Concomitant polymorphism in an organometallic ruthenium(II) complex with an N,N′-donor ligand

The simultaneous crystallization of different polymorphs, i.e. concomitant polymorphism, is a phenomenon which, when properly recognized and studied, can provide useful information for a variety of disciplines. It is rare for ruthenium complexes, although it has been observed. In the synthesis of the ruthenium(II) complex chlorido­(η⁶-p-cymene)(dimethyl 2,2′-bypyridine-4,5-di­carboxyl­ate-κ²N,N′)ruthenium(II) hexa­fluorido­phosphate, [RuCl(C₁₀H₁₄)(C₁₄H₁₂N₂O₄)]PF₆, concomitant polymorphs were crystallized under the same conditions. The colour of both crystals was orange, but the shapes, as well as the orientation of the p-cymene and meth­oxy­carbonyl ­groups, were different. The crystal structures of both isomers show approximately the same bond lengths. In the asymmetric unit, there is one cation and one anion. Due to the absence of strong hydrogen bonds, only weak inter­molecular inter­actions were observed. The Hirshfeld surface and two-dimensional fingerprint plots of both isomers satisfactorily explain the difference in the melting points.

Computing details

For both structures, data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and DIAMOND (Bergerhoff et al., 1996); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Chlorido(η⁶-p-cymene)(dimethyl 2,2'-bypyridine-4,5-dicarboxylate-κ²N,N')ruthenium(II)hexafluoridophosphate (A)

Crystal data

[RuCl(C10H14)(C14H12N2O4)]PF6	F(000) = 1384
Mr = 687.96	Dx = 1.691 Mg m^−3
Monoclinic, P21/c	Ag Kα radiation, λ = 0.56083 Å
a = 7.5508 (1) Å	Cell parameters from 1024970 reflections
b = 23.0248 (2) Å	θ = 2.1–36.5°
c = 15.8985 (1) Å	µ = 0.43 mm^−1
β = 102.081 (1)°	T = 100 K
V = 2702.83 (5) Å^3	Block, orange
Z = 4	0.31 × 0.2 × 0.15 mm

Data collection

Stoe StadiVari diffractometer	4855 reflections with I > 2σ(I)
rotation method scans	Rint = 0.032
Absorption correction: integration (X-AREA; Stoe & Cie, 2002)	θmax = 20.5°, θmin = 2.1°
Tmin = 0.901, Tmax = 0.937	h = −9→9
134822 measured reflections	k = −28→28
5431 independent reflections	l = −19→19

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.026	w = 1/[σ^2(Fo^2) + (0.0182P)^2 + 4.1599P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.063	(Δ/σ)max = 0.002
S = 1.08	Δρmax = 0.44 e Å^−3
5431 reflections	Δρmin = −0.43 e Å^−3
358 parameters	Extinction correction: SHELXL2017 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
354 restraints	Extinction coefficient: 0.00082 (18)
Primary atom site location: dual

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Experiments were performed on a Stoe STADIVARI diffractometer with a Dectris Pilatus 300 K detector and Ag Kα radiation at 100 K using a nitrogen gas open-flow cooler Oxford Cryostream Cobra. Data reduction and cell refinement were carried out using X-RED and X-AREA software (Stoe & Cie, 2002). The crystal structures were determined by a dual-space method using the SHELXT program (Sheldrick, 2015a), and then refined with full-matrix least-squares methods based on F² (SHELXL2017; Sheldrick, 2015b) in the OLEX² software (Dolomanov et al., 2009).

