[(1,2,5,6-η)-Cyclo­octa-1,5-diene](1-ethyl-3-isopropyl-1,3-imidazol-2-yl­idene)(tri­phenyl­phosphane)rhodium(I) tetra­fluorido­borate

A new N-heterocyclic cationic rhodium(I) complex with a tetra­fluorido­borate counter-anion, [Rh(C₈H₁₄N₂)(C₈H₁₂)(C₁₈H₁₅P)]BF₄, has been prepared and structurally characterized. The cationic complex exhibits a distorted square-planar environment around the rhodium(I) ion. Two connections are made from rhodium(I) to the carbon atom of an N-heterocylic carbene ligand and to the phospho­rus atom of a tri­phenyl­phosphane ligand. The remaining two coordination sites are made via a bidentate inter­action from the two olefinic bonds of cyclo­octa­diene to the rhodium(I) ion. The compound includes an out-sphere tetra­fluorido­borate counter-anion. Within the crystal of the compound exist several weak inter­molecular C—H...F inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.016
• wR factor = 0.041
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        9.8 Ratio
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of         B1 Check
PLAT245_ALERT_2_C U(iso) H28A      Smaller than U(eq) C28       by      0.016 Ang   2
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12      ..F1       .       2.57 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H32B     ..F2       .       2.57 Ang.

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          2 Report
PLAT164_ALERT_4_G Nr. of Refined C-H H-Atoms in Heavy-Atom Struct.          4 Note
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

[(1,2,5,6-η)-Cycloocta-1,5-diene](1-ethyl-3-isopropyl-1,3-imidazol-2-ylidene)(triphenylphosphane)rhodium(I) tetrafluoridoborate

Crystal data

[Rh(C8H14N2)(C8H12)(C18H15P)]BF4	F(000) = 1440
Mr = 698.38	Dx = 1.490 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 17.4184 (15) Å	Cell parameters from 9851 reflections
b = 10.2177 (8) Å	θ = 2.4–27.2°
c = 18.5136 (16) Å	µ = 0.65 mm^−1
β = 109.164 (3)°	T = 100 K
V = 3112.4 (5) Å^3	Plate, yellow–orange
Z = 4	0.40 × 0.26 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer	6836 independent reflections
Radiation source: sealed tube	6747 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 8 pixels mm^-1	θmax = 27.2°, θmin = 2.3°
φ and ω scans	h = −22→22
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −13→13
Tmin = 0.672, Tmax = 0.746	l = −23→23
