.2685 | 0.5503 | 0.027* | |
C41 | 0.5690 (2) | 0.2201 (7) | 0.55652 (18) | 0.0236 (12) | |
H41 | 0.5587 | 0.2024 | 0.5236 | 0.028* | |
C42 | 0.5290 (2) | 0.2073 (7) | 0.58903 (18) | 0.0237 (12) | |
H42 | 0.4923 | 0.1828 | 0.5776 | 0.028* | |
C43 | 0.5438 (2) | 0.2303 (7) | 0.63622 (18) | 0.0223 (11) | |
H43 | 0.5172 | 0.2222 | 0.6577 | 0.027* | |
C44 | 0.5990 (2) | 0.2664 (6) | 0.65380 (17) | 0.0164 (10) | |
C45 | 0.6156 (2) | 0.2860 (7) | 0.70265 (17) | 0.0169 (10) | |
H45 | 0.5892 | 0.2777 | 0.7244 | 0.020* | |
C46 | 0.8346 (2) | 0.3182 (7) | 0.83287 (17) | 0.0183 (11) | |
H46A | 0.8328 | 0.4006 | 0.8052 | 0.028* | |
H46B | 0.8332 | 0.1886 | 0.8222 | 0.028* | |
H46C | 0.8685 | 0.3401 | 0.8533 | 0.028* | |
C47 | 0.6361 (2) | 0.2234 (7) | 0.90457 (18) | 0.0217 (11) | |
H47A | 0.6578 | 0.1134 | 0.8975 | 0.026* | |
H47B | 0.6443 | 0.2498 | 0.9389 | 0.026* | |
C48 | 0.5764 (2) | 0.1718 (7) | 0.89511 (19) | 0.0246 (12) | |
H48A | 0.5690 | 0.0651 | 0.9154 | 0.029* | |
H48B | 0.5684 | 0.1324 | 0.8616 | 0.029* | |
C49 | 0.5389 (2) | 0.3319 (7) | 0.90469 (19) | 0.0229 (11) | |
H49A | 0.5518 | 0.3891 | 0.9356 | 0.028* | |
H49B | 0.5404 | 0.4277 | 0.8798 | 0.028* | |
C50 | 0.4805 (2) | 0.2693 (8) | 0.9054 (2) | 0.0328 (14) | |
H50A | 0.4576 | 0.3775 | 0.9097 | 0.049* | |
H50B | 0.4783 | 0.1822 | 0.9316 | 0.049* | |
H50C | 0.4680 | 0.2079 | 0.8753 | 0.049* | |
C51 | 0.6336 (2) | 0.7244 (7) | 0.84806 (17) | 0.0185 (11) | |
H51A | 0.6049 | 0.7546 | 0.8684 | 0.022* | |
H51B | 0.6636 | 0.8138 | 0.8560 | 0.022* | |
C52 | 0.61069 (19) | 0.7563 (7) | 0.79624 (17) | 0.0182 (11) | |
H52A | 0.6091 | 0.8918 | 0.7902 | 0.022* | |
H52B | 0.6361 | 0.7021 | 0.7755 | 0.022* | |
C53 | 0.5552 (2) | 0.6757 (7) | 0.78225 (18) | 0.0220 (11) | |
H53A | 0.5294 | 0.7298 | 0.8027 | 0.026* | |
H53B | 0.5564 | 0.5399 | 0.7878 | 0.026* | |
C54 | 0.5348 (2) | 0.7132 (8) | 0.73038 (19) | 0.0292 (13) | |
H54A | 0.4967 | 0.6758 | 0.7242 | 0.044* | |
H54B | 0.5565 | 0.6418 | 0.7099 | 0.044* | |
H54C | 0.5381 | 0.8460 | 0.7237 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.01504 (18) | 0.01007 (16) | 0.01526 (16) | 0.00157 (13) | 0.00262 (12) | 0.00071 (12) |
Sn2 | 0.01455 (18) | 0.01240 (16) | 0.01387 (16) | 0.00251 (13) | 0.00139 (12) | −0.00070 (13) |
Cl1 | 0.0267 (7) | 0.0260 (7) | 0.0248 (7) | 0.0067 (6) | −0.0070 (5) | 0.0001 (5) |
Cl2 | 0.0198 (6) | 0.0236 (6) | 0.0222 (6) | 0.0062 (5) | −0.0030 (5) | 0.0017 (5) |
N1 | 0.020 (2) | 0.012 (2) | 0.015 (2) | 0.0007 (17) | 0.0031 (17) | −0.0005 (16) |
N2 | 0.018 (2) | 0.014 (2) | 0.014 (2) | 0.0022 (17) | 0.0020 (16) | 0.0017 (16) |
N3 | 0.018 (2) | 0.0119 (19) | 0.0124 (19) | 0.0017 (16) | 0.0003 (16) | −0.0001 (15) |
N4 | 0.021 (2) | 0.012 (2) | 0.013 (2) | 0.0044 (17) | 0.0009 (16) | −0.0008 (16) |
O1 | 0.0158 (18) | 0.0165 (17) | 0.0218 (17) | 0.0034 (14) | 0.0014 (14) | −0.0027 (14) |
O2 | 0.0186 (18) | 0.0145 (17) | 0.0179 (17) | 0.0014 (14) | 0.0039 (14) | −0.0009 (14) |
