(2,2-Bi­pyridine-κ2N,N′)chlorido­[η6-1-methyl-4-(propan-2-yl)benzene]­ruthenium(II) tetra­phenyl­borate

Thapa, R.; Kilyanek, S.M.

doi:10.1107/S241431461901006X

(2,2-Bipyridine-κ²N,N′)chlorido[η⁶-1-methyl-4-(propan-2-yl)benzene]ruthenium(II) tetraphenylborate

The title complex, [RuCl(C₁₀H₁₄)(C₁₀H₈N₂)](C₂₄H₂₀B), has monoclinic (P2₁) symmetry at 100 K. It was prepared by the reaction of the dichlorido[1-methyl-4-(propan-2-yl)benzene]ruthenium(II) dimer with 2,2′-bipyridine, followed by the addition of ammonium tetraphenylborate. The 1-methyl-4-(propan-2-yl)benzene group, the 2,2′-bipyridine unit and a chloride ion coordinate the ruthenium(II) atom, with the 1-methyl-4-(propan-2-yl)benzene ring and bipyridine moieties trans to each other. In the crystal, the complex cations are linked by C—H

Cl hydrogen bonds, forming chains parallel to [010]. These chains are linked by a number of C—H

π interactions, involving the phenyl rings of the tetraphenylborate anion and a pyridine ring of the bpy ligand, resulting in the formation of layers parallel to (10 $\overline{1}$ ).

Keywords: crystal structure; organometallic complex; ruthenium(II); p-cymene; C—H

Cl hydrogen bonding; C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S241431461901006X/su4172sup1.cif Contains datablocks I, Global
	Structure factor file (CIF format) https://doi.org/10.1107/S241431461901006X/su4172Isup2.hkl Contains datablock I

CCDC reference: 1940325

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.025
wR factor = 0.062
Data-to-parameter ratio = 41.2

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF019_ALERT_1_A  _diffrn_standards_number is missing
            Number of standards used in measurement.
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report

Alert level G
PLAT013_ALERT_1_G No       _shelx_hkl_checksum Found in CIF ......     Please Check
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         19 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...         11 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         16 Info

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(2,2-Bipyridine-κ²N,N')chlorido[η⁶-1-methyl-4-(propan-2-yl)benzene]ruthenium(II) tetraphenylborate top

Crystal data top

[RuCl(C₁₀H₁₄)(C₁₀H₈N₂)](C₂₄H₂₀B)	F(000) = 772
M_r = 746.12	D_x = 1.367 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 14.1396 (15) Å	Cell parameters from 9150 reflections
b = 9.4811 (11) Å	θ = 4.3–37.1°
c = 14.3009 (15) Å	µ = 0.54 mm⁻¹
β = 109.013 (4)°	T = 100 K
V = 1812.6 (3) Å³	Block, orange
Z = 2	0.27 × 0.15 × 0.10 mm

Data collection top

Bruker Photon II cpad diffractometer	17627 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.040
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 37.1°, θ_min = 2.5°
T_min = 0.391, T_max = 0.439	h = −23→23
57149 measured reflections	k = −16→16
18389 independent reflections	l = −24→24

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.025	w = 1/[σ²(F_o²) + (0.028P)² + 0.240P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.062	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.43 e Å⁻³
18389 reflections	Δρ_min = −0.60 e Å⁻³
446 parameters	Extinction correction: (SHELXL2018; Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0054 (9)
Primary atom site location: dual	Absolute structure: Flack x determined using 7947 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.014 (7)

Special details top

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.

Refinement. Hydrogen atoms were included in calculated positions and treated as riding on the parent C atom: C—H = 0.95–1.00 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.

