Crystal structure of a 1,1-dibutyl-1H,3H-naphtho[1,8-cd][1,2,6]oxastannaborinin-3-ol

Breitwieser, K.; Chen, P.

doi:10.1107/S2056989021000712

Crystal structure of a 1,1-dibutyl-1H,3H-naphtho[1,8-cd][1,2,6]oxastannaborinin-3-ol

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.

Keywords: crystal structure; boron; tin; heterocycle; stannaborininol.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021000712/zq2260sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989021000712/zq2260Isup2.hkl Contains datablock I

CCDC reference: 2057745

checkCIF report

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

Computing details top

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-1H,3H-naphtho[1,8-cd][1,2,6]oxastannaborinin-3-ol top

Crystal data top

[Sn(C₄H₉)₂(C₁₀H₇BO₂)]	F(000) = 1632
M_r = 402.88	D_x = 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	R_int = 0.033
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2018)	θ_max = 79.6°, θ_min = 4.5°
T_min = 0.234, T_max = 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(F_o²) + (0.0359P)² + 2.7329P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
3923 reflections	Δρ_max = 0.45 e Å⁻³
264 parameters	Δρ_min = −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	U_iso*/U_eq	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.

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