O3 | 0.0180 (19) | 0.037 (2) | 0.0202 (18) | −0.0022 (17) | 0.0053 (15) | −0.0045 (17) |
O4 | 0.0200 (18) | 0.0168 (17) | 0.0195 (17) | 0.0036 (15) | −0.0007 (14) | −0.0050 (14) |
O5 | 0.0149 (18) | 0.0212 (18) | 0.0158 (16) | −0.0008 (14) | 0.0034 (14) | −0.0036 (14) |
O6 | 0.0142 (19) | 0.038 (2) | 0.0196 (18) | 0.0012 (16) | 0.0028 (14) | −0.0021 (17) |
C1 | 0.018 (3) | 0.008 (2) | 0.022 (2) | −0.0023 (19) | 0.001 (2) | 0.0013 (19) |
C2 | 0.015 (2) | 0.009 (2) | 0.023 (2) | 0.0003 (19) | 0.0003 (19) | 0.001 (2) |
C3 | 0.023 (3) | 0.010 (2) | 0.021 (2) | 0.000 (2) | 0.004 (2) | −0.001 (2) |
C4 | 0.022 (3) | 0.014 (2) | 0.016 (2) | −0.002 (2) | 0.000 (2) | −0.0022 (19) |
C5 | 0.021 (3) | 0.012 (2) | 0.023 (3) | 0.000 (2) | −0.003 (2) | 0.001 (2) |
C6 | 0.021 (3) | 0.011 (2) | 0.023 (3) | 0.001 (2) | 0.002 (2) | −0.002 (2) |
C7 | 0.021 (3) | 0.004 (2) | 0.022 (3) | −0.0004 (19) | 0.003 (2) | −0.0012 (18) |
C8 | 0.020 (3) | 0.008 (2) | 0.016 (2) | 0.0071 (19) | 0.005 (2) | −0.0004 (18) |
C9 | 0.018 (3) | 0.009 (2) | 0.021 (2) | 0.0017 (19) | 0.003 (2) | 0.0001 (19) |
C10 | 0.011 (2) | 0.015 (2) | 0.025 (3) | 0.0046 (19) | 0.007 (2) | −0.001 (2) |
C11 | 0.017 (3) | 0.017 (3) | 0.024 (3) | 0.004 (2) | 0.010 (2) | 0.002 (2) |
C12 | 0.022 (3) | 0.011 (2) | 0.021 (2) | 0.005 (2) | 0.005 (2) | 0.0002 (19) |
C13 | 0.031 (3) | 0.014 (2) | 0.022 (3) | 0.003 (2) | 0.006 (2) | 0.002 (2) |
C14 | 0.042 (3) | 0.018 (3) | 0.015 (2) | 0.007 (2) | 0.000 (2) | 0.000 (2) |
C15 | 0.029 (3) | 0.023 (3) | 0.023 (3) | 0.000 (2) | −0.006 (2) | 0.001 (2) |
C16 | 0.025 (3) | 0.022 (3) | 0.022 (3) | 0.000 (2) | 0.002 (2) | 0.002 (2) |
C17 | 0.020 (3) | 0.010 (2) | 0.020 (2) | 0.004 (2) | 0.003 (2) | 0.0007 (19) |
C18 | 0.019 (3) | 0.011 (2) | 0.020 (2) | 0.003 (2) | 0.007 (2) | −0.0010 (19) |
C19 | 0.020 (3) | 0.016 (2) | 0.023 (3) | 0.000 (2) | 0.002 (2) | 0.000 (2) |
C20 | 0.019 (3) | 0.013 (2) | 0.023 (3) | 0.004 (2) | 0.006 (2) | 0.002 (2) |
C21 | 0.023 (3) | 0.017 (2) | 0.019 (2) | −0.002 (2) | 0.003 (2) | 0.002 (2) |
C22 | 0.027 (3) | 0.022 (3) | 0.029 (3) | −0.002 (2) | 0.004 (2) | 0.007 (2) |
C23 | 0.029 (3) | 0.017 (3) | 0.058 (4) | −0.002 (2) | 0.011 (3) | 0.004 (3) |
C24 | 0.020 (3) | 0.009 (2) | 0.019 (2) | 0.006 (2) | 0.004 (2) | 0.0058 (19) |
C25 | 0.018 (3) | 0.023 (3) | 0.024 (3) | 0.006 (2) | 0.001 (2) | 0.004 (2) |
C26 | 0.022 (3) | 0.025 (3) | 0.022 (3) | 0.008 (2) | 0.004 (2) | 0.007 (2) |
C27 | 0.036 (3) | 0.034 (3) | 0.029 (3) | 0.014 (3) | 0.003 (3) | 0.009 (3) |
C28 | 0.015 (2) | 0.011 (2) | 0.017 (2) | −0.0028 (19) | 0.0004 (19) | −0.0012 (18) |
C29 | 0.009 (2) | 0.012 (2) | 0.019 (2) | −0.0032 (19) | 0.0009 (18) | −0.0004 (19) |
C30 | 0.017 (3) | 0.013 (2) | 0.021 (2) | −0.004 (2) | 0.006 (2) | −0.004 (2) |
C31 | 0.018 (3) | 0.013 (2) | 0.019 (2) | −0.003 (2) | 0.001 (2) | −0.0006 (19) |
C32 | 0.010 (2) | 0.012 (2) | 0.022 (3) | 0.0022 (19) | −0.0038 (19) | −0.0013 (19) |
