(η³-All­yl)bromo­(η⁵-cyclo­penta­dien­yl)(phenyl­amino­diphenyl­phosphine-κP)ruthenium(IV) hexa­fluoro­phosphate

The title compound, [RuBr(η⁵-C₅H₅)(η³-C₃H₅)(C₁₈H₁₆NP)]PF₆, contains a half-sandwich cyclo­penta­dienylruthenium(IV) complex with a three-legged piano-stool structure and an intra­molecular N—H...Br hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.023
• wR factor = 0.056
• Data-to-parameter ratio = 21.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          5
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ru     -   Br      ..       5.91 su
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         P2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SHELXTL (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(η³-Allyl)bromo(η⁵-cyclopentadienyl)(phenylaminodiphenylphosphine- κP)ruthenium(IV) hexafluorophosphate

Crystal data

[RuBr(C5H5)(C3H7)(C18H16NP)]PF6	F(000) = 2816
Mr = 709.40	Dx = 1.787 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1001 reflections
a = 15.384 (2) Å	θ = 2.7–29.8°
b = 17.603 (2) Å	µ = 2.29 mm^−1
c = 19.469 (2) Å	T = 123 K
V = 5272.4 (11) Å^3	Block, orange
Z = 8	0.38 × 0.31 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer	7663 independent reflections
Radiation source: fine-focus sealed tube	6108 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω scans	θmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
Tmin = 0.458, Tmax = 0.564	k = −24→24
59992 measured reflections	l = −27→26

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.056	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0224P)^2 + 3.5883P] where P = (Fo^2 + 2Fc^2)/3
7663 reflections	(Δ/σ)max = 0.002
352 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Experimental. Smart old, 4 x 606 omega scan frames, 0.3 ° and 20 sec per frame

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. 1) Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

2) N-bound and allyl-bound hydrogen atoms refined unrestrained. All other hydrogen refined with the riding model.

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

	x	y	z	Uiso*/Ueq
