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metal-organic compounds
The six-coordinate Sn atom in bis(diisopropylammonium) diphenyldioxalatostannate(IV), [(C3H7)2NH2]2+ [(C6H5)2Sn(O2CCO2)]2-, exists in a cis-C2SnO4 octahedral coordination sphere [Sn-C 2.139 (7) and 2.144 (7) Å; C-Sn-C 103.8 (3)°]. The ammonium cations and the stannate anions are linked by hydrogen bonds into a zigzag chain, running along the c axis of the monoclinic cell.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019457/bt6339sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019457/bt6339Isup2.hkl |
CCDC reference: 225660
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.014 Å
- R factor = 0.080
- wR factor = 0.166
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.56 Ratio PLAT223_ALERT_4_B Large Solvent/Anion H Ueq(max)/Ueq(min) ... 4.11 Ratio PLAT331_ALERT_2_B Small Av. Phenyl C-C Dist. C7 - C12 = 1.36 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C8 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C9 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C7 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C17 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C20 PLAT331_ALERT_2_C Small Av. Phenyl C-C Dist. C1 - C6 = 1.37 Ang. PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 14 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C13 - C14 = 1.54 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C15 - C16 = 1.55 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Bis(diisopropylammonium) diphenyldioxalatostannate top
Crystal data top
[Sn(C6H5)2(C2O4)2]2C6H16N | F(000) = 1352 |
Mr = 653.33 | Dx = 1.374 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4647 (5) Å | Cell parameters from 5007 reflections |
b = 20.901 (1) Å | θ = 2.5–27.6° |
c = 15.9940 (8) Å | µ = 0.86 mm−1 |
β = 93.364 (1)° | T = 298 K |
V = 3158.6 (3) Å3 | Parallelepiped, colorless |
Z = 4 | 0.29 × 0.18 × 0.12 mm |
Data collection top
Bruker APEX area-detector diffractometer | 5563 independent reflections |
Radiation source: fine-focus sealed tube | 5505 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scan | θmax = 25.0°, θmin = 1.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.705, Tmax = 0.905 | k = −24→24 |