C33 | 0.011 (2) | 0.009 (2) | 0.022 (2) | −0.0018 (18) | 0.0026 (19) | −0.0027 (19) |
C34 | 0.019 (3) | 0.009 (2) | 0.019 (2) | −0.0020 (19) | 0.002 (2) | −0.0008 (19) |
C35 | 0.014 (3) | 0.010 (2) | 0.022 (2) | 0.0049 (19) | 0.002 (2) | −0.0015 (19) |
C36 | 0.017 (3) | 0.010 (2) | 0.017 (2) | 0.0046 (19) | 0.0026 (19) | 0.0000 (19) |
C37 | 0.010 (2) | 0.014 (2) | 0.025 (3) | 0.0009 (19) | 0.004 (2) | −0.003 (2) |
C38 | 0.013 (2) | 0.021 (3) | 0.019 (2) | 0.004 (2) | 0.0044 (19) | 0.000 (2) |
C39 | 0.017 (3) | 0.012 (2) | 0.018 (2) | 0.007 (2) | 0.0003 (19) | 0.0004 (19) |
C40 | 0.029 (3) | 0.017 (3) | 0.020 (3) | 0.005 (2) | 0.000 (2) | 0.000 (2) |
C41 | 0.030 (3) | 0.020 (3) | 0.019 (3) | 0.003 (2) | −0.004 (2) | −0.003 (2) |
C42 | 0.025 (3) | 0.018 (3) | 0.026 (3) | −0.003 (2) | −0.006 (2) | 0.002 (2) |
C43 | 0.023 (3) | 0.020 (3) | 0.024 (3) | −0.002 (2) | 0.002 (2) | 0.000 (2) |
C44 | 0.017 (3) | 0.012 (2) | 0.020 (2) | 0.003 (2) | −0.001 (2) | 0.0004 (19) |
C45 | 0.016 (3) | 0.014 (2) | 0.021 (2) | 0.005 (2) | 0.003 (2) | −0.001 (2) |
C46 | 0.023 (3) | 0.015 (2) | 0.017 (2) | 0.001 (2) | 0.001 (2) | −0.001 (2) |
C47 | 0.027 (3) | 0.015 (2) | 0.024 (3) | 0.002 (2) | 0.006 (2) | 0.004 (2) |
C48 | 0.034 (3) | 0.017 (3) | 0.024 (3) | −0.007 (2) | 0.008 (2) | 0.000 (2) |
C49 | 0.023 (3) | 0.017 (3) | 0.029 (3) | 0.002 (2) | −0.001 (2) | 0.004 (2) |
C50 | 0.023 (3) | 0.025 (3) | 0.052 (4) | −0.006 (2) | 0.011 (3) | −0.007 (3) |
C51 | 0.019 (3) | 0.019 (3) | 0.018 (2) | 0.003 (2) | 0.005 (2) | 0.001 (2) |
C52 | 0.011 (2) | 0.020 (3) | 0.024 (3) | 0.004 (2) | 0.003 (2) | 0.004 (2) |
C53 | 0.013 (3) | 0.021 (3) | 0.032 (3) | 0.003 (2) | 0.002 (2) | 0.005 (2) |
C54 | 0.030 (3) | 0.027 (3) | 0.029 (3) | 0.001 (3) | −0.007 (2) | 0.000 (2) |
Sn1—O1 | 2.067 (3) | C23—H23C | 0.9800 |
Sn1—C20 | 2.126 (5) | C24—C25 | 1.522 (7) |
Sn1—C24 | 2.132 (4) | C24—H24A | 0.9900 |
Sn1—O2 | 2.150 (3) | C24—H24B | 0.9900 |
Sn1—N1 | 2.186 (4) | C25—C26 | 1.526 (7) |
Sn2—O4 | 2.073 (3) | C25—H25A | 0.9900 |
Sn2—C47 | 2.123 (5) | C25—H25B | 0.9900 |
Sn2—C51 | 2.135 (5) | C26—C27 | 1.528 (7) |
Sn2—O5 | 2.155 (3) | C26—H26A | 0.9900 |
Sn2—N3 | 2.198 (4) | C26—H26B | 0.9900 |
Cl1—C5 | 1.751 (5) | C27—H27A | 0.9800 |
Cl2—C32 | 1.748 (5) | C27—H27B | 0.9800 |
N1—C7 | 1.316 (6) | C27—H27C | 0.9800 |
N1—N2 | 1.395 (5) | C28—C29 | 1.406 (7) |
N2—C8 | 1.316 (6) | C28—C33 | 1.421 (7) |
N3—C34 | 1.304 (6) | C28—C34 | 1.469 (6) |
N3—N4 | 1.399 (5) | C29—C30 | 1.402 (6) |
N4—C35 | 1.319 (6) | C30—C31 | 1.378 (7) |
O1—C2 | 1.331 (6) | C30—H30 | 0.9500 |
O2—C8 | 1.294 (6) | C31—C32 | 1.383 (7) |
O3—C10 | 1.353 (6) | C31—H31 | 0.9500 |
O3—H3A | 0.8400 | C32—C33 | 1.364 (7) |
O4—C29 | 1.333 (6) | C33—H33 | 0.9500 |
O5—C35 | 1.291 (6) | C34—C46 | 1.498 (7) |
O6—C37 | 1.362 (6) | C35—C36 | 1.478 (6) |
O6—H6A | 0.8400 | C36—C45 | 1.375 (7) |
C1—C2 | 1.417 (7) | C36—C37 | 1.419 (7) |
C1—C6 | 1.418 (7) | C37—C38 | 1.375 (7) |
C1—C7 | 1.469 (7) | C38—C39 | 1.418 (7) |
