Diminished electron density in the Vaska-type rhodium(I) complex trans-[Rh(NCBH₃)(CO)(PPh₃)₂]

Vaska-type complexes, i.e. trans-[RhX(CO)(PPh₃)₂] (X is a halogen or pseudo­halogen), undergo a range of reactions and exhibit considerable catalytic activity. The electron density on the Rh^I atom in these complexes plays an im­portant role in their reactivity. Many cyano­trihydridoborate (BH₃CN⁻) com­plexes of Group 6–8 transition metals have been synthesized and structurally characterized, an exception being the rhodium(I) complex. Carbon­yl(cyano­trihydridoborato-κN)bis­(tri­phenyl­phosphine-κP)rhodium(I), [Rh(NCBH₃)(CO)(C₁₈H₁₅P)₂], was prepared by the metathesis reaction of sodium cyano­tri­hydridoborate with trans-[RhCl(CO)(PPh₃)₂], and was characterized by single-crystal X-ray diffraction analysis and IR, ¹H, ¹³C and ¹¹B NMR spectroscopy. The X-ray diffraction data indicate that the cyano­trihydridoborate ligand coordinates to the Rh^I atom through the N atom in a trans position with respect to the carbonyl ligand; this was also confirmed by the IR and NMR data. The carbonyl stretching frequency ν(CO) and the carbonyl carbon ¹J_C–Rh and ¹J_C–P coupling constants of the C_ipso atoms of the triphenylphosphine groups reflect the diminished electron density on the central Rh^I atom compared to the parent trans-[RhCl(CO)(PPh₃)₂] complex.

Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Carbonyl(cyanotrihydridoborato-κN)bis(triphenylphosphine-κP)rhodium(I)

Crystal data

[Rh(CH3BN)(CO)(C18H15P)2]	F(000) = 1424
Mr = 695.31	Dx = 1.411 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 13.9227 (1) Å	Cell parameters from 33390 reflections
b = 12.3500 (1) Å	θ = 4.2–73.5°
c = 19.7966 (1) Å	µ = 5.38 mm^−1
β = 105.987 (1)°	T = 123 K
V = 3272.28 (4) Å^3	Plate, yellow
Z = 4	0.23 × 0.13 × 0.04 mm

Data collection

Agilent SuperNova Single Source diffractometer with an Atlas detector	6570 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source	6129 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.027
Detector resolution: 5.1773 pixels mm^-1	θmax = 73.7°, θmin = 3.3°
ω scans	h = −17→17
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	k = −14→15
Tmin = 0.186, Tmax = 0.706	l = −24→24
45590 measured reflections

Refinement

Refinement on F^2	72 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.021	H-atom parameters constrained
wR(F^2) = 0.056	w = 1/[σ^2(Fo^2) + (0.0325P)^2 + 1.0597P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.003
6570 reflections	Δρmax = 0.36 e Å^−3
452 parameters	Δρmin = −0.56 e Å^−3

Special details

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.37.31d (release 11-02-2014 CrysAlis171 .NET) (compiled Feb 11 2014,18:09:27) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Crystallographic data and details of diffraction experiment for (2) are given in the Table 1 and deposited in Cambridge Crystallographic Data Centre under the code CCDC 1450635.