Ru	0.148779 (9)	0.134798 (8)	0.605796 (7)	0.01689 (4)
Br	0.029085 (12)	0.189698 (12)	0.531800 (10)	0.02634 (5)
P1	0.24155 (3)	0.21871 (2)	0.54451 (2)	0.01549 (8)
N	0.19318 (10)	0.30321 (8)	0.53603 (8)	0.0191 (3)
H	0.1447 (15)	0.3000 (12)	0.5461 (11)	0.023*
C1	0.08118 (13)	0.19397 (12)	0.69272 (10)	0.0268 (4)
H1	0.0331	0.2273	0.6871	0.032*
C2	0.16914 (13)	0.21552 (11)	0.69175 (9)	0.0254 (4)
H2	0.1907	0.2656	0.6853	0.030*
C3	0.22009 (14)	0.14913 (12)	0.70221 (9)	0.0286 (4)
H3	0.2817	0.1468	0.7040	0.034*
C4	0.16225 (16)	0.08720 (12)	0.70954 (10)	0.0331 (5)
H4	0.1783	0.0358	0.7173	0.040*
C5	0.07585 (15)	0.11517 (12)	0.70334 (10)	0.0317 (5)
H5	0.0240	0.0859	0.7059	0.038*
C6	0.08673 (16)	0.02695 (12)	0.57282 (12)	0.0323 (5)
H6A	0.0302 (17)	0.0321 (14)	0.5551 (13)	0.039*
H6B	0.0950 (16)	−0.0037 (14)	0.6121 (12)	0.039*
C7	0.15826 (15)	0.04358 (11)	0.53082 (11)	0.0286 (4)
H7	0.1506 (15)	0.0607 (13)	0.4847 (13)	0.034*
C8	0.23949 (15)	0.04690 (11)	0.56311 (11)	0.0269 (4)
H8A	0.2460 (15)	0.0159 (13)	0.6016 (12)	0.032*
H8B	0.2888 (15)	0.0640 (13)	0.5360 (12)	0.032*
C9	0.34123 (11)	0.23882 (10)	0.59094 (9)	0.0191 (3)
C10	0.40091 (12)	0.18133 (11)	0.60605 (10)	0.0238 (4)
H10	0.3899	0.1307	0.5915	0.029*
C11	0.47605 (13)	0.19814 (12)	0.64218 (10)	0.0281 (4)
H11	0.5170	0.1591	0.6517	0.034*
C12	0.49168 (13)	0.27098 (13)	0.66431 (10)	0.0290 (4)
H12	0.5436	0.2822	0.6887	0.035*
C13	0.43227 (14)	0.32786 (12)	0.65127 (10)	0.0278 (4)
H13	0.4429	0.3779	0.6674	0.033*
C14	0.35713 (12)	0.31228 (11)	0.61467 (9)	0.0222 (4)
H14	0.3164	0.3516	0.6057	0.027*
C15	0.27440 (11)	0.19074 (10)	0.45869 (9)	0.0177 (3)
C16	0.21067 (12)	0.19012 (11)	0.40794 (9)	0.0223 (4)
H16	0.1519	0.2007	0.4194	0.027*
C17	0.23355 (14)	0.17401 (11)	0.34056 (10)	0.0273 (4)
H17	0.1902	0.1736	0.3058	0.033*
C18	0.31866 (14)	0.15867 (12)	0.32380 (10)	0.0294 (4)
H18	0.3338	0.1480	0.2775	0.035*
C19	0.38196 (14)	0.15869 (12)	0.37387 (10)	0.0275 (4)
H19	0.4405	0.1477	0.3621	0.033*
C20	0.36014 (12)	0.17477 (10)	0.44135 (10)	0.0226 (4)
H20	0.4038	0.1749	0.4758	0.027*
C21	0.20837 (12)	0.35822 (10)	0.48411 (9)	0.0197 (3)
C22	0.13944 (13)	0.40404 (10)	0.46374 (10)	0.0258 (4)