18836 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.016	w = 1/[σ^2(Fo^2) + (0.0222P)^2 + 1.084P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.041	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.54 e Å^−3
6836 reflections	Δρmin = −0.29 e Å^−3
407 parameters	Absolute structure: Flack x determined using 3291 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013).
3 restraints	Absolute structure parameter: −0.024 (5)
Primary atom site location: dual

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.

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

	x	y	z	Uiso*/Ueq
Rh1	0.42545 (2)	0.32086 (2)	0.63412 (2)	0.01052 (5)
P1	0.36044 (4)	0.27657 (7)	0.50515 (3)	0.01170 (12)
C13	0.26691 (15)	0.1786 (2)	0.47885 (13)	0.0134 (4)
C7	0.42233 (14)	0.2032 (2)	0.45283 (13)	0.0143 (4)
C1	0.32858 (13)	0.4316 (2)	0.45497 (12)	0.0139 (4)
C5	0.24118 (15)	0.5609 (2)	0.35082 (14)	0.0201 (5)
H5	0.1947	0.5676	0.3063	0.024*
C3	0.35696 (16)	0.6616 (2)	0.44367 (15)	0.0203 (5)
H3	0.3899	0.7365	0.4621	0.024*
C2	0.37622 (14)	0.5425 (2)	0.48234 (13)	0.0164 (4)
H2	0.4220	0.5367	0.5276	0.020*
C4	0.28943 (17)	0.6700 (2)	0.37831 (15)	0.0216 (5)
H4	0.2760	0.7511	0.3521	0.026*
C6	0.26108 (14)	0.4415 (2)	0.38862 (13)	0.0166 (4)
H6	0.2286	0.3665	0.3692	0.020*
C12	0.45805 (14)	0.0810 (2)	0.47564 (13)	0.0171 (4)
H12	0.4470	0.0344	0.5155	0.021*
C8	0.43965 (15)	0.2706 (2)	0.39424 (13)	0.0177 (5)
H8	0.4159	0.3540	0.3786	0.021*
C11	0.50971 (15)	0.0276 (2)	0.44006 (14)	0.0201 (5)
H11	0.5334	−0.0560	0.4553	0.024*
C10	0.52700 (15)	0.0957 (3)	0.38225 (14)	0.0226 (5)
H10	0.5633	0.0597	0.3588	0.027*
C9	0.49115 (15)	0.2166 (3)	0.35885 (14)	0.0220 (5)
H9	0.5019	0.2624	0.3185	0.026*
C16	0.12602 (15)	0.0287 (2)	0.45403 (14)	0.0207 (5)
H16	0.0784	−0.0224	0.4463	0.025*
C17	0.12845 (15)	0.1572 (2)	0.47878 (14)	0.0192 (5)
H17	0.0824	0.1943	0.4877	0.023*
C14	0.26341 (14)	0.0492 (2)	0.45292 (13)	0.0182 (5)
H14	0.3092	0.0119	0.4436	0.022*
C15	0.19314 (15)	−0.0249 (2)	0.44067 (14)	0.0219 (5)
H15	0.1913	−0.1126	0.4231	0.026*
C18	0.19802 (15)	0.2314 (2)	0.49049 (13)	0.0162 (5)
H18	0.1988	0.3198	0.5067	0.019*
C19	0.31402 (18)	0.3416 (3)	0.64607 (16)	0.0123 (5)
N2	0.26421 (12)	0.4462 (2)	0.63903 (12)	0.0146 (4)
N1	0.27282 (11)	0.24015 (19)	0.66333 (11)	0.0139 (4)
C20	0.19801 (14)	0.2803 (2)	0.66586 (13)	0.0174 (4)
H20	0.1582	0.2270	0.6763	0.021*
C21	0.19237 (13)	0.4093 (2)	0.65064 (13)	0.0161 (4)
H21	0.1478	0.4646	0.6483	0.019*
C31	0.48989 (13)	0.4414 (2)	0.73577 (12)	0.0154 (4)