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Rh1	0.73503 (2)	0.56499 (2)	0.41983 (2)	0.02494 (5)
N1	0.82165 (11)	0.53014 (11)	0.51849 (7)	0.0326 (3)
C1	0.87733 (15)	0.50901 (14)	0.57081 (9)	0.0370 (4)
B1	0.9596 (3)	0.4798 (2)	0.64131 (13)	0.0686 (9)
H1A	1.0164	0.4480	0.6303	0.103*
H1B	0.9324	0.4293	0.6680	0.103*
H1C	0.9799	0.5444	0.6684	0.103*
C2	0.65934 (13)	0.59485 (13)	0.33044 (10)	0.0346 (4)
O1	0.61246 (11)	0.61247 (11)	0.27439 (7)	0.0492 (4)
P1	0.69357 (3)	0.38432 (3)	0.39413 (2)	0.02617 (9)
C111	0.74308 (13)	0.28177 (13)	0.46076 (8)	0.0300 (3)
C112	0.84580 (14)	0.28016 (14)	0.49117 (9)	0.0344 (4)
H112	0.8858	0.3332	0.4794	0.041*
C113	0.88900 (15)	0.19970 (14)	0.53907 (9)	0.0395 (4)
H113	0.9576	0.1994	0.5597	0.047*
C114	0.82958 (17)	0.12001 (14)	0.55588 (9)	0.0417 (5)
H114	0.8584	0.0660	0.5878	0.050*
C115	0.72795 (17)	0.12046 (14)	0.52548 (10)	0.0436 (5)
H115	0.6885	0.0664	0.5367	0.052*
C116	0.68388 (15)	0.20139 (13)	0.47805 (10)	0.0373 (4)
H116	0.6151	0.2017	0.4580	0.045*
C121	0.55822 (12)	0.37601 (11)	0.37490 (8)	0.0252 (3)
C122	0.51429 (12)	0.39827 (12)	0.42911 (8)	0.0279 (3)
H122	0.5546	0.4086	0.4746	0.033*
C123	0.41169 (13)	0.40499 (14)	0.41564 (9)	0.0323 (3)
H123	0.3832	0.4190	0.4521	0.039*
C124	0.35131 (14)	0.39082 (17)	0.34787 (10)	0.0419 (4)
H124	0.2823	0.3961	0.3386	0.050*
C125	0.39386 (15)	0.36882 (19)	0.29399 (10)	0.0482 (5)
H125	0.3531	0.3591	0.2485	0.058*
C126	0.49690 (14)	0.36117 (15)	0.30718 (9)	0.0374 (4)
H126	0.5249	0.3461	0.2706	0.045*
C131	0.7183 (7)	0.3134 (6)	0.3137 (4)	0.0225 (14)	0.5
C132	0.7846 (6)	0.3640 (5)	0.2844 (4)	0.0324 (14)	0.5
H132	0.8072	0.4336	0.2983	0.039*	0.5
C133	0.8175 (5)	0.3098 (7)	0.2336 (3)	0.0413 (16)	0.5
H133	0.8650	0.3418	0.2148	0.050*	0.5
C134	0.7806 (5)	0.2101 (6)	0.2111 (3)	0.0482 (15)	0.5
H134	0.8020	0.1747	0.1764	0.058*	0.5
C135	0.7119 (5)	0.1615 (4)	0.2395 (3)	0.0502 (13)	0.5
H135	0.6865	0.0937	0.2235	0.060*	0.5
C136	0.6799 (4)	0.2130 (5)	0.2921 (3)	0.0361 (11)	0.5
H136	0.6339	0.1803	0.3119	0.043*	0.5
C141	0.7377 (7)	0.3386 (7)	0.3256 (5)	0.0234 (14)	0.5
C142	0.7972 (6)	0.3993 (5)	0.2942 (4)	0.0253 (11)	0.5
H142	0.8127	0.4703	0.3090	0.030*	0.5
C143	0.8349 (4)	0.3567 (4)	0.2405 (3)	0.0316 (12)	0.5
H143	0.8722	0.4000	0.2187	0.038*	0.5
C144	0.8157 (5)	0.2506 (6)	0.2208 (3)	0.0350 (13)	0.5
H144	0.8410	0.2219	0.1858	0.042*	0.5
C145	0.7602 (4)	0.1862 (4)	0.2518 (3)	0.0367 (10)	0.5
H145	0.7480	0.1144	0.2381	0.044*	0.5
C146	0.7218 (4)	0.2292 (5)	0.3043 (3)	0.0302 (11)	0.5
H146	0.6849	0.1849	0.3257	0.036*	0.5
P2	0.74681 (3)	0.74960 (3)	0.44377 (2)	0.02491 (8)
