A novel oxastannaborininol, 1,1-dibutyl-1H,3H-naphtho[1,8-cd][1,2,6]oxastannaborinin-3-ol, has been synthesized and crystallized. It is the first reported compound with a heterocycle containing an Sn–O–B unit.
Supporting information
CCDC reference: 2057745
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean
(C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.024
- wR factor = 0.066
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level A
DIFF019_ALERT_1_A _diffrn_standards_number is missing
Number of standards used in measurement.
DIFF020_ALERT_1_A _diffrn_standards_interval_count and
_diffrn_standards_interval_time are missing. Number of measurements
between standards or time (min) between standards.
DIFF022_ALERT_1_A _diffrn_standards_decay_% is missing
Percentage decrease in standards intensity.
Alert level C
PLAT220_ALERT_2_C NonSolvent Resd 1 C Ueq(max)/Ueq(min) Range 3.6 Ratio
Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 20 Note
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing .............. 0.00010 Ang.
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records 4 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records 1 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Sn1 --C17 . 9.2 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Sn1A --C17 . 14.4 s.u.
PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 41% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 18 Note
PLAT721_ALERT_1_G Bond Calc 0.96000, Rep 0.97000 Dev... 0.01 Ang.
C1A -H1AA 1.555 1.555 ........ # 62 Check
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms .... ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 167 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 41 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 6 Info
3 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
15 ALERT level G = General information/check it is not something unexpected
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 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
7 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
1,1-Dibutyl-1
H,3
H-naphtho[1,8-
cd][1,2,6]oxastannaborinin-3-ol
top
Crystal data top
[Sn(C4H9)2(C10H7BO2)] | F(000) = 1632 |
Mr = 402.88 | Dx = 1.468 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54184 Å |
a = 30.1386 (6) Å | Cell parameters from 21527 reflections |
b = 11.2948 (1) Å | θ = 4.5–79.4° |
c = 16.4726 (3) Å | µ = 11.17 mm−1 |