H22	0.0842	0.3985	0.4849	0.031*
C23	0.15124 (16)	0.45765 (12)	0.41279 (12)	0.0342 (5)
H23	0.1040	0.4889	0.3991	0.041*
C24	0.23166 (16)	0.46618 (12)	0.38148 (10)	0.0333 (5)
H24	0.2395	0.5027	0.3461	0.040*
C25	0.30009 (15)	0.42118 (11)	0.40223 (10)	0.0291 (4)
H25	0.3553	0.4269	0.3810	0.035*
C26	0.28925 (13)	0.36774 (10)	0.45377 (10)	0.0229 (4)
H26	0.3371	0.3377	0.4683	0.027*
P2	0.08985 (3)	0.45969 (3)	0.71205 (3)	0.02291 (10)
F1	0.09284 (9)	0.45228 (8)	0.79356 (6)	0.0389 (3)
F2	0.08631 (10)	0.46776 (10)	0.63130 (7)	0.0523 (4)
F3	0.10440 (9)	0.54896 (7)	0.71982 (9)	0.0504 (4)
F4	0.07580 (8)	0.37021 (7)	0.70614 (8)	0.0392 (3)
F5	−0.01296 (7)	0.47169 (7)	0.71596 (7)	0.0329 (3)
F6	0.19293 (8)	0.44701 (8)	0.70859 (7)	0.0373 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru	0.01981 (7)	0.01607 (6)	0.01479 (6)	0.00108 (5)	0.00204 (5)	0.00094 (5)
Br	0.01704 (8)	0.03527 (10)	0.02670 (10)	0.00016 (8)	−0.00174 (7)	0.00550 (8)
P1	0.0164 (2)	0.01586 (19)	0.01421 (19)	0.00133 (16)	−0.00037 (16)	0.00038 (15)
N	0.0165 (7)	0.0195 (7)	0.0212 (7)	0.0030 (6)	0.0035 (6)	0.0030 (6)
C1	0.0317 (10)	0.0315 (10)	0.0173 (9)	0.0078 (8)	0.0072 (8)	−0.0007 (8)
C2	0.0353 (11)	0.0269 (9)	0.0141 (8)	0.0013 (8)	0.0036 (8)	−0.0050 (7)
C3	0.0308 (10)	0.0411 (12)	0.0139 (8)	0.0069 (9)	−0.0016 (7)	−0.0017 (8)
C4	0.0515 (14)	0.0284 (10)	0.0193 (9)	0.0097 (10)	0.0040 (9)	0.0067 (8)
C5	0.0381 (12)	0.0353 (11)	0.0218 (10)	−0.0058 (9)	0.0107 (9)	0.0028 (8)
C6	0.0376 (12)	0.0220 (9)	0.0374 (12)	−0.0071 (9)	0.0013 (10)	−0.0050 (9)
C7	0.0411 (12)	0.0178 (8)	0.0268 (10)	−0.0011 (8)	0.0029 (9)	−0.0069 (8)
C8	0.0368 (11)	0.0181 (8)	0.0258 (10)	0.0054 (8)	0.0049 (9)	−0.0021 (7)
C9	0.0180 (8)	0.0238 (8)	0.0155 (8)	−0.0002 (7)	−0.0003 (6)	0.0003 (6)
C10	0.0230 (9)	0.0261 (9)	0.0224 (9)	0.0028 (7)	−0.0033 (7)	−0.0006 (7)
C11	0.0223 (9)	0.0399 (11)	0.0222 (9)	0.0048 (8)	−0.0025 (8)	0.0051 (8)
C12	0.0224 (9)	0.0472 (12)	0.0174 (9)	−0.0098 (9)	−0.0046 (7)	0.0060 (8)
C13	0.0341 (11)	0.0303 (10)	0.0190 (9)	−0.0111 (8)	−0.0036 (8)	0.0016 (8)
C14	0.0254 (9)	0.0236 (8)	0.0177 (8)	−0.0026 (8)	−0.0014 (7)	0.0012 (7)
C15	0.0197 (8)	0.0168 (7)	0.0165 (8)	−0.0003 (6)	0.0028 (6)	0.0010 (6)