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

	x	y	z	Uiso*/Ueq
Ru1	0.43287 (2)	0.43630 (2)	0.17895 (2)	0.01398 (6)
Cl1	0.71487 (6)	0.47314 (3)	0.15467 (3)	0.02063 (12)
P1	0.76281 (8)	0.76799 (3)	0.62004 (4)	0.02531 (14)
F5	0.7207 (2)	0.77491 (7)	0.71382 (9)	0.0363 (4)
F2	0.8549 (2)	0.70573 (7)	0.64619 (9)	0.0341 (3)
F1	0.6725 (2)	0.83018 (7)	0.59251 (9)	0.0351 (4)
F4	0.9544 (2)	0.79887 (7)	0.65259 (11)	0.0407 (4)
F3	0.5692 (2)	0.73729 (8)	0.58842 (10)	0.0418 (4)
O1	0.6367 (2)	0.56305 (7)	0.47184 (9)	0.0211 (3)
F6	0.8021 (2)	0.76028 (8)	0.52562 (9)	0.0449 (4)
O3	1.0316 (2)	0.40099 (10)	0.58311 (10)	0.0381 (5)
N2	0.5497 (2)	0.35429 (8)	0.18116 (11)	0.0179 (4)
N1	0.5789 (2)	0.42892 (8)	0.30524 (10)	0.0150 (4)
O4	0.7607 (2)	0.38524 (9)	0.61449 (10)	0.0360 (5)
O2	0.8223 (3)	0.51491 (8)	0.57788 (10)	0.0352 (4)
C20	0.2271 (3)	0.49864 (10)	0.20468 (13)	0.0187 (4)
H20	0.229516	0.524555	0.251407	0.022*
C16	0.2775 (3)	0.47759 (10)	0.06153 (13)	0.0170 (4)
H16	0.317524	0.489432	0.011360	0.020*
C17	0.2122 (3)	0.42119 (10)	0.06621 (13)	0.0181 (4)
H17	0.206212	0.395685	0.018728	0.022*
C4	0.7588 (3)	0.36782 (10)	0.41203 (13)	0.0189 (4)
H4	0.813373	0.331136	0.427696	0.023*
C9	0.6620 (3)	0.37742 (10)	0.32822 (13)	0.0166 (4)
C11	0.7286 (3)	0.51683 (10)	0.50659 (13)	0.0200 (5)
C19	0.1641 (3)	0.44044 (10)	0.21018 (13)	0.0191 (4)
H19	0.128332	0.428107	0.261182	0.023*
C10	0.6432 (3)	0.33458 (10)	0.25836 (13)	0.0174 (4)
C24	0.0879 (3)	0.34018 (11)	0.14704 (15)	0.0261 (5)
H24A	0.145079	0.314703	0.111104	0.039*
H24B	−0.043914	0.339060	0.126728	0.039*
H24C	0.119114	0.326900	0.206884	0.039*
C15	0.2856 (3)	0.51810 (10)	0.13100 (13)	0.0171 (4)
C1	0.6032 (3)	0.47264 (10)	0.36227 (12)	0.0165 (4)
H1	0.551069	0.509369	0.344619	0.020*
C18	0.1540 (3)	0.40105 (10)	0.14154 (13)	0.0189 (4)
C21	0.3598 (3)	0.57842 (10)	0.12238 (13)	0.0194 (4)
H21	0.477206	0.574441	0.103215	0.023*
C7	0.6115 (3)	0.26466 (11)	0.11703 (15)	0.0248 (5)
H7	0.599633	0.241198	0.067008	0.030*
C2	0.7013 (3)	0.46646 (10)	0.44610 (13)	0.0173 (4)
C8	0.5366 (3)	0.31985 (11)	0.11199 (14)	0.0223 (5)
H8	0.473689	0.333782	0.057665	0.027*
C3	0.7747 (3)	0.41199 (10)	0.47209 (13)	0.0184 (4)
C13	0.8541 (3)	0.39851 (11)	0.56549 (13)	0.0215 (5)
C12	0.6672 (3)	0.61597 (11)	0.52218 (15)	0.0270 (5)
H12A	0.592573	0.647240	0.491376	0.040*
H12B	0.795348	0.626816	0.531255	0.040*
H12C	0.634426	0.609643	0.577937	0.040*
C23	0.2278 (3)	0.61215 (11)	0.05308 (15)	0.0288 (5)
H23A	0.209031	0.590824	−0.001414	0.043*
H23B	0.278175	0.650569	0.045642	0.043*
H23C	0.111686	0.616601	0.070732	0.043*
C6	0.7040 (3)	0.24422 (11)	0.19597 (15)	0.0256 (5)
H6	0.755821	0.206459	0.201046	0.031*
C22	0.3945 (4)	0.61264 (12)	0.20592 (16)	0.0355 (6)
H22A	0.280189	0.618184	0.224794	0.053*
H22B	0.446206	0.650581	0.196728	0.053*
H22C	0.479636	0.591242	0.250113	0.053*
C5	0.7196 (3)	0.27988 (10)	0.26759 (14)	0.0226 (5)
H5	0.782332	0.266760	0.322411	0.027*
C14	1.1188 (4)	0.38799 (19)	0.67244 (18)	0.0594 (11)
H14A	1.249092	0.382514	0.676641	0.089*