23125 measured reflections | l = −19→19 |
Refinement top
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)] = 0.080 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.166 | H-atom parameters constrained |
S = 1.30 | w = 1/[σ2(Fo2) + (0.0485P)2 + 12.4071P] where P = (Fo2 + 2Fc2)/3 |
5563 reflections | (Δ/σ)max = 0.001 |
352 parameters | Δρmax = 1.14 e Å−3 |
0 restraints | Δρmin = −1.40 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.27877 (5) | 0.33312 (2) | 0.24929 (3) | 0.0380 (2) | |
O1 | 0.1871 (5) | 0.4262 (2) | 0.2226 (3) | 0.048 (1) | |
O2 | 0.2052 (7) | 0.5109 (3) | 0.1410 (4) | 0.070 (2) | |
O3 | 0.3927 (5) | 0.3677 (2) | 0.1478 (3) | 0.050 (1) | |
O4 | 0.4152 (7) | 0.4505 (3) | 0.0633 (4) | 0.074 (2) | |
O5 | 0.4193 (5) | 0.3950 (2) | 0.3273 (3) | 0.044 (1) | |
O6 | 0.4422 (5) | 0.4365 (3) | 0.4547 (3) | 0.055 (1) | |
O7 | 0.1722 (5) | 0.3440 (2) | 0.3617 (3) | 0.040 (1) | |
O8 | 0.1684 (5) | 0.4050 (3) | 0.4757 (3) | 0.050 (1) | |
N1 | 0.3349 (6) | 0.5865 (3) | 0.0161 (4) | 0.045 (1) | |
N2 | 0.2759 (5) | 0.5230 (3) | 0.5553 (3) | 0.039 (1) | |
C1 | 0.4210 (7) | 0.2561 (3) | 0.2808 (4) | 0.040 (2) | |
C2 | 0.3788 (9) | 0.1941 (4) | 0.2688 (5) | 0.060 (2) | |
C3 | 0.465 (1) | 0.1425 (4) | 0.2920 (7) | 0.076 (3) | |
C4 | 0.596 (1) | 0.1530 (5) | 0.3264 (6) | 0.076 (3) | |
C5 | 0.642 (1) | 0.2130 (5) | 0.3401 (8) | 0.090 (3) | |
C6 | 0.554 (1) | 0.2644 (4) | 0.3156 (7) | 0.075 (3) | |
C7 | 0.1025 (8) | 0.2871 (3) | 0.1840 (5) | 0.046 (2) | |
C8 | 0.119 (1) | 0.2565 (6) | 0.1107 (7) | 0.105 (4) | |
C9 | 0.011 (2) | 0.2240 (6) | 0.0670 (9) | 0.125 (6) | |
C10 | −0.115 (2) | 0.2208 (5) | 0.0973 (9) | 0.100 (4) | |
C11 | −0.136 (1) | 0.2495 (7) | 0.1701 (8) | 0.102 (4) | |
C12 | −0.027 (1) | 0.2833 (5) | 0.2128 (5) | 0.072 (3) | |
C13 | 0.2409 (8) | 0.4580 (3) | 0.1644 (5) | 0.046 (2) | |
C14 | 0.3590 (8) | 0.4229 (3) | 0.1202 (4) | 0.046 (2) | |
C15 | 0.3755 (6) | 0.4078 (3) | 0.3983 (4) | 0.036 (1) | |
C16 | 0.2245 (6) | 0.3843 (3) | 0.4146 (4) | 0.035 (1) | |
C17 | 0.221 (1) | 0.5944 (4) | −0.0521 (5) | 0.062 (2) | |
C18 | 0.219 (2) | 0.5357 (8) | −0.1048 (9) | 0.148 (7) | |