C211	0.62427 (13)	0.81437 (15)	0.41329 (8)	0.0348 (4)
C212	0.61247 (17)	0.92239 (17)	0.39291 (10)	0.0448 (5)
H212	0.6681	0.9649	0.3945	0.054*
C213	0.51675 (19)	0.9667 (2)	0.37006 (11)	0.0607 (7)
H213	0.5088	1.0388	0.3559	0.073*
C214	0.43431 (18)	0.9047 (2)	0.36835 (11)	0.0644 (8)
H214	0.3708	0.9348	0.3529	0.077*
C215	0.44537 (15)	0.7987 (2)	0.38930 (11)	0.0574 (6)
H215	0.3893	0.7575	0.3889	0.069*
C216	0.54004 (13)	0.75242 (19)	0.41123 (9)	0.0430 (5)
H216	0.5470	0.6800	0.4245	0.052*
C221	0.79140 (12)	0.78914 (12)	0.53606 (8)	0.0287 (3)
C222	0.72855 (14)	0.83414 (13)	0.57257 (9)	0.0341 (4)
H222	0.6612	0.8449	0.5500	0.041*
C223	0.76682 (17)	0.86292 (14)	0.64285 (10)	0.0413 (4)
H223	0.7247	0.8928	0.6671	0.050*
C224	0.86659 (17)	0.84758 (14)	0.67696 (9)	0.0412 (4)
H224	0.8918	0.8685	0.7236	0.049*
C225	0.92912 (15)	0.80071 (14)	0.64131 (9)	0.0372 (4)
H225	0.9961	0.7889	0.6644	0.045*
C226	0.89155 (13)	0.77142 (13)	0.57118 (9)	0.0314 (3)
H226	0.9336	0.7398	0.5475	0.038*
C231	0.82451 (12)	0.82938 (12)	0.40206 (8)	0.0255 (3)
C232	0.85997 (15)	0.93094 (12)	0.42820 (9)	0.0338 (4)
H232	0.8507	0.9548	0.4705	0.041*
C233	0.90894 (15)	0.99662 (13)	0.39167 (10)	0.0370 (4)
H233	0.9319	1.0645	0.4093	0.044*
C234	0.92371 (14)	0.96111 (13)	0.32870 (9)	0.0325 (3)
H234	0.9553	1.0058	0.3036	0.039*
C235	0.89148 (12)	0.85938 (13)	0.30336 (8)	0.0289 (3)
H235	0.9027	0.8351	0.2617	0.035*
C236	0.84240 (11)	0.79315 (12)	0.33991 (8)	0.0259 (3)
H236	0.8214	0.7244	0.3229	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rh1	0.02319 (7)	0.02207 (7)	0.02976 (7)	0.00205 (4)	0.00763 (5)	0.01014 (4)
N1	0.0433 (8)	0.0251 (7)	0.0302 (7)	0.0081 (6)	0.0114 (6)	0.0069 (6)
C1	0.0586 (11)	0.0243 (8)	0.0285 (8)	0.0063 (8)	0.0127 (8)	0.0030 (6)
B1	0.116 (3)	0.0364 (12)	0.0319 (11)	−0.0026 (14)	−0.0152 (13)	0.0041 (10)
C2	0.0331 (9)	0.0222 (7)	0.0449 (10)	−0.0041 (6)	0.0047 (7)	0.0115 (7)
O1	0.0528 (8)	0.0356 (7)	0.0443 (7)	−0.0076 (6)	−0.0116 (6)	0.0153 (6)
P1	0.0332 (2)	0.02002 (18)	0.02971 (19)	0.00715 (15)	0.01613 (16)	0.00809 (14)
C111	0.0450 (9)	0.0221 (7)	0.0283 (7)	0.0138 (7)	0.0191 (7)	0.0070 (6)
C112	0.0470 (10)	0.0258 (8)	0.0332 (8)	0.0119 (7)	0.0155 (7)	0.0045 (6)
C113	0.0556 (11)	0.0311 (9)	0.0317 (8)	0.0194 (8)	0.0119 (8)	0.0022 (7)
C114	0.0731 (13)	0.0288 (9)	0.0295 (8)	0.0263 (9)	0.0246 (9)	0.0096 (7)
C115	0.0711 (13)	0.0268 (8)	0.0474 (10)	0.0201 (9)	0.0407 (10)	0.0151 (8)
C116	0.0519 (11)	0.0256 (8)	0.0438 (9)	0.0140 (7)	0.0291 (8)	0.0122 (7)
C121	0.0352 (8)	0.0135 (6)	0.0293 (7)	−0.0021 (6)	0.0127 (6)	0.0013 (5)