β = 139.457 (4)° | T = 200 K |
V = 3644.9 (2) Å3 | Plate, clear colourless |
Z = 8 | 0.26 × 0.13 × 0.02 mm |
Data collection top
Rigaku Oxford Diffraction XtaLAB Synergy, Dualflex, Pilatus 300K diffractometer | 3724 reflections with I > 2σ(I) |
ω scans | Rint = 0.033 |
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2018) | θmax = 79.6°, θmin = 4.5° |
Tmin = 0.234, Tmax = 1.000 | h = −38→29 |
28847 measured reflections | k = −14→14 |
3923 independent reflections | l = −17→20 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.024 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.066 | w = 1/[σ2(Fo2) + (0.0359P)2 + 2.7329P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
3923 reflections | Δρmax = 0.45 e Å−3 |
264 parameters | Δρmin = −0.39 e Å−3 |
167 restraints | |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Sn1 | 0.80127 (4) | 0.57065 (8) | 0.24979 (9) | 0.03908 (16) | 0.705 (6) |
O1 | 0.75421 (8) | 0.66412 (13) | 0.09740 (13) | 0.0452 (3) | |
O2 | 0.66330 (9) | 0.77545 (16) | −0.07920 (16) | 0.0560 (4) | |
H2 | 0.6923 (15) | 0.790 (3) | −0.079 (3) | 0.084* | |
C18 | 0.65789 (11) | 0.61897 (17) | 0.12184 (19) | 0.0411 (4) | |
C17 | 0.72252 (13) | 0.56497 (18) | 0.2265 (2) | 0.0465 (5) | |
C9 | 0.64190 (11) | 0.68493 (18) | 0.02737 (19) | 0.0427 (4) | |
C13 | 0.60618 (13) | 0.6048 (2) | 0.1109 (2) | 0.0498 (5) | |
C16 | 0.73393 (15) | 0.5022 (2) | 0.3129 (3) | 0.0606 (6) | |
H16 | 0.776391 | 0.467551 | 0.380439 | 0.073* | |
C12 | 0.54116 (13) | 0.6536 (3) | 0.0087 (3) | 0.0628 (6) | |
H12 | 0.507856 | 0.643613 | 0.002056 | 0.075* | |
C15 | 0.68324 (17) | 0.4895 (3) | 0.3016 (3) | 0.0676 (7) | |
H15 | 0.692174 | 0.447318 | 0.361363 | 0.081* | |
B1 | 0.69046 (12) | 0.7075 (2) | 0.0188 (2) | 0.0403 (4) | |
C14 | 0.62094 (16) | 0.5390 (2) | 0.2029 (3) | 0.0609 (6) | |
H14 | 0.587231 | 0.529701 | 0.195310 | 0.073* | |
C10 | 0.57682 (13) | 0.7313 (2) | −0.0696 (2) | 0.0571 (6) | |
H10 | 0.565960 | 0.775310 | −0.130655 | 0.069* | |
C11 | 0.52614 (14) | 0.7150 (3) | −0.0803 (3) | 0.0698 (7) | |
H11 | 0.482665 | 0.746192 | −0.148228 | 0.084* | |
C7 | 0.9197 (5) | 0.8346 (9) | 0.5547 (9) | 0.0641 (11) | 0.705 (6) |
H7A | 0.927199 | 0.892715 | 0.522732 | 0.077* | 0.705 (6) |
H7B | 0.962017 | 0.791753 | 0.621729 | 0.077* | 0.705 (6) |
C6 | 0.8653 (4) | 0.7496 (5) | 0.4523 (7) | 0.0553 (11) | 0.705 (6) |
H6A | 0.823204 | 0.793127 | 0.385509 | 0.066* | 0.705 (6) |