C19 | 0.083 (1) | 0.6058 (6) | −0.0181 (7) | 0.099 (4) | |
C20 | 0.3693 (9) | 0.6434 (4) | 0.0707 (5) | 0.056 (2) | |
C21 | 0.470 (1) | 0.6221 (6) | 0.1418 (6) | 0.091 (3) | |
C22 | 0.428 (1) | 0.6979 (4) | 0.0218 (7) | 0.085 (3) | |
C23 | 0.2518 (8) | 0.5130 (4) | 0.6461 (4) | 0.050 (2) | |
C24 | 0.1006 (9) | 0.4960 (5) | 0.6579 (5) | 0.073 (3) | |
C25 | 0.356 (1) | 0.4641 (5) | 0.6786 (6) | 0.074 (3) | |
C26 | 0.1860 (7) | 0.5697 (4) | 0.5071 (5) | 0.050 (2) | |
C27 | 0.2337 (9) | 0.5731 (4) | 0.4193 (5) | 0.064 (2) | |
C28 | 0.188 (1) | 0.6340 (4) | 0.5487 (7) | 0.076 (3) | |
H1n1 | 0.4146 | 0.5744 | −0.0075 | 0.054* | |
H1n2 | 0.3096 | 0.5542 | 0.0493 | 0.054* | |
H2n1 | 0.3666 | 0.5351 | 0.5516 | 0.047* | |
H2n2 | 0.2659 | 0.4849 | 0.5295 | 0.047* | |
H2 | 0.2891 | 0.1862 | 0.2441 | 0.072* | |
H3 | 0.4322 | 0.1009 | 0.2838 | 0.091* | |
H4 | 0.6543 | 0.1186 | 0.3407 | 0.091* | |
H5 | 0.7307 | 0.2203 | 0.3658 | 0.108* | |
H6 | 0.5882 | 0.3058 | 0.3234 | 0.090* | |
H8 | 0.2081 | 0.2573 | 0.0887 | 0.125* | |
H9 | 0.0276 | 0.2044 | 0.0162 | 0.150* | |
H10 | −0.1882 | 0.1989 | 0.0684 | 0.120* | |
H11 | −0.2246 | 0.2470 | 0.1925 | 0.123* | |
H12 | −0.0454 | 0.3038 | 0.2627 | 0.087* | |
H17 | 0.2450 | 0.6311 | −0.0867 | 0.075* | |
H18a | 0.1473 | 0.5397 | −0.1493 | 0.222* | |
H18b | 0.1996 | 0.4991 | −0.0710 | 0.222* | |
H18c | 0.3098 | 0.5304 | −0.1281 | 0.222* | |
H19a | 0.0873 | 0.6441 | 0.0150 | 0.149* | |
H19b | 0.0591 | 0.5702 | 0.0162 | 0.149* | |
H19c | 0.0128 | 0.6106 | −0.0634 | 0.149* | |
H20 | 0.2816 | 0.6579 | 0.0944 | 0.067* | |
H21a | 0.4282 | 0.5875 | 0.1712 | 0.136* | |
H21b | 0.4883 | 0.6573 | 0.1796 | 0.136* | |
H21c | 0.5569 | 0.6081 | 0.1200 | 0.136* | |
H22a | 0.3602 | 0.7099 | −0.0226 | 0.127* | |
H22b | 0.5143 | 0.6848 | −0.0015 | 0.127* | |
H22c | 0.4456 | 0.7338 | 0.0583 | 0.127* | |
H23 | 0.2726 | 0.5533 | 0.6757 | 0.060* | |
H24a | 0.0873 | 0.4902 | 0.7164 | 0.109* | |
H24b | 0.0774 | 0.4570 | 0.6284 | 0.109* | |
H24c | 0.0402 | 0.5297 | 0.6363 | 0.109* | |
H25a | 0.3438 | 0.4568 | 0.7370 | 0.111* | |
H25b | 0.4503 | 0.4791 | 0.6714 | 0.111* | |
H25c | 0.3407 | 0.4248 | 0.6483 | 0.111* | |
H26 | 0.0884 | 0.5538 | 0.5044 | 0.059* | |
H27a | 0.2313 | 0.5311 | 0.3950 | 0.096* | |