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

	x	y	z	U_iso*/U_eq
Ru1	0.18068 (2)	0.51286 (2)	0.07448 (2)	0.01075 (3)
Cl1	0.12759 (4)	0.74527 (5)	0.01726 (4)	0.01957 (8)
N1	0.09601 (10)	0.54459 (14)	0.16818 (10)	0.0145 (2)
N2	0.27945 (9)	0.61963 (14)	0.19404 (10)	0.0126 (2)
C1	0.22538 (12)	0.28724 (16)	0.09615 (11)	0.0146 (2)
C2	0.12355 (14)	0.29922 (19)	0.03465 (13)	0.0150 (3)
H2	0.070093	0.263351	0.060173	0.018*
C3	0.09526 (13)	0.38097 (18)	−0.05258 (11)	0.0166 (3)
H3	0.022771	0.401613	−0.086461	0.020*
C4	0.16818 (13)	0.45675 (19)	−0.08118 (12)	0.0182 (3)
C5	0.26946 (13)	0.45044 (19)	−0.01971 (12)	0.0181 (3)
H5	0.319034	0.518072	−0.030787	0.022*
C6	0.29636 (12)	0.36769 (18)	0.06801 (12)	0.0160 (3)
H6	0.364984	0.379252	0.116869	0.019*
C7	0.25764 (13)	0.19334 (18)	0.18562 (12)	0.0179 (3)
H7	0.321125	0.232642	0.232325	0.022*
C8	0.18197 (17)	0.1836 (3)	0.24075 (17)	0.0333 (5)
H8A	0.169370	0.278072	0.261917	0.050*
H8B	0.208624	0.122886	0.298870	0.050*
H8C	0.119277	0.143665	0.196898	0.050*
C9	0.2809 (2)	0.0474 (2)	0.15284 (17)	0.0327 (5)
H9A	0.219180	0.004466	0.109425	0.049*
H9B	0.309489	−0.012467	0.211108	0.049*
H9C	0.329040	0.056781	0.117002	0.049*
C10	0.13714 (16)	0.5463 (2)	−0.17228 (13)	0.0259 (4)
H10A	0.137720	0.489475	−0.229329	0.039*
H10B	0.183840	0.625332	−0.163962	0.039*
H10C	0.069533	0.582760	−0.183212	0.039*
C11	−0.00049 (11)	0.5078 (3)	0.14594 (12)	0.0215 (3)
H11	−0.032789	0.461693	0.084867	0.026*
C12	−0.05456 (14)	0.5350 (2)	0.20943 (15)	0.0283 (5)
H12	−0.122792	0.507808	0.191893	0.034*
C13	−0.00786 (15)	0.6023 (3)	0.29879 (16)	0.0278 (4)
H13	−0.043449	0.620928	0.343492	0.033*
C14	0.09145 (13)	0.6420 (2)	0.32182 (13)	0.0206 (3)
H14	0.124927	0.688474	0.382439	0.025*
C15	0.14161 (11)	0.61250 (17)	0.25445 (11)	0.0145 (2)
C16	0.24499 (11)	0.65497 (16)	0.26890 (11)	0.0128 (2)
C17	0.30385 (12)	0.72922 (17)	0.35107 (12)	0.0163 (3)
H17	0.278860	0.751998	0.403353	0.020*
C18	0.39957 (12)	0.76962 (17)	0.35571 (13)	0.0182 (3)
H18	0.441031	0.820014	0.411425	0.022*
C19	0.43407 (12)	0.73577 (18)	0.27837 (13)	0.0186 (3)
H19	0.499069	0.763543	0.279754	0.022*
C20	0.37197 (11)	0.66058 (17)	0.19884 (12)	0.0161 (3)
H20	0.395644	0.637128	0.145788	0.019*
C1A	0.23530 (11)	0.77267 (17)	0.60471 (11)	0.0132 (2)
C2A	0.23565 (12)	0.88711 (16)	0.54243 (11)	0.0152 (2)
H2A	0.298056	0.920629	0.539820	0.018*
C3A	0.14809 (14)	0.95384 (18)	0.48412 (13)	0.0196 (3)
H3A	0.152034	1.030055	0.442426	0.023*
C4A	0.05535 (14)	0.9094 (2)	0.48677 (13)	0.0217 (3)
H4A	−0.004269	0.954885	0.447650	0.026*
C5A	0.05165 (13)	0.7970 (2)	0.54779 (13)	0.0217 (3)
H5A	−0.010993	0.765367	0.550926	0.026*