C2—C3 | 1.406 (7) | C38—H38 | 0.9500 |
C3—C4 | 1.374 (7) | C39—C44 | 1.414 (7) |
C3—H3 | 0.9500 | C39—C40 | 1.418 (7) |
C4—C5 | 1.385 (7) | C40—C41 | 1.359 (8) |
C4—H4 | 0.9500 | C40—H40 | 0.9500 |
C5—C6 | 1.365 (7) | C41—C42 | 1.431 (8) |
C6—H6 | 0.9500 | C41—H41 | 0.9500 |
C7—C19 | 1.496 (7) | C42—C43 | 1.358 (7) |
C8—C9 | 1.476 (6) | C42—H42 | 0.9500 |
C9—C18 | 1.377 (7) | C43—C44 | 1.427 (7) |
C9—C10 | 1.431 (7) | C43—H43 | 0.9500 |
C10—C11 | 1.369 (7) | C44—C45 | 1.408 (7) |
C11—C12 | 1.407 (7) | C45—H45 | 0.9500 |
C11—H11 | 0.9500 | C46—H46A | 0.9800 |
C12—C13 | 1.427 (7) | C46—H46B | 0.9800 |
C12—C17 | 1.427 (7) | C46—H46C | 0.9800 |
C13—C14 | 1.370 (8) | C47—C48 | 1.524 (7) |
C13—H13 | 0.9500 | C47—H47A | 0.9900 |
C14—C15 | 1.402 (8) | C47—H47B | 0.9900 |
C14—H14 | 0.9500 | C48—C49 | 1.525 (7) |
C15—C16 | 1.363 (7) | C48—H48A | 0.9900 |
C15—H15 | 0.9500 | C48—H48B | 0.9900 |
C16—C17 | 1.424 (7) | C49—C50 | 1.519 (7) |
C16—H16 | 0.9500 | C49—H49A | 0.9900 |
C17—C18 | 1.405 (7) | C49—H49B | 0.9900 |
C18—H18 | 0.9500 | C50—H50A | 0.9800 |
C19—H19A | 0.9800 | C50—H50B | 0.9800 |
C19—H19B | 0.9800 | C50—H50C | 0.9800 |
C19—H19C | 0.9800 | C51—C52 | 1.533 (7) |
C20—C21 | 1.525 (7) | C51—H51A | 0.9900 |
C20—H20A | 0.9900 | C51—H51B | 0.9900 |
C20—H20B | 0.9900 | C52—C53 | 1.507 (7) |
C21—C22 | 1.514 (7) | C52—H52A | 0.9900 |
C21—H21A | 0.9900 | C52—H52B | 0.9900 |
C21—H21B | 0.9900 | C53—C54 | 1.526 (7) |
C22—C23 | 1.514 (8) | C53—H53A | 0.9900 |
C22—H22A | 0.9900 | C53—H53B | 0.9900 |
C22—H22B | 0.9900 | C54—H54A | 0.9800 |
C23—H23A | 0.9800 | C54—H54B | 0.9800 |
C23—H23B | 0.9800 | C54—H54C | 0.9800 |
O1—Sn1—C20 | 99.15 (17) | C24—C25—H25A | 108.9 |
O1—Sn1—C24 | 91.79 (16) | C26—C25—H25A | 108.9 |
C20—Sn1—C24 | 134.95 (19) | C24—C25—H25B | 108.9 |
O1—Sn1—O2 | 153.02 (13) | C26—C25—H25B | 108.9 |
C20—Sn1—O2 | 95.08 (16) | H25A—C25—H25B | 107.7 |
C24—Sn1—O2 | 94.22 (15) | C25—C26—C27 | 110.9 (5) |
O1—Sn1—N1 | 81.61 (14) | C25—C26—H26A | 109.5 |
C20—Sn1—N1 | 109.07 (16) | C27—C26—H26A | 109.5 |
C24—Sn1—N1 | 115.74 (17) | C25—C26—H26B | 109.5 |
O2—Sn1—N1 | 72.08 (13) | C27—C26—H26B | 109.5 |
O4—Sn2—C47 | 98.34 (17) | H26A—C26—H26B | 108.1 |
O4—Sn2—C51 | 90.85 (17) | C26—C27—H27A | 109.5 |
C47—Sn2—C51 | 135.8 (2) | C26—C27—H27B | 109.5 |
O4—Sn2—O5 | 152.42 (13) | H27A—C27—H27B | 109.5 |
C47—Sn2—O5 | 94.55 (17) | C26—C27—H27C | 109.5 |
C51—Sn2—O5 | 96.75 (16) | H27A—C27—H27C | 109.5 |
O4—Sn2—N3 | 80.65 (14) | H27B—C27—H27C | 109.5 |
C47—Sn2—N3 | 109.41 (17) | C29—C28—C33 | 118.4 (4) |
C51—Sn2—N3 | 114.78 (17) | C29—C28—C34 | 123.4 (4) |
O5—Sn2—N3 | 72.08 (13) | C33—C28—C34 | 118.2 (4) |
C7—N1—N2 | 117.5 (4) | O4—C29—C30 | 118.3 (4) |
C7—N1—Sn1 | 128.4 (3) | O4—C29—C28 | 122.4 (4) |
N2—N1—Sn1 | 114.1 (3) | C30—C29—C28 | 119.3 (4) |
C8—N2—N1 | 111.1 (4) | C31—C30—C29 | 121.4 (4) |
C34—N3—N4 | 117.7 (4) | C31—C30—H30 | 119.3 |
C34—N3—Sn2 | 129.0 (3) | C29—C30—H30 | 119.3 |
N4—N3—Sn2 | 113.3 (3) | C30—C31—C32 | 118.8 (4) |
