(Benzyl­amine-N)(η5-cyclo­penta­dienyl)­bis­(tri­phenyl­phosphine-P)­ruthenium(II) tetra­fluoro­borate

Cabeza, J.A.; Río, I.; Navarro, M.E.; García-Granda, S.

doi:10.1107/S1600536801004469

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(Benzylamine-N)(η⁵-cyclopentadienyl)bis(triphenylphosphine-P)ruthenium(II) tetrafluoroborate

J. A. Cabeza, I. Río, M. E. Navarro and S. García-Granda

The reaction of [RuCl(Cp)(PPh₃)₂] with Ag[BF₄] in tetrahydrofuran, in the presence of benzylamine, leads to the mononuclear title compound [Ru(Cp)(H₂NCH₂Ph)(PPh₃)₂]BF₄, where Cp is cyclopentadienyl (C₅H₅). The Ru atom presents a pseudo-octahedral environment with the Cp ligand occupying three facial coordination sites, while the remaining coordination positions are occupied by the P atoms of the two triphenylphosphine ligands and by the N atom of the benzylamine ligand. The [BF₄]⁻ counter-ion remains uncoordinated.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801004469/ci6016sup1.cif Contains datablocks I, e5b
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801004469/ci6016Isup2.hkl Contains datablock I

CCDC reference: 162803

checkCIF report

Key indicators

Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.009 Å
R factor = 0.047
wR factor = 0.133
Data-to-parameter ratio = 13.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           69.83
         From the CIF: _reflns_number_total               7148
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         7694
         Completeness (_total/calc)             92.90%
          Alert C: < 95% complete

RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.141

PLAT_420  Alert C D-H Without Acceptor       N(1)   -   H(99B)            ?


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

Comment top

Hydroamination of alkenes and alkynes, which constitutes the formal addition of an N—H bond across a carbon–carbon multiple bond, represents an attractive route to numerous classes of organonitrogen molecules, such as alkylated amines, enamines or imines (Müller & Beller, 1998). Recent advances in catalytic aminations are based on early-transition-metal and f-element complexes (Schaverien, 1994). However, catalytic additions of amines H—NR₂ to non-activated double or triple bonds mediated by late-transition-metal complexes are still rare (Schaverien, 1994). In this context, we have synthesized the Ru^II complex [(Cp)Ru(H₂NCH₂Ph)(PPh₃)₂][BF₄], (I), to use as a catalyst precursor for amination reactions. The synthesis and crystal structure reported herein is part of this study.

Experimental top

Ag[BF₄] (26.8 mg, 0.138 mmol) was added to a solution of benzylamine (15 µL, 0.138 mmol) and [Ru(Cp)Cl(PPh₃)₂] (100 mg, 0.138 mmol) in tetrahydrofuran (20 ml) under a nitrogen atmosphere. The color changed immediately to yellow and an off-white solid precipitated. The mixture was stirred at room temperature for 30 min and filtered over celite. The solvent was removed under reduced pressure and the residue redissolved in dichloromethane and precipitated with hexanes. The yellow solid was washed with hexanes (2 × 10 ml) and dried under vacuum to afford 104 mg (85%) of the title compound.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: DIRDIF (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: EUCLID (Spek, 1982); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. View of the structure of (I) showing XX% probability ellipsoids.

(Benzylamine-N)(η⁵-cyclopentadienyl)bis(triphenylphosphine-P)ruthenium(II) tetrafluoroborate top

Crystal data top

[Ru(C₅H₅)(C₇H₉N)(C₁₈H₁₅P)₂]BF₄	D_x = 1.445 Mg m⁻³
M_r = 884.66	Cu Kα radiation, λ = 1.54179 Å
Orthorhombic, Pbca	Cell parameters from 22652 reflections
a = 13.4255 (3) Å	θ = 1.5–70.1°
b = 21.1335 (6) Å	µ = 4.31 mm⁻¹
c = 28.6552 (8) Å	T = 200 K
V = 8130.3 (4) Å³	Block, yellow
Z = 8	0.08 × 0.05 × 0.03 mm
F(000) = 3632

Data collection top

KappaCCD diffractometer	7148 independent reflections
Radiation source: fine-focus sealed tube	3839 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.141
Detector resolution: 9.0 pixels mm^-1	θ_max = 69.8°, θ_min = 3.1°
CCD scans	h = 0→16
Absorption correction: empirical (using intensity measurements) (XABS2; Parkin et al., 1995)	k = 0→24
T_min = 0.701, T_max = 0.898	l = 0→34
54625 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ²(F_o²) + (0.0449P)² + ] where P = (F_o² + 2F_c²)/3
7148 reflections	(Δ/σ)_max < 0.001
530 parameters	Δρ_max = 0.86 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Ru(C₅H₅)(C₇H₉N)(C₁₈H₁₅P)₂]BF₄	V = 8130.3 (4) Å³
M_r = 884.66	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 13.4255 (3) Å	µ = 4.31 mm⁻¹
b = 21.1335 (6) Å	T = 200 K
c = 28.6552 (8) Å	0.08 × 0.05 × 0.03 mm

Data collection top

KappaCCD diffractometer	7148 independent reflections
Absorption correction: empirical (using intensity measurements) (XABS2; Parkin et al., 1995)	3839 reflections with I > 2σ(I)
T_min = 0.701, T_max = 0.898	R_int = 0.141
54625 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	Δρ_max = 0.86 e Å⁻³
7148 reflections	Δρ_min = −0.59 e Å⁻³
530 parameters

Special details top

Experimental. Anal. and spectroscopic data: Calcd for C₄₈H₄₄BF₄NP₂Ru (884.66): C, 65.17; H, 5.01; N, 1.58. Found: C, 64.96; H, 4.89; N, 1.50. ¹H NMR (CD₂Cl₂): δ 7.53–7.03 (m, 35 H, Ph), 6.55 (s, br, 2 H, NH₂), 4.55 (s, 5 H, Cp), 2.54 (s, br, 2 H, CH₂) p.p.m.. ³¹P NMR (CD₂Cl₂): δ 44.48 (s) p.p.m.. ¹⁹F NMR (CD₂Cl₂): δ -152.23 (s) p.p.m..