H31	0.4558	0.5126	0.7465	0.018*
C30	0.47546 (17)	0.3193 (2)	0.76080 (15)	0.0142 (5)
H30	0.4329	0.3191	0.7862	0.017*
C27	0.54248 (14)	0.2242 (2)	0.64930 (13)	0.0162 (4)
H27	0.5386	0.1482	0.6143	0.019*
C34	0.54342 (18)	0.3440 (3)	0.61543 (18)	0.0166 (6)
H34	0.5402	0.3386	0.5606	0.020*
C28	0.58720 (15)	0.1936 (3)	0.73303 (14)	0.0196 (5)
C29	0.53265 (16)	0.2061 (3)	0.78260 (14)	0.0189 (5)
H29A	0.5008	0.1245	0.7784	0.023*
H29B	0.5672	0.2160	0.8367	0.023*
C32	0.57237 (15)	0.4875 (3)	0.73428 (14)	0.0198 (5)
C33	0.58371 (16)	0.4668 (3)	0.65570 (16)	0.0213 (6)
H33A	0.5610	0.5432	0.6227	0.026*
H33B	0.6426	0.4626	0.6630	0.026*
C22	0.30159 (15)	0.1041 (2)	0.67200 (13)	0.0169 (5)
H22A	0.3530	0.0991	0.6603	0.020*
H22B	0.2610	0.0487	0.6345	0.020*
C24	0.28426 (14)	0.5819 (2)	0.62459 (13)	0.0156 (4)
H24	0.3375	0.5809	0.6150	0.019*
C23	0.31568 (15)	0.0504 (2)	0.75187 (14)	0.0207 (5)
H23A	0.3354	−0.0399	0.7547	0.031*
H23B	0.2645	0.0522	0.7632	0.031*
H23C	0.3562	0.1043	0.7893	0.031*
C26	0.22038 (16)	0.6381 (3)	0.55409 (15)	0.0232 (5)
H26A	0.2152	0.5815	0.5100	0.035*
H26B	0.2368	0.7260	0.5439	0.035*
H26C	0.1680	0.6429	0.5630	0.035*
C25	0.29387 (17)	0.6662 (2)	0.69523 (16)	0.0241 (5)
H25A	0.2414	0.6733	0.7038	0.036*
H25B	0.3127	0.7537	0.6873	0.036*
H25C	0.3337	0.6258	0.7399	0.036*
B1	0.47942 (19)	0.8319 (3)	0.63945 (18)	0.0216 (6)
F1	0.50775 (10)	0.81699 (16)	0.57787 (10)	0.0298 (4)
F2	0.45538 (12)	0.71358 (17)	0.65886 (12)	0.0393 (4)
F3	0.41466 (19)	0.9168 (2)	0.61969 (17)	0.0748 (10)
F4	0.54203 (14)	0.8787 (3)	0.70204 (13)	0.0667 (8)
H28A	0.6405 (16)	0.253 (3)	0.7537 (14)	0.004 (6)*
H32A	0.618 (2)	0.446 (3)	0.7789 (19)	0.027 (8)*
H32B	0.5747 (19)	0.577 (3)	0.7442 (17)	0.024 (8)*
H28B	0.605 (2)	0.102 (4)	0.736 (2)	0.039 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rh1	0.00993 (7)	0.01155 (8)	0.00951 (7)	−0.00034 (8)	0.00241 (5)	−0.00038 (7)
P1	0.0128 (3)	0.0112 (3)	0.0105 (3)	0.0005 (2)	0.0031 (2)	−0.0004 (2)
C13	0.0128 (11)	0.0147 (11)	0.0111 (10)	−0.0018 (8)	0.0017 (8)	0.0006 (8)
C7	0.0111 (10)	0.0183 (11)	0.0129 (10)	−0.0018 (8)	0.0030 (8)	−0.0042 (8)
C1	0.0148 (10)	0.0152 (11)	0.0119 (10)	0.0024 (8)	0.0044 (8)	0.0019 (8)
C5	0.0215 (12)	0.0231 (12)	0.0136 (10)	0.0027 (10)	0.0031 (9)	0.0035 (9)
C3	0.0227 (12)	0.0174 (12)	0.0216 (12)	−0.0043 (9)	0.0082 (10)	0.0001 (9)
C2	0.0174 (11)	0.0170 (11)	0.0143 (10)	−0.0005 (9)	0.0044 (8)	−0.0008 (9)
C4	0.0279 (13)	0.0174 (12)	0.0209 (12)	0.0036 (9)	0.0099 (11)	0.0062 (9)