C122	0.0327 (8)	0.0241 (7)	0.0270 (7)	−0.0013 (6)	0.0087 (6)	−0.0021 (6)
C123	0.0322 (8)	0.0320 (8)	0.0353 (8)	−0.0051 (7)	0.0138 (7)	−0.0015 (7)
C124	0.0307 (9)	0.0524 (11)	0.0411 (9)	−0.0185 (8)	0.0073 (7)	−0.0001 (8)
C125	0.0441 (11)	0.0664 (13)	0.0310 (9)	−0.0280 (10)	0.0050 (8)	−0.0064 (9)
C126	0.0476 (10)	0.0377 (9)	0.0305 (8)	−0.0160 (8)	0.0168 (7)	−0.0072 (7)
C131	0.038 (4)	0.015 (4)	0.016 (3)	0.005 (2)	0.009 (2)	−0.005 (2)
C132	0.026 (2)	0.044 (4)	0.022 (2)	0.004 (3)	−0.0008 (17)	−0.005 (3)
C133	0.033 (3)	0.061 (5)	0.032 (3)	0.008 (4)	0.012 (2)	0.003 (4)
C134	0.056 (4)	0.060 (4)	0.028 (2)	0.030 (3)	0.011 (3)	−0.007 (3)
C135	0.078 (4)	0.034 (3)	0.036 (2)	0.021 (3)	0.011 (3)	−0.0056 (18)
C136	0.058 (3)	0.020 (2)	0.031 (2)	0.003 (2)	0.014 (2)	−0.0030 (16)
C141	0.036 (3)	0.012 (3)	0.020 (3)	0.005 (2)	0.005 (2)	−0.005 (2)
C142	0.024 (2)	0.029 (3)	0.024 (3)	0.000 (2)	0.0085 (18)	−0.003 (2)
C143	0.028 (2)	0.039 (3)	0.031 (2)	0.005 (2)	0.0139 (18)	0.006 (2)
C144	0.039 (3)	0.039 (4)	0.027 (3)	0.013 (3)	0.009 (2)	−0.001 (3)
C145	0.048 (3)	0.031 (2)	0.029 (2)	0.0110 (19)	0.007 (2)	−0.0034 (17)
C146	0.038 (3)	0.027 (3)	0.026 (2)	0.000 (2)	0.009 (2)	0.0008 (16)
P2	0.02629 (18)	0.02312 (18)	0.02792 (18)	0.00674 (14)	0.01181 (14)	0.00907 (14)
C211	0.0341 (8)	0.0471 (10)	0.0274 (8)	0.0184 (8)	0.0157 (7)	0.0135 (7)
C212	0.0519 (12)	0.0492 (11)	0.0398 (10)	0.0289 (9)	0.0234 (9)	0.0192 (8)
C213	0.0710 (15)	0.0741 (15)	0.0440 (11)	0.0520 (13)	0.0276 (11)	0.0276 (11)
C214	0.0505 (13)	0.111 (2)	0.0361 (10)	0.0524 (14)	0.0202 (9)	0.0251 (12)
C215	0.0345 (10)	0.1048 (19)	0.0374 (10)	0.0248 (11)	0.0173 (8)	0.0179 (11)
C216	0.0331 (9)	0.0663 (13)	0.0336 (9)	0.0147 (9)	0.0159 (7)	0.0177 (9)
C221	0.0385 (8)	0.0210 (7)	0.0301 (8)	0.0060 (6)	0.0154 (7)	0.0103 (6)
C222	0.0466 (10)	0.0268 (8)	0.0348 (8)	0.0108 (7)	0.0213 (7)	0.0127 (7)
C223	0.0690 (13)	0.0286 (8)	0.0357 (9)	0.0118 (8)	0.0301 (9)	0.0109 (7)
C224	0.0725 (13)	0.0260 (8)	0.0275 (8)	0.0034 (8)	0.0178 (8)	0.0099 (7)
C225	0.0499 (10)	0.0273 (8)	0.0326 (8)	0.0006 (7)	0.0080 (7)	0.0108 (7)
C226	0.0392 (9)	0.0253 (8)	0.0317 (8)	0.0047 (7)	0.0130 (7)	0.0065 (6)
C231	0.0304 (8)	0.0200 (7)	0.0294 (7)	0.0075 (6)	0.0137 (6)	0.0057 (6)
C232	0.0538 (11)	0.0209 (7)	0.0351 (8)	0.0056 (7)	0.0265 (8)	0.0014 (6)
C233	0.0622 (11)	0.0159 (7)	0.0406 (9)	−0.0007 (7)	0.0271 (8)	−0.0010 (7)
C234	0.0462 (9)	0.0232 (7)	0.0343 (8)	−0.0008 (7)	0.0217 (7)	0.0042 (6)
C235	0.0352 (8)	0.0271 (8)	0.0284 (7)	0.0003 (6)	0.0154 (6)	−0.0012 (6)
C236	0.0297 (7)	0.0200 (7)	0.0297 (7)	0.0015 (6)	0.0114 (6)	0.0007 (6)