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. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2292 (4)	0.2018 (3)	0.01116 (18)	0.0382 (16)
H1	0.2570	0.1634	0.0021	0.046*
C2	0.1254 (4)	0.2147 (3)	0.02001 (18)	0.0365 (15)
H2	0.0735	0.1859	0.0170	0.044*
C3	0.1160 (4)	0.2779 (3)	0.03387 (19)	0.0379 (16)
H3	0.0568	0.2978	0.0420	0.046*
C4	0.2113 (4)	0.3064 (3)	0.03359 (19)	0.0412 (16)
H4	0.2258	0.3481	0.0414	0.049*
C5	0.2806 (4)	0.2597 (3)	0.01917 (18)	0.0375 (15)
H5	0.3487	0.2659	0.0155	0.045*
C6	0.1960 (5)	0.3456 (3)	0.1543 (2)	0.0431 (17)
C101	0.1579 (4)	0.3765 (3)	0.1983 (2)	0.0419 (16)
C102	0.0915 (4)	0.4260 (3)	0.1969 (2)	0.0516 (19)
H102	0.0681	0.4403	0.1683	0.062*
C103	0.0592 (5)	0.4548 (4)	0.2372 (3)	0.073 (2)
H103	0.0148	0.4885	0.2357	0.087*
C104	0.0935 (6)	0.4331 (4)	0.2805 (3)	0.069 (2)
H104	0.0714	0.4519	0.3080	0.083*
C105	0.1589 (5)	0.3847 (4)	0.2819 (2)	0.060 (2)
H105	0.1824	0.3705	0.3106	0.071*
C106	0.1911 (5)	0.3561 (3)	0.2417 (2)	0.0528 (18)
H106	0.2359	0.3226	0.2435	0.063*
C201	0.1490 (4)	0.1016 (3)	0.16953 (19)	0.0350 (15)
C202	0.1086 (4)	0.1404 (3)	0.2043 (2)	0.0444 (17)
H202	0.0776	0.1781	0.1961	0.053*
C203	0.1141 (4)	0.1230 (3)	0.2508 (2)	0.0494 (18)
H203	0.0879	0.1495	0.2736	0.059*
C204	0.1583 (5)	0.0665 (4)	0.2636 (2)	0.054 (2)
H204	0.1632	0.0554	0.2949	0.065*
C205	0.1951 (5)	0.0270 (3)	0.2295 (2)	0.056 (2)
H205	0.2240	−0.0115	0.2377	0.068*
C206	0.1890 (4)	0.0443 (3)	0.1832 (2)	0.0460 (17)
H206	0.2125	0.0166	0.1605	0.055*
C301	0.1740 (4)	0.0677 (3)	0.0715 (2)	0.0306 (14)
C302	0.2648 (4)	0.0382 (3)	0.0759 (2)	0.0410 (16)
H302	0.3076	0.0502	0.0998	0.049*
C303	0.2938 (4)	−0.0095 (3)	0.0451 (2)	0.0398 (16)
H303	0.3540	−0.0304	0.0494	0.048*
C304	0.2324 (4)	−0.0256 (3)	0.0080 (2)	0.0389 (16)
H304	0.2520	−0.0566	−0.0131	0.047*
C305	0.1436 (4)	0.0043 (3)	0.0027 (2)	0.0380 (15)
H305	0.1027	−0.0061	−0.0223	0.046*
C306	0.1128 (4)	0.0506 (3)	0.0346 (2)	0.0349 (15)
H306	0.0511	0.0699	0.0310	0.042*
C401	0.0016 (4)	0.1296 (3)	0.10744 (19)	0.0308 (14)
C402	−0.0487 (4)	0.0738 (3)	0.1190 (2)	0.0387 (16)
H402	−0.0119	0.0382	0.1271	0.046*
C403	−0.1502 (4)	0.0698 (3)	0.1187 (2)	0.0432 (17)
H403	−0.1816	0.0321	0.1267	0.052*
C404	−0.2064 (4)	0.1224 (3)	0.1063 (2)	0.0412 (16)
H404	−0.2756	0.1199	0.1058	0.049*
C405	−0.1599 (4)	0.1779 (3)	0.0950 (2)	0.0433 (17)
H405	−0.1974	0.2132	0.0869	0.052*
C406	−0.0562 (4)	0.1815 (3)	0.09562 (18)	0.0353 (15)
H406	−0.0252	0.2195	0.0880	0.042*
C501	0.3856 (4)	0.2273 (3)	0.18252 (19)	0.0330 (14)
C502	0.3480 (4)	0.1803 (3)	0.2120 (2)	0.0439 (17)
H502	0.3184	0.1445	0.1991	0.053*
C503	0.3542 (4)	0.1861 (3)	0.2597 (2)	0.0482 (18)
H503	0.3300	0.1540	0.2788	0.058*
C504	0.3958 (4)	0.2388 (3)	0.2792 (2)	0.0477 (18)
H504	0.3981	0.2429	0.3115	0.057*
C505	0.4337 (4)	0.2850 (3)	0.2516 (2)	0.0464 (17)