C16	0.0234 (9)	0.0266 (9)	0.0170 (8)	−0.0001 (7)	0.0001 (7)	0.0002 (7)
C17	0.0342 (11)	0.0293 (10)	0.0183 (9)	−0.0026 (8)	−0.0012 (8)	−0.0012 (7)
C18	0.0409 (12)	0.0279 (10)	0.0193 (9)	−0.0035 (9)	0.0093 (8)	−0.0042 (8)
C19	0.0258 (10)	0.0281 (9)	0.0286 (10)	−0.0028 (8)	0.0111 (8)	−0.0056 (8)
C20	0.0219 (9)	0.0221 (9)	0.0239 (9)	−0.0016 (7)	0.0023 (7)	−0.0019 (7)
C21	0.0256 (9)	0.0161 (8)	0.0175 (8)	−0.0015 (7)	−0.0034 (7)	0.0003 (6)
C22	0.0256 (10)	0.0204 (9)	0.0314 (10)	0.0008 (7)	−0.0056 (8)	0.0012 (8)
C23	0.0452 (13)	0.0224 (9)	0.0350 (11)	0.0016 (9)	−0.0166 (10)	0.0047 (8)
C24	0.0546 (14)	0.0232 (9)	0.0220 (9)	−0.0076 (9)	−0.0080 (9)	0.0059 (8)
C25	0.0412 (12)	0.0235 (9)	0.0227 (10)	−0.0094 (9)	0.0034 (9)	−0.0011 (8)
C26	0.0271 (9)	0.0198 (8)	0.0218 (9)	−0.0013 (7)	−0.0002 (7)	0.0000 (7)
P2	0.0220 (2)	0.0202 (2)	0.0266 (3)	−0.00144 (19)	−0.00109 (19)	0.00317 (19)
F1	0.0370 (7)	0.0528 (8)	0.0267 (7)	−0.0061 (6)	−0.0023 (5)	0.0005 (6)
F2	0.0458 (8)	0.0857 (11)	0.0256 (7)	0.0094 (8)	−0.0007 (6)	0.0139 (7)
F3	0.0448 (8)	0.0215 (6)	0.0849 (12)	−0.0077 (6)	−0.0016 (8)	0.0074 (7)
F4	0.0365 (7)	0.0206 (6)	0.0606 (9)	0.0010 (5)	−0.0089 (6)	−0.0060 (6)
F5	0.0229 (6)	0.0314 (6)	0.0445 (7)	0.0034 (5)	−0.0020 (5)	−0.0048 (5)
F6	0.0213 (6)	0.0469 (8)	0.0436 (8)	0.0005 (5)	0.0026 (5)	0.0074 (6)

Geometric parameters (Å, º)

Ru—C1	2.243 (2)	C11—C12	1.374 (3)
Ru—C2	2.218 (2)	C11—H11	0.9500
Ru—C3	2.189 (2)	C12—C13	1.379 (3)
Ru—C4	2.196 (2)	C12—H12	0.9500
Ru—C5	2.233 (2)	C13—C14	1.385 (3)
Ru—C6	2.220 (2)	C13—H13	0.9500
Ru—C7	2.175 (2)	C14—H14	0.9500
Ru—C8	2.243 (2)	C15—C20	1.390 (2)
Ru—P1	2.3754 (5)	C15—C16	1.392 (2)
Ru—Br	2.5298 (3)	C16—C17	1.387 (3)
C6—C7	1.402 (3)	C16—H16	0.9500
C7—C8	1.400 (3)	C17—C18	1.376 (3)
P1—C9	1.815 (2)	C17—H17	0.9500
P1—C15	1.814 (2)	C18—C19	1.378 (3)
P1—N	1.6714 (15)	C18—H18	0.9500
N—C21	1.419 (2)	C19—C20	1.385 (3)
N—H	0.77 (2)	C19—H19	0.9500
C1—C2	1.406 (3)	C20—H20	0.9500
C1—C5	1.405 (3)	C21—C26	1.387 (3)
C1—H1	0.9500	C21—C22	1.390 (3)
C2—C3	1.422 (3)	C22—C23	1.381 (3)
C2—H2	0.9500	C22—H22	0.9500
C3—C4	1.414 (3)	C23—C24	1.387 (3)
