Tetrel bond in the triphenyltin(IV) chloride–cyclo­hexyl­diphenyl­phosphane oxide (1/1) cocrystal

The single-crystal X-ray diffraction structure of the title compound, [SnCl(C₆H₅)₃]·C₁₈H₂₁OP, is reported. The 1:1 cocrystal features a short and directional tetrel bond between tin and oxygen. The tin–oxygen distance is 2.346 (4) Å, representing 62% of the sum of the van der Waals radii of Sn and O. The Cl—Sn...O angle is 174.0 (1)° and this nearly linear arrangement is consistent with a tetrel bond formed via a σ-hole opposite the tin–chlorine covalent bond. Some weak C—H...Cl inter­actions are noted between adjacent mol­ecules.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.052
• wR factor = 0.116
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.967 Why?
PLAT234_ALERT_4_C Large Hirshfeld Difference C25      --C26      .       0.18 Ang.
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C21 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C19 Check
PLAT331_ALERT_2_C Small Aver Phenyl C-C Dist C19      --C24      .       1.37 Ang.
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.01072 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.749 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.598        188 Report

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        273 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        273 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H1       ..CL1      .       2.87 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H18      ..CL1      .       2.88 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          5 Note
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.4 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   9 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   2 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
   5 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b).

Triphenyltin(IV) chloride–cyclohexyldiphenylphosphane oxide (1/1)

Crystal data

[SnCl(C6H5)3]·C18H21OP	F(000) = 1368
Mr = 669.76	Dx = 1.388 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.548 (2) Å	Cell parameters from 4222 reflections
b = 10.7496 (15) Å	θ = 2.3–21.9°
c = 18.665 (3) Å	µ = 0.96 mm^−1
β = 105.110 (4)°	T = 273 K
V = 3205.4 (8) Å^3	Plate, colourless
Z = 4	0.31 × 0.17 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer	2948 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.090
ω and πhi scans	θmax = 25.1°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→13
Tmin = 0.621, Tmax = 0.745	k = −12→12
19012 measured reflections	l = −22→21
5547 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0456P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max = 0.001
5547 reflections	Δρmax = 1.08 e Å^−3
361 parameters	Δρmin = −0.62 e Å^−3
0 restraints

Special details

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.