H6B | 0.857484 | 0.692717 | 0.484475 | 0.066* | 0.705 (6) |
C1 | 0.8221 (5) | 0.3983 (7) | 0.2290 (11) | 0.0757 (19) | 0.705 (6) |
H1A | 0.854211 | 0.357484 | 0.308673 | 0.091* | 0.705 (6) |
H1B | 0.780202 | 0.352665 | 0.169737 | 0.091* | 0.705 (6) |
C5 | 0.8825 (3) | 0.6821 (5) | 0.3978 (6) | 0.0555 (11) | 0.705 (6) |
H5A | 0.923203 | 0.634959 | 0.462947 | 0.067* | 0.705 (6) |
H5B | 0.891816 | 0.738315 | 0.367705 | 0.067* | 0.705 (6) |
C8 | 0.9005 (7) | 0.8980 (10) | 0.6062 (8) | 0.0776 (15) | 0.705 (6) |
H8A | 0.855991 | 0.932701 | 0.538591 | 0.116* | 0.705 (6) |
H8B | 0.933280 | 0.959032 | 0.662845 | 0.116* | 0.705 (6) |
H8C | 0.900010 | 0.842311 | 0.649544 | 0.116* | 0.705 (6) |
C3A | 0.9362 (9) | 0.469 (2) | 0.2939 (13) | 0.131 (9) | 0.295 (6) |
H3AA | 0.980912 | 0.440122 | 0.340706 | 0.158* | 0.295 (6) |
H3AB | 0.940412 | 0.552561 | 0.313166 | 0.158* | 0.295 (6) |
C2 | 0.8516 (4) | 0.4040 (4) | 0.1841 (8) | 0.110 (2) | 0.705 (6) |
H2A | 0.859231 | 0.324071 | 0.175231 | 0.132* | 0.705 (6) |
H2B | 0.818392 | 0.441013 | 0.102315 | 0.132* | 0.705 (6) |
C4 | 0.9615 (5) | 0.4669 (7) | 0.2585 (10) | 0.142 (3) | 0.705 (6) |
H4A | 0.943675 | 0.519424 | 0.193075 | 0.213* | 0.705 (6) |
H4B | 0.962191 | 0.387520 | 0.238623 | 0.213* | 0.705 (6) |
H4C | 1.007051 | 0.490615 | 0.335834 | 0.213* | 0.705 (6) |
C4A | 0.8861 (8) | 0.4541 (14) | 0.1525 (11) | 0.117 (6) | 0.295 (6) |
H4AA | 0.840486 | 0.445560 | 0.109470 | 0.176* | 0.295 (6) |
H4AB | 0.898299 | 0.384852 | 0.138891 | 0.176* | 0.295 (6) |
H4AC | 0.888484 | 0.522479 | 0.121278 | 0.176* | 0.295 (6) |
C3 | 0.9174 (5) | 0.4718 (7) | 0.2707 (12) | 0.149 (5) | 0.705 (6) |
H3A | 0.906412 | 0.554416 | 0.264650 | 0.179* | 0.705 (6) |
H3B | 0.945236 | 0.446432 | 0.354910 | 0.179* | 0.705 (6) |
C2A | 0.9121 (6) | 0.4051 (10) | 0.3302 (14) | 0.091 (4) | 0.295 (6) |
H2AA | 0.941594 | 0.426381 | 0.416263 | 0.110* | 0.295 (6) |
H2AB | 0.919817 | 0.321779 | 0.330202 | 0.110* | 0.295 (6) |
C1A | 0.8408 (11) | 0.4164 (14) | 0.261 (3) | 0.100 (8) | 0.295 (6) |
H1AA | 0.833837 | 0.357857 | 0.293132 | 0.120* | 0.295 (6) |
H1AB | 0.810547 | 0.396319 | 0.173984 | 0.120* | 0.295 (6) |
Sn1A | 0.8101 (2) | 0.5864 (4) | 0.2649 (3) | 0.0696 (7) | 0.295 (6) |
C5A | 0.8830 (9) | 0.7164 (16) | 0.4067 (17) | 0.0555 (11) | 0.295 (6) |
H5AA | 0.926737 | 0.677223 | 0.474024 | 0.067* | 0.295 (6) |
H5AB | 0.888251 | 0.774727 | 0.371250 | 0.067* | 0.295 (6) |