C35—N4—N3 | 110.9 (4) | C30—C31—H31 | 120.6 |
C2—O1—Sn1 | 122.5 (3) | C32—C31—H31 | 120.6 |
C8—O2—Sn1 | 112.6 (3) | C33—C32—C31 | 121.9 (4) |
C10—O3—H3A | 109.5 | C33—C32—Cl2 | 119.7 (4) |
C29—O4—Sn2 | 122.5 (3) | C31—C32—Cl2 | 118.4 (4) |
C35—O5—Sn2 | 112.1 (3) | C32—C33—C28 | 120.1 (4) |
C37—O6—H6A | 109.5 | C32—C33—H33 | 119.9 |
C2—C1—C6 | 118.1 (4) | C28—C33—H33 | 119.9 |
C2—C1—C7 | 123.9 (4) | N3—C34—C28 | 119.7 (4) |
C6—C1—C7 | 118.0 (4) | N3—C34—C46 | 120.0 (4) |
O1—C2—C3 | 117.8 (4) | C28—C34—C46 | 120.3 (4) |
O1—C2—C1 | 123.2 (4) | O5—C35—N4 | 124.5 (4) |
C3—C2—C1 | 118.9 (4) | O5—C35—C36 | 117.8 (4) |
C4—C3—C2 | 122.0 (5) | N4—C35—C36 | 117.7 (4) |
C4—C3—H3 | 119.0 | C45—C36—C37 | 118.7 (4) |
C2—C3—H3 | 119.0 | C45—C36—C35 | 117.9 (4) |
C3—C4—C5 | 118.4 (5) | C37—C36—C35 | 123.4 (4) |
C3—C4—H4 | 120.8 | O6—C37—C38 | 117.8 (4) |
C5—C4—H4 | 120.8 | O6—C37—C36 | 121.6 (4) |
C6—C5—C4 | 122.1 (5) | C38—C37—C36 | 120.5 (4) |
C6—C5—Cl1 | 119.3 (4) | C37—C38—C39 | 120.9 (4) |
C4—C5—Cl1 | 118.5 (4) | C37—C38—H38 | 119.6 |
C5—C6—C1 | 120.5 (5) | C39—C38—H38 | 119.6 |
C5—C6—H6 | 119.8 | C44—C39—C38 | 118.9 (4) |
C1—C6—H6 | 119.8 | C44—C39—C40 | 118.8 (5) |
N1—C7—C1 | 119.9 (4) | C38—C39—C40 | 122.4 (5) |
N1—C7—C19 | 120.2 (4) | C41—C40—C39 | 120.9 (5) |
C1—C7—C19 | 119.9 (4) | C41—C40—H40 | 119.6 |
O2—C8—N2 | 123.9 (4) | C39—C40—H40 | 119.6 |
O2—C8—C9 | 117.8 (4) | C40—C41—C42 | 120.6 (5) |
N2—C8—C9 | 118.3 (4) | C40—C41—H41 | 119.7 |
C18—C9—C10 | 118.9 (4) | C42—C41—H41 | 119.7 |
C18—C9—C8 | 118.7 (4) | C43—C42—C41 | 119.8 (5) |
C10—C9—C8 | 122.4 (4) | C43—C42—H42 | 120.1 |
O3—C10—C11 | 118.8 (4) | C41—C42—H42 | 120.1 |
O3—C10—C9 | 121.6 (4) | C42—C43—C44 | 120.7 (5) |
C11—C10—C9 | 119.6 (5) | C42—C43—H43 | 119.7 |
C10—C11—C12 | 121.7 (5) | C44—C43—H43 | 119.7 |
C10—C11—H11 | 119.2 | C45—C44—C39 | 118.8 (4) |
C12—C11—H11 | 119.2 | C45—C44—C43 | 121.8 (5) |
C11—C12—C13 | 122.6 (5) | C39—C44—C43 | 119.3 (4) |
C11—C12—C17 | 119.3 (4) | C36—C45—C44 | 122.2 (5) |
C13—C12—C17 | 118.1 (5) | C36—C45—H45 | 118.9 |
C14—C13—C12 | 120.5 (5) | C44—C45—H45 | 118.9 |
C14—C13—H13 | 119.7 | C34—C46—H46A | 109.5 |
C12—C13—H13 | 119.7 | C34—C46—H46B | 109.5 |
C13—C14—C15 | 121.0 (5) | H46A—C46—H46B | 109.5 |
C13—C14—H14 | 119.5 | C34—C46—H46C | 109.5 |
C15—C14—H14 | 119.5 | H46A—C46—H46C | 109.5 |
C16—C15—C14 | 120.5 (5) | H46B—C46—H46C | 109.5 |
C16—C15—H15 | 119.7 | C48—C47—Sn2 | 117.3 (3) |
C14—C15—H15 | 119.7 | C48—C47—H47A | 108.0 |
C15—C16—C17 | 120.4 (5) | Sn2—C47—H47A | 108.0 |
C15—C16—H16 | 119.8 | C48—C47—H47B | 108.0 |
C17—C16—H16 | 119.8 | Sn2—C47—H47B | 108.0 |
C18—C17—C16 | 122.6 (5) | H47A—C47—H47B | 107.2 |
C18—C17—C12 | 117.9 (5) | C47—C48—C49 | 112.7 (4) |
C16—C17—C12 | 119.5 (5) | C47—C48—H48A | 109.0 |
C9—C18—C17 | 122.5 (5) | C49—C48—H48A | 109.0 |
C9—C18—H18 | 118.7 | C47—C48—H48B | 109.0 |
C17—C18—H18 | 118.7 | C49—C48—H48B | 109.0 |
C7—C19—H19A | 109.5 | H48A—C48—H48B | 107.8 |