Geometric parameters (Å, º)

Rh1—N1	2.0389 (14)	C141—C142	1.385 (14)
Rh1—C2	1.8305 (18)	C141—C146	1.414 (7)
Rh1—P1	2.3257 (4)	C142—H142	0.9300
Rh1—P2	2.3253 (4)	C142—C143	1.410 (11)
N1—C1	1.140 (2)	C143—H143	0.9300
C1—B1	1.584 (3)	C143—C144	1.373 (7)
B1—H1A	0.9600	C144—H144	0.9300
B1—H1B	0.9600	C144—C145	1.367 (8)
B1—H1C	0.9600	C145—H145	0.9300
C2—O1	1.143 (2)	C145—C146	1.398 (8)
P1—C111	1.8216 (15)	C146—H146	0.9300
P1—C121	1.8197 (16)	P2—C211	1.8296 (16)
P1—C131	1.929 (8)	P2—C221	1.8268 (17)
P1—C141	1.732 (10)	P2—C231	1.8207 (15)
C111—C112	1.391 (3)	C211—C212	1.390 (3)
C111—C116	1.392 (2)	C211—C216	1.391 (3)
C112—H112	0.9300	C212—H212	0.9300
C112—C113	1.391 (2)	C212—C213	1.396 (3)
C113—H113	0.9300	C213—H213	0.9300
C113—C114	1.384 (3)	C213—C214	1.373 (4)
C114—H114	0.9300	C214—H214	0.9300
C114—C115	1.377 (3)	C214—C215	1.369 (4)
C115—H115	0.9300	C215—H215	0.9300
C115—C116	1.393 (2)	C215—C216	1.392 (3)
C116—H116	0.9300	C216—H216	0.9300
C121—C122	1.401 (2)	C221—C222	1.395 (2)
C121—C126	1.389 (2)	C221—C226	1.394 (2)
C122—H122	0.9300	C222—H222	0.9300
C122—C123	1.382 (2)	C222—C223	1.392 (3)
C123—H123	0.9300	C223—H223	0.9300
C123—C124	1.384 (3)	C223—C224	1.380 (3)
C124—H124	0.9300	C224—H224	0.9300
C124—C125	1.382 (3)	C224—C225	1.389 (3)
C125—H125	0.9300	C225—H225	0.9300
C125—C126	1.389 (3)	C225—C226	1.390 (2)
C126—H126	0.9300	C226—H226	0.9300
C131—C132	1.370 (14)	C231—C232	1.394 (2)
C131—C136	1.371 (7)	C231—C236	1.395 (2)
C132—H132	0.9300	C232—H232	0.9300
C132—C133	1.387 (11)	C232—C233	1.385 (2)
C133—H133	0.9300	C233—H233	0.9300
C133—C134	1.361 (9)	C233—C234	1.389 (2)
C134—H134	0.9300	C234—H234	0.9300
C134—C135	1.375 (9)	C234—C235	1.381 (2)
C135—H135	0.9300	C235—H235	0.9300
C135—C136	1.392 (8)	C235—C236	1.390 (2)
C136—H136	0.9300	C236—H236	0.9300
N1—Rh1—P1	93.02 (4)	C142—C141—P1	124.1 (5)
N1—Rh1—P2	91.25 (4)	C142—C141—C146	116.6 (8)
C2—Rh1—N1	178.72 (7)	C146—C141—P1	119.0 (7)
C2—Rh1—P1	86.54 (5)	C141—C142—H142	119.0
C2—Rh1—P2	89.37 (5)	C141—C142—C143	121.9 (5)
P2—Rh1—P1	169.933 (14)	C143—C142—H142	119.0
C1—N1—Rh1	173.47 (15)	C142—C143—H143	120.4
N1—C1—B1	176.7 (2)	C144—C143—C142	119.1 (6)
C1—B1—H1A	109.5	C144—C143—H143	120.4
C1—B1—H1B	109.5	C143—C144—H144	119.4
C1—B1—H1C	109.5	C145—C144—C143	121.2 (6)
H1A—B1—H1B	109.5	C145—C144—H144	119.4
H1A—B1—H1C	109.5	C144—C145—H145	120.3
H1B—B1—H1C	109.5	C144—C145—C146	119.5 (5)
O1—C2—Rh1	179.25 (18)	C146—C145—H145	120.3
C111—P1—Rh1	119.15 (6)	C141—C146—H146	119.2
C111—P1—C131	99.4 (3)	C145—C146—C141	121.6 (6)
C121—P1—Rh1	106.28 (5)	C145—C146—H146	119.2
C121—P1—C111	106.02 (7)	C211—P2—Rh1	110.76 (7)
C121—P1—C131	102.2 (3)	C221—P2—Rh1	116.83 (5)
C131—P1—Rh1	121.8 (2)	C221—P2—C211	104.01 (8)