C6A | 0.8671 (11) | 0.7814 (15) | 0.4627 (19) | 0.0553 (11) | 0.295 (6) |
H6AA | 0.827565 | 0.831359 | 0.398553 | 0.066* | 0.295 (6) |
H6AB | 0.854627 | 0.723469 | 0.486213 | 0.066* | 0.295 (6) |
C7A | 0.9231 (13) | 0.856 (3) | 0.574 (2) | 0.0641 (11) | 0.295 (6) |
H7AA | 0.931733 | 0.920516 | 0.547875 | 0.077* | 0.295 (6) |
H7AB | 0.964334 | 0.808857 | 0.633969 | 0.077* | 0.295 (6) |
C8A | 0.9093 (18) | 0.908 (3) | 0.637 (2) | 0.0776 (15) | 0.295 (6) |
H8AA | 0.879434 | 0.974810 | 0.589615 | 0.116* | 0.295 (6) |
H8AB | 0.951534 | 0.932796 | 0.719433 | 0.116* | 0.295 (6) |
H8AC | 0.888151 | 0.849241 | 0.640933 | 0.116* | 0.295 (6) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.0426 (2) | 0.0423 (2) | 0.04336 (19) | 0.00587 (15) | 0.03572 (17) | 0.00775 (15) |
O1 | 0.0546 (8) | 0.0530 (8) | 0.0488 (7) | 0.0110 (6) | 0.0450 (7) | 0.0129 (6) |
O2 | 0.0562 (9) | 0.0733 (11) | 0.0550 (9) | 0.0151 (8) | 0.0468 (8) | 0.0221 (8) |
C18 | 0.0557 (11) | 0.0377 (9) | 0.0490 (10) | −0.0046 (8) | 0.0451 (10) | −0.0059 (8) |
C17 | 0.0602 (13) | 0.0475 (11) | 0.0514 (12) | −0.0012 (9) | 0.0478 (11) | 0.0012 (8) |
C9 | 0.0521 (11) | 0.0445 (10) | 0.0475 (10) | 0.0001 (8) | 0.0423 (10) | −0.0010 (8) |
C13 | 0.0656 (13) | 0.0488 (11) | 0.0632 (13) | −0.0119 (10) | 0.0568 (12) | −0.0116 (10) |
C16 | 0.0771 (16) | 0.0629 (15) | 0.0624 (14) | 0.0033 (12) | 0.0587 (14) | 0.0109 (11) |
C12 | 0.0598 (14) | 0.0779 (17) | 0.0756 (16) | −0.0075 (12) | 0.0584 (14) | −0.0072 (13) |
C15 | 0.095 (2) | 0.0702 (16) | 0.0759 (17) | −0.0076 (15) | 0.0759 (17) | 0.0055 (13) |
B1 | 0.0510 (12) | 0.0406 (10) | 0.0437 (11) | 0.0022 (9) | 0.0399 (10) | 0.0014 (9) |
C14 | 0.0834 (17) | 0.0627 (14) | 0.0767 (16) | −0.0206 (13) | 0.0720 (16) | −0.0132 (13) |
C10 | 0.0570 (13) | 0.0690 (15) | 0.0602 (13) | 0.0105 (11) | 0.0486 (12) | 0.0125 (11) |
C11 | 0.0553 (14) | 0.091 (2) | 0.0741 (17) | 0.0102 (13) | 0.0522 (14) | 0.0107 (15) |
C7 | 0.084 (2) | 0.058 (4) | 0.062 (3) | 0.003 (2) | 0.059 (2) | −0.0001 (19) |
C6 | 0.0703 (16) | 0.047 (4) | 0.066 (2) | −0.001 (3) | 0.0567 (16) | −0.002 (2) |
C1 | 0.093 (4) | 0.040 (2) | 0.132 (5) | 0.010 (2) | 0.096 (4) | 0.012 (3) |
C5 | 0.0517 (13) | 0.066 (4) | 0.0520 (16) | 0.003 (2) | 0.0403 (13) | −0.006 (2) |
C8 | 0.123 (4) | 0.062 (3) | 0.078 (5) | 0.003 (3) | 0.084 (5) | 0.000 (3) |
C3A | 0.094 (10) | 0.25 (3) | 0.098 (9) | −0.067 (13) | 0.087 (8) | −0.059 (12) |