H505	0.4625	0.3208	0.2649	0.056*
C506	0.4291 (4)	0.2787 (3)	0.2038 (2)	0.0407 (16)
H506	0.4565	0.3103	0.1852	0.049*
C601	0.4622 (4)	0.2808 (3)	0.10145 (18)	0.0307 (14)
C602	0.5645 (4)	0.2695 (3)	0.10628 (19)	0.0385 (15)
H602	0.5868	0.2293	0.1144	0.046*
C603	0.6329 (5)	0.3177 (3)	0.0990 (2)	0.0441 (17)
H603	0.7006	0.3095	0.1022	0.053*
C604	0.6011 (5)	0.3779 (3)	0.08687 (19)	0.0448 (17)
H604	0.6470	0.4103	0.0825	0.054*
C605	0.5017 (5)	0.3891 (3)	0.0814 (2)	0.0441 (17)
H605	0.4801	0.4291	0.0725	0.053*
C606	0.4327 (4)	0.3416 (3)	0.08905 (19)	0.0388 (15)
H606	0.3652	0.3505	0.0858	0.047*
C701	0.4420 (4)	0.1484 (3)	0.1025 (2)	0.0319 (15)
C702	0.4809 (4)	0.1053 (3)	0.1335 (2)	0.0347 (15)
H702	0.4728	0.1111	0.1655	0.042*
C703	0.5327 (4)	0.0528 (3)	0.1167 (2)	0.0420 (16)
H703	0.5577	0.0231	0.1375	0.050*
C704	0.5470 (4)	0.0447 (3)	0.0697 (2)	0.0416 (16)
H704	0.5816	0.0095	0.0589	0.050*
C705	0.5103 (4)	0.0888 (3)	0.0384 (2)	0.0412 (16)
H705	0.5209	0.0839	0.0065	0.049*
C706	0.4580 (4)	0.1398 (3)	0.0550 (2)	0.0388 (16)
H706	0.4327	0.1693	0.0340	0.047*
B1	−0.0797 (6)	0.1300 (4)	0.5999 (3)	0.046 (2)
F1	−0.0521 (3)	0.17286 (18)	0.63475 (13)	0.0697 (11)
F2	−0.1162 (2)	0.1655 (2)	0.56299 (13)	0.0726 (12)
F3	−0.1481 (3)	0.08874 (19)	0.61643 (15)	0.0820 (13)
F4	0.0061 (2)	0.09946 (16)	0.58534 (12)	0.0528 (10)
N1	0.1617 (4)	0.2799 (3)	0.14729 (19)	0.0349 (13)
P1	0.13861 (10)	0.13308 (7)	0.11007 (5)	0.0309 (4)
P2	0.37115 (11)	0.22016 (7)	0.11873 (5)	0.0309 (4)
Ru1	0.21194 (3)	0.22838 (2)	0.085300 (14)	0.02903 (16)
H6A	0.276 (4)	0.341 (3)	0.1557 (18)	0.052 (18)*
H6B	0.173 (3)	0.372 (2)	0.1289 (16)	0.020 (14)*
H99A	0.099 (3)	0.279 (2)	0.1487 (15)	0.006 (14)*
H99B	0.179 (6)	0.255 (4)	0.176 (3)	0.14 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.052 (4)	0.041 (4)	0.022 (3)	0.006 (3)	0.001 (3)	−0.002 (3)
C2	0.036 (4)	0.046 (4)	0.028 (4)	0.002 (3)	−0.008 (3)	−0.002 (3)
C3	0.035 (4)	0.044 (4)	0.035 (4)	0.007 (3)	−0.007 (3)	0.004 (3)
C4	0.057 (4)	0.033 (4)	0.034 (4)	−0.001 (4)	−0.004 (3)	0.006 (3)
C5	0.039 (4)	0.045 (4)	0.029 (4)	−0.003 (3)	0.002 (3)	0.008 (3)
C6	0.054 (5)	0.036 (4)	0.039 (4)	0.005 (4)	−0.002 (4)	−0.003 (3)
C101	0.039 (4)	0.046 (4)	0.041 (4)	0.002 (3)	−0.001 (3)	−0.015 (3)
C102	0.043 (4)	0.058 (5)	0.053 (5)	0.010 (4)	−0.006 (4)	−0.009 (4)
C103	0.056 (5)	0.066 (6)	0.097 (7)	0.019 (4)	0.012 (5)	−0.027 (5)
C104	0.076 (6)	0.070 (6)	0.062 (6)	−0.012 (5)	0.030 (5)	−0.032 (5)
C105	0.071 (5)	0.069 (6)	0.039 (5)	−0.007 (5)	0.006 (4)	0.002 (4)
C106	0.061 (5)	0.050 (5)	0.048 (5)	0.007 (4)	0.001 (4)	−0.008 (4)
C201	0.032 (4)	0.042 (4)	0.031 (4)	−0.002 (3)	0.001 (3)	−0.003 (3)
C202	0.041 (4)	0.044 (4)	0.048 (4)	0.000 (3)	0.010 (3)	0.010 (4)
C203	0.044 (4)	0.070 (5)	0.034 (4)	−0.010 (4)	0.014 (3)	−0.006 (4)