C3—H3	0.9500	C23—H23	0.9500
C4—C5	1.423 (3)	C24—C25	1.378 (3)
C4—H4	0.9500	C24—H24	0.9500
C5—H5	0.9500	C25—C26	1.385 (3)
C6—H6A	0.94 (3)	C25—H25	0.9500
C6—H6B	0.94 (2)	C26—H26	0.9500
C7—H7	0.95 (2)	P2—F2	1.5795 (14)
C8—H8A	0.93 (2)	P2—F1	1.5929 (13)
C8—H8B	0.97 (2)	P2—F3	1.5944 (14)
C9—C14	1.395 (3)	P2—F4	1.5941 (13)
C9—C10	1.398 (3)	P2—F5	1.5974 (13)
C10—C11	1.385 (3)	P2—F6	1.6029 (13)
C10—H10	0.9500
C7—Ru—P1	94.68 (6)	C7—C6—H6A	119.4 (16)
C7—Ru—Br	87.06 (6)	Ru—C6—H6A	115.0 (15)
P1—Ru—Br	85.053 (15)	C7—C6—H6B	119.1 (16)
C6—C7—C8	116.6 (2)	Ru—C6—H6B	101.3 (15)
P1—N—C21	127.17 (13)	H6A—C6—H6B	119 (2)
C7—Ru—C3	128.83 (8)	C8—C7—Ru	74.19 (11)
C7—Ru—C4	109.22 (8)	C6—C7—Ru	73.14 (12)
C3—Ru—C4	37.63 (8)	C8—C7—H7	121.3 (14)
C7—Ru—C2	165.94 (8)	C6—C7—H7	121.2 (14)
C3—Ru—C2	37.64 (7)	Ru—C7—H7	113.0 (14)
C4—Ru—C2	62.43 (8)	C7—C8—Ru	68.89 (11)
C7—Ru—C6	37.19 (8)	C7—C8—H8A	115.6 (15)
C3—Ru—C6	124.20 (9)	Ru—C8—H8A	99.9 (14)
C4—Ru—C6	88.87 (9)	C7—C8—H8B	117.8 (14)
C2—Ru—C6	145.79 (8)	Ru—C8—H8B	118.2 (14)
C7—Ru—C5	119.36 (8)	H8A—C8—H8B	122 (2)
C3—Ru—C5	62.63 (8)	C14—C9—C10	119.10 (17)
C4—Ru—C5	37.46 (8)	C14—C9—P1	119.60 (14)
C2—Ru—C5	61.85 (8)	C10—C9—P1	121.24 (14)
C6—Ru—C5	84.12 (8)	C11—C10—C9	120.03 (18)
C7—Ru—C1	151.69 (8)	C11—C10—H10	120.0
C3—Ru—C1	62.08 (8)	C9—C10—H10	120.0
C4—Ru—C1	61.77 (8)	C12—C11—C10	120.31 (19)
C2—Ru—C1	36.73 (7)	C12—C11—H11	119.8
C6—Ru—C1	114.58 (8)	C10—C11—H11	119.8
C5—Ru—C1	36.59 (8)	C11—C12—C13	120.26 (18)
C7—Ru—C8	36.91 (8)	C11—C12—H12	119.9
C3—Ru—C8	94.90 (8)	C13—C12—H12	119.9
C4—Ru—C8	91.08 (8)	C12—C13—C14	120.26 (19)
C2—Ru—C8	129.32 (8)	C12—C13—H13	119.9
C6—Ru—C8	64.56 (8)	C14—C13—H13	119.9
C5—Ru—C8	121.40 (8)	C13—C14—C9	120.02 (18)
C1—Ru—C8	152.66 (7)	C13—C14—H14	120.0
C3—Ru—P1	93.32 (6)	C9—C14—H14	120.0
C4—Ru—P1	129.97 (7)	C20—C15—C16	119.63 (17)
C2—Ru—P1	84.01 (5)	C20—C15—P1	122.88 (14)
C6—Ru—P1	130.16 (6)	C16—C15—P1	117.37 (13)
C5—Ru—P1	145.63 (6)	C17—C16—C15	119.61 (18)
C1—Ru—P1	111.64 (6)	C17—C16—H16	120.2
C8—Ru—P1	82.47 (6)	C15—C16—H16	120.2
C3—Ru—Br	144.02 (5)	C18—C17—C16	120.37 (19)
C4—Ru—Br	137.56 (6)	C18—C17—H17	119.8
C2—Ru—Br	106.73 (5)	C16—C17—H17	119.8