Refinement. Crystallographic data for the title compound were collected from a single crystal mounted on a MiTeGen MicroMount using parabar oil. Data were collected on a Bruker Kappa APEXII single-crystal diffractometer equipped with a sealed tube Mo Kα source (λ = 0.71073 Å), a TRIUMPH monochromator, and an APEXII CCD detector. Data were collected at 273 K. Raw data collection and processing were performed with the APEX3 software package from Bruker. Initial unit-cell parameters were determined from 36 data frames from select ω scans. Semi-empirical absorption corrections based on equivalent reflections were applied. Systematic absences in the diffraction data set and unit-cell parameters were consistent with the assigned space group. The initial structural solutions were determined using SHELXT (Sheldrick, 2015b) direct methods, and refined with full-matrix least-squares procedures based on F² using SHELXT and ShelXle. The structure was deposited with the Cambridge Structural Database, entry 2267964.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Sn1	0.74139 (3)	0.42607 (4)	0.61347 (3)	0.03965 (17)
Cl1	0.73072 (12)	0.49797 (15)	0.48345 (10)	0.0583 (5)
P1	0.75522 (10)	0.33662 (14)	0.81497 (10)	0.0371 (4)
O1	0.7432 (2)	0.3773 (3)	0.7364 (2)	0.0453 (11)
C1	0.6708 (4)	0.2398 (5)	0.8277 (3)	0.0405 (17)
H1	0.689087	0.199472	0.876358	0.049*
C2	0.6492 (4)	0.1379 (6)	0.7680 (4)	0.066 (2)
H2A	0.634718	0.176145	0.719269	0.079*
H2AB	0.697817	0.085500	0.771633	0.079*
C3	0.5761 (5)	0.0578 (7)	0.7768 (5)	0.084 (3)
H3A	0.561586	−0.001785	0.736459	0.101*
H3AB	0.593000	0.011609	0.822989	0.101*
C4	0.4999 (5)	0.1360 (8)	0.7770 (5)	0.093 (3)
H4A	0.478894	0.174469	0.728660	0.111*
H4AB	0.456136	0.082823	0.785875	0.111*
C5	0.5204 (5)	0.2359 (7)	0.8358 (5)	0.084 (3)
H5A	0.535447	0.197608	0.884526	0.101*
H5AB	0.471428	0.287535	0.832419	0.101*
C6	0.5928 (4)	0.3169 (6)	0.8262 (4)	0.068 (2)
H6A	0.575657	0.360988	0.779322	0.081*
H6AB	0.606258	0.378255	0.865633	0.081*
C7	0.7615 (4)	0.4664 (5)	0.8759 (4)	0.0374 (16)
C8	0.7922 (5)	0.4522 (6)	0.9517 (4)	0.064 (2)
H8	0.811506	0.375067	0.971498	0.077*
C9	0.7940 (5)	0.5540 (8)	0.9986 (4)	0.081 (3)
H9	0.811615	0.543443	1.049801	0.097*
C10	0.7702 (5)	0.6682 (7)	0.9697 (5)	0.074 (3)
H10	0.774125	0.736428	1.001112	0.089*
C11	0.7409 (5)	0.6832 (6)	0.8954 (5)	0.064 (2)
