Crystal structure of ruthenocenecarbo­nitrile

The ruthenocenecarbo­nitrile mol­ecule exhibits mirror symmetry in the solid state.

Key indicators

• Single-crystal X-ray study
• T = 110 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.012
• wR factor = 0.032
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         11 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          2 Note

Alert level G
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          2 Report
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

Ruthenocenecarbonitrile

Crystal data

[Ru(C5H5)(C6H4N)]	F(000) = 252
Mr = 256.26	Dx = 1.947 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
a = 7.2023 (2) Å	Cell parameters from 26762 reflections
b = 8.6802 (2) Å	θ = 3.5–28.7°
c = 7.2922 (1) Å	µ = 1.74 mm^−1
β = 106.497 (2)°	T = 110 K
V = 437.12 (2) Å^3	Block, yellow green
Z = 2	0.38 × 0.30 × 0.30 mm

Data collection

Oxford Gemini S CCD diffractometer	900 independent reflections
Radiation source: fine-focus sealed tube	877 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
ω scans	θmax = 26.0°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	h = −8→8
Tmin = 0.849, Tmax = 1.000	k = −10→10
27710 measured reflections	l = −8→8

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)] = 0.012	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.032	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0218P)^2 + 0.1909P] where P = (Fo^2 + 2Fc^2)/3
900 reflections	(Δ/σ)max < 0.001
67 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.39 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. 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 (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.4152 (3)	0.2500	−0.0364 (3)	0.0162 (4)
C2	−0.3084 (3)	0.2500	0.1617 (3)	0.0142 (4)
C3	−0.24721 (18)	0.11497 (16)	0.27791 (19)	0.0142 (3)
H3C	−0.2679	0.0130	0.2382	0.017*
C4	−0.14854 (18)	0.16776 (15)	0.46603 (18)	0.0145 (3)
H4C	−0.0935	0.1053	0.5710	0.017*
C5	0.1429 (3)	0.2500	0.0334 (3)	0.0185 (4)
H5C	0.0744	0.2500	−0.0957	0.022*
C6	0.20428 (19)	0.11674 (17)	0.1491 (2)	0.0175 (3)
H6C	0.1832	0.0149	0.1089	0.021*
C7	0.30392 (17)	0.16746 (16)	0.33757 (19)	0.0158 (3)
H7C	0.3591	0.1045	0.4420	0.019*
N1	−0.5024 (2)	0.2500	−0.1949 (3)	0.0244 (4)
Ru1	0.00474 (2)	0.2500	0.26311 (2)	0.00953 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0120 (8)	0.0168 (9)	0.0198 (10)	0.000	0.0045 (7)	0.000
C2	0.0093 (8)	0.0168 (9)	0.0170 (9)	0.000	0.0044 (7)	0.000
C3	0.0111 (6)	0.0148 (7)	0.0182 (6)	−0.0022 (5)	0.0065 (5)	−0.0003 (5)
C4	0.0145 (6)	0.0163 (7)	0.0146 (6)	0.0003 (5)	0.0072 (5)	0.0029 (5)
C5	0.0155 (9)	0.0283 (11)	0.0145 (9)	0.000	0.0087 (7)	0.000
C6	0.0143 (6)	0.0190 (7)	0.0222 (7)	0.0005 (5)	0.0101 (5)	−0.0047 (6)
C7	0.0098 (6)	0.0191 (7)	0.0193 (6)	0.0033 (5)	0.0054 (5)	0.0029 (5)
N1	0.0222 (9)	0.0274 (10)	0.0208 (9)	0.000	0.0015 (7)	0.000
Ru1	0.00850 (10)	0.00992 (10)	0.01040 (10)	0.000	0.00305 (6)	0.000

Geometric parameters (Å, º)