C6A	0.13943 (12)	0.73070 (19)	0.60434 (12)	0.0181 (3)
H6A	0.134581	0.653307	0.644725	0.022*
C7A	0.36590 (11)	0.75614 (16)	0.78984 (11)	0.0129 (2)
C8A	0.30762 (13)	0.8527 (2)	0.82111 (12)	0.0197 (3)
H8AA	0.247185	0.885698	0.774408	0.024*
C9A	0.33465 (16)	0.9025 (2)	0.91823 (14)	0.0268 (4)
H9AA	0.293176	0.968914	0.935999	0.032*
C10A	0.42176 (14)	0.8554 (2)	0.98886 (13)	0.0228 (3)
H10D	0.439700	0.887490	1.055300	0.027*
C11A	0.48227 (13)	0.7604 (2)	0.96048 (12)	0.0202 (3)
H11A	0.542283	0.727121	1.007701	0.024*
C12A	0.45494 (12)	0.71423 (19)	0.86297 (12)	0.0173 (3)
H12A	0.498421	0.651443	0.844919	0.021*
C13A	0.31168 (10)	0.5213 (2)	0.67714 (9)	0.0126 (2)
C14A	0.34015 (13)	0.43489 (17)	0.76138 (12)	0.0161 (3)
H14A	0.376568	0.475869	0.823269	0.019*
C15A	0.31722 (14)	0.29086 (19)	0.75824 (14)	0.0202 (3)
H15A	0.337552	0.236845	0.817420	0.024*
C16A	0.26504 (14)	0.22670 (18)	0.66926 (14)	0.0212 (3)
H16A	0.249287	0.129060	0.666635	0.025*
C17A	0.23636 (14)	0.3084 (2)	0.58416 (14)	0.0206 (3)
H17A	0.200600	0.266322	0.522461	0.025*
C18A	0.25953 (13)	0.45161 (18)	0.58838 (12)	0.0177 (3)
H18A	0.239247	0.504547	0.528734	0.021*
C19A	0.43290 (11)	0.71807 (15)	0.63904 (11)	0.0122 (2)
C20A	0.47654 (11)	0.61317 (16)	0.59733 (11)	0.0140 (2)
H20A	0.449422	0.520595	0.590472	0.017*
C21A	0.55858 (12)	0.63956 (18)	0.56539 (12)	0.0156 (2)
H21A	0.586610	0.565195	0.538421	0.019*
C22A	0.59897 (12)	0.77414 (18)	0.57306 (11)	0.0161 (3)
H22A	0.653725	0.793064	0.550248	0.019*
C23A	0.55809 (12)	0.88118 (17)	0.61471 (12)	0.0158 (3)
H23A	0.584916	0.973856	0.620306	0.019*
C24A	0.47790 (12)	0.85237 (16)	0.64813 (12)	0.0146 (2)
H24A	0.452554	0.926073	0.678224	0.018*
B1A	0.33633 (12)	0.69173 (18)	0.67724 (12)	0.0124 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ru1	0.01025 (4)	0.01104 (4)	0.01128 (4)	0.00032 (4)	0.00393 (3)	0.00047 (4)
Cl1	0.01740 (17)	0.01448 (16)	0.02383 (19)	0.00399 (13)	0.00261 (14)	0.00439 (14)
N1	0.0140 (5)	0.0145 (5)	0.0164 (5)	−0.0034 (4)	0.0068 (4)	−0.0035 (4)
N2	0.0110 (5)	0.0118 (5)	0.0148 (5)	0.0004 (4)	0.0038 (4)	0.0013 (4)
C1	0.0170 (6)	0.0115 (5)	0.0142 (6)	0.0018 (5)	0.0038 (5)	−0.0009 (4)
C2	0.0173 (7)	0.0132 (6)	0.0130 (6)	−0.0003 (5)	0.0028 (5)	−0.0014 (5)
C3	0.0181 (6)	0.0178 (6)	0.0124 (6)	0.0009 (5)	0.0030 (5)	−0.0014 (5)
C4	0.0217 (7)	0.0216 (7)	0.0125 (6)	0.0042 (6)	0.0074 (5)	0.0011 (5)
C5	0.0191 (7)	0.0217 (7)	0.0166 (6)	0.0028 (5)	0.0099 (6)	0.0014 (5)
C6	0.0154 (6)	0.0169 (6)	0.0162 (6)	0.0035 (5)	0.0057 (5)	−0.0009 (5)
C7	0.0206 (7)	0.0150 (6)	0.0147 (6)	−0.0003 (5)	0.0010 (5)	0.0018 (5)
C8	0.0301 (10)	0.0434 (13)	0.0271 (9)	0.0023 (9)	0.0103 (8)	0.0167 (9)