C6	0.0175 (11)	0.0175 (11)	0.0134 (10)	−0.0010 (9)	0.0033 (9)	−0.0007 (8)
C12	0.0179 (11)	0.0172 (11)	0.0149 (10)	−0.0002 (9)	0.0035 (9)	−0.0030 (8)
C8	0.0193 (11)	0.0177 (12)	0.0147 (11)	−0.0021 (9)	0.0037 (9)	−0.0013 (9)
C11	0.0179 (11)	0.0196 (12)	0.0214 (11)	0.0015 (9)	0.0046 (9)	−0.0051 (9)
C10	0.0200 (12)	0.0263 (13)	0.0233 (12)	−0.0025 (10)	0.0097 (10)	−0.0106 (10)
C9	0.0240 (13)	0.0255 (13)	0.0189 (12)	−0.0060 (10)	0.0104 (10)	−0.0033 (10)
C16	0.0186 (11)	0.0222 (12)	0.0190 (11)	−0.0084 (10)	0.0029 (9)	0.0015 (9)
C17	0.0156 (11)	0.0249 (12)	0.0161 (11)	−0.0014 (9)	0.0038 (9)	0.0009 (9)
C14	0.0199 (11)	0.0154 (11)	0.0189 (11)	−0.0006 (9)	0.0058 (9)	−0.0019 (9)
C15	0.0246 (12)	0.0162 (12)	0.0221 (12)	−0.0045 (10)	0.0039 (10)	−0.0024 (9)
C18	0.0189 (12)	0.0158 (11)	0.0125 (11)	−0.0011 (9)	0.0033 (9)	−0.0021 (9)
C19	0.0122 (12)	0.0131 (12)	0.0095 (11)	−0.0012 (10)	0.0008 (10)	−0.0020 (9)
N2	0.0127 (9)	0.0148 (10)	0.0159 (10)	−0.0011 (7)	0.0041 (8)	−0.0029 (8)
N1	0.0137 (9)	0.0123 (9)	0.0163 (9)	−0.0011 (7)	0.0060 (7)	−0.0017 (7)
C20	0.0143 (11)	0.0218 (12)	0.0179 (11)	−0.0030 (9)	0.0078 (9)	−0.0033 (9)
C21	0.0115 (10)	0.0205 (11)	0.0171 (11)	−0.0011 (8)	0.0056 (8)	−0.0045 (9)
C31	0.0146 (10)	0.0175 (11)	0.0117 (10)	−0.0016 (8)	0.0014 (8)	−0.0035 (8)
C30	0.0154 (12)	0.0203 (14)	0.0058 (10)	−0.0019 (8)	0.0019 (9)	−0.0013 (8)
C27	0.0120 (10)	0.0198 (12)	0.0163 (11)	0.0038 (9)	0.0040 (9)	−0.0026 (9)
C34	0.0097 (13)	0.0261 (14)	0.0147 (13)	−0.0019 (11)	0.0051 (10)	−0.0033 (11)
C28	0.0155 (12)	0.0234 (13)	0.0167 (12)	0.0063 (9)	0.0011 (9)	0.0004 (9)
C29	0.0196 (12)	0.0213 (12)	0.0122 (10)	0.0036 (9)	0.0003 (9)	0.0039 (9)
C32	0.0173 (11)	0.0218 (13)	0.0184 (11)	−0.0061 (9)	0.0034 (9)	−0.0034 (9)
C33	0.0145 (11)	0.0256 (14)	0.0228 (13)	−0.0082 (10)	0.0048 (10)	−0.0012 (10)
C22	0.0228 (12)	0.0100 (10)	0.0205 (11)	−0.0001 (9)	0.0107 (9)	−0.0006 (8)
C24	0.0166 (11)	0.0126 (10)	0.0176 (11)	0.0005 (8)	0.0057 (9)	−0.0005 (8)
C23	0.0237 (12)	0.0165 (11)	0.0219 (12)	−0.0013 (9)	0.0076 (10)	0.0004 (9)
C26	0.0229 (12)	0.0224 (12)	0.0240 (12)	0.0059 (10)	0.0071 (10)	0.0052 (10)
C25	0.0265 (13)	0.0206 (13)	0.0271 (13)	−0.0041 (10)	0.0114 (11)	−0.0088 (10)
B1	0.0235 (14)	0.0155 (13)	0.0303 (15)	−0.0024 (10)	0.0149 (12)	0.0009 (10)
F1	0.0230 (8)	0.0435 (10)	0.0252 (8)	0.0038 (6)	0.0111 (7)	0.0005 (6)
F2	0.0433 (10)	0.0233 (8)	0.0547 (12)	−0.0095 (7)	0.0207 (9)	0.0074 (8)
F3	0.0900 (19)	0.0630 (13)	0.102 (2)	0.0594 (15)	0.0729 (19)	0.0508 (15)