C204	0.049 (4)	0.079 (6)	0.035 (4)	−0.006 (4)	0.002 (4)	0.019 (4)
C205	0.063 (5)	0.057 (5)	0.049 (5)	0.012 (4)	−0.004 (4)	0.018 (4)
C206	0.054 (4)	0.040 (4)	0.044 (4)	0.001 (3)	0.001 (4)	0.003 (3)
C301	0.029 (3)	0.029 (4)	0.034 (4)	−0.004 (3)	0.001 (3)	−0.003 (3)
C302	0.039 (4)	0.035 (4)	0.049 (4)	0.000 (3)	−0.004 (3)	−0.007 (3)
C303	0.033 (3)	0.031 (4)	0.055 (4)	0.003 (3)	0.002 (3)	0.000 (3)
C304	0.042 (4)	0.034 (4)	0.040 (4)	0.007 (3)	0.008 (3)	−0.005 (3)
C305	0.040 (4)	0.035 (4)	0.039 (4)	−0.006 (3)	−0.005 (3)	−0.007 (3)
C306	0.034 (4)	0.034 (4)	0.036 (4)	0.002 (3)	−0.002 (3)	0.004 (3)
C401	0.021 (3)	0.036 (4)	0.036 (4)	−0.002 (3)	0.000 (3)	−0.003 (3)
C402	0.030 (4)	0.037 (4)	0.049 (4)	0.004 (3)	0.003 (3)	0.001 (3)
C403	0.038 (4)	0.045 (4)	0.047 (4)	−0.012 (3)	0.010 (3)	0.000 (3)
C404	0.028 (3)	0.048 (5)	0.048 (4)	−0.005 (3)	−0.002 (3)	−0.004 (3)
C405	0.037 (4)	0.047 (4)	0.045 (4)	0.013 (3)	−0.002 (3)	−0.004 (3)
C406	0.027 (3)	0.039 (4)	0.040 (4)	−0.002 (3)	0.004 (3)	−0.009 (3)
C501	0.030 (3)	0.038 (4)	0.031 (4)	−0.001 (3)	0.003 (3)	0.002 (3)
C502	0.034 (4)	0.059 (5)	0.038 (4)	−0.009 (3)	−0.004 (3)	−0.002 (4)
C503	0.042 (4)	0.069 (5)	0.033 (4)	−0.010 (4)	−0.004 (3)	0.013 (4)
C504	0.035 (4)	0.070 (5)	0.038 (4)	0.003 (4)	−0.004 (3)	−0.009 (4)
C505	0.044 (4)	0.059 (5)	0.036 (4)	−0.003 (3)	−0.006 (3)	−0.007 (4)
C506	0.045 (4)	0.038 (4)	0.039 (4)	−0.007 (3)	0.000 (3)	−0.004 (3)
C601	0.033 (4)	0.035 (4)	0.024 (3)	−0.004 (3)	0.004 (3)	0.001 (3)
C602	0.036 (4)	0.037 (4)	0.042 (4)	0.000 (3)	0.006 (3)	−0.005 (3)
C603	0.035 (4)	0.046 (5)	0.051 (4)	−0.004 (3)	0.002 (3)	0.000 (3)
C604	0.054 (4)	0.045 (5)	0.035 (4)	−0.018 (4)	0.002 (3)	−0.006 (3)
C605	0.050 (4)	0.038 (4)	0.044 (4)	−0.007 (3)	0.000 (3)	0.009 (3)
C606	0.034 (3)	0.041 (4)	0.041 (4)	−0.003 (3)	−0.001 (3)	0.000 (3)
C701	0.021 (3)	0.038 (4)	0.036 (4)	−0.003 (3)	0.001 (3)	−0.004 (3)
C702	0.034 (4)	0.030 (4)	0.040 (4)	−0.005 (3)	−0.008 (3)	−0.004 (3)
C703	0.035 (4)	0.040 (4)	0.050 (5)	−0.008 (3)	−0.013 (3)	0.007 (3)
C704	0.033 (4)	0.027 (4)	0.065 (5)	−0.005 (3)	0.007 (4)	−0.005 (3)
C705	0.039 (4)	0.042 (4)	0.042 (4)	0.002 (3)	0.011 (3)	−0.001 (3)
C706	0.038 (4)	0.034 (4)	0.044 (4)	0.009 (3)	0.004 (3)	0.006 (3)
B1	0.047 (5)	0.041 (5)	0.050 (5)	0.002 (4)	−0.005 (4)	−0.003 (4)
F1	0.079 (3)	0.066 (3)	0.064 (3)	0.007 (2)	−0.001 (2)	−0.018 (2)
F2	0.058 (2)	0.093 (3)	0.067 (3)	0.014 (2)	−0.018 (2)	0.011 (2)
F3	0.055 (3)	0.060 (3)	0.131 (4)	−0.010 (2)	0.028 (3)	0.003 (3)
F4	0.042 (2)	0.052 (2)	0.064 (3)	0.0091 (18)	0.0008 (19)	−0.005 (2)
N1	0.027 (3)	0.037 (4)	0.041 (4)	0.001 (3)	0.002 (3)	0.003 (3)
P1	0.0286 (8)	0.0286 (9)	0.0355 (9)	0.0002 (7)	−0.0001 (7)	0.0006 (7)
P2	0.0292 (9)	0.0321 (9)	0.0314 (9)	−0.0007 (7)	0.0018 (7)	0.0004 (7)
Ru1	0.0292 (3)	0.0285 (3)	0.0294 (3)	0.0006 (2)	−0.0001 (2)	0.0000 (2)