H14B	1.066576	0.352436	0.690899	0.089*
H14C	1.099110	0.420329	0.709495	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru1	0.01171 (10)	0.01808 (12)	0.01125 (10)	0.00089 (7)	0.00036 (7)	0.00044 (8)
Cl1	0.0136 (2)	0.0296 (3)	0.0185 (2)	0.0002 (2)	0.00308 (18)	0.0041 (2)
P1	0.0265 (3)	0.0268 (4)	0.0200 (3)	0.0011 (2)	−0.0012 (2)	0.0032 (2)
F5	0.0526 (9)	0.0323 (9)	0.0226 (7)	0.0036 (7)	0.0052 (6)	0.0009 (6)
F2	0.0450 (9)	0.0240 (8)	0.0286 (7)	0.0032 (6)	−0.0029 (6)	0.0007 (6)
F1	0.0361 (8)	0.0330 (9)	0.0339 (8)	0.0106 (6)	0.0017 (6)	0.0106 (6)
F4	0.0267 (8)	0.0308 (9)	0.0597 (10)	−0.0003 (6)	−0.0019 (7)	0.0050 (8)
F3	0.0333 (8)	0.0465 (11)	0.0413 (9)	−0.0089 (7)	−0.0020 (7)	−0.0057 (7)
O1	0.0211 (7)	0.0224 (9)	0.0190 (7)	−0.0017 (6)	0.0023 (6)	−0.0048 (6)
F6	0.0559 (10)	0.0557 (12)	0.0255 (8)	0.0158 (8)	0.0139 (7)	0.0076 (7)
O3	0.0166 (8)	0.0760 (15)	0.0194 (8)	0.0016 (8)	−0.0016 (6)	0.0162 (9)
N2	0.0143 (8)	0.0213 (10)	0.0170 (8)	−0.0001 (7)	0.0011 (6)	−0.0006 (7)
N1	0.0126 (8)	0.0180 (10)	0.0137 (8)	0.0000 (7)	0.0013 (6)	0.0017 (7)
O4	0.0216 (8)	0.0655 (14)	0.0199 (8)	−0.0044 (8)	0.0021 (7)	0.0149 (8)
O2	0.0439 (11)	0.0369 (12)	0.0185 (8)	0.0024 (8)	−0.0080 (7)	−0.0047 (7)
C20	0.0130 (9)	0.0256 (13)	0.0167 (9)	0.0042 (8)	0.0012 (7)	−0.0016 (8)
C16	0.0146 (9)	0.0206 (12)	0.0146 (9)	0.0021 (8)	0.0005 (7)	0.0036 (8)
C17	0.0140 (9)	0.0241 (12)	0.0136 (9)	0.0016 (8)	−0.0028 (7)	−0.0003 (8)
C4	0.0154 (10)	0.0224 (13)	0.0187 (10)	0.0028 (8)	0.0031 (8)	0.0050 (8)
C9	0.0127 (9)	0.0207 (12)	0.0171 (9)	0.0005 (8)	0.0044 (7)	0.0017 (8)
C11	0.0168 (10)	0.0272 (13)	0.0160 (10)	−0.0037 (9)	0.0031 (8)	−0.0007 (9)
C19	0.0119 (9)	0.0293 (13)	0.0158 (9)	0.0024 (8)	0.0025 (7)	0.0029 (9)
C10	0.0129 (9)	0.0213 (12)	0.0177 (10)	−0.0009 (8)	0.0028 (7)	−0.0001 (8)
C24	0.0224 (11)	0.0274 (14)	0.0260 (11)	−0.0056 (9)	−0.0005 (9)	0.0037 (10)
C15	0.0118 (9)	0.0213 (12)	0.0164 (9)	0.0031 (8)	−0.0010 (7)	0.0016 (8)
C1	0.0158 (9)	0.0191 (12)	0.0143 (9)	−0.0008 (8)	0.0027 (7)	0.0014 (8)
C18	0.0102 (9)	0.0241 (13)	0.0199 (10)	−0.0003 (8)	−0.0021 (7)	0.0023 (9)
C21	0.0176 (10)	0.0201 (12)	0.0195 (10)	0.0018 (8)	0.0017 (8)	0.0009 (8)
C7	0.0231 (11)	0.0230 (13)	0.0275 (11)	0.0006 (9)	0.0035 (9)	−0.0078 (9)
C2	0.0122 (9)	0.0244 (12)	0.0155 (9)	−0.0020 (8)	0.0033 (7)	0.0011 (8)
C8	0.0192 (10)	0.0253 (13)	0.0209 (10)	−0.0004 (9)	0.0002 (8)	−0.0038 (9)
C3	0.0123 (9)	0.0275 (13)	0.0156 (10)	−0.0010 (8)	0.0032 (7)	0.0040 (8)
C13	0.0179 (10)	0.0283 (14)	0.0168 (10)	0.0012 (9)	0.0005 (8)	0.0036 (9)
C12	0.0274 (12)	0.0242 (14)	0.0305 (12)	−0.0049 (10)	0.0087 (10)	−0.0100 (10)
C23	0.0291 (12)	0.0231 (14)	0.0308 (12)	0.0036 (10)	−0.0015 (10)	0.0046 (10)
C6	0.0244 (11)	0.0199 (13)	0.0329 (12)	0.0025 (9)	0.0072 (9)	0.0014 (10)
C22	0.0520 (16)	0.0250 (15)	0.0262 (12)	−0.0117 (12)	0.0004 (11)	−0.0022 (10)
C5	0.0214 (11)	0.0230 (13)	0.0234 (11)	0.0027 (9)	0.0047 (8)	0.0038 (9)
C14	0.0252 (14)	0.120 (3)	0.0273 (14)	0.0009 (17)	−0.0068 (11)	0.0328 (17)