H27b | 0.3285 | 0.5895 | 0.4203 | 0.096* | |
H27c | 0.1717 | 0.6009 | 0.3864 | 0.096* | |
H28a | 0.1584 | 0.6297 | 0.6048 | 0.114* | |
H28b | 0.1251 | 0.6625 | 0.5177 | 0.114* | |
H28c | 0.2825 | 0.6511 | 0.5503 | 0.114* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0440 (3) | 0.0331 (3) | 0.0375 (3) | 0.0003 (2) | 0.006 (2) | −0.0027 (2) |
O1 | 0.052 (3) | 0.033 (3) | 0.061 (3) | 0.009 (2) | 0.015 (2) | −0.001 (2) |
O2 | 0.091 (4) | 0.043 (3) | 0.076 (4) | 0.019 (3) | 0.026 (3) | 0.015 (3) |
O3 | 0.061 (3) | 0.039 (3) | 0.053 (3) | 0.009 (2) | 0.023 (2) | 0.004 (2) |
O4 | 0.085 (4) | 0.057 (4) | 0.083 (4) | 0.015 (3) | 0.040 (4) | 0.024 (3) |
O5 | 0.039 (3) | 0.043 (3) | 0.051 (3) | −0.008 (2) | 0.013 (2) | −0.012 (2) |
O6 | 0.032 (3) | 0.071 (4) | 0.060 (3) | −0.004 (2) | 0.001 (2) | −0.021 (3) |
O7 | 0.042 (3) | 0.040 (3) | 0.037 (2) | −0.008 (2) | 0.010 (2) | −0.006 (2) |
O8 | 0.038 (3) | 0.064 (3) | 0.049 (3) | −0.004 (2) | 0.011 (2) | −0.016 (3) |
N1 | 0.045 (3) | 0.043 (3) | 0.048 (3) | 0.008 (3) | 0.006 (3) | 0.005 (3) |
N2 | 0.030 (3) | 0.045 (3) | 0.042 (3) | −0.004 (2) | 0.006 (2) | −0.008 (3) |
C1 | 0.041 (4) | 0.040 (4) | 0.039 (4) | 0.002 (3) | 0.002 (3) | 0.001 (3) |
C2 | 0.061 (5) | 0.049 (5) | 0.070 (6) | 0.001 (4) | 0.002 (4) | −0.001 (4) |
C3 | 0.080 (7) | 0.042 (5) | 0.107 (8) | 0.004 (4) | 0.018 (6) | 0.004 (5) |
C4 | 0.076 (7) | 0.062 (6) | 0.089 (7) | 0.030 (5) | 0.009 (5) | 0.017 (5) |
C5 | 0.061 (6) | 0.086 (8) | 0.121 (9) | 0.023 (5) | −0.020 (6) | −0.011 (7) |
C6 | 0.078 (7) | 0.045 (5) | 0.101 (8) | 0.006 (4) | −0.007 (5) | −0.008 (5) |
C7 | 0.050 (4) | 0.036 (4) | 0.051 (4) | 0.003 (3) | −0.020 (3) | −0.016 (3) |
C8 | 0.074 (7) | 0.12 (1) | 0.113 (9) | 0.025 (6) | −0.026 (6) | −0.070 (8) |
C9 | 0.099 (9) | 0.13 (1) | 0.14 (1) | 0.032 (8) | −0.049 (9) | −0.10 (1) |
C10 | 0.11 (1) | 0.061 (6) | 0.1391) | −0.002 (6) | −0.058 (8) | −0.015 (7) |
C11 | 0.066 (7) | 0.14 (1) | 0.095 (8) | −0.039 (7) | −0.023 (6) | 0.034 (8) |
C12 | 0.068 (6) | 0.099 (7) | 0.049 (5) | −0.018 (5) | −0.008 (4) | 0.003 (5) |
C13 | 0.055 (5) | 0.038 (4) | 0.047 (4) | 0.002 (3) | 0.007 (3) | −0.005 (3) |