C2 | 0.163 (6) | 0.063 (3) | 0.188 (7) | 0.031 (3) | 0.157 (6) | 0.013 (3) |
C4 | 0.176 (8) | 0.098 (4) | 0.244 (11) | 0.024 (5) | 0.185 (9) | 0.019 (6) |
C4A | 0.095 (10) | 0.087 (9) | 0.094 (8) | 0.003 (7) | 0.050 (8) | −0.011 (7) |
C3 | 0.165 (7) | 0.094 (5) | 0.291 (13) | 0.022 (5) | 0.202 (9) | 0.007 (6) |
C2A | 0.095 (8) | 0.061 (6) | 0.146 (12) | 0.022 (5) | 0.099 (9) | 0.031 (7) |
C1A | 0.124 (13) | 0.057 (9) | 0.17 (2) | 0.030 (9) | 0.127 (16) | 0.039 (10) |
Sn1A | 0.0836 (12) | 0.0915 (15) | 0.0617 (9) | 0.0361 (8) | 0.0630 (9) | 0.0338 (8) |
C5A | 0.0517 (13) | 0.066 (4) | 0.0520 (16) | 0.003 (2) | 0.0403 (13) | −0.006 (2) |
C6A | 0.0703 (16) | 0.047 (4) | 0.066 (2) | −0.001 (3) | 0.0567 (16) | −0.002 (2) |
C7A | 0.084 (2) | 0.058 (4) | 0.062 (3) | 0.003 (2) | 0.059 (2) | −0.0001 (19) |
C8A | 0.123 (4) | 0.062 (3) | 0.078 (5) | 0.003 (3) | 0.084 (5) | 0.000 (3) |
Geometric parameters (Å, º) top
Sn1—O1 | 2.0041 (17) | C8—H8A | 0.9600 |
Sn1—C17 | 2.098 (3) | C8—H8B | 0.9600 |
Sn1—C1 | 2.151 (6) | C8—H8C | 0.9600 |
Sn1—C5 | 2.110 (5) | C3A—H3AA | 0.9700 |
O1—B1 | 1.352 (3) | C3A—H3AB | 0.9700 |
O1—Sn1A | 2.040 (3) | C3A—C4A | 1.546 (13) |
O2—H2 | 0.882 (18) | C3A—C2A | 1.439 (12) |
O2—B1 | 1.362 (3) | C2—H2A | 0.9700 |
C18—C17 | 1.427 (3) | C2—H2B | 0.9700 |
C18—C9 | 1.439 (3) | C2—C3 | 1.501 (9) |
C18—C13 | 1.435 (3) | C4—H4A | 0.9600 |
C17—C16 | 1.380 (3) | C4—H4B | 0.9600 |
C17—Sn1A | 2.210 (4) | C4—H4C | 0.9600 |
C9—B1 | 1.594 (3) | C4—C3 | 1.489 (8) |
C9—C10 | 1.382 (3) | C4A—H4AA | 0.9600 |
C13—C12 | 1.401 (4) | C4A—H4AB | 0.9600 |
C13—C14 | 1.422 (4) | C4A—H4AC | 0.9600 |
C16—H16 | 0.9300 | C3—H3A | 0.9700 |
C16—C15 | 1.399 (4) | C3—H3B | 0.9700 |
C12—H12 | 0.9300 | C2A—H2AA | 0.9700 |
C12—C11 | 1.352 (4) | C2A—H2AB | 0.9700 |
C15—H15 | 0.9300 | C2A—C1A | 1.483 (13) |
C15—C14 | 1.357 (4) | C1A—H1AA | 0.9700 |
C14—H14 | 0.9300 | C1A—H1AB | 0.9700 |
C10—H10 | 0.9300 | C1A—Sn1A | 2.157 (13) |
C10—C11 | 1.410 (3) | Sn1A—C5A | 2.154 (12) |
C11—H11 | 0.9300 | C5A—H5AA | 0.9700 |
C7—H7A | 0.9700 | C5A—H5AB | 0.9700 |
C7—H7B | 0.9700 | C5A—C6A | 1.513 (12) |
C7—C6 | 1.500 (6) | C6A—H6AA | 0.9700 |
C7—C8 | 1.521 (7) | C6A—H6AB | 0.9700 |
C6—H6A | 0.9700 | C6A—C7A | 1.489 (13) |
C6—H6B | 0.9700 | C7A—H7AA | 0.9700 |
C6—C5 | 1.535 (6) | C7A—H7AB | 0.9700 |
C1—H1A | 0.9700 | C7A—C8A | 1.498 (13) |
C1—H1B | 0.9700 | C8A—H8AA | 0.9600 |
C1—C2 | 1.530 (9) | C8A—H8AB | 0.9600 |
