Two isomers of [1-benzyl-4-(pyridin-2-yl-κN)-1H-1,2,3-triazole-κN³]di­chlorido­bis­(dimethyl sulfoxide-κS)ruthenium(II)

Reaction of [RuCl₂(DMSO)₄] with 1-benzyl-4-(pyridin-2-yl)-1H-1,2,3-triazole yields two of the four possible isomers of the title compound.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.004 Å
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.025
• wR factor = 0.067
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Datablock: 2


Alert level C
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.596         29 Report

Alert level G
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.71 mm
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ru1      --S2       .        8.7 s.u.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT794_ALERT_5_G Tentative Bond Valency for Ru1       (III)     .       3.84 Info
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        80% Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   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
   7 ALERT level G = General information/check it is not something unexpected

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




Datablock: 3


Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          3 Check

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.49 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.596        195 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.96A   From Ru1             2.09 eA-3

Alert level G
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT063_ALERT_4_G Crystal Size Likely too Large for Beam Size ....       0.67 mm
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.005 Degree
PLAT794_ALERT_5_G Tentative Bond Valency for Ru1       (III)     .       3.96 Info
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        98% Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

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

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

---

Computing details

For both structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

(OC-6-14)-[1-Benzyl-4-(pyridin-2-yl-κN)-1H-1,2,3-triazole-κN³]dichloridobis(dimethyl sulfoxide-κS)ruthenium(II) (2)

Crystal data

[RuCl2(C14H12N4)(C2H6OS)2]	Dx = 1.658 Mg m^−3
Mr = 564.50	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pbca	Cell parameters from 9998 reflections
a = 21.3094 (11) Å	θ = 3.9–66.5°
b = 9.4213 (5) Å	µ = 9.70 mm^−1
c = 22.5267 (12) Å	T = 90 K
V = 4522.5 (4) Å^3	Needle, yellow
Z = 8	0.71 × 0.16 × 0.04 mm
F(000) = 2288

Data collection

Bruker Kappa APEXII CCD DUO diffractometer	3970 independent reflections
Radiation source: IµS microfocus	3628 reflections with I > 2σ(I)
QUAZAR multilayer optics monochromator	Rint = 0.043
φ and ω scans	θmax = 66.7°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −24→23
Tmin = 0.349, Tmax = 0.715	k = −11→9
34572 measured reflections	l = −26→26