Geometric parameters (Å, º)

Ru1—Cl1	2.3972 (5)	C9—C10	1.470 (3)
Ru1—N2	2.0813 (19)	C11—C2	1.493 (3)
Ru1—N1	2.0856 (16)	C19—H19	0.9500
Ru1—C20	2.215 (2)	C19—C18	1.409 (3)
Ru1—C16	2.202 (2)	C10—C5	1.380 (3)
Ru1—C17	2.2045 (19)	C24—H24A	0.9800
Ru1—C19	2.190 (2)	C24—H24B	0.9800
Ru1—C15	2.238 (2)	C24—H24C	0.9800
Ru1—C18	2.219 (2)	C24—C18	1.497 (3)
P1—F5	1.5964 (15)	C15—C21	1.515 (3)
P1—F2	1.6094 (16)	C1—H1	0.9500
P1—F1	1.6068 (16)	C1—C2	1.390 (3)
P1—F4	1.5981 (16)	C21—H21	1.0000
P1—F3	1.6070 (16)	C21—C23	1.533 (3)
P1—F6	1.5997 (16)	C21—C22	1.519 (3)
O1—C11	1.326 (3)	C7—H7	0.9500
O1—C12	1.450 (3)	C7—C8	1.386 (3)
O3—C13	1.312 (3)	C7—C6	1.385 (3)
O3—C14	1.466 (3)	C2—C3	1.398 (3)
N2—C10	1.359 (3)	C8—H8	0.9500
N2—C8	1.343 (3)	C3—C13	1.513 (3)
N1—C9	1.355 (3)	C12—H12A	0.9800
N1—C1	1.341 (3)	C12—H12B	0.9800
O4—C13	1.195 (3)	C12—H12C	0.9800
O2—C11	1.205 (3)	C23—H23A	0.9800
C20—H20	0.9500	C23—H23B	0.9800
C20—C19	1.431 (3)	C23—H23C	0.9800
C20—C15	1.409 (3)	C6—H6	0.9500
C16—H16	0.9500	C6—C5	1.389 (3)
C16—C17	1.397 (3)	C22—H22A	0.9800
C16—C15	1.437 (3)	C22—H22B	0.9800
C17—H17	0.9500	C22—H22C	0.9800
C17—C18	1.436 (3)	C5—H5	0.9500
C4—H4	0.9500	C14—H14A	0.9800
C4—C9	1.397 (3)	C14—H14B	0.9800
C4—C3	1.383 (3)	C14—H14C	0.9800
N2—Ru1—Cl1	86.34 (5)	O2—C11—O1	125.1 (2)
N2—Ru1—N1	76.88 (7)	O2—C11—C2	123.5 (2)
N2—Ru1—C20	153.61 (8)	Ru1—C19—H19	128.5
N2—Ru1—C16	123.69 (7)	C20—C19—Ru1	72.01 (11)
N2—Ru1—C17	96.66 (7)	C20—C19—H19	119.3
N2—Ru1—C19	116.43 (8)	C18—C19—Ru1	72.48 (12)
N2—Ru1—C15	161.39 (7)	C18—C19—C20	121.36 (19)
N2—Ru1—C18	92.73 (8)	C18—C19—H19	119.3
N1—Ru1—Cl1	82.84 (5)	N2—C10—C9	114.08 (19)
N1—Ru1—C20	97.19 (7)	N2—C10—C5	121.8 (2)
N1—Ru1—C16	158.75 (8)	C5—C10—C9	124.04 (19)
N1—Ru1—C17	158.01 (7)	H24A—C24—H24B	109.5
N1—Ru1—C19	96.53 (7)	H24A—C24—H24C	109.5
N1—Ru1—C15	121.43 (7)	H24B—C24—H24C	109.5
N1—Ru1—C18	120.61 (7)	C18—C24—H24A	109.5
C20—Ru1—Cl1	118.78 (6)	C18—C24—H24B	109.5
C20—Ru1—C15	36.87 (7)	C18—C24—H24C	109.5
C20—Ru1—C18	67.88 (8)	C20—C15—Ru1	70.68 (12)
C16—Ru1—Cl1	92.53 (6)	C20—C15—C16	117.6 (2)
C16—Ru1—C20	66.86 (8)	C20—C15—C21	123.58 (19)
C16—Ru1—C17	36.96 (8)	C16—C15—Ru1	69.74 (12)
C16—Ru1—C15	37.76 (8)	C16—C15—C21	118.84 (18)
C16—Ru1—C18	67.88 (8)	C21—C15—Ru1	129.45 (14)
C17—Ru1—Cl1	118.07 (6)	N1—C1—H1	118.6
C17—Ru1—C20	79.19 (8)	N1—C1—C2	122.8 (2)
C17—Ru1—C15	67.59 (8)	C2—C1—H1	118.6
C17—Ru1—C18	37.90 (8)	C17—C18—Ru1	70.51 (11)
C19—Ru1—Cl1	156.58 (7)	C17—C18—C24	121.0 (2)
C19—Ru1—C20	37.90 (8)	C19—C18—Ru1	70.26 (12)
C19—Ru1—C16	79.57 (8)	C19—C18—C17	117.5 (2)
C19—Ru1—C17	67.21 (8)	C19—C18—C24	121.5 (2)
C19—Ru1—C15	67.83 (8)	C24—C18—Ru1	129.52 (15)
C19—Ru1—C18	37.26 (8)	C15—C21—H21	108.2
C15—Ru1—Cl1	92.42 (6)	C15—C21—C23	109.40 (18)
C18—Ru1—Cl1	155.71 (6)	C15—C21—C22	113.33 (19)
C18—Ru1—C15	80.81 (8)	C23—C21—H21	108.2
F5—P1—F2	90.43 (8)	C22—C21—H21	108.2
F5—P1—F1	90.53 (8)	C22—C21—C23	109.4 (2)
F5—P1—F4	89.84 (9)	C8—C7—H7	120.5
F5—P1—F3	89.42 (9)	C6—C7—H7	120.5
F5—P1—F6	178.98 (11)	C6—C7—C8	119.1 (2)
F1—P1—F2	179.00 (9)	C1—C2—C11	120.8 (2)
F1—P1—F3	90.02 (9)	C1—C2—C3	118.3 (2)
F4—P1—F2	89.98 (9)	C3—C2—C11	120.91 (18)
F4—P1—F1	89.74 (9)	N2—C8—C7	122.3 (2)
F4—P1—F3	179.22 (10)	N2—C8—H8	118.8
F4—P1—F6	91.15 (10)	C7—C8—H8	118.8
F3—P1—F2	90.27 (9)	C4—C3—C2	118.93 (19)
F6—P1—F2	89.35 (9)	C4—C3—C13	119.1 (2)
F6—P1—F1	89.70 (9)	C2—C3—C13	121.7 (2)
F6—P1—F3	89.59 (9)	O3—C13—C3	112.20 (18)
C11—O1—C12	115.84 (17)	O4—C13—O3	126.0 (2)
C13—O3—C14	115.45 (19)	O4—C13—C3	121.71 (19)
C10—N2—Ru1	117.15 (14)	O1—C12—H12A	109.5
C8—N2—Ru1	124.31 (15)	O1—C12—H12B	109.5
C8—N2—C10	118.54 (19)	O1—C12—H12C	109.5
C9—N1—Ru1	116.90 (14)	H12A—C12—H12B	109.5
C1—N1—Ru1	124.01 (14)	H12A—C12—H12C	109.5
C1—N1—C9	118.97 (17)	H12B—C12—H12C	109.5
Ru1—C20—H20	130.7	C21—C23—H23A	109.5
C19—C20—Ru1	70.09 (12)	C21—C23—H23B	109.5
C19—C20—H20	119.5	C21—C23—H23C	109.5
C15—C20—Ru1	72.45 (12)	H23A—C23—H23B	109.5
C15—C20—H20	119.5	H23A—C23—H23C	109.5
C15—C20—C19	121.0 (2)	H23B—C23—H23C	109.5
Ru1—C16—H16	129.0	C7—C6—H6	120.6
C17—C16—Ru1	71.62 (11)	C7—C6—C5	118.8 (2)
C17—C16—H16	119.3	C5—C6—H6	120.6
C17—C16—C15	121.40 (19)	C21—C22—H22A	109.5
C15—C16—Ru1	72.50 (11)	C21—C22—H22B	109.5
C15—C16—H16	119.3	C21—C22—H22C	109.5
Ru1—C17—H17	130.2	H22A—C22—H22B	109.5
C16—C17—Ru1	71.41 (11)	H22A—C22—H22C	109.5
C16—C17—H17	119.4	H22B—C22—H22C	109.5
C16—C17—C18	121.2 (2)	C10—C5—C6	119.4 (2)
C18—C17—Ru1	71.60 (11)	C10—C5—H5	120.3
C18—C17—H17	119.4	C6—C5—H5	120.3
C9—C4—H4	120.2	O3—C14—H14A	109.5
C3—C4—H4	120.2	O3—C14—H14B	109.5
C3—C4—C9	119.7 (2)	O3—C14—H14C	109.5
N1—C9—C4	121.0 (2)	H14A—C14—H14B	109.5
N1—C9—C10	114.66 (17)	H14A—C14—H14C	109.5
C4—C9—C10	124.3 (2)	H14B—C14—H14C	109.5
O1—C11—C2	111.44 (17)

Chlorido(η⁶-cymene)(dimethyl 2,2'-bypyridine-4,5-dicarboxylate-κ²N,N')ruthenium(II)hexafluoridophosphate (B)

Crystal data

[RuCl(C10H14)(C14H12N2O4)]PF6	F(000) = 1384
Mr = 687.96	Dx = 1.710 Mg m^−3
Monoclinic, P21/n	Ag Kα radiation, λ = 0.56083 Å
a = 11.4706 (3) Å	Cell parameters from 941262 reflections
b = 16.9700 (4) Å	θ = 1.9–40.2°
c = 13.9242 (4) Å	µ = 0.44 mm^−1
β = 99.550 (2)°	T = 100 K
V = 2672.87 (12) Å^3	Rod, orange
Z = 4	0.18 × 0.14 × 0.12 mm