C14 | 0.054 (4) | 0.045 (4) | 0.038 (4) | −0.003 (3) | 0.009 (3) | 0.009 (3) |
C15 | 0.028 (3) | 0.038 (4) | 0.041 (4) | 0.005 (3) | −0.007 (3) | −0.008 (3) |
C16 | 0.030 (3) | 0.036 (3) | 0.039 (4) | 0.004 (3) | −0.001 (3) | 0.000 (3) |
C17 | 0.072 (6) | 0.060 (5) | 0.053 (5) | 0.002 (4) | −0.008 (4) | 0.008 (4) |
C18 | 0.15 (1) | 0.17 (2) | 0.12 (1) | 0.03 (1) | −0.037 (9) | −0.09 (1) |
C19 | 0.068 (7) | 0.13 (1) | 0.097 (8) | 0.013 (7) | −0.010 (6) | 0.016 (8) |
C20 | 0.059 (5) | 0.052 (4) | 0.057 (5) | 0.004 (4) | 0.005 (4) | −0.009 (4) |
C21 | 0.091 (8) | 0.100 (8) | 0.079 (7) | −0.010 (6) | −0.023 (6) | −0.001 (6) |
C22 | 0.104 (8) | 0.049 (5) | 0.101 (8) | −0.004 (5) | −0.004 (6) | −0.015 (5) |
C23 | 0.054 (5) | 0.060 (5) | 0.035 (4) | −0.007 (4) | 0.001 (3) | −0.011 (3) |
C24 | 0.051 (5) | 0.117 (8) | 0.051 (5) | −0.017 (5) | 0.009 (4) | −0.003 (5) |
C25 | 0.083 (7) | 0.083 (7) | 0.055 (5) | −0.004 (5) | −0.006 (5) | 0.010 (5) |
C26 | 0.029 (4) | 0.051 (4) | 0.068 (5) | −0.005 (3) | −0.001 (3) | 0.008 (4) |
C27 | 0.062 (5) | 0.068 (6) | 0.061 (5) | −0.001 (4) | 0.000 (4) | 0.021 (4) |
C28 | 0.066 (6) | 0.052 (5) | 0.110 (8) | 0.006 (4) | 0.003 (5) | −0.014 (5) |
Geometric parameters (Å, º) top
Sn1—C1 | 2.139 (7) | N1—H1n2 | 0.90 |
Sn1—C7 | 2.144 (7) | N2—H2n1 | 0.90 |
Sn1—O1 | 2.162 (5) | N2—H2n2 | 0.90 |
Sn1—O3 | 2.128 (5) | C2—H2 | 0.93 |
Sn1—O5 | 2.191 (5) | C3—H3 | 0.93 |
Sn1—O7 | 2.124 (4) | C4—H4 | 0.93 |
O1—C13 | 1.275 (8) | C5—H5 | 0.93 |
O2—C13 | 1.209 (9) | C6—H6 | 0.93 |
O3—C14 | 1.269 (8) | C8—H8 | 0.93 |
O4—C14 | 1.226 (8) | C9—H9 | 0.93 |
O5—C15 | 1.261 (8) | C10—H10 | 0.93 |
O6—C15 | 1.227 (8) | C11—H11 | 0.93 |
O7—C16 | 1.272 (8) | C12—H12 | 0.93 |
O8—C16 | 1.219 (8) | C17—H17 | 0.98 |
N1—C17 | 1.50 (1) | C18—H18a | 0.96 |
N1—C20 | 1.499 (9) | C18—H18b | 0.96 |
N2—C23 | 1.499 (8) | C18—H18c | 0.96 |
N2—C26 | 1.481 (9) | C19—H19a | 0.96 |
C1—C6 | 1.36 (1) | C19—H19b | 0.96 |
C1—C2 | 1.37 (1) | C19—H19c | 0.96 |
C2—C3 | 1.39 (1) | C20—H20 | 0.98 |
C3—C4 | 1.34 (1) | C21—H21a | 0.96 |
C4—C5 | 1.34 (1) | C21—H21b | 0.96 |
C5—C6 | 1.40 (1) | C21—H21c | 0.96 |
C7—C12 | 1.34 (1) | C22—H22a | 0.96 |
C7—C8 | 1.35 (1) | C22—H22b | 0.96 |
C8—C9 | 1.38 (2) | C22—H22c | 0.96 |