C9	0.0478 (13)	0.0140 (7)	0.0293 (9)	0.0052 (7)	0.0030 (9)	0.0013 (6)
C10	0.0283 (8)	0.0346 (10)	0.0167 (7)	0.0058 (7)	0.0102 (6)	0.0087 (6)
C11	0.0166 (5)	0.0260 (7)	0.0241 (6)	−0.0095 (8)	0.0097 (5)	−0.0094 (9)
C12	0.0196 (7)	0.0391 (14)	0.0321 (8)	−0.0112 (7)	0.0167 (7)	−0.0118 (8)
C13	0.0237 (8)	0.0388 (11)	0.0277 (9)	−0.0077 (8)	0.0178 (7)	−0.0091 (8)
C14	0.0210 (7)	0.0255 (8)	0.0186 (7)	−0.0030 (6)	0.0109 (6)	−0.0058 (6)
C15	0.0141 (6)	0.0152 (6)	0.0149 (6)	−0.0020 (5)	0.0058 (5)	−0.0028 (5)
C16	0.0127 (5)	0.0110 (5)	0.0140 (5)	−0.0001 (4)	0.0036 (5)	0.0000 (4)
C17	0.0174 (6)	0.0135 (6)	0.0156 (6)	−0.0001 (5)	0.0019 (5)	−0.0016 (5)
C18	0.0158 (6)	0.0135 (6)	0.0199 (7)	−0.0013 (5)	−0.0015 (5)	−0.0008 (5)
C19	0.0129 (6)	0.0165 (6)	0.0233 (7)	−0.0027 (5)	0.0018 (5)	0.0024 (5)
C20	0.0115 (6)	0.0163 (6)	0.0206 (7)	−0.0011 (5)	0.0053 (5)	0.0018 (5)
C1A	0.0143 (6)	0.0127 (6)	0.0125 (5)	0.0005 (5)	0.0043 (5)	−0.0012 (4)
C2A	0.0180 (6)	0.0122 (6)	0.0148 (6)	−0.0001 (5)	0.0047 (5)	−0.0008 (4)
C3A	0.0240 (7)	0.0140 (7)	0.0179 (7)	0.0032 (5)	0.0032 (6)	0.0009 (5)
C4A	0.0194 (7)	0.0208 (7)	0.0208 (7)	0.0063 (6)	0.0009 (6)	−0.0001 (6)
C5A	0.0140 (6)	0.0276 (8)	0.0221 (7)	0.0028 (6)	0.0040 (6)	0.0014 (6)
C6A	0.0139 (6)	0.0224 (7)	0.0177 (6)	0.0010 (5)	0.0046 (5)	0.0043 (5)
C7A	0.0127 (6)	0.0132 (6)	0.0133 (5)	−0.0013 (4)	0.0049 (5)	−0.0014 (4)
C8A	0.0189 (7)	0.0225 (7)	0.0160 (6)	0.0040 (6)	0.0034 (5)	−0.0057 (5)
C9A	0.0266 (8)	0.0325 (10)	0.0205 (8)	0.0056 (7)	0.0067 (7)	−0.0106 (7)
C10A	0.0239 (8)	0.0290 (9)	0.0146 (6)	−0.0043 (7)	0.0052 (6)	−0.0060 (6)
C11A	0.0166 (6)	0.0271 (8)	0.0146 (6)	−0.0033 (6)	0.0021 (5)	−0.0016 (5)
C12A	0.0139 (6)	0.0212 (7)	0.0156 (6)	0.0003 (5)	0.0032 (5)	−0.0017 (5)
C13A	0.0123 (4)	0.0129 (5)	0.0139 (4)	−0.0005 (6)	0.0059 (4)	−0.0006 (6)
C14A	0.0193 (6)	0.0147 (6)	0.0147 (6)	0.0003 (5)	0.0064 (5)	0.0000 (5)
C15A	0.0251 (8)	0.0154 (6)	0.0218 (7)	−0.0001 (6)	0.0100 (6)	0.0023 (5)
C16A	0.0237 (8)	0.0148 (6)	0.0285 (8)	−0.0044 (6)	0.0130 (7)	−0.0023 (6)
C17A	0.0200 (7)	0.0184 (7)	0.0235 (7)	−0.0057 (6)	0.0071 (6)	−0.0061 (6)
C18A	0.0186 (7)	0.0169 (7)	0.0165 (6)	−0.0038 (5)	0.0041 (5)	−0.0015 (5)
C19A	0.0120 (5)	0.0117 (5)	0.0125 (5)	−0.0003 (4)	0.0035 (4)	−0.0004 (4)
C20A	0.0151 (6)	0.0117 (5)	0.0156 (6)	−0.0002 (4)	0.0056 (5)	−0.0005 (4)
C21A	0.0144 (6)	0.0167 (6)	0.0170 (6)	0.0003 (5)	0.0069 (5)	−0.0019 (5)
C22A	0.0130 (6)	0.0203 (7)	0.0156 (6)	−0.0015 (5)	0.0054 (5)	0.0016 (5)
C23A	0.0147 (6)	0.0143 (6)	0.0173 (6)	−0.0035 (5)	0.0035 (5)	0.0012 (5)
C24A	0.0142 (6)	0.0125 (6)	0.0171 (6)	−0.0012 (5)	0.0050 (5)	−0.0015 (5)
B1A	0.0125 (6)	0.0128 (6)	0.0116 (6)	−0.0009 (5)	0.0036 (5)	−0.0010 (5)