Data collection

Stoe StadiVari diffractometer	5016 reflections with I > 2σ(I)
Radiation source: Ag-Ims	Rint = 0.023
rotation method scans	θmax = 20.5°, θmin = 1.9°
Absorption correction: integration (X-AREA; Stoe & Cie, 2002)	h = −14→14
Tmin = 0.927, Tmax = 0.948	k = −21→21
88420 measured reflections	l = −17→17
5467 independent reflections

Refinement

Refinement on F^2	561 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.023	H-atom parameters constrained
wR(F^2) = 0.058	w = 1/[σ^2(Fo^2) + (0.0256P)^2 + 2.7584P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.005
5467 reflections	Δρmax = 0.80 e Å^−3
420 parameters	Δρmin = −0.41 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Experiments were performed on a Stoe STADIVARI diffractometer with a Dectris Pilatus 300 K detector and Ag Kα radiation at 100 K using a nitrogen gas open-flow cooler Oxford Cryostream Cobra. Data reduction and cell refinement were carried out using X-RED and X-AREA software (Stoe & Cie, 2002). The crystal structures were determined by a dual-space method using the SHELXT program (Sheldrick, 2015a), and then refined with full-matrix least-squares methods based on F² (SHELXL2017; Sheldrick, 2015b) in the OLEX² software (Dolomanov et al., 2009).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ru1	0.69396 (2)	0.68662 (2)	0.62562 (2)	0.01256 (5)
Cl1	0.75634 (4)	0.55232 (3)	0.64174 (3)	0.02048 (10)
P1	0.1655 (2)	0.76656 (12)	0.51539 (16)	0.0221 (4)	0.6
O4	0.17020 (11)	0.51981 (9)	0.74333 (10)	0.0269 (3)
O1	0.38778 (12)	0.53253 (8)	0.88365 (9)	0.0226 (3)
O3	0.15646 (11)	0.48712 (8)	0.58581 (10)	0.0232 (3)
N1	0.52931 (12)	0.64150 (8)	0.64119 (10)	0.0141 (3)
O2	0.30130 (12)	0.65207 (8)	0.86854 (9)	0.0254 (3)
N2	0.61952 (12)	0.65576 (9)	0.48363 (10)	0.0151 (3)
C9	0.46191 (14)	0.61054 (10)	0.56093 (12)	0.0132 (3)
C15	0.66514 (15)	0.81414 (10)	0.64136 (13)	0.0162 (3)
C5	0.45479 (16)	0.59763 (10)	0.37893 (12)	0.0174 (3)
H5	0.378631	0.574126	0.371046	0.021*
C10	0.51150 (14)	0.62094 (10)	0.47074 (12)	0.0140 (3)
C8	0.67286 (16)	0.66681 (11)	0.40535 (13)	0.0194 (4)
H8	0.748675	0.690875	0.414391	0.023*
C4	0.35622 (14)	0.57151 (10)	0.56594 (12)	0.0141 (3)
H4	0.310924	0.549318	0.509061	0.017*
C17	0.79107 (16)	0.73186 (11)	0.76477 (13)	0.0194 (4)
H17	0.803795	0.708791	0.827807	0.023*
C1	0.49199 (15)	0.63552 (10)	0.72760 (12)	0.0163 (3)
H1	0.539695	0.656852	0.783891	0.020*
C3	0.31794 (14)	0.56546 (10)	0.65531 (12)	0.0147 (3)
C16	0.68981 (16)	0.77809 (10)	0.73494 (13)	0.0180 (3)
H16	0.635715	0.785593	0.778923	0.022*
C18	0.87455 (15)	0.71932 (11)	0.70142 (14)	0.0207 (4)
C2	0.38628 (15)	0.59927 (10)	0.73710 (12)	0.0155 (3)
C23	0.50805 (18)	0.86144 (12)	0.50289 (15)	0.0284 (4)
H23A	0.565408	0.887804	0.468892	0.043*
H23B	0.432255	0.889308	0.489492	0.043*
H23C	0.497222	0.806898	0.480029	0.043*
C6	0.51075 (17)	0.60910 (11)	0.29925 (13)	0.0205 (4)
H6	0.473787	0.592958	0.236178	0.025*
C7	0.62148 (17)	0.64447 (11)	0.31245 (13)	0.0212 (4)
H7	0.661150	0.653133	0.258672	0.025*
C19	0.85261 (15)	0.75428 (11)	0.60807 (14)	0.0201 (4)
H19	0.907541	0.747211	0.564689	0.024*
C21	0.55365 (16)	0.86194 (11)	0.61237 (14)	0.0205 (4)
H21	0.490931	0.838197	0.645325	0.025*
C11	0.35108 (15)	0.59837 (11)	0.83671 (12)	0.0172 (3)
C20	0.74866 (16)	0.80009 (10)	0.57850 (13)	0.0179 (3)
H20	0.734796	0.821888	0.514780	0.022*
C13	0.20671 (14)	0.52238 (10)	0.66742 (13)	0.0171 (3)
C22	0.57498 (19)	0.94615 (12)	0.65060 (17)	0.0306 (5)
H22A	0.603588	0.944795	0.720925	0.046*
H22B	0.500838	0.975927	0.637583	0.046*
H22C	0.634190	0.971653	0.617776	0.046*
C12	0.35119 (19)	0.52333 (13)	0.97799 (14)	0.0296 (4)
H12A	0.264759	0.525610	0.970111	0.044*
H12B	0.385342	0.565802	1.021435	0.044*
H12C	0.378785	0.472350	1.006077	0.044*
C14	0.05311 (17)	0.43939 (13)	0.59413 (16)	0.0299 (5)
H14A	0.028180	0.410560	0.533200	0.045*
H14B	−0.011348	0.473653	0.606953	0.045*
H14C	0.072946	0.401848	0.647827	0.045*
C24	0.97821 (16)	0.66570 (12)	0.73146 (16)	0.0282 (4)
H24A	0.957177	0.625317	0.775909	0.042*
H24B	1.045444	0.696444	0.764449	0.042*
H24C	0.999714	0.640314	0.673643	0.042*
F1	0.0875 (8)	0.8272 (6)	0.5641 (8)	0.0446 (14)	0.6
F2	0.1808 (9)	0.8373 (5)	0.4446 (6)	0.047 (2)	0.6
F5	0.0504 (3)	0.7519 (2)	0.4364 (2)	0.0322 (8)	0.6
F6	0.2392 (3)	0.70915 (17)	0.4574 (2)	0.0384 (7)	0.6
F4	0.1294 (2)	0.69421 (16)	0.57644 (19)	0.0355 (6)	0.6
F3A	0.2686 (3)	0.8434 (3)	0.5904 (3)	0.0545 (11)	0.4
F6A	0.2795 (4)	0.7395 (3)	0.4914 (3)	0.0426 (11)	0.4
F4A	0.1789 (8)	0.7293 (3)	0.6176 (4)	0.106 (3)	0.4
F5A	0.0812 (6)	0.7322 (4)	0.4642 (6)	0.093 (3)	0.4
F3	0.2796 (2)	0.7804 (2)	0.59465 (17)	0.0549 (8)	0.6
P1A	0.1760 (3)	0.78689 (19)	0.5282 (3)	0.0234 (7)	0.4
F2A	0.1982 (13)	0.8474 (7)	0.4471 (9)	0.0359 (17)	0.4
F1A	0.0790 (9)	0.8319 (9)	0.5763 (10)	0.0269 (15)	0.4