H11	0.723488	0.761391	0.876009	0.077*
C12	0.7366 (4)	0.5823 (6)	0.8480 (4)	0.0486 (18)
H12	0.716663	0.593431	0.796977	0.058*
C13	0.8527 (4)	0.2548 (5)	0.8477 (3)	0.0407 (17)
C14	0.9247 (5)	0.3158 (6)	0.8458 (4)	0.061 (2)
H14	0.920827	0.397493	0.828876	0.074*
C15	1.0024 (5)	0.2619 (8)	0.8677 (5)	0.076 (2)
H15	1.049931	0.306512	0.865676	0.091*
C16	1.0092 (6)	0.1404 (8)	0.8928 (5)	0.085 (3)
H16	1.061254	0.102139	0.908556	0.102*
C17	0.9372 (5)	0.0774 (7)	0.8939 (4)	0.075 (2)
H17	0.940741	−0.005004	0.909617	0.090*
C18	0.8603 (4)	0.1338 (6)	0.8723 (4)	0.0526 (19)
H18	0.812718	0.089502	0.874382	0.063*
C19	0.6260 (4)	0.3297 (6)	0.5840 (3)	0.0414 (17)
C20	0.6255 (4)	0.2067 (7)	0.5648 (4)	0.070 (2)
H20	0.675363	0.168679	0.562754	0.084*
C21	0.5530 (5)	0.1384 (7)	0.5487 (5)	0.091 (3)
H21	0.554667	0.054460	0.537100	0.109*
C22	0.4785 (5)	0.1921 (8)	0.5494 (5)	0.080 (3)
H22	0.429551	0.145177	0.538574	0.096*
C23	0.4765 (5)	0.3139 (8)	0.5661 (4)	0.067 (2)
H23	0.425880	0.352059	0.565347	0.081*
C24	0.5496 (5)	0.3818 (6)	0.5843 (4)	0.063 (2)
H24	0.547573	0.465132	0.597188	0.076*
C25	0.7582 (4)	0.6126 (5)	0.6541 (4)	0.0381 (17)
C26	0.6976 (4)	0.7008 (6)	0.6302 (4)	0.057 (2)
H26	0.648295	0.679564	0.595325	0.068*
C27	0.7085 (5)	0.8211 (6)	0.6573 (5)	0.070 (2)
H27	0.666909	0.880293	0.640582	0.085*
C28	0.7811 (6)	0.8529 (6)	0.7090 (5)	0.072 (3)
H28	0.788339	0.933676	0.727340	0.087*
C29	0.8420 (5)	0.7677 (7)	0.7334 (4)	0.069 (2)
H29	0.891609	0.789705	0.767645	0.082*
C30	0.8296 (5)	0.6455 (6)	0.7064 (4)	0.0529 (19)
H30	0.870562	0.585861	0.724317	0.063*
C31	0.8464 (4)	0.3065 (5)	0.6194 (3)	0.0375 (16)
C32	0.8992 (4)	0.3271 (6)	0.5743 (4)	0.053 (2)
H32	0.889843	0.395901	0.543017	0.064*
C33	0.9659 (4)	0.2488 (7)	0.5739 (4)	0.065 (2)
H33	1.000849	0.265544	0.543254	0.078*
C34	0.9795 (5)	0.1462 (7)	0.6194 (5)	0.068 (2)
H34	1.023708	0.092630	0.619618	0.081*
C35	0.9280 (5)	0.1233 (6)	0.6643 (5)	0.068 (2)
H35	0.937693	0.054158	0.695318	0.081*
C36	0.8610 (4)	0.2022 (6)	0.6642 (4)	0.054 (2)
H36	0.825900	0.184534	0.694567	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0529 (3)	0.0298 (2)	0.0381 (3)	0.0012 (2)	0.0154 (2)	−0.0019 (2)
Cl1	0.0890 (14)	0.0499 (11)	0.0404 (13)	0.0168 (10)	0.0248 (10)	0.0063 (8)
P1	0.0485 (11)	0.0284 (9)	0.0367 (12)	−0.0030 (8)	0.0152 (9)	0.0011 (8)
O1	0.065 (3)	0.047 (3)	0.028 (3)	−0.006 (2)	0.018 (2)	0.000 (2)