C5—H5A | 0.9700 | C8A—H8AC | 0.9600 |
C5—H5B | 0.9700 | | |
| | | |
O1—Sn1—C17 | 99.30 (8) | H8B—C8—H8C | 109.5 |
O1—Sn1—C1 | 107.0 (3) | H3AA—C3A—H3AB | 108.1 |
O1—Sn1—C5 | 103.2 (2) | C4A—C3A—H3AA | 109.6 |
C17—Sn1—C1 | 111.7 (2) | C4A—C3A—H3AB | 109.6 |
C17—Sn1—C5 | 112.8 (2) | C2A—C3A—H3AA | 109.6 |
C5—Sn1—C1 | 120.1 (3) | C2A—C3A—H3AB | 109.6 |
B1—O1—Sn1 | 121.92 (13) | C2A—C3A—C4A | 110.4 (11) |
B1—O1—Sn1A | 124.28 (15) | C1—C2—H2A | 108.9 |
B1—O2—H2 | 113 (2) | C1—C2—H2B | 108.9 |
C17—C18—C9 | 123.78 (18) | H2A—C2—H2B | 107.7 |
C17—C18—C13 | 117.34 (19) | C3—C2—C1 | 113.2 (7) |
C13—C18—C9 | 118.9 (2) | C3—C2—H2A | 108.9 |
C18—C17—Sn1 | 121.60 (15) | C3—C2—H2B | 108.9 |
C18—C17—Sn1A | 122.42 (16) | H4A—C4—H4B | 109.5 |
C16—C17—Sn1 | 117.84 (19) | H4A—C4—H4C | 109.5 |
C16—C17—C18 | 120.5 (2) | H4B—C4—H4C | 109.5 |
C16—C17—Sn1A | 117.0 (2) | C3—C4—H4A | 109.5 |
C18—C9—B1 | 127.12 (19) | C3—C4—H4B | 109.5 |
C10—C9—C18 | 117.46 (19) | C3—C4—H4C | 109.5 |
C10—C9—B1 | 115.39 (18) | C3A—C4A—H4AA | 109.5 |
C12—C13—C18 | 120.0 (2) | C3A—C4A—H4AB | 109.5 |
C12—C13—C14 | 120.3 (2) | C3A—C4A—H4AC | 109.5 |
C14—C13—C18 | 119.6 (2) | H4AA—C4A—H4AB | 109.5 |
C17—C16—H16 | 119.2 | H4AA—C4A—H4AC | 109.5 |
C17—C16—C15 | 121.7 (3) | H4AB—C4A—H4AC | 109.5 |
C15—C16—H16 | 119.2 | C2—C3—H3A | 107.0 |
C13—C12—H12 | 119.5 | C2—C3—H3B | 106.9 |
C11—C12—C13 | 121.0 (2) | C4—C3—C2 | 121.5 (9) |
C11—C12—H12 | 119.5 | C4—C3—H3A | 106.9 |
C16—C15—H15 | 120.2 | C4—C3—H3B | 106.9 |
C14—C15—C16 | 119.6 (2) | H3A—C3—H3B | 106.7 |
C14—C15—H15 | 120.2 | C3A—C2A—H2AA | 106.9 |
O1—B1—O2 | 118.44 (18) | C3A—C2A—H2AB | 106.9 |
O1—B1—C9 | 126.12 (18) | C3A—C2A—C1A | 121.8 (14) |
O2—B1—C9 | 115.44 (18) | H2AA—C2A—H2AB | 106.7 |
C13—C14—H14 | 119.4 | C1A—C2A—H2AA | 106.9 |
C15—C14—C13 | 121.3 (2) | C1A—C2A—H2AB | 106.9 |
C15—C14—H14 | 119.4 | C2A—C1A—H1AA | 108.0 |
C9—C10—H10 | 118.5 | C2A—C1A—H1AB | 108.0 |
C9—C10—C11 | 123.1 (2) | C2A—C1A—Sn1A | 117.2 (11) |
C11—C10—H10 | 118.5 | H1AA—C1A—H1AB | 107.2 |
C12—C11—C10 | 119.6 (3) | Sn1A—C1A—H1AA | 108.0 |
C12—C11—H11 | 120.2 | Sn1A—C1A—H1AB | 108.0 |
C10—C11—H11 | 120.2 | O1—Sn1A—C17 | 94.66 (15) |
H7A—C7—H7B | 107.9 | O1—Sn1A—C1A | 105.8 (10) |
C6—C7—H7A | 109.2 | O1—Sn1A—C5A | 106.7 (7) |
C6—C7—H7B | 109.2 | C1A—Sn1A—C17 | 110.1 (4) |
C6—C7—C8 | 112.1 (6) | C5A—Sn1A—C17 | 113.4 (5) |
C8—C7—H7A | 109.2 | C5A—Sn1A—C1A | 122.2 (8) |