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru1	0.01265 (8)	0.01407 (9)	0.01132 (8)	−0.00220 (6)	0.00299 (6)	−0.00002 (6)
Cl1	0.0212 (2)	0.0158 (2)	0.0226 (2)	0.00044 (16)	−0.00192 (16)	−0.00102 (16)
P1	0.0193 (6)	0.0304 (11)	0.0170 (6)	0.0011 (6)	0.0039 (4)	0.0050 (7)
O4	0.0208 (6)	0.0378 (8)	0.0243 (7)	−0.0078 (6)	0.0101 (5)	−0.0016 (6)
O1	0.0271 (7)	0.0253 (7)	0.0180 (6)	0.0060 (5)	0.0114 (5)	0.0051 (5)
O3	0.0175 (6)	0.0273 (7)	0.0254 (7)	−0.0093 (5)	0.0054 (5)	−0.0044 (6)
N1	0.0147 (7)	0.0150 (7)	0.0129 (7)	−0.0006 (5)	0.0031 (5)	0.0002 (5)
O2	0.0363 (8)	0.0225 (7)	0.0206 (7)	0.0044 (6)	0.0142 (6)	−0.0006 (5)
N2	0.0173 (7)	0.0148 (7)	0.0137 (7)	0.0006 (5)	0.0039 (5)	0.0009 (5)
C9	0.0152 (8)	0.0109 (8)	0.0134 (8)	0.0027 (6)	0.0022 (6)	0.0001 (6)
C15	0.0177 (8)	0.0125 (8)	0.0185 (8)	−0.0038 (6)	0.0035 (6)	−0.0017 (6)
C5	0.0205 (8)	0.0160 (8)	0.0150 (8)	0.0006 (7)	0.0009 (6)	0.0010 (7)
C10	0.0170 (8)	0.0110 (8)	0.0138 (8)	0.0023 (6)	0.0024 (6)	0.0014 (6)
C8	0.0198 (8)	0.0228 (9)	0.0168 (8)	0.0015 (7)	0.0065 (7)	0.0023 (7)
C4	0.0146 (7)	0.0123 (8)	0.0148 (8)	0.0009 (6)	0.0009 (6)	−0.0008 (6)
C17	0.0209 (8)	0.0199 (9)	0.0157 (8)	−0.0069 (7)	−0.0015 (7)	−0.0018 (7)
C1	0.0172 (8)	0.0183 (9)	0.0139 (8)	−0.0025 (6)	0.0036 (6)	−0.0017 (7)
C3	0.0133 (7)	0.0129 (8)	0.0181 (8)	0.0021 (6)	0.0034 (6)	0.0003 (6)
C16	0.0207 (8)	0.0168 (9)	0.0171 (8)	−0.0058 (7)	0.0049 (7)	−0.0053 (7)
C18	0.0150 (8)	0.0191 (9)	0.0263 (9)	−0.0059 (7)	−0.0015 (7)	−0.0022 (7)
C2	0.0164 (8)	0.0160 (8)	0.0151 (8)	0.0014 (6)	0.0057 (6)	0.0009 (6)
C23	0.0290 (10)	0.0262 (10)	0.0274 (10)	0.0055 (8)	−0.0026 (8)	0.0012 (8)
C6	0.0286 (9)	0.0196 (9)	0.0125 (8)	0.0047 (7)	0.0010 (7)	0.0001 (7)
C7	0.0278 (9)	0.0230 (9)	0.0143 (8)	0.0051 (7)	0.0079 (7)	0.0039 (7)
C19	0.0161 (8)	0.0197 (9)	0.0262 (9)	−0.0070 (7)	0.0084 (7)	−0.0018 (7)
C21	0.0192 (8)	0.0184 (9)	0.0244 (9)	0.0004 (7)	0.0048 (7)	0.0006 (7)
C11	0.0150 (8)	0.0223 (9)	0.0150 (8)	−0.0038 (7)	0.0043 (6)	−0.0006 (7)
C20	0.0200 (8)	0.0165 (8)	0.0181 (8)	−0.0058 (7)	0.0054 (7)	0.0016 (7)
C13	0.0129 (8)	0.0172 (9)	0.0214 (9)	0.0015 (6)	0.0033 (6)	0.0006 (7)
C22	0.0317 (11)	0.0206 (10)	0.0396 (12)	0.0047 (8)	0.0060 (9)	−0.0069 (9)
C12	0.0377 (11)	0.0334 (11)	0.0214 (10)	0.0083 (9)	0.0161 (8)	0.0100 (8)
C14	0.0206 (9)	0.0323 (11)	0.0372 (11)	−0.0131 (8)	0.0062 (8)	−0.0044 (9)
C24	0.0167 (9)	0.0276 (10)	0.0372 (11)	−0.0011 (8)	−0.0043 (8)	0.0002 (9)
F1	0.057 (3)	0.044 (3)	0.043 (3)	−0.0207 (19)	0.039 (2)	−0.0214 (19)
F2	0.084 (6)	0.031 (3)	0.035 (2)	−0.004 (3)	0.034 (2)	0.0034 (18)
F5	0.0330 (15)	0.0394 (16)	0.0204 (10)	0.0031 (11)	−0.0065 (10)	−0.0021 (10)
F6	0.0491 (17)	0.0390 (17)	0.0327 (16)	0.0267 (13)	0.0232 (13)	0.0184 (11)
F4	0.0321 (12)	0.0445 (16)	0.0329 (13)	0.0091 (10)	0.0144 (10)	0.0193 (11)
F3A	0.0196 (16)	0.097 (3)	0.044 (2)	−0.004 (2)	−0.0015 (14)	−0.031 (2)
F6A	0.053 (3)	0.044 (3)	0.037 (3)	0.028 (2)	0.024 (2)	0.0148 (18)
F4A	0.203 (8)	0.063 (4)	0.082 (4)	0.070 (4)	0.108 (5)	0.050 (3)
F5A	0.065 (4)	0.076 (5)	0.153 (7)	−0.045 (4)	0.060 (4)	−0.084 (5)
F3	0.0246 (12)	0.104 (2)	0.0325 (13)	−0.0192 (14)	−0.0051 (9)	0.0033 (16)
P1A	0.0250 (11)	0.0230 (14)	0.0257 (12)	0.0016 (9)	0.0149 (8)	0.0030 (9)
F2A	0.039 (3)	0.023 (3)	0.056 (4)	−0.014 (2)	0.038 (2)	−0.002 (2)
F1A	0.025 (3)	0.038 (3)	0.024 (3)	−0.009 (2)	0.020 (2)	−0.020 (2)