C141—P1—Rh1	111.3 (3)	C231—P2—Rh1	117.10 (5)
C141—P1—C111	101.3 (3)	C231—P2—C211	103.32 (7)
C141—P1—C121	112.9 (3)	C231—P2—C221	103.19 (7)
C112—C111—P1	117.54 (12)	C212—C211—P2	122.69 (15)
C112—C111—C116	119.43 (15)	C212—C211—C216	119.20 (17)
C116—C111—P1	122.84 (14)	C216—C211—P2	118.10 (14)
C111—C112—H112	119.8	C211—C212—H212	120.1
C111—C112—C113	120.36 (17)	C211—C212—C213	119.8 (2)
C113—C112—H112	119.8	C213—C212—H212	120.1
C112—C113—H113	120.1	C212—C213—H213	119.8
C114—C113—C112	119.82 (19)	C214—C213—C212	120.4 (2)
C114—C113—H113	120.1	C214—C213—H213	119.8
C113—C114—H114	119.9	C213—C214—H214	119.9
C115—C114—C113	120.16 (16)	C215—C214—C213	120.18 (19)
C115—C114—H114	119.9	C215—C214—H214	119.9
C114—C115—H115	119.8	C214—C215—H215	119.8
C114—C115—C116	120.44 (18)	C214—C215—C216	120.4 (2)
C116—C115—H115	119.8	C216—C215—H215	119.8
C111—C116—C115	119.79 (19)	C211—C216—C215	120.1 (2)
C111—C116—H116	120.1	C211—C216—H216	120.0
C115—C116—H116	120.1	C215—C216—H216	120.0
C122—C121—P1	118.29 (12)	C222—C221—P2	122.41 (13)
C126—C121—P1	122.36 (12)	C226—C221—P2	118.35 (12)
C126—C121—C122	118.90 (15)	C226—C221—C222	119.24 (16)
C121—C122—H122	119.7	C221—C222—H222	120.1
C123—C122—C121	120.68 (15)	C223—C222—C221	119.85 (18)
C123—C122—H122	119.7	C223—C222—H222	120.1
C122—C123—H123	120.0	C222—C223—H223	119.6
C122—C123—C124	119.94 (16)	C224—C223—C222	120.71 (16)
C124—C123—H123	120.0	C224—C223—H223	119.6
C123—C124—H124	120.1	C223—C224—H224	120.1
C125—C124—C123	119.87 (17)	C223—C224—C225	119.73 (17)
C125—C124—H124	120.1	C225—C224—H224	120.1
C124—C125—H125	119.7	C224—C225—H225	120.0
C124—C125—C126	120.55 (17)	C224—C225—C226	119.99 (18)
C126—C125—H125	119.7	C226—C225—H225	120.0
C121—C126—C125	120.07 (16)	C221—C226—H226	119.8
C121—C126—H126	120.0	C225—C226—C221	120.47 (16)
C125—C126—H126	120.0	C225—C226—H226	119.8
C132—C131—P1	115.9 (4)	C232—C231—P2	120.82 (11)
C132—C131—C136	122.0 (7)	C232—C231—C236	119.01 (14)
C136—C131—P1	121.7 (6)	C236—C231—P2	119.95 (12)
C131—C132—H132	120.5	C231—C232—H232	119.7
C131—C132—C133	118.9 (6)	C233—C232—C231	120.53 (15)
C133—C132—H132	120.5	C233—C232—H232	119.7
C132—C133—H133	119.9	C232—C233—H233	120.0
C134—C133—C132	120.2 (6)	C232—C233—C234	119.98 (16)
C134—C133—H133	119.9	C234—C233—H233	120.0
C133—C134—H134	119.9	C233—C234—H234	120.0
C133—C134—C135	120.3 (5)	C235—C234—C233	119.96 (15)
C135—C134—H134	119.9	C235—C234—H234	120.0
C134—C135—H135	119.7	C234—C235—H235	119.9
C134—C135—C136	120.5 (6)	C234—C235—C236	120.23 (14)
C136—C135—H135	119.7	C236—C235—H235	119.9
C131—C136—C135	118.0 (7)	C231—C236—H236	119.9
C131—C136—H136	121.0	C235—C236—C231	120.22 (14)
C135—C136—H136	121.0	C235—C236—H236	119.9