Geometric parameters (Å, º) top

C1—C5	1.422 (7)	C401—P1	1.843 (5)
C1—C2	1.442 (7)	C402—C403	1.365 (7)
C1—Ru1	2.210 (5)	C402—H402	0.9300
C1—H1	0.9300	C403—C404	1.389 (8)
C2—C3	1.398 (8)	C403—H403	0.9300
C2—Ru1	2.221 (5)	C404—C405	1.368 (8)
C2—H2	0.9300	C404—H404	0.9300
C3—C4	1.414 (7)	C405—C406	1.395 (7)
C3—Ru1	2.219 (5)	C405—H405	0.9300
C3—H3	0.9300	C406—H406	0.9300
C4—C5	1.418 (7)	C501—C506	1.376 (7)
C4—Ru1	2.217 (6)	C501—C502	1.397 (8)
C4—H4	0.9300	C501—P2	1.844 (6)
C5—Ru1	2.208 (5)	C502—C503	1.377 (7)
C5—H5	0.9300	C502—H502	0.9300
C6—N1	1.477 (8)	C503—C504	1.365 (8)
C6—C101	1.511 (8)	C503—H503	0.9300
C6—H6A	1.08 (5)	C504—C505	1.357 (8)
C6—H6B	0.96 (4)	C504—H504	0.9300
C101—C102	1.375 (8)	C505—C506	1.379 (7)
C101—C106	1.390 (8)	C505—H505	0.9300
C102—C103	1.374 (9)	C506—H506	0.9300
C102—H102	0.9300	C601—C606	1.389 (7)
C103—C104	1.400 (10)	C601—C602	1.402 (7)
C103—H103	0.9300	C601—P2	1.840 (6)
C104—C105	1.349 (9)	C602—C603	1.387 (7)
C104—H104	0.9300	C602—H602	0.9300
C105—C106	1.371 (8)	C603—C604	1.386 (8)
C105—H105	0.9300	C603—H603	0.9300
C106—H106	0.9300	C604—C605	1.364 (7)
C201—C206	1.381 (8)	C604—H604	0.9300
C201—C202	1.399 (7)	C605—C606	1.384 (7)
C201—P1	1.834 (6)	C605—H605	0.9300
C202—C203	1.385 (8)	C606—H606	0.9300
C202—H202	0.9300	C701—C702	1.378 (7)
C203—C204	1.381 (8)	C701—C706	1.390 (7)
C203—H203	0.9300	C701—P2	1.849 (6)
C204—C205	1.378 (8)	C702—C703	1.394 (7)
C204—H204	0.9300	C702—H702	0.9300
C205—C206	1.378 (8)	C703—C704	1.370 (8)
C205—H205	0.9300	C703—H703	0.9300
C206—H206	0.9300	C704—C705	1.385 (8)
C301—C302	1.374 (7)	C704—H704	0.9300
C301—C306	1.388 (7)	C705—C706	1.371 (7)
C301—P1	1.831 (6)	C705—H705	0.9300
C302—C303	1.395 (7)	C706—H706	0.9300
C302—H302	0.9300	B1—F3	1.351 (8)
C303—C304	1.387 (7)	B1—F4	1.384 (8)
C303—H303	0.9300	B1—F2	1.387 (8)
C304—C305	1.357 (7)	B1—F1	1.398 (8)
C304—H304	0.9300	N1—Ru1	2.190 (5)
C305—C306	1.401 (7)	N1—H99A	0.84 (4)
C305—H305	0.9300	N1—H99B	1.00 (8)
C306—H306	0.9300	P1—Ru1	2.3514 (15)
C401—C406	1.386 (7)	P2—Ru1	2.3487 (15)
C401—C402	1.399 (7)