C1	0.048 (4)	0.032 (4)	0.040 (5)	−0.003 (3)	0.009 (3)	0.004 (3)
C2	0.078 (6)	0.061 (5)	0.063 (6)	−0.023 (4)	0.025 (5)	−0.011 (4)
C3	0.098 (7)	0.072 (6)	0.082 (7)	−0.052 (6)	0.021 (5)	−0.012 (5)
C4	0.069 (7)	0.097 (7)	0.103 (9)	−0.027 (6)	0.007 (6)	0.027 (6)
C5	0.050 (5)	0.074 (6)	0.131 (9)	−0.002 (5)	0.029 (5)	0.017 (6)
C6	0.054 (5)	0.056 (5)	0.096 (7)	0.003 (4)	0.025 (5)	0.002 (4)
C7	0.050 (4)	0.031 (4)	0.033 (5)	0.012 (3)	0.015 (3)	0.001 (3)
C8	0.101 (6)	0.051 (5)	0.036 (5)	0.017 (4)	0.008 (4)	−0.005 (4)
C9	0.128 (8)	0.079 (6)	0.028 (5)	0.018 (5)	0.005 (5)	−0.008 (4)
C10	0.115 (7)	0.048 (5)	0.064 (7)	0.009 (5)	0.030 (6)	−0.016 (5)
C11	0.095 (6)	0.043 (5)	0.064 (6)	0.002 (4)	0.037 (5)	−0.001 (4)
C12	0.060 (5)	0.043 (4)	0.046 (5)	0.000 (4)	0.020 (4)	−0.001 (4)
C13	0.046 (4)	0.038 (4)	0.043 (5)	−0.005 (3)	0.019 (3)	−0.002 (3)
C14	0.063 (5)	0.042 (4)	0.084 (7)	−0.005 (4)	0.027 (5)	0.000 (4)
C15	0.041 (5)	0.093 (7)	0.095 (7)	0.000 (5)	0.021 (5)	0.001 (5)
C16	0.069 (6)	0.083 (6)	0.112 (8)	0.031 (5)	0.039 (6)	0.017 (6)
C17	0.076 (6)	0.068 (5)	0.090 (7)	0.030 (5)	0.037 (5)	0.026 (5)
C18	0.052 (5)	0.048 (4)	0.066 (6)	0.004 (4)	0.030 (4)	0.008 (4)
C19	0.057 (5)	0.035 (4)	0.032 (4)	−0.002 (3)	0.010 (4)	−0.003 (3)
C20	0.045 (5)	0.065 (5)	0.092 (7)	−0.006 (4)	0.003 (4)	−0.038 (5)
C21	0.062 (6)	0.062 (5)	0.137 (9)	−0.010 (5)	0.003 (6)	−0.038 (5)
C22	0.058 (6)	0.075 (6)	0.095 (8)	−0.018 (5)	0.000 (5)	−0.021 (5)
C23	0.040 (5)	0.081 (6)	0.077 (7)	0.007 (5)	0.006 (4)	−0.009 (5)
C24	0.065 (6)	0.052 (5)	0.068 (6)	0.007 (4)	0.010 (5)	−0.012 (4)
C25	0.050 (5)	0.030 (4)	0.038 (5)	0.007 (3)	0.017 (4)	0.007 (3)
C26	0.062 (5)	0.051 (5)	0.057 (6)	−0.008 (4)	0.015 (4)	0.001 (4)
C27	0.074 (6)	0.035 (4)	0.108 (8)	0.015 (4)	0.032 (6)	0.007 (4)
C28	0.099 (7)	0.033 (4)	0.101 (8)	−0.014 (5)	0.054 (6)	−0.019 (5)
C29	0.083 (6)	0.050 (5)	0.071 (6)	−0.015 (5)	0.017 (5)	−0.015 (4)
C30	0.069 (5)	0.042 (4)	0.048 (5)	0.003 (4)	0.014 (4)	0.002 (4)
C31	0.047 (4)	0.034 (4)	0.032 (4)	0.000 (3)	0.011 (3)	0.002 (3)
C32	0.055 (5)	0.042 (4)	0.064 (6)	0.008 (4)	0.016 (4)	0.009 (4)
C33	0.056 (5)	0.072 (6)	0.071 (6)	0.003 (4)	0.024 (4)	0.003 (5)
C34	0.069 (6)	0.061 (5)	0.074 (7)	0.020 (5)	0.020 (5)	−0.006 (5)
C35	0.087 (7)	0.047 (5)	0.063 (6)	0.027 (5)	0.009 (5)	0.004 (4)
C36	0.068 (5)	0.047 (4)	0.050 (5)	0.005 (4)	0.021 (4)	−0.001 (4)