Geometric parameters (Å, º)

Ru1—Cl1	2.3881 (5)	C17—C18	1.421 (3)
Ru1—N1	2.0823 (14)	C1—H1	0.9500
Ru1—N2	2.0862 (14)	C1—C2	1.386 (2)
Ru1—C15	2.2056 (17)	C3—C2	1.394 (2)
Ru1—C17	2.2063 (17)	C3—C13	1.504 (2)
Ru1—C16	2.1801 (17)	C16—H16	0.9500
Ru1—C18	2.2332 (17)	C18—C19	1.413 (3)
Ru1—C19	2.1995 (17)	C18—C24	1.501 (3)
Ru1—C20	2.1607 (17)	C2—C11	1.508 (2)
P1—F1	1.588 (3)	C23—H23A	0.9800
P1—F2	1.581 (3)	C23—H23B	0.9800
P1—F5	1.591 (2)	C23—H23C	0.9800
P1—F6	1.595 (2)	C23—C21	1.527 (3)
P1—F4	1.587 (2)	C6—H6	0.9500
P1—F3	1.583 (2)	C6—C7	1.389 (3)
O4—C13	1.201 (2)	C7—H7	0.9500
O1—C11	1.327 (2)	C19—H19	0.9500
O1—C12	1.452 (2)	C19—C20	1.426 (3)
O3—C13	1.328 (2)	C21—H21	1.0000
O3—C14	1.456 (2)	C21—C22	1.530 (3)
N1—C9	1.355 (2)	C20—H20	0.9500
N1—C1	1.346 (2)	C22—H22A	0.9800
O2—C11	1.199 (2)	C22—H22B	0.9800
N2—C10	1.358 (2)	C22—H22C	0.9800
N2—C8	1.349 (2)	C12—H12A	0.9800
C9—C10	1.473 (2)	C12—H12B	0.9800
C9—C4	1.393 (2)	C12—H12C	0.9800
C15—C16	1.425 (2)	C14—H14A	0.9800
C15—C21	1.512 (2)	C14—H14B	0.9800
C15—C20	1.421 (2)	C14—H14C	0.9800
C5—H5	0.9500	C24—H24A	0.9800
C5—C10	1.392 (2)	C24—H24B	0.9800
C5—C6	1.385 (3)	C24—H24C	0.9800
C8—H8	0.9500	F3A—P1A	1.578 (3)
C8—C7	1.382 (3)	F6A—P1A	1.588 (3)
C4—H4	0.9500	F4A—P1A	1.578 (3)
C4—C3	1.390 (2)	F5A—P1A	1.586 (3)
C17—H17	0.9500	P1A—F2A	1.579 (3)
C17—C16	1.406 (3)	P1A—F1A	1.586 (3)
N1—Ru1—Cl1	84.38 (4)	C2—C3—C13	118.74 (15)
N1—Ru1—N2	76.75 (5)	Ru1—C16—H16	129.6
N1—Ru1—C15	101.36 (6)	C15—C16—Ru1	72.01 (10)
N1—Ru1—C17	111.77 (6)	C15—C16—H16	118.7
N1—Ru1—C16	93.66 (6)	C17—C16—Ru1	72.32 (10)
N1—Ru1—C18	145.93 (6)	C17—C16—C15	122.60 (16)
N1—Ru1—C19	170.06 (6)	C17—C16—H16	118.7
N1—Ru1—C20	132.33 (6)	C17—C18—Ru1	70.30 (10)
N2—Ru1—Cl1	85.34 (4)	C17—C18—C24	120.13 (17)
N2—Ru1—C15	107.21 (6)	C19—C18—Ru1	70.12 (10)
N2—Ru1—C17	170.83 (6)	C19—C18—C17	118.20 (16)
N2—Ru1—C16	141.95 (6)	C19—C18—C24	121.53 (18)
N2—Ru1—C18	135.40 (6)	C24—C18—Ru1	127.66 (13)
N2—Ru1—C19	103.99 (6)	C1—C2—C3	119.14 (15)
N2—Ru1—C20	91.70 (6)	C1—C2—C11	117.69 (15)
C15—Ru1—Cl1	167.04 (5)	C3—C2—C11	123.17 (15)
C15—Ru1—C17	68.50 (7)	H23A—C23—H23B	109.5
C15—Ru1—C18	81.47 (7)	H23A—C23—H23C	109.5
C17—Ru1—Cl1	98.61 (5)	H23B—C23—H23C	109.5
C17—Ru1—C18	37.34 (7)	C21—C23—H23A	109.5
C16—Ru1—Cl1	130.90 (5)	C21—C23—H23B	109.5
C16—Ru1—C15	37.91 (7)	C21—C23—H23C	109.5
C16—Ru1—C17	37.39 (7)	C5—C6—H6	120.3
C16—Ru1—C18	67.61 (7)	C5—C6—C7	119.33 (16)
C16—Ru1—C19	79.64 (7)	C7—C6—H6	120.3
C18—Ru1—Cl1	87.29 (5)	C8—C7—C6	118.74 (16)
C19—Ru1—Cl1	105.55 (5)	C8—C7—H7	120.6
C19—Ru1—C15	68.85 (7)	C6—C7—H7	120.6
C19—Ru1—C17	67.01 (7)	Ru1—C19—H19	130.8