C6—Ru—Br	81.31 (7)	C17—C18—C19	120.30 (18)
C5—Ru—Br	100.24 (6)	C17—C18—H18	119.8
C1—Ru—Br	85.11 (5)	C19—C18—H18	119.8
C8—Ru—Br	120.36 (6)	C18—C19—C20	119.99 (19)
N—P1—C15	105.95 (8)	C18—C19—H19	120.0
N—P1—C9	104.59 (8)	C20—C19—H19	120.0
C15—P1—C9	106.04 (8)	C19—C20—C15	120.09 (18)
N—P1—Ru	109.60 (6)	C19—C20—H20	120.0
C15—P1—Ru	117.47 (6)	C15—C20—H20	120.0
C9—P1—Ru	112.26 (6)	C26—C21—C22	119.51 (17)
C21—N—H	112.9 (17)	C26—C21—N	122.24 (16)
P1—N—H	109.9 (16)	C22—C21—N	118.26 (17)
C2—C1—C5	108.95 (18)	C23—C22—C21	120.1 (2)
C2—C1—Ru	70.66 (11)	C23—C22—H22	120.0
C5—C1—Ru	71.32 (11)	C21—C22—H22	120.0
C2—C1—H1	125.5	C22—C23—C24	120.4 (2)
C5—C1—H1	125.5	C22—C23—H23	119.8
Ru—C1—H1	124.1	C24—C23—H23	119.8
C1—C2—C3	107.87 (18)	C25—C24—C23	119.36 (19)
C1—C2—Ru	72.61 (11)	C25—C24—H24	120.3
C3—C2—Ru	70.08 (11)	C23—C24—H24	120.3
C1—C2—H2	126.1	C24—C25—C26	120.7 (2)
C3—C2—H2	126.1	C24—C25—H25	119.6
Ru—C2—H2	122.9	C26—C25—H25	119.6
C4—C3—C2	107.53 (19)	C25—C26—C21	119.89 (18)
C4—C3—Ru	71.48 (12)	C25—C26—H26	120.1
C2—C3—Ru	72.28 (11)	C21—C26—H26	120.1
C4—C3—H3	126.2	F2—P2—F1	179.44 (9)
C2—C3—H3	126.2	F2—P2—F3	90.61 (9)
Ru—C3—H3	121.7	F1—P2—F3	88.98 (8)
C3—C4—C5	108.21 (18)	F2—P2—F4	90.70 (9)
C3—C4—Ru	70.89 (11)	F1—P2—F4	89.71 (8)
C5—C4—Ru	72.66 (11)	F3—P2—F4	178.67 (9)
C3—C4—H4	125.9	F2—P2—F5	90.08 (8)
C5—C4—H4	125.9	F1—P2—F5	89.54 (7)
Ru—C4—H4	122.2	F3—P2—F5	90.24 (7)
C1—C5—C4	107.43 (19)	F4—P2—F5	89.99 (7)
C1—C5—Ru	72.10 (11)	F2—P2—F6	90.27 (8)
C4—C5—Ru	69.88 (11)	F1—P2—F6	90.11 (7)
C1—C5—H5	126.3	F3—P2—F6	90.13 (8)
C4—C5—H5	126.3	F4—P2—F6	89.63 (7)
Ru—C5—H5	123.4	F5—P2—F6	179.49 (8)
C7—C6—Ru	69.67 (11)
C7—Ru—P1—N	129.18 (9)	C1—Ru—C4—C5	37.08 (12)
C3—Ru—P1—N	−101.40 (8)	C8—Ru—C4—C5	−146.33 (13)
C4—Ru—P1—N	−110.84 (9)	P1—Ru—C4—C5	132.60 (11)
C2—Ru—P1—N	−64.87 (8)	Br—Ru—C4—C5	−6.00 (17)
C6—Ru—P1—N	116.81 (11)	C2—C1—C5—C4	0.4 (2)
C5—Ru—P1—N	−58.36 (13)	Ru—C1—C5—C4	61.30 (14)
C1—Ru—P1—N	−40.18 (8)	C2—C1—C5—Ru	−60.94 (13)
C8—Ru—P1—N	164.10 (8)	C3—C4—C5—C1	−0.4 (2)
Br—Ru—P1—N	42.56 (6)	Ru—C4—C5—C1	−62.73 (14)
C7—Ru—P1—C15	8.26 (9)	C3—C4—C5—Ru	62.36 (14)
C3—Ru—P1—C15	137.68 (8)	C7—Ru—C5—C1	−159.53 (13)
C4—Ru—P1—C15	128.24 (10)	C3—Ru—C5—C1	79.21 (14)