C7—C19—H19B | 109.5 | C50—C49—C48 | 112.4 (4) |
H19A—C19—H19B | 109.5 | C50—C49—H49A | 109.1 |
C7—C19—H19C | 109.5 | C48—C49—H49A | 109.1 |
H19A—C19—H19C | 109.5 | C50—C49—H49B | 109.1 |
H19B—C19—H19C | 109.5 | C48—C49—H49B | 109.1 |
C21—C20—Sn1 | 114.7 (3) | H49A—C49—H49B | 107.9 |
C21—C20—H20A | 108.6 | C49—C50—H50A | 109.5 |
Sn1—C20—H20A | 108.6 | C49—C50—H50B | 109.5 |
C21—C20—H20B | 108.6 | H50A—C50—H50B | 109.5 |
Sn1—C20—H20B | 108.6 | C49—C50—H50C | 109.5 |
H20A—C20—H20B | 107.6 | H50A—C50—H50C | 109.5 |
C22—C21—C20 | 112.4 (4) | H50B—C50—H50C | 109.5 |
C22—C21—H21A | 109.1 | C52—C51—Sn2 | 117.0 (3) |
C20—C21—H21A | 109.1 | C52—C51—H51A | 108.1 |
C22—C21—H21B | 109.1 | Sn2—C51—H51A | 108.1 |
C20—C21—H21B | 109.1 | C52—C51—H51B | 108.1 |
H21A—C21—H21B | 107.9 | Sn2—C51—H51B | 108.1 |
C21—C22—C23 | 112.9 (5) | H51A—C51—H51B | 107.3 |
C21—C22—H22A | 109.0 | C53—C52—C51 | 115.2 (4) |
C23—C22—H22A | 109.0 | C53—C52—H52A | 108.5 |
C21—C22—H22B | 109.0 | C51—C52—H52A | 108.5 |
C23—C22—H22B | 109.0 | C53—C52—H52B | 108.5 |
H22A—C22—H22B | 107.8 | C51—C52—H52B | 108.5 |
C22—C23—H23A | 109.5 | H52A—C52—H52B | 107.5 |
C22—C23—H23B | 109.5 | C52—C53—C54 | 112.4 (4) |
H23A—C23—H23B | 109.5 | C52—C53—H53A | 109.1 |
C22—C23—H23C | 109.5 | C54—C53—H53A | 109.1 |
H23A—C23—H23C | 109.5 | C52—C53—H53B | 109.1 |
H23B—C23—H23C | 109.5 | C54—C53—H53B | 109.1 |
C25—C24—Sn1 | 115.3 (3) | H53A—C53—H53B | 107.8 |
C25—C24—H24A | 108.5 | C53—C54—H54A | 109.5 |
Sn1—C24—H24A | 108.5 | C53—C54—H54B | 109.5 |
C25—C24—H24B | 108.5 | H54A—C54—H54B | 109.5 |
Sn1—C24—H24B | 108.5 | C53—C54—H54C | 109.5 |
H24A—C24—H24B | 107.5 | H54A—C54—H54C | 109.5 |
C24—C25—C26 | 113.5 (4) | H54B—C54—H54C | 109.5 |
O1—Sn1—N1—C7 | −27.5 (4) | C11—C12—C17—C16 | 178.7 (5) |
C20—Sn1—N1—C7 | 69.4 (4) | C13—C12—C17—C16 | −0.2 (7) |
C24—Sn1—N1—C7 | −115.4 (4) | C10—C9—C18—C17 | −1.1 (7) |
O2—Sn1—N1—C7 | 158.6 (4) | C8—C9—C18—C17 | 178.9 (4) |
O1—Sn1—N1—N2 | 153.6 (3) | C16—C17—C18—C9 | −177.2 (5) |
C20—Sn1—N1—N2 | −109.6 (3) | C12—C17—C18—C9 | 1.2 (7) |
C24—Sn1—N1—N2 | 65.7 (3) | O1—Sn1—C20—C21 | −79.3 (4) |
O2—Sn1—N1—N2 | −20.3 (3) | C24—Sn1—C20—C21 | 22.6 (5) |
C7—N1—N2—C8 | −162.1 (4) | O2—Sn1—C20—C21 | 123.7 (4) |
Sn1—N1—N2—C8 | 17.0 (5) | N1—Sn1—C20—C21 | −163.5 (3) |
O4—Sn2—N3—C34 | 23.2 (4) | Sn1—C20—C21—C22 | −60.6 (5) |
C47—Sn2—N3—C34 | −72.5 (4) | C20—C21—C22—C23 | 178.3 (4) |
C51—Sn2—N3—C34 | 109.8 (4) | O1—Sn1—C24—C25 | −169.9 (4) |
O5—Sn2—N3—C34 | −161.0 (4) | C20—Sn1—C24—C25 | 85.2 (4) |
O4—Sn2—N3—N4 | −153.8 (3) | O2—Sn1—C24—C25 | −16.3 (4) |
C47—Sn2—N3—N4 | 110.6 (3) | N1—Sn1—C24—C25 | −88.4 (4) |
C51—Sn2—N3—N4 | −67.2 (3) | Sn1—C24—C25—C26 | 170.4 (3) |
O5—Sn2—N3—N4 | 22.1 (3) | C24—C25—C26—C27 | 179.2 (4) |
C34—N3—N4—C35 | 163.4 (4) | Sn2—O4—C29—C30 | −135.1 (4) |
Sn2—N3—N4—C35 | −19.3 (4) | Sn2—O4—C29—C28 | 46.9 (6) |
C20—Sn1—O1—C2 | −61.1 (4) | C33—C28—C29—O4 | 178.6 (4) |
C24—Sn1—O1—C2 | 162.8 (4) | C34—C28—C29—O4 | −0.2 (7) |