Geometric parameters (Å, º) top

Ru1—Cl1	2.3851 (5)	C19—C20	1.386 (2)
Ru1—N1	2.0892 (13)	C19—H19	0.9500
Ru1—N2	2.0839 (13)	C20—H20	0.9500
Ru1—C1	2.2234 (16)	C1A—C2A	1.405 (2)
Ru1—C2	2.1863 (18)	C1A—C6A	1.411 (2)
Ru1—C3	2.2123 (16)	C1A—B1A	1.655 (2)
Ru1—C4	2.2391 (16)	C2A—C3A	1.399 (2)
Ru1—C5	2.2005 (16)	C2A—H2A	0.9500
Ru1—C6	2.1626 (16)	C3A—C4A	1.390 (3)
N1—C11	1.3423 (19)	C3A—H3A	0.9500
N1—C15	1.354 (2)	C4A—C5A	1.389 (3)
N2—C20	1.345 (2)	C4A—H4A	0.9500
N2—C16	1.355 (2)	C5A—C6A	1.391 (2)
C1—C6	1.419 (2)	C5A—H5A	0.9500
C1—C2	1.426 (3)	C6A—H6A	0.9500
C1—C7	1.502 (2)	C7A—C8A	1.399 (2)
C2—C3	1.411 (2)	C7A—C12A	1.407 (2)
C2—H2	1.0000	C7A—B1A	1.644 (2)
C3—C4	1.422 (2)	C8A—C9A	1.397 (2)
C3—H3	1.0000	C8A—H8AA	0.9500
C4—C5	1.417 (2)	C9A—C10A	1.388 (3)
C4—C10	1.496 (2)	C9A—H9AA	0.9500
C5—C6	1.422 (2)	C10A—C11A	1.391 (3)
C5—H5	1.0000	C10A—H10D	0.9500
C6—H6	1.0000	C11A—C12A	1.391 (2)
C7—C8	1.525 (3)	C11A—H11A	0.9500
C7—C9	1.531 (3)	C12A—H12A	0.9500
C7—H7	1.0000	C13A—C14A	1.403 (2)
C8—H8A	0.9800	C13A—C18A	1.408 (2)
C8—H8B	0.9800	C13A—B1A	1.653 (3)
C8—H8C	0.9800	C14A—C15A	1.401 (2)
C9—H9A	0.9800	C14A—H14A	0.9500
C9—H9B	0.9800	C15A—C16A	1.386 (3)
C9—H9C	0.9800	C15A—H15A	0.9500
C10—H10A	0.9800	C16A—C17A	1.387 (3)
C10—H10B	0.9800	C16A—H16A	0.9500
C10—H10C	0.9800	C17A—C18A	1.394 (3)
C11—C12	1.388 (2)	C17A—H17A	0.9500
C11—H11	0.9500	C18A—H18A	0.9500
C12—C13	1.388 (3)	C19A—C20A	1.402 (2)
C12—H12	0.9500	C19A—C24A	1.410 (2)
C13—C14	1.386 (3)	C19A—B1A	1.647 (2)
C13—H13	0.9500	C20A—C21A	1.401 (2)
C14—C15	1.398 (2)	C20A—H20A	0.9500
C14—H14	0.9500	C21A—C22A	1.388 (2)
C15—C16	1.465 (2)	C21A—H21A	0.9500
C16—C17	1.390 (2)	C22A—C23A	1.394 (2)
C17—C18	1.387 (2)	C22A—H22A	0.9500
C17—H17	0.9500	C23A—C24A	1.393 (2)
C18—C19	1.384 (3)	C23A—H23A	0.9500
C18—H18	0.9500	C24A—H24A	0.9500