C9—C10 | 1.32 (2) | C23—H23 | 0.98 |
C10—C11 | 1.34 (2) | C24—H24a | 0.96 |
C11—C12 | 1.39 (1) | C24—H24b | 0.96 |
C13—C14 | 1.54 (1) | C24—H24c | 0.96 |
C15—C16 | 1.547 (9) | C25—H25a | 0.96 |
C17—C19 | 1.46 (1) | C25—H25b | 0.96 |
C17—C18 | 1.49 (1) | C25—H25c | 0.96 |
C20—C22 | 1.51 (1) | C26—H26 | 0.98 |
C20—C21 | 1.51 (1) | C27—H27a | 0.96 |
C23—C25 | 1.49 (1) | C27—H27b | 0.96 |
C23—C24 | 1.50 (1) | C27—H27c | 0.96 |
C26—C28 | 1.50 (1) | C28—H28a | 0.96 |
C26—C27 | 1.50 (1) | C28—H28b | 0.96 |
N1—H1n1 | 0.90 | C28—H28c | 0.96 |
C1—Sn1—C7 | 103.8 (3) | C5—C4—H4 | 119.9 |
C1—Sn1—O1 | 164.4 (2) | C4—C5—H5 | 120.3 |
C1—Sn1—O3 | 95.5 (2) | C6—C5—H5 | 120.3 |
C1—Sn1—O5 | 87.6 (2) | C1—C6—H6 | 118.8 |
C1—Sn1—O7 | 101.8 (2) | C5—C6—H6 | 118.8 |
C7—Sn1—O1 | 90.9 (2) | C7—C8—H8 | 118.3 |
C7—Sn1—O3 | 101.3 (3) | C9—C8—H8 | 118.3 |
C7—Sn1—O5 | 166.2 (2) | C10—C9—H9 | 120.1 |
C7—Sn1—O7 | 93.8 (2) | C8—C9—H9 | 120.1 |
O1—Sn1—O3 | 76.0 (2) | C9—C10—H10 | 120.5 |
O1—Sn1—O5 | 78.8 (2) | C11—C10—H10 | 120.5 |
O1—Sn1—O7 | 82.3 (2) | C10—C11—H11 | 119.7 |
O3—Sn1—O7 | 153.6 (2) | C12—C11—H11 | 119.7 |
O3—Sn1—O5 | 85.2 (2) | C7—C12—H12 | 119.0 |
O7—Sn1—O5 | 76.0 (2) | C11—C12—H12 | 119.0 |
C13—O1—Sn1 | 116.2 (4) | C19—C17—H17 | 108.7 |
C14—O3—Sn1 | 116.5 (4) | C18—C17—H17 | 108.7 |
C15—O5—Sn1 | 114.7 (4) | N1—C17—H17 | 108.7 |
C16—O7—Sn1 | 116.6 (4) | C17—C18—H18a | 109.5 |
C17—N1—C20 | 117.4 (6) | C17—C18—H18b | 109.5 |
C26—N2—C23 | 118.8 (6) | H18a—C18—H18b | 109.5 |
C6—C1—C2 | 115.8 (7) | C17—C18—H18c | 109.5 |
C6—C1—Sn1 | 123.8 (6) | H18a—C18—H18c | 109.5 |
C2—C1—Sn1 | 120.4 (6) | H18b—C18—H18c | 109.5 |
C1—C2—C3 | 122.5 (8) | C17—C19—H19a | 109.5 |
C4—C3—C2 | 119.6 (9) | C17—C19—H19b | 109.5 |
C3—C4—C5 | 120.2 (9) | H19a—C19—H19b | 109.5 |
C4—C5—C6 | 119.4 (9) | C17—C19—H19c | 109.5 |
C1—C6—C5 | 122.4 (9) | H19a—C19—H19c | 109.5 |
C12—C7—C8 | 115.3 (8) | H19b—C19—H19c | 109.5 |
C12—C7—Sn1 | 124.2 (6) | N1—C20—H20 | 108.1 |
C8—C7—Sn1 | 120.5 (7) | C22—C20—H20 | 108.1 |
C7—C8—C9 | 123 (1) | C21—C20—H20 | 108.1 |
C10—C9—C8 | 120 (1) | C20—C21—H21a | 109.5 |
C9—C10—C11 | 119 (1) | C20—C21—H21b | 109.5 |
C10—C11—C12 | 121 (1) | H21a—C21—H21b | 109.5 |
C7—C12—C11 | 122 (1) | C20—C21—H21c | 109.5 |