C2—Ru—P1—C15	174.21 (8)	C4—Ru—C5—C1	116.98 (19)
C6—Ru—P1—C15	−4.11 (11)	C2—Ru—C5—C1	36.46 (12)
C5—Ru—P1—C15	−179.29 (12)	C6—Ru—C5—C1	−147.18 (14)
C1—Ru—P1—C15	−161.11 (9)	C8—Ru—C5—C1	157.48 (12)
C8—Ru—P1—C15	43.17 (8)	P1—Ru—C5—C1	29.11 (19)
Br—Ru—P1—C15	−78.37 (7)	Br—Ru—C5—C1	−67.14 (13)
C7—Ru—P1—C9	−115.06 (9)	C7—Ru—C5—C4	83.50 (15)
C3—Ru—P1—C9	14.36 (8)	C3—Ru—C5—C4	−37.76 (13)
C4—Ru—P1—C9	4.92 (10)	C2—Ru—C5—C4	−80.52 (14)
C2—Ru—P1—C9	50.89 (8)	C6—Ru—C5—C4	95.84 (14)
C6—Ru—P1—C9	−127.43 (11)	C1—Ru—C5—C4	−116.98 (19)
C5—Ru—P1—C9	57.40 (13)	C8—Ru—C5—C4	40.50 (16)
C1—Ru—P1—C9	75.58 (9)	P1—Ru—C5—C4	−87.86 (15)
C8—Ru—P1—C9	−80.14 (8)	Br—Ru—C5—C4	175.89 (12)
Br—Ru—P1—C9	158.32 (6)	C3—Ru—C6—C7	−111.01 (14)
C15—P1—N—C21	−26.98 (17)	C4—Ru—C6—C7	−124.81 (14)
C9—P1—N—C21	84.82 (17)	C2—Ru—C6—C7	−156.33 (14)
Ru—P1—N—C21	−154.64 (14)	C5—Ru—C6—C7	−162.05 (15)
C7—Ru—C1—C2	158.82 (16)	C1—Ru—C6—C7	177.15 (13)
C3—Ru—C1—C2	37.97 (12)	C8—Ru—C6—C7	−33.07 (13)
C4—Ru—C1—C2	80.85 (13)	P1—Ru—C6—C7	20.69 (17)
C6—Ru—C1—C2	155.18 (12)	Br—Ru—C6—C7	96.62 (13)
C5—Ru—C1—C2	118.82 (18)	Ru—C6—C7—C8	61.98 (15)
C8—Ru—C1—C2	73.4 (2)	C3—Ru—C7—C8	−27.22 (16)
P1—Ru—C1—C2	−44.00 (12)	C4—Ru—C7—C8	−64.47 (14)
Br—Ru—C1—C2	−126.70 (11)	C2—Ru—C7—C8	−13.2 (4)
C7—Ru—C1—C5	40.0 (2)	C6—Ru—C7—C8	−124.9 (2)
C3—Ru—C1—C5	−80.85 (14)	C5—Ru—C7—C8	−104.26 (14)
C4—Ru—C1—C5	−37.96 (13)	C1—Ru—C7—C8	−130.34 (17)
C2—Ru—C1—C5	−118.82 (18)	P1—Ru—C7—C8	70.86 (12)
C6—Ru—C1—C5	36.36 (16)	Br—Ru—C7—C8	155.65 (12)
C8—Ru—C1—C5	−45.4 (2)	C3—Ru—C7—C6	97.64 (16)
P1—Ru—C1—C5	−162.81 (12)	C4—Ru—C7—C6	60.39 (16)
Br—Ru—C1—C5	114.49 (13)	C2—Ru—C7—C6	111.7 (3)
C5—C1—C2—C3	−0.2 (2)	C5—Ru—C7—C6	20.60 (17)
Ru—C1—C2—C3	−61.57 (13)	C1—Ru—C7—C6	−5.5 (2)
C5—C1—C2—Ru	61.35 (14)	C8—Ru—C7—C6	124.86 (19)
C7—Ru—C2—C1	−135.1 (3)	P1—Ru—C7—C6	−164.28 (13)
C3—Ru—C2—C1	−117.10 (17)	Br—Ru—C7—C6	−79.49 (13)
C4—Ru—C2—C1	−78.90 (13)	C6—C7—C8—Ru	−61.41 (16)
C6—Ru—C2—C1	−42.8 (2)	C3—Ru—C8—C7	159.05 (13)
C5—Ru—C2—C1	−36.32 (12)	C4—Ru—C8—C7	121.55 (13)
C8—Ru—C2—C1	−145.32 (12)	C2—Ru—C8—C7	175.89 (12)
P1—Ru—C2—C1	139.52 (11)	C6—Ru—C8—C7	33.31 (13)
Br—Ru—C2—C1	56.53 (12)	C5—Ru—C8—C7	98.27 (14)