N2—Ru1—N1	76.98 (5)	C13—C12—C11	119.30 (16)
N2—Ru1—C6	91.73 (6)	C13—C12—H12	120.3
N1—Ru1—C6	135.94 (6)	C11—C12—H12	120.3
N2—Ru1—C2	139.09 (6)	C14—C13—C12	119.00 (17)
N1—Ru1—C2	93.45 (6)	C14—C13—H13	120.5
C6—Ru1—C2	67.64 (7)	C12—C13—H13	120.5
N2—Ru1—C5	105.63 (6)	C13—C14—C15	118.96 (16)
N1—Ru1—C5	172.63 (6)	C13—C14—H14	120.5
C6—Ru1—C5	38.04 (6)	C15—C14—H14	120.5
C2—Ru1—C5	80.06 (7)	N1—C15—C14	121.67 (14)
N2—Ru1—C3	171.53 (6)	N1—C15—C16	114.60 (13)
N1—Ru1—C3	109.54 (6)	C14—C15—C16	123.70 (14)
C6—Ru1—C3	79.82 (6)	N2—C16—C17	121.53 (14)
C2—Ru1—C3	37.42 (6)	N2—C16—C15	114.82 (13)
C5—Ru1—C3	67.23 (7)	C17—C16—C15	123.62 (14)
N2—Ru1—C1	105.60 (5)	C18—C17—C16	119.10 (15)
N1—Ru1—C1	104.21 (6)	C18—C17—H17	120.5
C6—Ru1—C1	37.73 (6)	C16—C17—H17	120.5
C2—Ru1—C1	37.73 (7)	C19—C18—C17	119.35 (15)
C5—Ru1—C1	68.51 (6)	C19—C18—H18	120.3
C3—Ru1—C1	67.98 (6)	C17—C18—H18	120.3
N2—Ru1—C4	138.24 (6)	C18—C19—C20	118.74 (15)
N1—Ru1—C4	142.73 (6)	C18—C19—H19	120.6
C6—Ru1—C4	67.79 (6)	C20—C19—H19	120.6
C2—Ru1—C4	67.55 (7)	N2—C20—C19	122.40 (16)
C5—Ru1—C4	37.20 (6)	N2—C20—H20	118.8
C3—Ru1—C4	37.25 (6)	C19—C20—H20	118.8
C1—Ru1—C4	80.61 (6)	C2A—C1A—C6A	114.66 (14)
N2—Ru1—Cl1	83.37 (4)	C2A—C1A—B1A	125.09 (14)
N1—Ru1—Cl1	84.55 (4)	C6A—C1A—B1A	120.23 (14)
C6—Ru1—Cl1	136.99 (5)	C3A—C2A—C1A	122.83 (16)
C2—Ru1—Cl1	135.91 (4)	C3A—C2A—H2A	118.6
C5—Ru1—Cl1	102.53 (5)	C1A—C2A—H2A	118.6
C3—Ru1—Cl1	102.34 (5)	C4A—C3A—C2A	120.43 (16)
C1—Ru1—Cl1	168.54 (4)	C4A—C3A—H3A	119.8
C4—Ru1—Cl1	87.95 (5)	C2A—C3A—H3A	119.8
C11—N1—C15	119.01 (14)	C5A—C4A—C3A	118.61 (16)
C11—N1—Ru1	124.14 (11)	C5A—C4A—H4A	120.7
C15—N1—Ru1	116.78 (10)	C3A—C4A—H4A	120.7
C20—N2—C16	118.85 (14)	C4A—C5A—C6A	120.18 (17)
C20—N2—Ru1	124.25 (11)	C4A—C5A—H5A	119.9
C16—N2—Ru1	116.82 (10)	C6A—C5A—H5A	119.9
C6—C1—C2	116.57 (14)	C5A—C6A—C1A	123.28 (16)
C6—C1—C7	120.89 (14)	C5A—C6A—H6A	118.4
C2—C1—C7	122.53 (15)	C1A—C6A—H6A	118.4
C6—C1—Ru1	68.81 (9)	C8A—C7A—C12A	115.15 (14)
C2—C1—Ru1	69.72 (9)	C8A—C7A—B1A	124.60 (14)
C7—C1—Ru1	133.03 (11)	C12A—C7A—B1A	120.25 (13)
C3—C2—C1	121.83 (17)	C9A—C8A—C7A	122.68 (16)
C3—C2—Ru1	72.29 (10)	C9A—C8A—H8AA	118.7
C1—C2—Ru1	72.55 (9)	C7A—C8A—H8AA	118.7
C3—C2—H2	118.6	C10A—C9A—C8A	120.37 (18)