F4	0.0626 (14)	0.1002 (19)	0.0541 (13)	−0.0596 (14)	0.0418 (12)	−0.0510 (13)

Geometric parameters (Å, º)

Rh1—P1	2.3265 (6)	N2—C24	1.476 (3)
Rh1—C19	2.035 (3)	N1—C20	1.382 (3)
Rh1—C31	2.221 (2)	N1—C22	1.468 (3)
Rh1—C30	2.218 (3)	C20—H20	0.9500
Rh1—C27	2.198 (2)	C20—C21	1.345 (4)
Rh1—C34	2.206 (3)	C21—H21	0.9500
P1—C13	1.837 (3)	C31—H31	1.0000
P1—C7	1.830 (2)	C31—C30	1.383 (3)
P1—C1	1.828 (2)	C31—C32	1.521 (3)
C13—C14	1.401 (3)	C30—H30	1.0000
C13—C18	1.396 (3)	C30—C29	1.493 (3)
C7—C12	1.398 (3)	C27—H27	1.0000
C7—C8	1.398 (3)	C27—C34	1.377 (4)
C1—C2	1.397 (3)	C27—C28	1.521 (3)
C1—C6	1.398 (3)	C34—H34	1.0000
C5—H5	0.9500	C34—C33	1.510 (4)
C5—C4	1.389 (4)	C28—C29	1.528 (3)
C5—C6	1.392 (3)	C28—H28A	1.07 (3)
C3—H3	0.9500	C28—H28B	0.98 (4)
C3—C2	1.396 (3)	C29—H29A	0.9900
C3—C4	1.386 (4)	C29—H29B	0.9900
C2—H2	0.9500	C32—C33	1.546 (4)
C4—H4	0.9500	C32—H32A	1.03 (3)
C6—H6	0.9500	C32—H32B	0.93 (3)
C12—H12	0.9500	C33—H33A	0.9900
C12—C11	1.390 (3)	C33—H33B	0.9900
C8—H8	0.9500	C22—H22A	0.9900
C8—C9	1.387 (3)	C22—H22B	0.9900
C11—H11	0.9500	C22—C23	1.520 (3)
C11—C10	1.390 (4)	C24—H24	1.0000
C10—H10	0.9500	C24—C26	1.522 (3)
C10—C9	1.388 (4)	C24—C25	1.528 (3)
C9—H9	0.9500	C23—H23A	0.9800
C16—H16	0.9500	C23—H23B	0.9800
C16—C17	1.386 (4)	C23—H23C	0.9800
C16—C15	1.385 (4)	C26—H26A	0.9800
C17—H17	0.9500	C26—H26B	0.9800
C17—C18	1.385 (3)	C26—H26C	0.9800
C14—H14	0.9500	C25—H25A	0.9800
C14—C15	1.394 (3)	C25—H25B	0.9800
C15—H15	0.9500	C25—H25C	0.9800
C18—H18	0.9500	B1—F1	1.391 (3)
C19—N2	1.355 (4)	B1—F2	1.365 (3)
C19—N1	1.357 (3)	B1—F3	1.374 (4)
N2—C21	1.389 (3)	B1—F4	1.390 (4)
C19—Rh1—P1	88.37 (8)	N2—C21—H21	126.5
C19—Rh1—C31	94.87 (10)	C20—C21—N2	106.9 (2)
C19—Rh1—C30	86.75 (11)	C20—C21—H21	126.5
C19—Rh1—C27	155.53 (10)	Rh1—C31—H31	113.9
C19—Rh1—C34	167.59 (8)	C30—C31—Rh1	71.74 (14)
C31—Rh1—P1	156.62 (6)	C30—C31—H31	113.9
C30—Rh1—P1	166.84 (6)	C30—C31—C32	124.2 (2)
C30—Rh1—C31	36.30 (9)	C32—C31—Rh1	111.97 (15)
C27—Rh1—P1	99.34 (6)	C32—C31—H31	113.9
C27—Rh1—C31	87.21 (9)	Rh1—C30—H30	113.8
C27—Rh1—C30	80.55 (9)	C31—C30—Rh1	71.96 (14)
C27—Rh1—C34	36.45 (10)	C31—C30—H30	113.8
C34—Rh1—P1	91.40 (8)	C31—C30—C29	127.7 (2)
C34—Rh1—C31	80.55 (10)	C29—C30—Rh1	106.70 (16)
C34—Rh1—C30	95.97 (11)	C29—C30—H30	113.8
C13—P1—Rh1	117.95 (8)	Rh1—C27—H27	113.8
C7—P1—Rh1	116.76 (8)	C34—C27—Rh1	72.06 (16)
C7—P1—C13	105.19 (11)	C34—C27—H27	113.8
C1—P1—Rh1	108.50 (8)	C34—C27—C28	124.6 (2)