C5—C1—C2	106.1 (5)	C405—C406—H406	119.4
C5—C1—Ru1	71.2 (3)	C506—C501—C502	116.5 (5)
C2—C1—Ru1	71.4 (3)	C506—C501—P2	123.2 (5)
C5—C1—H1	127.0	C502—C501—P2	120.2 (5)
C2—C1—H1	127.0	C503—C502—C501	121.0 (6)
Ru1—C1—H1	122.2	C503—C502—H502	119.5
C3—C2—C1	108.5 (5)	C501—C502—H502	119.5
C3—C2—Ru1	71.6 (3)	C504—C503—C502	120.3 (6)
C1—C2—Ru1	70.6 (3)	C504—C503—H503	119.8
C3—C2—H2	125.7	C502—C503—H503	119.8
C1—C2—H2	125.7	C505—C504—C503	120.1 (6)
Ru1—C2—H2	123.7	C505—C504—H504	119.9
C2—C3—C4	108.9 (5)	C503—C504—H504	119.9
C2—C3—Ru1	71.7 (3)	C504—C505—C506	119.5 (6)
C4—C3—Ru1	71.3 (3)	C504—C505—H505	120.2
C2—C3—H3	125.5	C506—C505—H505	120.2
C4—C3—H3	125.5	C501—C506—C505	122.5 (6)
Ru1—C3—H3	123.0	C501—C506—H506	118.8
C3—C4—C5	107.3 (5)	C505—C506—H506	118.8
C3—C4—Ru1	71.5 (3)	C606—C601—C602	117.6 (5)
C5—C4—Ru1	71.0 (3)	C606—C601—P2	121.6 (4)
C3—C4—H4	126.3	C602—C601—P2	120.4 (5)
C5—C4—H4	126.3	C603—C602—C601	120.6 (6)
Ru1—C4—H4	122.9	C603—C602—H602	119.7
C4—C5—C1	109.1 (5)	C601—C602—H602	119.7
C4—C5—Ru1	71.6 (3)	C604—C603—C602	120.5 (6)
C1—C5—Ru1	71.3 (3)	C604—C603—H603	119.8
C4—C5—H5	125.4	C602—C603—H603	119.8
C1—C5—H5	125.4	C605—C604—C603	119.3 (6)
Ru1—C5—H5	123.3	C605—C604—H604	120.3
N1—C6—C101	114.4 (5)	C603—C604—H604	120.3
N1—C6—H6A	103 (3)	C604—C605—C606	120.7 (6)
C101—C6—H6A	110 (3)	C604—C605—H605	119.6
N1—C6—H6B	109 (3)	C606—C605—H605	119.6
C101—C6—H6B	106 (3)	C605—C606—C601	121.3 (5)
H6A—C6—H6B	114 (4)	C605—C606—H606	119.3
C102—C101—C106	118.0 (6)	C601—C606—H606	119.3
C102—C101—C6	121.6 (6)	C702—C701—C706	119.1 (5)
C106—C101—C6	120.3 (6)	C702—C701—P2	125.1 (5)
C103—C102—C101	121.1 (7)	C706—C701—P2	115.7 (4)
C103—C102—H102	119.4	C701—C702—C703	119.5 (6)
C101—C102—H102	119.4	C701—C702—H702	120.3
C102—C103—C104	119.7 (7)	C703—C702—H702	120.3
C102—C103—H103	120.2	C704—C703—C702	120.6 (6)
C104—C103—H103	120.2	C704—C703—H703	119.7
C105—C104—C103	119.3 (7)	C702—C703—H703	119.7
C105—C104—H104	120.4	C703—C704—C705	120.2 (6)
C103—C104—H104	120.4	C703—C704—H704	119.9
C104—C105—C106	121.0 (7)	C705—C704—H704	119.9
C104—C105—H105	119.5	C706—C705—C704	119.2 (6)
C106—C105—H105	119.5	C706—C705—H705	120.4
C105—C106—C101	120.9 (7)	C704—C705—H705	120.4
C105—C106—H106	119.5	C705—C706—C701	121.4 (6)
C101—C106—H106	119.5	C705—C706—H706	119.3
C206—C201—C202	117.5 (6)	C701—C706—H706	119.3
C206—C201—P1	127.7 (5)	F3—B1—F4	111.8 (6)
C202—C201—P1	114.8 (5)	F3—B1—F2	112.1 (6)
C203—C202—C201	120.6 (6)	F4—B1—F2	108.4 (6)
C203—C202—H202	119.7	F3—B1—F1	110.3 (6)
C201—C202—H202	119.7	F4—B1—F1	107.3 (6)
C204—C203—C202	120.5 (6)	F2—B1—F1	106.7 (6)
C204—C203—H203	119.7	C6—N1—Ru1	118.8 (4)
C202—C203—H203	119.7	C6—N1—H99A	110 (3)
C205—C204—C203	119.3 (6)	Ru1—N1—H99A	109 (3)
C205—C204—H204	120.4	C6—N1—H99B	109 (5)
C203—C204—H204	120.4	Ru1—N1—H99B	109 (5)
C206—C205—C204	120.0 (6)	H99A—N1—H99B	100 (5)
C206—C205—H205	120.0	C301—P1—C201	105.5 (3)
C204—C205—H205	120.0	C301—P1—C401	101.8 (3)
C205—C206—C201	122.0 (6)	C201—P1—C401	95.7 (3)
C205—C206—H206	119.0	C301—P1—Ru1	110.79 (18)
C201—C206—H206	119.0	C201—P1—Ru1	123.98 (19)
C302—C301—C306	118.4 (5)	C401—P1—Ru1	116.1 (2)
C302—C301—P1	121.2 (4)	C601—P2—C501	98.1 (3)
C306—C301—P1	120.2 (4)	C601—P2—C701	99.3 (3)
C301—C302—C303	121.2 (6)	C501—P2—C701	105.2 (3)
C301—C302—H302	119.4	C601—P2—Ru1	116.31 (19)
C303—C302—H302	119.4	C501—P2—Ru1	119.61 (17)
C304—C303—C302	119.7 (6)	C701—P2—Ru1	115.19 (18)
C304—C303—H303	120.1	N1—Ru1—C5	132.5 (2)
C302—C303—H303	120.1	N1—Ru1—C1	159.8 (2)
C305—C304—C303	119.6 (6)	C5—Ru1—C1	37.56 (19)
C305—C304—H304	120.2	N1—Ru1—C4	99.8 (2)
C303—C304—H304	120.2	C5—Ru1—C4	37.38 (19)
C304—C305—C306	120.7 (6)	C1—Ru1—C4	63.1 (2)
C304—C305—H305	119.6	N1—Ru1—C3	97.2 (2)
C306—C305—H305	119.6	C5—Ru1—C3	62.0 (2)
C301—C306—C305	120.3 (5)	C1—Ru1—C3	62.7 (2)
C301—C306—H306	119.9	C4—Ru1—C3	37.18 (18)
C305—C306—H306	119.9	N1—Ru1—C2	125.9 (2)
C406—C401—C402	117.1 (5)	C5—Ru1—C2	62.2 (2)
C406—C401—P1	122.5 (4)	C1—Ru1—C2	38.00 (18)
C402—C401—P1	120.4 (4)	C4—Ru1—C2	62.1 (2)
C403—C402—C401	122.1 (6)	C3—Ru1—C2	36.70 (19)
C403—C402—H402	118.9	N1—Ru1—P2	89.22 (15)
C401—C402—H402	118.9	C5—Ru1—P2	89.58 (15)
C402—C403—C404	119.7 (6)	C1—Ru1—P2	106.13 (15)
C402—C403—H403	120.2	C4—Ru1—P2	109.35 (16)
C404—C403—H403	120.2	C3—Ru1—P2	146.50 (16)
C405—C404—C403	119.9 (5)	C2—Ru1—P2	144.09 (15)
C405—C404—H404	120.1	N1—Ru1—P1	93.00 (14)
C403—C404—H404	120.1	C5—Ru1—P1	133.65 (17)
C404—C405—C406	120.0 (6)	C1—Ru1—P1	96.70 (17)
C404—C405—H405	120.0	C4—Ru1—P1	146.84 (16)
C406—C405—H405	120.0	C3—Ru1—P1	111.17 (16)
C401—C406—C405	121.2 (6)	C2—Ru1—P1	85.65 (16)
C401—C406—H406	119.4	P2—Ru1—P1	101.22 (5)