O2—Sn1—O1—C2 | 59.9 (5) | C33—C28—C29—C30 | 0.6 (7) |
N1—Sn1—O1—C2 | 47.0 (4) | C34—C28—C29—C30 | −178.2 (4) |
O1—Sn1—O2—C8 | 7.4 (5) | O4—C29—C30—C31 | −178.9 (4) |
C20—Sn1—O2—C8 | 129.2 (3) | C28—C29—C30—C31 | −0.9 (7) |
C24—Sn1—O2—C8 | −95.0 (3) | C29—C30—C31—C32 | 0.6 (7) |
N1—Sn1—O2—C8 | 20.7 (3) | C30—C31—C32—C33 | −0.1 (7) |
C47—Sn2—O4—C29 | 60.2 (4) | C30—C31—C32—Cl2 | 180.0 (4) |
C51—Sn2—O4—C29 | −163.2 (4) | C31—C32—C33—C28 | −0.2 (7) |
O5—Sn2—O4—C29 | −56.8 (5) | Cl2—C32—C33—C28 | 179.8 (4) |
N3—Sn2—O4—C29 | −48.2 (3) | C29—C28—C33—C32 | −0.1 (7) |
O4—Sn2—O5—C35 | −12.8 (5) | C34—C28—C33—C32 | 178.8 (4) |
C47—Sn2—O5—C35 | −130.6 (3) | N4—N3—C34—C28 | −177.1 (4) |
C51—Sn2—O5—C35 | 92.2 (3) | Sn2—N3—C34—C28 | 6.1 (6) |
N3—Sn2—O5—C35 | −21.7 (3) | N4—N3—C34—C46 | 1.0 (6) |
Sn1—O1—C2—C3 | 138.3 (4) | Sn2—N3—C34—C46 | −175.8 (3) |
Sn1—O1—C2—C1 | −43.3 (6) | C29—C28—C34—N3 | −26.8 (7) |
C6—C1—C2—O1 | −178.1 (4) | C33—C28—C34—N3 | 154.4 (4) |
C7—C1—C2—O1 | −0.7 (7) | C29—C28—C34—C46 | 155.1 (5) |
C6—C1—C2—C3 | 0.2 (7) | C33—C28—C34—C46 | −23.7 (6) |
C7—C1—C2—C3 | 177.6 (4) | Sn2—O5—C35—N4 | 20.6 (6) |
O1—C2—C3—C4 | 178.2 (4) | Sn2—O5—C35—C36 | −159.9 (3) |
C1—C2—C3—C4 | −0.2 (7) | N3—N4—C35—O5 | −0.7 (6) |
C2—C3—C4—C5 | −0.7 (7) | N3—N4—C35—C36 | 179.8 (4) |
C3—C4—C5—C6 | 1.7 (8) | O5—C35—C36—C45 | −1.4 (7) |
C3—C4—C5—Cl1 | −179.2 (4) | N4—C35—C36—C45 | 178.1 (4) |
C4—C5—C6—C1 | −1.8 (8) | O5—C35—C36—C37 | 177.4 (4) |
Cl1—C5—C6—C1 | 179.1 (4) | N4—C35—C36—C37 | −3.1 (7) |
C2—C1—C6—C5 | 0.8 (7) | C45—C36—C37—O6 | 179.8 (4) |
C7—C1—C6—C5 | −176.8 (4) | C35—C36—C37—O6 | 1.0 (7) |
N2—N1—C7—C1 | 179.9 (4) | C45—C36—C37—C38 | 0.2 (7) |
Sn1—N1—C7—C1 | 0.9 (6) | C35—C36—C37—C38 | −178.6 (4) |
N2—N1—C7—C19 | 0.8 (6) | O6—C37—C38—C39 | 179.3 (4) |
Sn1—N1—C7—C19 | −178.2 (3) | C36—C37—C38—C39 | −1.1 (7) |
C2—C1—C7—N1 | 22.4 (7) | C37—C38—C39—C44 | 1.2 (7) |
C6—C1—C7—N1 | −160.2 (4) | C37—C38—C39—C40 | −178.3 (5) |
C2—C1—C7—C19 | −158.6 (5) | C44—C39—C40—C41 | −1.2 (7) |
C6—C1—C7—C19 | 18.8 (6) | C38—C39—C40—C41 | 178.3 (5) |
Sn1—O2—C8—N2 | −20.6 (6) | C39—C40—C41—C42 | 1.6 (8) |
Sn1—O2—C8—C9 | 159.9 (3) | C40—C41—C42—C43 | −0.8 (8) |
N1—N2—C8—O2 | 2.4 (6) | C41—C42—C43—C44 | −0.2 (8) |
N1—N2—C8—C9 | −178.2 (4) | C38—C39—C44—C45 | −0.5 (7) |
O2—C8—C9—C18 | 0.5 (6) | C40—C39—C44—C45 | 179.0 (4) |
N2—C8—C9—C18 | −179.0 (4) | C38—C39—C44—C43 | −179.4 (5) |
O2—C8—C9—C10 | −179.5 (4) | C40—C39—C44—C43 | 0.2 (7) |
N2—C8—C9—C10 | 1.1 (7) | C42—C43—C44—C45 | −178.3 (5) |
C18—C9—C10—O3 | −179.5 (4) | C42—C43—C44—C39 | 0.6 (7) |
C8—C9—C10—O3 | 0.5 (7) | C37—C36—C45—C44 | 0.6 (7) |
C18—C9—C10—C11 | −0.3 (7) | C35—C36—C45—C44 | 179.4 (4) |
C8—C9—C10—C11 | 179.6 (4) | C39—C44—C45—C36 | −0.4 (7) |
O3—C10—C11—C12 | −179.1 (4) | C43—C44—C45—C36 | 178.5 (5) |
C9—C10—C11—C12 | 1.7 (7) | O4—Sn2—C47—C48 | 143.3 (4) |
C10—C11—C12—C13 | 177.1 (5) | C51—Sn2—C47—C48 | 43.4 (5) |
C10—C11—C12—C17 | −1.7 (7) | O5—Sn2—C47—C48 | −61.2 (4) |