C1—N1	1.148 (3)	C5—Ru1	2.1780 (18)
C1—C2	1.431 (3)	C5—H5C	0.9300
C2—C3^i	1.4401 (17)	C6—C7	1.4274 (19)
C2—C3	1.4401 (17)	C6—Ru1	2.1848 (13)
C2—Ru1	2.1649 (18)	C6—H6C	0.9300
C3—C4	1.4294 (18)	C7—C7^i	1.433 (3)
C3—Ru1	2.1885 (13)	C7—Ru1	2.1878 (12)
C3—H3C	0.9300	C7—H7C	0.9300
C4—C4^i	1.428 (3)	Ru1—C6^i	2.1848 (13)
C4—Ru1	2.2013 (12)	Ru1—C7^i	2.1878 (12)
C4—H4C	0.9300	Ru1—C3^i	2.1885 (13)
C5—C6^i	1.4262 (18)	Ru1—C4^i	2.2013 (12)
C5—C6	1.4262 (18)
N1—C1—C2	179.4 (2)	C5—Ru1—C6	38.16 (5)
C1—C2—C3^i	125.52 (8)	C6^i—Ru1—C6	63.94 (8)
C1—C2—C3	125.52 (8)	C2—Ru1—C7^i	160.38 (4)
C3^i—C2—C3	108.96 (16)	C5—Ru1—C7^i	63.77 (6)
C1—C2—Ru1	123.64 (13)	C6^i—Ru1—C7^i	38.11 (5)
C3^i—C2—Ru1	71.57 (8)	C6—Ru1—C7^i	63.89 (5)
C3—C2—Ru1	71.57 (8)	C2—Ru1—C7	160.38 (4)
C4—C3—C2	106.82 (12)	C5—Ru1—C7	63.77 (6)
C4—C3—Ru1	71.48 (7)	C6^i—Ru1—C7	63.89 (5)
C2—C3—Ru1	69.80 (9)	C6—Ru1—C7	38.11 (5)
C4—C3—H3C	126.6	C7^i—Ru1—C7	38.23 (7)
C2—C3—H3C	126.6	C2—Ru1—C3^i	38.63 (4)
Ru1—C3—H3C	123.8	C5—Ru1—C3^i	127.17 (5)
C4^i—C4—C3	108.70 (8)	C6^i—Ru1—C3^i	112.30 (6)
C4^i—C4—Ru1	71.08 (3)	C6—Ru1—C3^i	161.19 (5)
C3—C4—Ru1	70.51 (7)	C7^i—Ru1—C3^i	125.76 (5)
C4^i—C4—H4C	125.7	C7—Ru1—C3^i	159.25 (5)
C3—C4—H4C	125.7	C2—Ru1—C3	38.63 (4)
Ru1—C4—H4C	124.4	C5—Ru1—C3	127.17 (5)
C6^i—C5—C6	108.40 (17)	C6^i—Ru1—C3	161.18 (5)
C6^i—C5—Ru1	71.18 (9)	C6—Ru1—C3	112.30 (6)
C6—C5—Ru1	71.18 (9)	C7^i—Ru1—C3	159.25 (5)
C6^i—C5—H5C	125.8	C7—Ru1—C3	125.76 (5)
C6—C5—H5C	125.8	C3^i—Ru1—C3	64.76 (7)
Ru1—C5—H5C	123.5	C2—Ru1—C4^i	63.69 (6)
C5—C6—C7	107.83 (13)	C5—Ru1—C4^i	160.55 (4)
C5—C6—Ru1	70.66 (9)	C6^i—Ru1—C4^i	126.43 (5)
C7—C6—Ru1	71.06 (7)	C6—Ru1—C4^i	159.58 (5)
C5—C6—H6C	126.1	C7^i—Ru1—C4^i	111.94 (5)
C7—C6—H6C	126.1	C7—Ru1—C4^i	125.87 (5)
Ru1—C6—H6C	123.8	C3^i—Ru1—C4^i	38.01 (5)
C6—C7—C7^i	107.97 (8)	C3—Ru1—C4^i	63.86 (5)
C6—C7—Ru1	70.83 (7)	C2—Ru1—C4	63.69 (6)
C7^i—C7—Ru1	70.88 (4)	C5—Ru1—C4	160.55 (4)
C6—C7—H7C	126.0	C6^i—Ru1—C4	159.58 (5)
C7^i—C7—H7C	126.0	C6—Ru1—C4	126.42 (5)
Ru1—C7—H7C	123.9	C7^i—Ru1—C4	125.87 (5)
C2—Ru1—C5	113.36 (7)	C7—Ru1—C4	111.94 (5)
C2—Ru1—C6^i	127.17 (5)	C3^i—Ru1—C4	63.86 (5)
C5—Ru1—C6^i	38.16 (5)	C3—Ru1—C4	38.01 (5)
C2—Ru1—C6	127.17 (5)	C4^i—Ru1—C4	37.84 (7)
C1—C2—C3—C4	−179.04 (16)	C2—C3—C4—Ru1	−61.20 (10)
C3^i—C2—C3—C4	0.13 (19)	C6^i—C5—C6—C7	0.1 (2)
Ru1—C2—C3—C4	62.30 (9)	Ru1—C5—C6—C7	−61.69 (9)
C1—C2—C3—Ru1	118.66 (18)	C6^i—C5—C6—Ru1	61.79 (12)
C3^i—C2—C3—Ru1	−62.17 (12)	C5—C6—C7—C7^i	−0.06 (12)
C2—C3—C4—C4^i	−0.08 (12)	Ru1—C6—C7—C7^i	−61.50 (4)
Ru1—C3—C4—C4^i	61.12 (4)	C5—C6—C7—Ru1	61.44 (10)

Symmetry code: (i) x, −y+1/2, z.