Geometric parameters (Å, º)

Sn1—C19	2.115 (6)	C15—C16	1.382 (10)
Sn1—C25	2.136 (6)	C15—H15	0.9300
Sn1—C31	2.141 (6)	C16—C17	1.375 (10)
Sn1—O1	2.346 (4)	C16—H16	0.9300
Sn1—Cl1	2.5089 (18)	C17—C18	1.372 (8)
P1—O1	1.493 (4)	C17—H17	0.9300
P1—C7	1.786 (6)	C18—H18	0.9300
P1—C13	1.798 (6)	C19—C20	1.370 (8)
P1—C1	1.807 (6)	C19—C24	1.384 (8)
C1—C6	1.527 (8)	C20—C21	1.371 (9)
C1—C2	1.537 (8)	C20—H20	0.9300
C1—H1	0.9800	C21—C22	1.366 (10)
C2—C3	1.528 (9)	C21—H21	0.9300
C2—H2A	0.9700	C22—C23	1.348 (9)
C2—H2AB	0.9700	C22—H22	0.9300
C3—C4	1.516 (10)	C23—C24	1.377 (9)
C3—H3A	0.9700	C23—H23	0.9300
C3—H3AB	0.9700	C24—H24	0.9300
C4—C5	1.510 (10)	C25—C26	1.367 (8)
C4—H4A	0.9700	C25—C30	1.369 (8)
C4—H4AB	0.9700	C26—C27	1.383 (9)
C5—C6	1.530 (9)	C26—H26	0.9300
C5—H5A	0.9700	C27—C28	1.373 (10)
C5—H5AB	0.9700	C27—H27	0.9300
C6—H6A	0.9700	C28—C29	1.350 (9)
C6—H6AB	0.9700	C28—H28	0.9300
C7—C12	1.372 (8)	C29—C30	1.402 (8)
C7—C8	1.382 (8)	C29—H29	0.9300
C8—C9	1.396 (9)	C30—H30	0.9300
C8—H8	0.9300	C31—C32	1.381 (8)
C9—C10	1.358 (9)	C31—C36	1.382 (8)
C9—H9	0.9300	C32—C33	1.390 (8)
C10—C11	1.355 (9)	C32—H32	0.9300
C10—H10	0.9300	C33—C34	1.374 (9)
C11—C12	1.390 (8)	C33—H33	0.9300
C11—H11	0.9300	C34—C35	1.364 (10)
C12—H12	0.9300	C34—H34	0.9300
C13—C14	1.369 (8)	C35—C36	1.397 (9)
C13—C18	1.375 (8)	C35—H35	0.9300
C14—C15	1.372 (9)	C36—H36	0.9300
C14—H14	0.9300
C19—Sn1—C25	125.2 (3)	C14—C13—P1	117.9 (5)
C19—Sn1—C31	112.6 (2)	C18—C13—P1	125.0 (5)
C25—Sn1—C31	121.1 (2)	C13—C14—C15	123.0 (7)
C19—Sn1—O1	85.74 (19)	C13—C14—H14	118.5
C25—Sn1—O1	83.99 (19)	C15—C14—H14	118.5
C31—Sn1—O1	90.7 (2)	C14—C15—C16	119.2 (8)
C19—Sn1—Cl1	93.90 (17)	C14—C15—H15	120.4
C25—Sn1—Cl1	91.37 (17)	C16—C15—H15	120.4
C31—Sn1—Cl1	94.95 (18)	C17—C16—C15	118.4 (8)
O1—Sn1—Cl1	174.01 (10)	C17—C16—H16	120.8
O1—P1—C7	111.5 (3)	C15—C16—H16	120.8
O1—P1—C13	110.8 (3)	C18—C17—C16	121.3 (7)
C7—P1—C13	105.5 (3)	C18—C17—H17	119.4
O1—P1—C1	112.9 (3)	C16—C17—H17	119.4
C7—P1—C1	106.6 (3)	C17—C18—C13	121.0 (7)
C13—P1—C1	109.2 (3)	C17—C18—H18	119.5
P1—O1—Sn1	172.1 (3)	C13—C18—H18	119.5
C6—C1—C2	109.7 (5)	C20—C19—C24	116.7 (6)
C6—C1—P1	111.3 (4)	C20—C19—Sn1	119.0 (5)
C2—C1—P1	110.9 (5)	C24—C19—Sn1	124.4 (5)
C6—C1—H1	108.3	C19—C20—C21	121.3 (7)
C2—C1—H1	108.3	C19—C20—H20	119.3
P1—C1—H1	108.3	C21—C20—H20	119.3
C3—C2—C1	111.4 (6)	C22—C21—C20	120.8 (7)
C3—C2—H2A	109.4	C22—C21—H21	119.6
C1—C2—H2A	109.4	C20—C21—H21	119.6
C3—C2—H2AB	109.4	C23—C22—C21	119.2 (7)
C1—C2—H2AB	109.4	C23—C22—H22	120.4
H2A—C2—H2AB	108.0	C21—C22—H22	120.4
C4—C3—C2	111.7 (7)	C22—C23—C24	120.0 (7)
C4—C3—H3A	109.3	C22—C23—H23	120.0
C2—C3—H3A	109.3	C24—C23—H23	120.0
C4—C3—H3AB	109.3	C23—C24—C19	121.9 (6)
C2—C3—H3AB	109.3	C23—C24—H24	119.0
H3A—C3—H3AB	107.9	C19—C24—H24	119.0
C5—C4—C3	111.5 (7)	C26—C25—C30	118.5 (6)
C5—C4—H4A	109.3	C26—C25—Sn1	121.3 (5)
C3—C4—H4A	109.3	C30—C25—Sn1	120.2 (5)
C5—C4—H4AB	109.3	C25—C26—C27	120.9 (7)
C3—C4—H4AB	109.3	C25—C26—H26	119.5