C8—C7—H7B | 109.2 | Sn1A—C5A—H5AA | 108.0 |
C7—C6—H6A | 108.7 | Sn1A—C5A—H5AB | 108.0 |
C7—C6—H6B | 108.7 | H5AA—C5A—H5AB | 107.3 |
C7—C6—C5 | 114.2 (5) | C6A—C5A—Sn1A | 117.2 (11) |
H6A—C6—H6B | 107.6 | C6A—C5A—H5AA | 108.0 |
C5—C6—H6A | 108.7 | C6A—C5A—H5AB | 108.0 |
C5—C6—H6B | 108.7 | C5A—C6A—H6AA | 108.3 |
Sn1—C1—H1A | 109.1 | C5A—C6A—H6AB | 108.3 |
Sn1—C1—H1B | 109.1 | H6AA—C6A—H6AB | 107.4 |
H1A—C1—H1B | 107.8 | C7A—C6A—C5A | 115.7 (13) |
C2—C1—Sn1 | 112.7 (5) | C7A—C6A—H6AA | 108.3 |
C2—C1—H1A | 109.1 | C7A—C6A—H6AB | 108.3 |
C2—C1—H1B | 109.1 | C6A—C7A—H7AA | 108.6 |
Sn1—C5—H5A | 109.4 | C6A—C7A—H7AB | 108.6 |
Sn1—C5—H5B | 109.4 | C6A—C7A—C8A | 114.7 (14) |
C6—C5—Sn1 | 111.2 (4) | H7AA—C7A—H7AB | 107.6 |
C6—C5—H5A | 109.4 | C8A—C7A—H7AA | 108.6 |
C6—C5—H5B | 109.4 | C8A—C7A—H7AB | 108.6 |
H5A—C5—H5B | 108.0 | C7A—C8A—H8AA | 109.5 |
C7—C8—H8A | 109.5 | C7A—C8A—H8AB | 109.5 |
C7—C8—H8B | 109.5 | C7A—C8A—H8AC | 109.5 |
C7—C8—H8C | 109.5 | H8AA—C8A—H8AB | 109.5 |
H8A—C8—H8B | 109.5 | H8AA—C8A—H8AC | 109.5 |
H8A—C8—H8C | 109.5 | H8AB—C8A—H8AC | 109.5 |
| | | |
Sn1—O1—B1—O2 | 176.60 (15) | C13—C18—C17—C16 | −0.2 (3) |
Sn1—O1—B1—C9 | −4.7 (3) | C13—C18—C17—Sn1A | −176.2 (2) |
Sn1—C17—C16—C15 | −177.2 (2) | C13—C18—C9—B1 | −177.74 (19) |
Sn1—C1—C2—C3 | 59.5 (9) | C13—C18—C9—C10 | 0.0 (3) |
C18—C17—C16—C15 | −0.1 (4) | C13—C12—C11—C10 | −0.7 (5) |
C18—C9—B1—O1 | 2.6 (3) | C16—C15—C14—C13 | −0.6 (4) |
C18—C9—B1—O2 | −178.7 (2) | C12—C13—C14—C15 | 179.0 (3) |
C18—C9—C10—C11 | −1.1 (4) | B1—C9—C10—C11 | 176.9 (3) |
C18—C13—C12—C11 | −0.4 (4) | C14—C13—C12—C11 | −179.1 (3) |
C18—C13—C14—C15 | 0.3 (4) | C10—C9—B1—O1 | −175.2 (2) |
C17—C18—C9—B1 | 1.6 (3) | C10—C9—B1—O2 | 3.6 (3) |
C17—C18—C9—C10 | 179.3 (2) | C7—C6—C5—Sn1 | −177.6 (7) |
C17—C18—C13—C12 | −178.6 (2) | C1—C2—C3—C4 | 167.2 (8) |
C17—C18—C13—C14 | 0.1 (3) | C8—C7—C6—C5 | −179.4 (8) |
C17—C16—C15—C14 | 0.5 (4) | C3A—C2A—C1A—Sn1A | −66 (3) |
C9—C18—C17—Sn1 | −2.6 (3) | C4A—C3A—C2A—C1A | −49 (3) |
C9—C18—C17—C16 | −179.5 (2) | Sn1A—O1—B1—O2 | 168.6 (2) |
C9—C18—C17—Sn1A | 4.4 (3) | Sn1A—O1—B1—C9 | −12.7 (3) |
C9—C18—C13—C12 | 0.8 (3) | Sn1A—C17—C16—C15 | 176.1 (3) |
C9—C18—C13—C14 | 179.5 (2) | Sn1A—C5A—C6A—C7A | 170.7 (19) |
C9—C10—C11—C12 | 1.5 (5) | C5A—C6A—C7A—C8A | −173 (2) |
C13—C18—C17—Sn1 | 176.78 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.88 (2) | 1.93 (2) | 2.805 (2) | 172 (3) |
Symmetry code: (i) −x+3/2, −y+3/2, −z. |