C11—C12—C13—C14 | −177.9 (5) | N3—Sn2—C47—C48 | −133.7 (4) |
C17—C12—C13—C14 | 1.0 (7) | Sn2—C47—C48—C49 | −57.6 (5) |
C12—C13—C14—C15 | −1.0 (8) | C47—C48—C49—C50 | −167.9 (5) |
C13—C14—C15—C16 | 0.3 (8) | O4—Sn2—C51—C52 | 150.9 (4) |
C14—C15—C16—C17 | 0.4 (8) | C47—Sn2—C51—C52 | −106.2 (4) |
C15—C16—C17—C18 | 177.9 (5) | O5—Sn2—C51—C52 | −2.6 (4) |
C15—C16—C17—C12 | −0.5 (7) | N3—Sn2—C51—C52 | 70.8 (4) |
C11—C12—C17—C18 | 0.2 (7) | Sn2—C51—C52—C53 | 75.6 (5) |
C13—C12—C17—C18 | −178.6 (4) | C51—C52—C53—C54 | 179.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···N2 | 0.84 | 1.85 | 2.602 (5) | 147 |
O6—H6A···N4 | 0.84 | 1.88 | 2.617 (5) | 146 |
Experimental details
Crystal data | |
Chemical formula | [Sn(C4H9)2(C19H13ClN2O3)] |
Mr | 585.67 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 24.8256 (13), 7.1994 (4), 28.3649 (15) |
β (°) | 96.376 (1) |
V (Å3) | 5038.3 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.15 |
Crystal size (mm) | 0.25 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.762, 0.846 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 37459, 8881, 8369 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.101, 1.32 |
No. of reflections | 8881 |
No. of parameters | 621 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0158P)2 + 27.1939P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.82, −1.50 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···N2 | 0.84 | 1.85 | 2.602 (5) | 147.4 |
O6—H6A···N4 | 0.84 | 1.88 | 2.617 (5) | 146.3 |
Schiff bases derived from substituted salicylaldehydes have been widely used as polydentate ligands in the preparation of metal complexes. The metal complexes of these hydrazones with substituted salicylaldehydes are known to possess potential biological activities such as antifungal, anticancer and many others [Bernhardt et al. (2006), Ainscough et al. (1999), Mohd Ali et al. (2004)]. We have earlier reported the synthesis and molecular structure of a diphenyltin complex of the Schiff base derived from the reaction of 3-hydroxy-2-naphthoic hydrazide with 5-chlorobenzaldehyde [Lee et al. (2009)]. The crystal structure of this complex consists of discrete molecules in which the tin atom is O,N, O'-chelated by the deprotonated Schiff base ligand. As an extension of our work in structural characterization of organotin with hydrazones, we report here the molecular structure of a dibutyltin complex of a Schiff base derived from the reaction of 3-hydroxy-2-naphthoic hydrazide with 5-chloro-2-hydroxyacetophenone. The unit cell of the title complex consists of two crystallographically independent molecules. In both molecules, the Schiff base ligand, N'-[1-(5-chloro-2-oxidophenyl)ethylidene-3-hydroxy-2-naphthohydrazone] forms a tridentate dianion which coordinated to the dibutyltin fragment in a distorted cis-C2NO2Sn trigonal bipyramidal configuration; the axial O—Sn—O angle are 153.03 (13)o and 152.41 (13)o.