C1—C2—H2	118.6	C10A—C9A—H9AA	119.8
Ru1—C2—H2	118.6	C8A—C9A—H9AA	119.8
C2—C3—C4	120.56 (15)	C9A—C10A—C11A	118.70 (16)
C2—C3—Ru1	70.29 (9)	C9A—C10A—H10D	120.6
C4—C3—Ru1	72.40 (9)	C11A—C10A—H10D	120.6
C2—C3—H3	119.1	C10A—C11A—C12A	120.01 (16)
C4—C3—H3	119.1	C10A—C11A—H11A	120.0
Ru1—C3—H3	119.1	C12A—C11A—H11A	120.0
C5—C4—C3	118.77 (15)	C11A—C12A—C7A	123.05 (16)
C5—C4—C10	120.99 (16)	C11A—C12A—H12A	118.5
C3—C4—C10	120.19 (16)	C7A—C12A—H12A	118.5
C5—C4—Ru1	69.92 (9)	C14A—C13A—C18A	114.82 (17)
C3—C4—Ru1	70.35 (9)	C14A—C13A—B1A	124.65 (13)
C10—C4—Ru1	129.54 (13)	C18A—C13A—B1A	120.52 (14)
C4—C5—C6	119.77 (15)	C15A—C14A—C13A	122.89 (16)
C4—C5—Ru1	72.88 (9)	C15A—C14A—H14A	118.6
C6—C5—Ru1	69.54 (9)	C13A—C14A—H14A	118.6
C4—C5—H5	119.6	C16A—C15A—C14A	120.36 (16)
C6—C5—H5	119.6	C16A—C15A—H15A	119.8
Ru1—C5—H5	119.6	C14A—C15A—H15A	119.8
C1—C6—C5	122.41 (15)	C15A—C16A—C17A	118.46 (16)
C1—C6—Ru1	73.46 (9)	C15A—C16A—H16A	120.8
C5—C6—Ru1	72.43 (9)	C17A—C16A—H16A	120.8
C1—C6—H6	118.4	C16A—C17A—C18A	120.57 (17)
C5—C6—H6	118.4	C16A—C17A—H17A	119.7
Ru1—C6—H6	118.4	C18A—C17A—H17A	119.7
C1—C7—C8	113.99 (15)	C17A—C18A—C13A	122.89 (17)
C1—C7—C9	108.11 (15)	C17A—C18A—H18A	118.6
C8—C7—C9	111.16 (18)	C13A—C18A—H18A	118.6
C1—C7—H7	107.8	C20A—C19A—C24A	115.58 (13)
C8—C7—H7	107.8	C20A—C19A—B1A	124.13 (13)
C9—C7—H7	107.8	C24A—C19A—B1A	120.29 (13)
C7—C8—H8A	109.5	C21A—C20A—C19A	122.55 (14)
C7—C8—H8B	109.5	C21A—C20A—H20A	118.7
H8A—C8—H8B	109.5	C19A—C20A—H20A	118.7
C7—C8—H8C	109.5	C22A—C21A—C20A	120.11 (15)
H8A—C8—H8C	109.5	C22A—C21A—H21A	119.9
H8B—C8—H8C	109.5	C20A—C21A—H21A	119.9
C7—C9—H9A	109.5	C21A—C22A—C23A	119.07 (14)
C7—C9—H9B	109.5	C21A—C22A—H22A	120.5
H9A—C9—H9B	109.5	C23A—C22A—H22A	120.5
C7—C9—H9C	109.5	C24A—C23A—C22A	120.06 (14)
H9A—C9—H9C	109.5	C24A—C23A—H23A	120.0
H9B—C9—H9C	109.5	C22A—C23A—H23A	120.0
C4—C10—H10A	109.5	C23A—C24A—C19A	122.58 (14)
C4—C10—H10B	109.5	C23A—C24A—H24A	118.7
H10A—C10—H10B	109.5	C19A—C24A—H24A	118.7
C4—C10—H10C	109.5	C7A—B1A—C19A	107.15 (12)
H10A—C10—H10C	109.5	C7A—B1A—C13A	110.50 (12)
H10B—C10—H10C	109.5	C19A—B1A—C13A	110.20 (12)
N1—C11—C12	122.04 (16)	C7A—B1A—C1A	109.50 (12)
N1—C11—H11	119.0	C19A—B1A—C1A	111.19 (12)
C12—C11—H11	119.0	C13A—B1A—C1A	108.31 (12)