C1—P1—C13	104.04 (11)	C28—C27—Rh1	111.44 (15)
C1—P1—C7	102.66 (11)	C28—C27—H27	113.8
C14—C13—P1	122.70 (19)	Rh1—C34—H34	114.1
C18—C13—P1	118.76 (17)	C27—C34—Rh1	71.49 (15)
C18—C13—C14	118.4 (2)	C27—C34—H34	114.1
C12—C7—P1	119.16 (17)	C27—C34—C33	125.9 (3)
C12—C7—C8	119.1 (2)	C33—C34—Rh1	108.50 (19)
C8—C7—P1	121.59 (18)	C33—C34—H34	114.1
C2—C1—P1	118.23 (17)	C27—C28—C29	112.6 (2)
C2—C1—C6	119.2 (2)	C27—C28—H28A	110.0 (14)
C6—C1—P1	122.49 (18)	C27—C28—H28B	108 (2)
C4—C5—H5	120.1	C29—C28—H28A	112.1 (14)
C4—C5—C6	119.9 (2)	C29—C28—H28B	107 (2)
C6—C5—H5	120.1	H28A—C28—H28B	107 (3)
C2—C3—H3	120.2	C30—C29—C28	113.2 (2)
C4—C3—H3	120.2	C30—C29—H29A	108.9
C4—C3—C2	119.6 (2)	C30—C29—H29B	108.9
C1—C2—H2	119.8	C28—C29—H29A	108.9
C3—C2—C1	120.4 (2)	C28—C29—H29B	108.9
C3—C2—H2	119.8	H29A—C29—H29B	107.8
C5—C4—H4	119.7	C31—C32—C33	112.8 (2)
C3—C4—C5	120.6 (2)	C31—C32—H32A	109.8 (17)
C3—C4—H4	119.7	C31—C32—H32B	106.3 (19)
C1—C6—H6	119.9	C33—C32—H32A	113.6 (17)
C5—C6—C1	120.3 (2)	C33—C32—H32B	108.0 (19)
C5—C6—H6	119.9	H32A—C32—H32B	106 (3)
C7—C12—H12	120.0	C34—C33—C32	113.4 (2)
C11—C12—C7	120.1 (2)	C34—C33—H33A	108.9
C11—C12—H12	120.0	C34—C33—H33B	108.9
C7—C8—H8	119.7	C32—C33—H33A	108.9
C9—C8—C7	120.6 (2)	C32—C33—H33B	108.9
C9—C8—H8	119.7	H33A—C33—H33B	107.7
C12—C11—H11	119.8	N1—C22—H22A	109.0
C12—C11—C10	120.4 (2)	N1—C22—H22B	109.0
C10—C11—H11	119.8	N1—C22—C23	112.86 (19)
C11—C10—H10	120.1	H22A—C22—H22B	107.8
C9—C10—C11	119.8 (2)	C23—C22—H22A	109.0
C9—C10—H10	120.1	C23—C22—H22B	109.0
C8—C9—C10	120.1 (2)	N2—C24—H24	108.1
C8—C9—H9	120.0	N2—C24—C26	111.1 (2)
C10—C9—H9	120.0	N2—C24—C25	109.91 (19)
C17—C16—H16	120.1	C26—C24—H24	108.1
C15—C16—H16	120.1	C26—C24—C25	111.4 (2)
C15—C16—C17	119.9 (2)	C25—C24—H24	108.1
C16—C17—H17	120.0	C22—C23—H23A	109.5
C18—C17—C16	120.0 (2)	C22—C23—H23B	109.5
C18—C17—H17	120.0	C22—C23—H23C	109.5
C13—C14—H14	119.8	H23A—C23—H23B	109.5
C15—C14—C13	120.4 (2)	H23A—C23—H23C	109.5
C15—C14—H14	119.8	H23B—C23—H23C	109.5
C16—C15—C14	120.2 (2)	C24—C26—H26A	109.5
C16—C15—H15	119.9	C24—C26—H26B	109.5
C14—C15—H15	119.9	C24—C26—H26C	109.5
C13—C18—H18	119.5	H26A—C26—H26B	109.5
C17—C18—C13	121.1 (2)	H26A—C26—H26C	109.5
C17—C18—H18	119.5	H26B—C26—H26C	109.5
N2—C19—Rh1	132.4 (2)	C24—C25—H25A	109.5
N2—C19—N1	104.7 (2)	C24—C25—H25B	109.5
N1—C19—Rh1	122.86 (19)	C24—C25—H25C	109.5
C19—N2—C21	110.6 (2)	H25A—C25—H25B	109.5
C19—N2—C24	125.2 (2)	H25A—C25—H25C	109.5
C21—N2—C24	124.2 (2)	H25B—C25—H25C	109.5