C5—C1—C2—C3	−1.3 (6)	C6—N1—Ru1—C5	−16.2 (6)
Ru1—C1—C2—C3	61.9 (4)	C6—N1—Ru1—C1	−67.6 (8)
C5—C1—C2—Ru1	−63.2 (4)	C6—N1—Ru1—C4	−37.0 (5)
C1—C2—C3—C4	0.8 (6)	C6—N1—Ru1—C3	−74.5 (5)
Ru1—C2—C3—C4	62.0 (4)	C6—N1—Ru1—C2	−99.5 (5)
C1—C2—C3—Ru1	−61.2 (4)	C6—N1—Ru1—P2	72.5 (5)
C2—C3—C4—C5	0.1 (6)	C6—N1—Ru1—P1	173.7 (5)
Ru1—C3—C4—C5	62.3 (4)	C4—C5—Ru1—N1	−35.2 (5)
C2—C3—C4—Ru1	−62.3 (4)	C1—C5—Ru1—N1	−153.7 (3)
C3—C4—C5—C1	−0.9 (6)	C4—C5—Ru1—C1	118.5 (5)
Ru1—C4—C5—C1	61.7 (4)	C1—C5—Ru1—C4	−118.5 (5)
C3—C4—C5—Ru1	−62.7 (4)	C4—C5—Ru1—C3	37.7 (3)
C2—C1—C5—C4	1.4 (6)	C1—C5—Ru1—C3	−80.8 (4)
Ru1—C1—C5—C4	−62.0 (4)	C4—C5—Ru1—C2	79.5 (4)
C2—C1—C5—Ru1	63.4 (4)	C1—C5—Ru1—C2	−39.1 (3)
N1—C6—C101—C102	−112.2 (7)	C4—C5—Ru1—P2	−123.7 (3)
N1—C6—C101—C106	69.2 (8)	C1—C5—Ru1—P2	117.7 (3)
C106—C101—C102—C103	0.2 (10)	C4—C5—Ru1—P1	131.1 (3)
C6—C101—C102—C103	−178.4 (6)	C1—C5—Ru1—P1	12.6 (4)
C101—C102—C103—C104	−0.6 (11)	C5—C1—Ru1—N1	71.0 (7)
C102—C103—C104—C105	0.9 (11)	C2—C1—Ru1—N1	−44.1 (8)
C103—C104—C105—C106	−0.8 (11)	C2—C1—Ru1—C5	−115.0 (5)
C104—C105—C106—C101	0.5 (10)	C5—C1—Ru1—C4	36.8 (3)
C102—C101—C106—C105	−0.2 (10)	C2—C1—Ru1—C4	−78.3 (4)
C6—C101—C106—C105	178.5 (6)	C5—C1—Ru1—C3	78.7 (4)
C206—C201—C202—C203	3.6 (9)	C2—C1—Ru1—C3	−36.3 (3)
P1—C201—C202—C203	−178.1 (4)	C5—C1—Ru1—C2	115.0 (5)
C201—C202—C203—C204	−1.0 (9)	C5—C1—Ru1—P2	−67.1 (3)
C202—C203—C204—C205	−1.4 (10)	C2—C1—Ru1—P2	177.8 (3)
C203—C204—C205—C206	1.1 (10)	C5—C1—Ru1—P1	−170.9 (3)
C204—C205—C206—C201	1.7 (10)	C2—C1—Ru1—P1	74.1 (3)
C202—C201—C206—C205	−4.0 (9)	C3—C4—Ru1—N1	−89.0 (4)
P1—C201—C206—C205	178.0 (5)	C5—C4—Ru1—N1	154.4 (3)
C306—C301—C302—C303	−2.2 (9)	C3—C4—Ru1—C5	116.6 (5)
P1—C301—C302—C303	−176.8 (5)	C3—C4—Ru1—C1	79.6 (4)
C301—C302—C303—C304	3.1 (9)	C5—C4—Ru1—C1	−36.9 (3)
C302—C303—C304—C305	−1.6 (9)	C5—C4—Ru1—C3	−116.6 (5)
C303—C304—C305—C306	−0.7 (9)	C3—C4—Ru1—C2	36.6 (3)
C302—C301—C306—C305	−0.1 (8)	C5—C4—Ru1—C2	−80.0 (4)
P1—C301—C306—C305	174.6 (4)	C3—C4—Ru1—P2	178.4 (3)
C304—C305—C306—C301	1.6 (9)	C5—C4—Ru1—P2	61.8 (3)
C406—C401—C402—C403	0.1 (9)	C3—C4—Ru1—P1	22.2 (5)
P1—C401—C402—C403	178.2 (4)	C5—C4—Ru1—P1	−94.3 (4)
C401—C402—C403—C404	0.4 (9)	C2—C3—Ru1—N1	−145.1 (3)
C402—C403—C404—C405	−0.6 (9)	C4—C3—Ru1—N1	96.8 (4)
C403—C404—C405—C406	0.3 (9)	C2—C3—Ru1—C5	80.2 (4)
C402—C401—C406—C405	−0.4 (8)	C4—C3—Ru1—C5	−37.9 (3)
P1—C401—C406—C405	−178.4 (4)	C2—C3—Ru1—C1	37.6 (3)
C404—C405—C406—C401	0.2 (9)	C4—C3—Ru1—C1	−80.5 (4)
C506—C501—C502—C503	0.4 (9)	C2—C3—Ru1—C4	118.2 (5)
P2—C501—C502—C503	−177.1 (4)	C4—C3—Ru1—C2	−118.2 (5)
C501—C502—C503—C504	1.3 (9)	C2—C3—Ru1—P2	115.4 (4)
C502—C503—C504—C505	−1.8 (9)	C4—C3—Ru1—P2	−2.8 (5)
C503—C504—C505—C506	0.6 (9)	C2—C3—Ru1—P1	−49.0 (4)
C502—C501—C506—C505	−1.7 (9)	C4—C3—Ru1—P1	−167.2 (3)
P2—C501—C506—C505	175.8 (4)	C3—C2—Ru1—N1	44.5 (4)
C504—C505—C506—C501	1.2 (9)	C1—C2—Ru1—N1	162.7 (3)
C606—C601—C602—C603	0.2 (8)	C3—C2—Ru1—C5	−79.6 (4)
P2—C601—C602—C603	−171.8 (4)	C1—C2—Ru1—C5	38.6 (3)
C601—C602—C603—C604	0.1 (9)	C3—C2—Ru1—C1	−118.2 (5)
C602—C603—C604—C605	−1.1 (9)	C3—C2—Ru1—C4	−37.1 (3)
C603—C604—C605—C606	1.7 (9)	C1—C2—Ru1—C4	81.1 (4)
C604—C605—C606—C601	−1.3 (9)	C1—C2—Ru1—C3	118.2 (5)
C602—C601—C606—C605	0.4 (8)	C3—C2—Ru1—P2	−121.8 (3)
P2—C601—C606—C605	172.3 (4)	C1—C2—Ru1—P2	−3.5 (5)
C706—C701—C702—C703	−2.1 (8)	C3—C2—Ru1—P1	135.1 (3)