C19—Ru1—C18	37.16 (7)	C18—C19—Ru1	72.72 (10)
C20—Ru1—Cl1	141.39 (5)	C18—C19—H19	119.8
C20—Ru1—C15	37.97 (6)	C18—C19—C20	120.49 (16)
C20—Ru1—C17	80.03 (7)	C20—C19—Ru1	69.45 (10)
C20—Ru1—C16	67.58 (7)	C20—C19—H19	119.8
C20—Ru1—C18	68.21 (7)	C15—C21—C23	113.45 (16)
C20—Ru1—C19	38.16 (7)	C15—C21—H21	107.6
F1—P1—F5	86.3 (5)	C15—C21—C22	109.20 (15)
F1—P1—F6	174.9 (5)	C23—C21—H21	107.6
F2—P1—F1	84.5 (6)	C23—C21—C22	111.15 (17)
F2—P1—F5	81.5 (4)	C22—C21—H21	107.6
F2—P1—F6	91.4 (4)	O1—C11—C2	110.49 (15)
F2—P1—F4	170.7 (4)	O2—C11—O1	126.13 (16)
F2—P1—F3	99.0 (4)	O2—C11—C2	123.31 (16)
F5—P1—F6	90.2 (2)	Ru1—C20—H20	128.2
F4—P1—F1	93.2 (5)	C15—C20—Ru1	72.73 (10)
F4—P1—F5	89.39 (18)	C15—C20—C19	122.05 (16)
F4—P1—F6	90.36 (18)	C15—C20—H20	119.0
F3—P1—F1	93.7 (4)	C19—C20—Ru1	72.39 (10)
F3—P1—F5	179.4 (3)	C19—C20—H20	119.0
F3—P1—F6	89.9 (2)	O4—C13—O3	124.87 (16)
F3—P1—F4	90.03 (18)	O4—C13—C3	122.86 (16)
C11—O1—C12	114.86 (14)	O3—C13—C3	112.27 (15)
C13—O3—C14	115.21 (15)	C21—C22—H22A	109.5
C9—N1—Ru1	117.38 (11)	C21—C22—H22B	109.5
C1—N1—Ru1	123.31 (11)	C21—C22—H22C	109.5
C1—N1—C9	119.04 (14)	H22A—C22—H22B	109.5
C10—N2—Ru1	117.10 (11)	H22A—C22—H22C	109.5
C8—N2—Ru1	124.18 (12)	H22B—C22—H22C	109.5
C8—N2—C10	118.70 (15)	O1—C12—H12A	109.5
N1—C9—C10	114.12 (14)	O1—C12—H12B	109.5
N1—C9—C4	121.67 (15)	O1—C12—H12C	109.5
C4—C9—C10	124.20 (15)	H12A—C12—H12B	109.5
C16—C15—Ru1	70.08 (10)	H12A—C12—H12C	109.5
C16—C15—C21	120.36 (16)	H12B—C12—H12C	109.5
C21—C15—Ru1	129.35 (12)	O3—C14—H14A	109.5
C20—C15—Ru1	69.30 (10)	O3—C14—H14B	109.5
C20—C15—C16	116.06 (16)	O3—C14—H14C	109.5
C20—C15—C21	123.54 (16)	H14A—C14—H14B	109.5
C10—C5—H5	120.4	H14A—C14—H14C	109.5
C6—C5—H5	120.4	H14B—C14—H14C	109.5
C6—C5—C10	119.19 (16)	C18—C24—H24A	109.5
N2—C10—C9	114.37 (14)	C18—C24—H24B	109.5
N2—C10—C5	121.48 (15)	C18—C24—H24C	109.5
C5—C10—C9	124.14 (15)	H24A—C24—H24B	109.5
N2—C8—H8	118.7	H24A—C24—H24C	109.5
N2—C8—C7	122.54 (17)	H24B—C24—H24C	109.5
C7—C8—H8	118.7	F3A—P1A—F6A	90.8 (3)
C9—C4—H4	120.4	F3A—P1A—F5A	178.4 (5)
C3—C4—C9	119.11 (15)	F3A—P1A—F2A	79.8 (6)
C3—C4—H4	120.4	F3A—P1A—F1A	86.1 (5)
Ru1—C17—H17	130.2	F4A—P1A—F3A	91.1 (4)
C16—C17—Ru1	70.30 (10)	F4A—P1A—F6A	91.2 (3)
C16—C17—H17	119.7	F4A—P1A—F5A	90.3 (5)
C16—C17—C18	120.57 (16)	F4A—P1A—F2A	169.2 (7)
C18—C17—Ru1	72.36 (10)	F4A—P1A—F1A	83.7 (7)
C18—C17—H17	119.7	F5A—P1A—F6A	90.1 (4)
N1—C1—H1	118.9	F2A—P1A—F6A	83.1 (6)
N1—C1—C2	122.14 (16)	F2A—P1A—F5A	98.9 (7)
C2—C1—H1	118.9	F2A—P1A—F1A	101.3 (9)
C4—C3—C2	118.84 (15)	F1A—P1A—F6A	174.0 (6)
C4—C3—C13	122.40 (15)	F1A—P1A—F5A	93.2 (6)