O2—C13—O1 | 125.9 (7) | H21a—C21—H21c | 109.5 |
O2—C13—C14 | 119.4 (7) | H21b—C21—H21c | 109.5 |
O1—C13—C14 | 114.7 (6) | C20—C22—H22a | 109.5 |
O4—C14—O3 | 125.1 (7) | C20—C22—H22b | 109.5 |
O4—C14—C13 | 118.3 (6) | H22a—C22—H22b | 109.5 |
O3—C14—C13 | 116.6 (6) | C20—C22—H22c | 109.5 |
O6—C15—O5 | 125.7 (6) | H22a—C22—H22c | 109.5 |
O6—C15—C16 | 118.2 (6) | H22b—C22—H22c | 109.5 |
O5—C15—C16 | 116.1 (5) | C25—C23—H23 | 108.1 |
O8—C16—O7 | 126.7 (6) | C24—C23—H23 | 108.1 |
O8—C16—C15 | 118.1 (6) | N2—C23—H23 | 108.1 |
O7—C16—C15 | 115.2 (5) | C23—C24—H24a | 109.5 |
C19—C17—C18 | 111 (1) | C23—C24—H24b | 109.5 |
C19—C17—N1 | 111.5 (8) | H24a—C24—H24b | 109.5 |
C18—C17—N1 | 107.9 (8) | C23—C24—H24c | 109.5 |
N1—C20—C22 | 111.8 (7) | H24a—C24—H24c | 109.5 |
N1—C20—C21 | 108.2 (7) | H24b—C24—H24c | 109.5 |
C22—C20—C21 | 112.4 (8) | C23—C25—H25a | 109.5 |
C25—C23—C24 | 114.2 (8) | C23—C25—H25b | 109.5 |
C25—C23—N2 | 107.4 (6) | H25a—C25—H25b | 109.5 |
C24—C23—N2 | 110.9 (6) | C23—C25—H25c | 109.5 |
N2—C26—C28 | 111.5 (7) | H25a—C25—H25c | 109.5 |
N2—C26—C27 | 108.8 (6) | H25b—C25—H25c | 109.5 |
C28—C26—C27 | 112.0 (7) | N2—C26—H26 | 108.1 |
C17—N1—H1n1 | 108.0 | C28—C26—H26 | 108.1 |
C20—N1—H1n1 | 108.0 | C27—C26—H26 | 108.1 |
C17—N1—H1n2 | 108.0 | C26—C27—H27a | 109.5 |
C20—N1—H1n2 | 108.0 | C26—C27—H27b | 109.5 |
H1n1—N1—H1n2 | 107.2 | H27a—C27—H27b | 109.5 |
C26—N2—H2n1 | 107.6 | C26—C27—H27c | 109.5 |
C23—N2—H2n1 | 107.6 | H27a—C27—H27c | 109.5 |
C26—N2—H2n2 | 107.6 | H27b—C27—H27c | 109.5 |
C23—N2—H2n2 | 107.6 | C26—C28—H28a | 109.5 |
H2n1—N2—H2n2 | 107.1 | C26—C28—H28b | 109.5 |
C1—C2—H2 | 118.7 | H28a—C28—H28b | 109.5 |
C3—C2—H2 | 118.7 | C26—C28—H28c | 109.5 |
C4—C3—H3 | 120.2 | H28a—C28—H28c | 109.5 |
C2—C3—H3 | 120.2 | H28b—C28—H28c | 109.5 |
C3—C4—H4 | 119.9 | ||
O7—Sn1—O1—C13 | 163.1 (5) | C1—Sn1—C7—C12 | 113.3 (7) |
O3—Sn1—O1—C13 | −1.8 (5) | O1—Sn1—C7—C12 | −72.2 (7) |
C1—Sn1—O1—C13 | 57 (1) | O5—Sn1—C7—C12 | −31 (2) |
C7—Sn1—O1—C13 | −103.2 (5) | O7—Sn1—C7—C8 | −166.4 (8) |
O5—Sn1—O1—C13 | 86.0 (5) | O3—Sn1—C7—C8 | 35.3 (8) |
O7—Sn1—O3—C14 | −35.0 (8) | C1—Sn1—C7—C8 | −63.2 (9) |
C1—Sn1—O3—C14 | −166.1 (5) | O1—Sn1—C7—C8 | 111.3 (8) |