P2—C701—C702—C703	179.8 (4)	C1—C2—Ru1—P1	−106.7 (3)
C701—C702—C703—C704	1.5 (8)	C601—P2—Ru1—N1	−95.3 (2)
C702—C703—C704—C705	0.1 (8)	C501—P2—Ru1—N1	22.2 (3)
C703—C704—C705—C706	−1.2 (9)	C701—P2—Ru1—N1	149.1 (2)
C704—C705—C706—C701	0.6 (9)	C601—P2—Ru1—C5	37.2 (3)
C702—C701—C706—C705	1.1 (8)	C501—P2—Ru1—C5	154.7 (3)
P2—C701—C706—C705	179.4 (4)	C701—P2—Ru1—C5	−78.4 (3)
C101—C6—N1—Ru1	−179.4 (4)	C601—P2—Ru1—C1	71.4 (3)
C302—C301—P1—C201	−56.5 (5)	C501—P2—Ru1—C1	−171.2 (3)
C306—C301—P1—C201	129.0 (5)	C701—P2—Ru1—C1	−44.2 (3)
C302—C301—P1—C401	−155.9 (5)	C601—P2—Ru1—C4	4.9 (3)
C306—C301—P1—C401	29.6 (5)	C501—P2—Ru1—C4	122.3 (3)
C302—C301—P1—Ru1	80.0 (5)	C701—P2—Ru1—C4	−110.7 (3)
C306—C301—P1—Ru1	−94.5 (4)	C601—P2—Ru1—C3	6.7 (4)
C206—C201—P1—C301	8.7 (6)	C501—P2—Ru1—C3	124.1 (4)
C202—C201—P1—C301	−169.3 (4)	C701—P2—Ru1—C3	−109.0 (4)
C206—C201—P1—C401	112.7 (6)	C601—P2—Ru1—C2	73.7 (3)
C202—C201—P1—C401	−65.3 (5)	C501—P2—Ru1—C2	−168.9 (3)
C206—C201—P1—Ru1	−120.4 (5)	C701—P2—Ru1—C2	−42.0 (4)
C202—C201—P1—Ru1	61.6 (5)	C601—P2—Ru1—P1	171.8 (2)
C406—C401—P1—C301	−126.0 (5)	C501—P2—Ru1—P1	−70.7 (2)
C402—C401—P1—C301	56.0 (5)	C701—P2—Ru1—P1	56.2 (2)
C406—C401—P1—C201	126.8 (5)	C301—P1—Ru1—N1	−172.6 (3)
C402—C401—P1—C201	−51.1 (5)	C201—P1—Ru1—N1	−45.7 (3)
C406—C401—P1—Ru1	−5.6 (5)	C401—P1—Ru1—N1	72.0 (2)
C402—C401—P1—Ru1	176.4 (4)	C301—P1—Ru1—C5	17.5 (3)
C606—C601—P2—C501	−99.2 (5)	C201—P1—Ru1—C5	144.4 (3)
C602—C601—P2—C501	72.4 (5)	C401—P1—Ru1—C5	−97.9 (3)
C606—C601—P2—C701	153.8 (5)	C301—P1—Ru1—C1	25.2 (2)
C602—C601—P2—C701	−34.5 (5)	C201—P1—Ru1—C1	152.1 (3)
C606—C601—P2—Ru1	29.6 (5)	C401—P1—Ru1—C1	−90.3 (2)
C602—C601—P2—Ru1	−158.8 (4)	C301—P1—Ru1—C4	74.3 (4)
C506—C501—P2—C601	17.4 (5)	C201—P1—Ru1—C4	−158.8 (4)
C502—C501—P2—C601	−165.2 (5)	C401—P1—Ru1—C4	−41.1 (4)
C506—C501—P2—C701	119.5 (5)	C301—P1—Ru1—C3	88.5 (3)
C502—C501—P2—C701	−63.2 (5)	C201—P1—Ru1—C3	−144.6 (3)
C506—C501—P2—Ru1	−109.1 (5)	C401—P1—Ru1—C3	−26.9 (3)
C502—C501—P2—Ru1	68.3 (5)	C301—P1—Ru1—C2	61.6 (2)
C702—C701—P2—C601	111.1 (5)	C201—P1—Ru1—C2	−171.5 (3)
C706—C701—P2—C601	−67.1 (5)	C401—P1—Ru1—C2	−53.8 (2)
C702—C701—P2—C501	10.0 (5)	C301—P1—Ru1—P2	−82.8 (2)
C706—C701—P2—C501	−168.2 (4)	C201—P1—Ru1—P2	44.1 (2)
C702—C701—P2—Ru1	−123.9 (4)	C401—P1—Ru1—P2	161.8 (2)
C706—C701—P2—Ru1	57.9 (5)

Experimental details

Crystal data
Chemical formula	[Ru(C₅H₅)(C₇H₉N)(C₁₈H₁₅P)₂]BF₄
M_r	884.66
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	200
a, b, c (Å)	13.4255 (3), 21.1335 (6), 28.6552 (8)
V (Å³)	8130.3 (4)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	4.31
Crystal size (mm)	0.08 × 0.05 × 0.03

Data collection
Diffractometer	KappaCCD diffractometer
Absorption correction	Empirical (using intensity measurements) (XABS2; Parkin et al., 1995)
T_min, T_max	0.701, 0.898
No. of measured, independent and observed [I > 2σ(I)] reflections	54625, 7148, 3839
R_int	0.141
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.133, 0.90
No. of reflections	7148
No. of parameters	530
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.86, −0.59

Computer programs: COLLECT (Nonius, 1998), HKL SCALEPACK (Otwinowski & Minor 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, DIRDIF (Beurskens et al., 1992), SHELXL97 (Sheldrick, 1997), EUCLID (Spek, 1982), SHELXL97.

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