H4A—C4—H4AB	108.0	C27—C26—H26	119.5
C4—C5—C6	110.7 (7)	C28—C27—C26	119.8 (7)
C4—C5—H5A	109.5	C28—C27—H27	120.1
C6—C5—H5A	109.5	C26—C27—H27	120.1
C4—C5—H5AB	109.5	C29—C28—C27	120.5 (7)
C6—C5—H5AB	109.5	C29—C28—H28	119.7
H5A—C5—H5AB	108.1	C27—C28—H28	119.7
C1—C6—C5	111.9 (5)	C28—C29—C30	119.2 (7)
C1—C6—H6A	109.2	C28—C29—H29	120.4
C5—C6—H6A	109.2	C30—C29—H29	120.4
C1—C6—H6AB	109.2	C25—C30—C29	121.1 (7)
C5—C6—H6AB	109.2	C25—C30—H30	119.4
H6A—C6—H6AB	107.9	C29—C30—H30	119.4
C12—C7—C8	118.9 (6)	C32—C31—C36	117.4 (6)
C12—C7—P1	120.4 (5)	C32—C31—Sn1	120.5 (5)
C8—C7—P1	120.7 (5)	C36—C31—Sn1	122.0 (5)
C7—C8—C9	119.9 (7)	C31—C32—C33	122.5 (6)
C7—C8—H8	120.1	C31—C32—H32	118.8
C9—C8—H8	120.1	C33—C32—H32	118.8
C10—C9—C8	120.2 (7)	C34—C33—C32	119.0 (7)
C10—C9—H9	119.9	C34—C33—H33	120.5
C8—C9—H9	119.9	C32—C33—H33	120.5
C11—C10—C9	120.3 (7)	C35—C34—C33	119.8 (7)
C11—C10—H10	119.9	C35—C34—H34	120.1
C9—C10—H10	119.9	C33—C34—H34	120.1
C10—C11—C12	120.3 (7)	C34—C35—C36	120.9 (7)
C10—C11—H11	119.9	C34—C35—H35	119.6
C12—C11—H11	119.9	C36—C35—H35	119.6
C7—C12—C11	120.4 (7)	C31—C36—C35	120.4 (7)
C7—C12—H12	119.8	C31—C36—H36	119.8
C11—C12—H12	119.8	C35—C36—H36	119.8
C14—C13—C18	117.1 (6)
O1—P1—C1—C6	−75.5 (5)	C1—P1—C13—C18	5.3 (7)
C7—P1—C1—C6	47.2 (5)	C18—C13—C14—C15	−0.6 (11)
C13—P1—C1—C6	160.7 (5)	P1—C13—C14—C15	−178.5 (6)
O1—P1—C1—C2	46.9 (5)	C13—C14—C15—C16	0.2 (12)
C7—P1—C1—C2	169.7 (5)	C14—C15—C16—C17	0.8 (13)
C13—P1—C1—C2	−76.8 (5)	C15—C16—C17—C18	−1.4 (13)
C6—C1—C2—C3	−54.9 (8)	C16—C17—C18—C13	1.0 (12)
P1—C1—C2—C3	−178.3 (5)	C14—C13—C18—C17	0.0 (10)
C1—C2—C3—C4	55.1 (9)	P1—C13—C18—C17	177.7 (5)
C2—C3—C4—C5	−55.3 (9)	C24—C19—C20—C21	−1.6 (11)
C3—C4—C5—C6	55.6 (9)	Sn1—C19—C20—C21	176.9 (6)
C2—C1—C6—C5	56.0 (8)	C19—C20—C21—C22	1.6 (13)
P1—C1—C6—C5	179.2 (5)	C20—C21—C22—C23	0.2 (14)
C4—C5—C6—C1	−56.7 (9)	C21—C22—C23—C24	−1.9 (13)
O1—P1—C7—C12	15.1 (6)	C22—C23—C24—C19	2.0 (12)
C13—P1—C7—C12	135.5 (5)	C20—C19—C24—C23	−0.2 (11)
C1—P1—C7—C12	−108.5 (6)	Sn1—C19—C24—C23	−178.6 (5)
O1—P1—C7—C8	−164.4 (5)	C30—C25—C26—C27	1.0 (10)
C13—P1—C7—C8	−44.0 (6)	Sn1—C25—C26—C27	179.4 (5)
C1—P1—C7—C8	72.0 (6)	C25—C26—C27—C28	−0.1 (12)
C12—C7—C8—C9	2.6 (11)	C26—C27—C28—C29	0.3 (13)
P1—C7—C8—C9	−177.9 (6)	C27—C28—C29—C30	−1.3 (12)
C7—C8—C9—C10	−3.7 (13)	C26—C25—C30—C29	−2.1 (11)
C8—C9—C10—C11	3.1 (13)	Sn1—C25—C30—C29	179.6 (5)
C9—C10—C11—C12	−1.4 (13)	C28—C29—C30—C25	2.2 (11)
C8—C7—C12—C11	−1.0 (10)	C36—C31—C32—C33	−1.2 (10)
P1—C7—C12—C11	179.5 (5)	Sn1—C31—C32—C33	−177.1 (5)
C10—C11—C12—C7	0.4 (11)	C31—C32—C33—C34	0.7 (11)
O1—P1—C13—C14	58.0 (6)	C32—C33—C34—C35	−0.3 (12)
C7—P1—C13—C14	−62.8 (6)	C33—C34—C35—C36	0.5 (12)
C1—P1—C13—C14	−177.0 (5)	C32—C31—C36—C35	1.3 (10)
O1—P1—C13—C18	−119.7 (6)	Sn1—C31—C36—C35	177.2 (5)
C7—P1—C13—C18	119.5 (6)	C34—C35—C36—C31	−1.0 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1^i	0.98	2.87	3.803 (6)	159
C18—H18···Cl1^i	0.93	2.88	3.637 (7)	139

Symmetry code: (i) x, −y+1/2, z+1/2.