C7—Sn1—O3—C14 | 88.6 (6) | O5—Sn1—C7—C8 | 152 (1) |
O1—Sn1—O3—C14 | 0.5 (5) | C12—C7—C8—C9 | 0.9 (17) |
O5—Sn1—O3—C14 | −79.1 (5) | Sn1—C7—C8—C9 | 178 (1) |
O7—Sn1—O5—C15 | 0.0 (4) | C7—C8—C9—C10 | −1 (2) |
O3—Sn1—O5—C15 | 161.5 (5) | C8—C9—C10—C11 | 0 (2) |
C1—Sn1—O5—C15 | −102.8 (5) | C9—C10—C11—C12 | 1 (2) |
C7—Sn1—O5—C15 | 43 (1) | C8—C7—C12—C11 | 1 (2) |
O1—Sn1—O5—C15 | 84.8 (5) | Sn1—C7—C12—C11 | −176.2 (8) |
O3—Sn1—O7—C16 | −37.8 (7) | C10—C11—C12—C7 | −2 (2) |
C1—Sn1—O7—C16 | 92.2 (5) | Sn1—O1—C13—O2 | −179.2 (7) |
C7—Sn1—O7—C16 | −162.9 (5) | Sn1—O1—C13—C14 | 2.6 (8) |
O1—Sn1—O7—C16 | −72.5 (4) | Sn1—O3—C14—O4 | 178.6 (7) |
O5—Sn1—O7—C16 | 7.8 (4) | Sn1—O3—C14—C13 | 0.6 (8) |
O7—Sn1—C1—C6 | −90.0 (7) | O2—C13—C14—O4 | 1.4 (12) |
O3—Sn1—C1—C6 | 70.0 (7) | O1—C13—C14—O4 | 179.7 (7) |
C7—Sn1—C1—C6 | 173.1 (7) | O2—C13—C14—O3 | 179.5 (7) |
O1—Sn1—C1—C6 | 14 (1) | O1—C13—C14—O3 | −2 (1) |
O5—Sn1—C1—C6 | −14.9 (7) | Sn1—O5—C15—O6 | 173.1 (6) |
O7—Sn1—C1—C2 | 87.8 (6) | Sn1—O5—C15—C16 | −6.4 (7) |
O3—Sn1—C1—C2 | −112.2 (6) | Sn1—O7—C16—O8 | 167.4 (6) |
C7—Sn1—C1—C2 | −9.1 (7) | Sn1—O7—C16—C15 | −13.2 (7) |
O1—Sn1—C1—C2 | −168.3 (7) | O6—C15—C16—O8 | 13.2 (9) |
O5—Sn1—C1—C2 | 162.9 (6) | O5—C15—C16—O8 | −167.2 (6) |
C6—C1—C2—C3 | 1.2 (13) | O6—C15—C16—O7 | −166.2 (6) |
Sn1—C1—C2—C3 | −176.8 (7) | O5—C15—C16—O7 | 13.3 (8) |
C1—C2—C3—C4 | −1 (2) | C20—N1—C17—C19 | −65 (1) |
C2—C3—C4—C5 | 2 (2) | C20—N1—C17—C18 | 172.3 (9) |
C3—C4—C5—C6 | −2 (2) | C17—N1—C20—C22 | −63.8 (9) |
C2—C1—C6—C5 | −2 (1) | C17—N1—C20—C21 | 171.9 (7) |
Sn1—C1—C6—C5 | 176.0 (8) | C26—N2—C23—C25 | −180.0 (6) |
C4—C5—C6—C1 | 3 (2) | C26—N2—C23—C24 | 54.7 (9) |
O7—Sn1—C7—C12 | 10.2 (8) | C23—N2—C26—C28 | 53.7 (9) |
O3—Sn1—C7—C12 | −148.1 (7) | C23—N2—C26—C27 | 177.8 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n2···O2 | 0.90 | 2.03 | 2.878 (8) | 157 |
N1—H1n2···O4 | 0.90 | 2.39 | 3.026 (8) | 128 |
N1—H1n1···O4i | 0.90 | 1.96 | 2.856 (8) | 178 |
N2—H2n2···O6 | 0.90 | 2.34 | 2.938 (7) | 124 |
N2—H2n1···O6ii | 0.90 | 1.91 | 2.812 (7) | 178 |
N2—H2n2···O8 | 0.90 | 2.07 | 2.931 (7) | 160 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1. |
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