C19—N1—C20	111.0 (2)	F2—B1—F1	109.9 (2)
C19—N1—C22	124.1 (2)	F2—B1—F3	109.5 (2)
C20—N1—C22	124.7 (2)	F2—B1—F4	108.1 (3)
N1—C20—H20	126.6	F3—B1—F1	109.4 (2)
C21—C20—N1	106.8 (2)	F3—B1—F4	110.8 (3)
C21—C20—H20	126.6	F4—B1—F1	109.2 (2)
Rh1—P1—C13—C14	−108.34 (19)	C4—C5—C6—C1	1.2 (4)
Rh1—P1—C13—C18	66.7 (2)	C4—C3—C2—C1	0.9 (4)
Rh1—P1—C7—C12	61.3 (2)	C6—C1—C2—C3	−0.4 (3)
Rh1—P1—C7—C8	−113.91 (18)	C6—C5—C4—C3	−0.7 (4)
Rh1—P1—C1—C2	31.68 (19)	C12—C7—C8—C9	0.4 (3)
Rh1—P1—C1—C6	−151.50 (17)	C12—C11—C10—C9	−1.3 (4)
Rh1—C19—N2—C21	178.1 (2)	C8—C7—C12—C11	−0.3 (3)
Rh1—C19—N2—C24	−4.5 (4)	C11—C10—C9—C8	1.5 (4)
Rh1—C19—N1—C20	−178.26 (17)	C16—C17—C18—C13	−0.9 (4)
Rh1—C19—N1—C22	−2.8 (3)	C17—C16—C15—C14	0.8 (4)
Rh1—C31—C30—C29	97.5 (3)	C14—C13—C18—C17	1.7 (3)
Rh1—C31—C32—C33	12.8 (3)	C15—C16—C17—C18	−0.3 (4)
Rh1—C30—C29—C28	43.2 (2)	C18—C13—C14—C15	−1.3 (3)
Rh1—C27—C34—C33	99.8 (3)	C19—N2—C21—C20	0.6 (3)
Rh1—C27—C28—C29	13.9 (3)	C19—N2—C24—C26	124.9 (2)
Rh1—C34—C33—C32	39.5 (3)	C19—N2—C24—C25	−111.3 (3)
P1—C13—C14—C15	173.84 (18)	C19—N1—C20—C21	−0.6 (3)
P1—C13—C18—C17	−173.57 (18)	C19—N1—C22—C23	118.0 (3)
P1—C7—C12—C11	−175.64 (18)	N2—C19—N1—C20	0.9 (3)
P1—C7—C8—C9	175.65 (19)	N2—C19—N1—C22	176.4 (2)
P1—C1—C2—C3	176.55 (18)	N1—C19—N2—C21	−0.9 (3)
P1—C1—C6—C5	−177.46 (18)	N1—C19—N2—C24	176.4 (2)
C13—P1—C7—C12	−71.6 (2)	N1—C20—C21—N2	0.0 (3)
C13—P1—C7—C8	113.2 (2)	C20—N1—C22—C23	−67.2 (3)
C13—P1—C1—C2	158.06 (18)	C21—N2—C24—C26	−58.0 (3)
C13—P1—C1—C6	−25.1 (2)	C21—N2—C24—C25	65.8 (3)
C13—C14—C15—C16	0.0 (4)	C31—C30—C29—C28	−36.6 (4)
C7—P1—C13—C14	23.9 (2)	C31—C32—C33—C34	−35.3 (3)
C7—P1—C13—C18	−161.03 (19)	C30—C31—C32—C33	95.1 (3)
C7—P1—C1—C2	−92.49 (19)	C27—C34—C33—C32	−40.7 (4)
C7—P1—C1—C6	84.3 (2)	C27—C28—C29—C30	−39.1 (3)
C7—C12—C11—C10	0.7 (4)	C34—C27—C28—C29	96.4 (3)
C7—C8—C9—C10	−1.0 (4)	C28—C27—C34—Rh1	−104.1 (2)
C1—P1—C13—C14	131.5 (2)	C28—C27—C34—C33	−4.3 (4)
C1—P1—C13—C18	−53.5 (2)	C32—C31—C30—Rh1	−104.6 (2)
C1—P1—C7—C12	179.85 (18)	C32—C31—C30—C29	−7.1 (4)
C1—P1—C7—C8	4.6 (2)	C22—N1—C20—C21	−176.0 (2)
C2—C1—C6—C5	−0.7 (3)	C24—N2—C21—C20	−176.8 (2)
C2—C3—C4—C5	−0.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···F1^i	0.95	2.57	3.245 (3)	129
C21—H21···F4^ii	0.95	2.52	3.082 (3)	118
C22—H22A···F3^i	0.99	2.39	3.120 (3)	130
C24—H24···F2	1.00	2.37	3.139 (3)	133
C32—H32B···F2	0.93 (3)	2.57 (3)	3.094 (3)	116 (2)
C28—H28B···F4^i	0.98 (4)	2.53 (4)	3.318 (4)	138 (3)

Symmetry codes: (i) x, y−1, z; (ii) x−1/2, y−1/2, z.