C7—Ru—C2—C3	−18.0 (4)	C1—Ru—C8—C7	128.08 (17)
C4—Ru—C2—C3	38.20 (12)	P1—Ru—C8—C7	−108.24 (12)
C6—Ru—C2—C3	74.34 (19)	Br—Ru—C8—C7	−28.50 (14)
C5—Ru—C2—C3	80.79 (14)	N—P1—C9—C14	4.67 (17)
C1—Ru—C2—C3	117.10 (17)	C15—P1—C9—C14	116.40 (15)
C8—Ru—C2—C3	−28.21 (16)	Ru—P1—C9—C14	−114.09 (14)
P1—Ru—C2—C3	−103.38 (12)	N—P1—C9—C10	−178.12 (15)
Br—Ru—C2—C3	173.63 (11)	C15—P1—C9—C10	−66.39 (16)
C1—C2—C3—C4	0.0 (2)	Ru—P1—C9—C10	63.13 (16)
Ru—C2—C3—C4	−63.21 (13)	C14—C9—C10—C11	−2.1 (3)
C1—C2—C3—Ru	63.20 (13)	P1—C9—C10—C11	−179.32 (15)
C7—Ru—C3—C4	−69.40 (15)	C9—C10—C11—C12	1.0 (3)
C2—Ru—C3—C4	116.14 (17)	C10—C11—C12—C13	0.6 (3)
C6—Ru—C3—C4	−22.98 (16)	C11—C12—C13—C14	−1.2 (3)
C5—Ru—C3—C4	37.59 (12)	C12—C13—C14—C9	0.1 (3)
C1—Ru—C3—C4	79.09 (13)	C10—C9—C14—C13	1.5 (3)
C8—Ru—C3—C4	−85.40 (13)	P1—C9—C14—C13	178.80 (14)
P1—Ru—C3—C4	−168.12 (12)	N—P1—C15—C20	122.11 (15)
Br—Ru—C3—C4	105.72 (13)	C9—P1—C15—C20	11.34 (17)
C7—Ru—C3—C2	174.47 (12)	Ru—P1—C15—C20	−115.08 (14)
C4—Ru—C3—C2	−116.14 (17)	N—P1—C15—C16	−53.90 (16)
C6—Ru—C3—C2	−139.12 (13)	C9—P1—C15—C16	−164.67 (14)
C5—Ru—C3—C2	−78.55 (13)	Ru—P1—C15—C16	68.91 (15)
C1—Ru—C3—C2	−37.05 (12)	C20—C15—C16—C17	−0.4 (3)
C8—Ru—C3—C2	158.46 (12)	P1—C15—C16—C17	175.78 (14)
P1—Ru—C3—C2	75.74 (11)	C15—C16—C17—C18	0.0 (3)
Br—Ru—C3—C2	−10.41 (18)	C16—C17—C18—C19	0.4 (3)
C2—C3—C4—C5	0.2 (2)	C17—C18—C19—C20	−0.5 (3)
Ru—C3—C4—C5	−63.50 (14)	C18—C19—C20—C15	0.1 (3)
C2—C3—C4—Ru	63.74 (13)	C16—C15—C20—C19	0.3 (3)
C7—Ru—C4—C3	129.45 (13)	P1—C15—C20—C19	−175.64 (14)
C2—Ru—C4—C3	−38.21 (12)	P1—N—C21—C26	−31.9 (3)
C6—Ru—C4—C3	161.16 (13)	P1—N—C21—C22	148.45 (15)
C5—Ru—C4—C3	−117.05 (18)	C26—C21—C22—C23	1.2 (3)
C1—Ru—C4—C3	−79.97 (13)	N—C21—C22—C23	−179.21 (18)
C8—Ru—C4—C3	96.63 (13)	C21—C22—C23—C24	0.1 (3)
P1—Ru—C4—C3	15.55 (15)	C22—C23—C24—C25	−0.7 (3)
Br—Ru—C4—C3	−123.05 (12)	C23—C24—C25—C26	0.1 (3)
C7—Ru—C4—C5	−113.50 (13)	C24—C25—C26—C21	1.2 (3)
C3—Ru—C4—C5	117.05 (18)	C22—C21—C26—C25	−1.8 (3)
C2—Ru—C4—C5	78.84 (13)	N—C21—C26—C25	178.59 (17)
C6—Ru—C4—C5	−81.79 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N—H···Br	0.77 (2)	2.65 (2)	3.2206 (16)	132 (2)