C6—C1—C2—C3	3.2 (2)	C18—C19—C20—N2	0.1 (3)
C7—C1—C2—C3	−175.93 (15)	C6A—C1A—C2A—C3A	−0.4 (2)
Ru1—C1—C2—C3	55.22 (15)	B1A—C1A—C2A—C3A	−178.56 (15)
C6—C1—C2—Ru1	−52.00 (13)	C1A—C2A—C3A—C4A	0.9 (3)
C7—C1—C2—Ru1	128.85 (15)	C2A—C3A—C4A—C5A	−0.5 (3)
C1—C2—C3—C4	−1.1 (3)	C3A—C4A—C5A—C6A	−0.3 (3)
Ru1—C2—C3—C4	54.22 (14)	C4A—C5A—C6A—C1A	0.9 (3)
C1—C2—C3—Ru1	−55.33 (14)	C2A—C1A—C6A—C5A	−0.5 (2)
C2—C3—C4—C5	−1.0 (2)	B1A—C1A—C6A—C5A	177.80 (16)
Ru1—C3—C4—C5	52.27 (14)	C12A—C7A—C8A—C9A	−1.0 (3)
C2—C3—C4—C10	−178.31 (16)	B1A—C7A—C8A—C9A	178.62 (18)
Ru1—C3—C4—C10	−125.06 (16)	C7A—C8A—C9A—C10A	−0.8 (3)
C2—C3—C4—Ru1	−53.25 (14)	C8A—C9A—C10A—C11A	1.3 (3)
C3—C4—C5—C6	0.8 (2)	C9A—C10A—C11A—C12A	−0.1 (3)
C10—C4—C5—C6	178.13 (16)	C10A—C11A—C12A—C7A	−1.8 (3)
Ru1—C4—C5—C6	53.30 (14)	C8A—C7A—C12A—C11A	2.3 (3)
C3—C4—C5—Ru1	−52.47 (14)	B1A—C7A—C12A—C11A	−177.37 (16)
C10—C4—C5—Ru1	124.83 (16)	C18A—C13A—C14A—C15A	−1.0 (2)
C2—C1—C6—C5	−3.4 (2)	B1A—C13A—C14A—C15A	179.59 (15)
C7—C1—C6—C5	175.78 (15)	C13A—C14A—C15A—C16A	0.6 (3)
Ru1—C1—C6—C5	−55.84 (14)	C14A—C15A—C16A—C17A	0.0 (3)
C2—C1—C6—Ru1	52.45 (13)	C15A—C16A—C17A—C18A	−0.1 (3)
C7—C1—C6—Ru1	−128.39 (14)	C16A—C17A—C18A—C13A	−0.4 (3)
C4—C5—C6—C1	1.4 (2)	C14A—C13A—C18A—C17A	0.9 (2)
Ru1—C5—C6—C1	56.31 (14)	B1A—C13A—C18A—C17A	−179.66 (15)
C4—C5—C6—Ru1	−54.87 (14)	C24A—C19A—C20A—C21A	−0.8 (2)
C6—C1—C7—C8	146.08 (18)	B1A—C19A—C20A—C21A	179.82 (14)
C2—C1—C7—C8	−34.8 (2)	C19A—C20A—C21A—C22A	−0.9 (2)
Ru1—C1—C7—C8	57.1 (2)	C20A—C21A—C22A—C23A	1.3 (2)
C6—C1—C7—C9	−89.8 (2)	C21A—C22A—C23A—C24A	0.1 (2)
C2—C1—C7—C9	89.3 (2)	C22A—C23A—C24A—C19A	−2.0 (2)
Ru1—C1—C7—C9	−178.77 (14)	C20A—C19A—C24A—C23A	2.3 (2)
C15—N1—C11—C12	−1.1 (3)	B1A—C19A—C24A—C23A	−178.31 (14)
Ru1—N1—C11—C12	−177.98 (18)	C8A—C7A—B1A—C19A	127.43 (16)
N1—C11—C12—C13	0.0 (4)	C12A—C7A—B1A—C19A	−52.97 (18)
C11—C12—C13—C14	0.7 (4)	C8A—C7A—B1A—C13A	−112.49 (17)
C12—C13—C14—C15	−0.2 (3)	C12A—C7A—B1A—C13A	67.11 (18)
C11—N1—C15—C14	1.6 (3)	C8A—C7A—B1A—C1A	6.7 (2)
Ru1—N1—C15—C14	178.68 (14)	C12A—C7A—B1A—C1A	−173.66 (14)
C11—N1—C15—C16	−176.66 (17)	C20A—C19A—B1A—C7A	129.97 (15)
Ru1—N1—C15—C16	0.40 (18)	C24A—C19A—B1A—C7A	−49.35 (18)
C13—C14—C15—N1	−0.9 (3)	C20A—C19A—B1A—C13A	9.70 (19)
C13—C14—C15—C16	177.17 (18)	C24A—C19A—B1A—C13A	−169.62 (13)
C20—N2—C16—C17	−1.6 (2)	C20A—C19A—B1A—C1A	−110.41 (16)
Ru1—N2—C16—C17	−178.47 (11)	C24A—C19A—B1A—C1A	70.27 (17)
C20—N2—C16—C15	176.78 (14)	C14A—C13A—B1A—C7A	−17.8 (2)
Ru1—N2—C16—C15	−0.12 (17)	C18A—C13A—B1A—C7A	162.90 (13)
N1—C15—C16—N2	−0.2 (2)	C14A—C13A—B1A—C19A	100.45 (16)
C14—C15—C16—N2	−178.42 (16)	C18A—C13A—B1A—C19A	−78.87 (17)
N1—C15—C16—C17	178.13 (14)	C14A—C13A—B1A—C1A	−137.72 (14)
C14—C15—C16—C17	−0.1 (3)	C18A—C13A—B1A—C1A	42.96 (18)
N2—C16—C17—C18	0.9 (2)	C2A—C1A—B1A—C7A	96.69 (17)
C15—C16—C17—C18	−177.30 (15)	C6A—C1A—B1A—C7A	−81.38 (18)
C16—C17—C18—C19	0.3 (2)	C2A—C1A—B1A—C19A	−21.5 (2)
C17—C18—C19—C20	−0.8 (2)	C6A—C1A—B1A—C19A	160.42 (14)
C16—N2—C20—C19	1.1 (2)	C2A—C1A—B1A—C13A	−142.74 (15)
Ru1—N2—C20—C19	177.71 (12)	C6A—C1A—B1A—C13A	39.19 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of rings C19A–C24A and N2/C16–C20, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1ⁱ	1.00	2.66	3.421 (2)	133
C11—H11···Cl1ⁱ	0.95	2.62	3.484 (2)	151
C7—H7···Cg1ⁱⁱ	1.00	2.67	3.616 (2)	158
C9—H9B···Cg2ⁱⁱⁱ	0.98	2.91	3.733 (2)	143
C18—H18···Cg1	0.95	2.73	3.431 (2)	131
C23A—H23A···Cg2^iv	0.95	2.60	3.461 (2)	151

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

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(2,2-Bi­pyridine-κ2N,N′)chlorido­[η6-1-methyl-4-(propan-2-yl)benzene]­ruthenium(II) tetra­phenyl­borate

Supporting information

Key indicators

checkCIF/PLATON results

(2,2-Bipyridine-κ²N,N′)chlorido[η⁶-1-methyl-4-(propan-2-yl)benzene]ruthenium(II) tetraphenylborate