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.067	w = 1/[σ^2(Fo^2) + (0.0391P)^2 + 3.2772P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
3970 reflections	Δρmax = 0.60 e Å^−3
266 parameters	Δρmin = −0.46 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
Ru1	0.09298 (2)	0.17864 (2)	0.37532 (2)	0.02143 (8)
Cl1	0.08456 (3)	0.01442 (6)	0.45541 (2)	0.02897 (14)
Cl2	0.11140 (3)	0.34903 (6)	0.29710 (2)	0.02744 (13)
S1	0.04525 (3)	0.34440 (6)	0.43372 (2)	0.02548 (13)
S2	0.00095 (3)	0.11879 (7)	0.33388 (3)	0.02991 (14)
O2	−0.05488 (9)	0.2095 (2)	0.34285 (9)	0.0476 (5)
O1	0.08383 (8)	0.4194 (2)	0.47853 (8)	0.0336 (4)
N1	0.18911 (8)	0.2124 (2)	0.40402 (8)	0.0224 (4)
N2	0.14267 (8)	0.0257 (2)	0.32734 (8)	0.0240 (4)
N3	0.12683 (9)	−0.0753 (2)	0.28984 (8)	0.0264 (4)
N4	0.18058 (9)	−0.1375 (2)	0.27335 (8)	0.0240 (4)
C1	0.21032 (11)	0.3039 (2)	0.44464 (10)	0.0261 (5)
H1	0.180986	0.362842	0.464654	0.031*
C2	0.27331 (12)	0.3162 (3)	0.45875 (11)	0.0301 (5)
H2	0.286609	0.383822	0.487405	0.036*
C3	0.31690 (11)	0.2297 (3)	0.43097 (11)	0.0297 (5)
H3	0.360309	0.237149	0.440043	0.036*
C4	0.29572 (11)	0.1328 (3)	0.38988 (10)	0.0256 (5)
H4	0.324292	0.070938	0.370413	0.031*
C5	0.23209 (11)	0.1268 (3)	0.37732 (9)	0.0230 (5)
C6	0.20593 (10)	0.0266 (2)	0.33525 (9)	0.0223 (5)
C7	0.23052 (10)	−0.0784 (2)	0.30006 (9)	0.0235 (4)
H7	0.273411	−0.103661	0.295568	0.028*
C8	0.18019 (11)	−0.2548 (3)	0.23009 (10)	0.0281 (5)
H8A	0.136727	−0.271837	0.216302	0.034*
H8AB	0.195534	−0.342585	0.249364	0.034*
C18	0.00697 (12)	0.1011 (3)	0.25524 (11)	0.0365 (6)
H18A	−0.033416	0.069712	0.239103	0.055*
H18B	0.039385	0.031020	0.245612	0.055*
H18C	0.018252	0.192946	0.237803	0.055*
C17	−0.02254 (14)	−0.0564 (3)	0.35314 (13)	0.0459 (7)
H17A	−0.058689	−0.084239	0.328895	0.069*
H17B	−0.034137	−0.059392	0.395224	0.069*
H17C	0.012264	−0.122196	0.345925	0.069*
C9	0.22158 (12)	−0.2194 (3)	0.17743 (10)	0.0317 (5)
C10	0.19814 (17)	−0.1376 (4)	0.13231 (13)	0.0518 (8)
H10	0.155735	−0.106577	0.133446	0.062*
C11	0.2363 (2)	−0.1000 (4)	0.08503 (15)	0.0686 (11)
H11	0.219937	−0.043315	0.053763	0.082*
C12	0.29860 (18)	−0.1453 (4)	0.08322 (15)	0.0614 (10)
H12	0.325403	−0.115599	0.051885	0.074*
C13	0.32091 (16)	−0.2331 (5)	0.12711 (14)	0.0592 (10)
H13	0.362443	−0.269291	0.124741	0.071*
C14	0.28276 (13)	−0.2694 (4)	0.17521 (13)	0.0476 (7)
H14	0.298593	−0.327775	0.206148	0.057*
C15	0.00646 (13)	0.4811 (3)	0.39304 (11)	0.0349 (6)
H15A	0.037764	0.541872	0.373815	0.052*
H15B	−0.019102	0.538224	0.420192	0.052*
H15C	−0.020607	0.438318	0.362755	0.052*
C16	−0.02029 (12)	0.2740 (3)	0.47367 (11)	0.0336 (5)
H16A	−0.050315	0.232593	0.445651	0.050*
H16B	−0.040715	0.350377	0.496027	0.050*
H16C	−0.005731	0.200585	0.501229	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru1	0.01644 (12)	0.02583 (12)	0.02202 (11)	0.00089 (6)	0.00003 (6)	−0.00100 (6)
Cl1	0.0250 (3)	0.0305 (3)	0.0313 (3)	0.0012 (2)	0.0041 (2)	0.0048 (2)
Cl2	0.0217 (3)	0.0355 (3)	0.0251 (3)	0.0012 (2)	−0.0010 (2)	0.0042 (2)
S1	0.0226 (3)	0.0286 (3)	0.0251 (3)	0.0031 (2)	0.0023 (2)	−0.0011 (2)
S2	0.0197 (3)	0.0379 (3)	0.0321 (3)	0.0011 (2)	−0.0021 (2)	−0.0057 (2)
O2	0.0265 (9)	0.0660 (13)	0.0503 (12)	0.0126 (9)	−0.0099 (8)	−0.0207 (10)
O1	0.0288 (9)	0.0383 (10)	0.0337 (9)	0.0039 (7)	0.0007 (7)	−0.0093 (8)
N1	0.0207 (9)	0.0259 (10)	0.0207 (9)	−0.0012 (7)	0.0015 (7)	0.0031 (7)
N2	0.0191 (9)	0.0286 (10)	0.0245 (9)	0.0002 (7)	−0.0009 (7)	−0.0011 (8)
N3	0.0218 (10)	0.0306 (11)	0.0268 (9)	0.0013 (8)	−0.0001 (7)	−0.0046 (8)
N4	0.0216 (9)	0.0277 (10)	0.0226 (9)	0.0011 (8)	0.0015 (7)	−0.0017 (8)
C1	0.0265 (12)	0.0273 (12)	0.0247 (11)	−0.0001 (9)	−0.0007 (9)	−0.0005 (9)
C2	0.0267 (13)	0.0300 (13)	0.0336 (13)	−0.0012 (9)	−0.0051 (10)	−0.0039 (10)
C3	0.0212 (11)	0.0316 (13)	0.0364 (12)	−0.0021 (10)	−0.0051 (9)	0.0017 (10)
C4	0.0198 (11)	0.0278 (12)	0.0293 (11)	0.0014 (9)	0.0001 (9)	0.0037 (10)
C5	0.0237 (12)	0.0230 (11)	0.0223 (11)	0.0006 (9)	0.0009 (8)	0.0043 (8)
C6	0.0191 (11)	0.0262 (12)	0.0217 (10)	−0.0002 (9)	−0.0001 (8)	0.0035 (9)
C7	0.0191 (11)	0.0270 (12)	0.0244 (10)	0.0002 (9)	0.0006 (8)	0.0019 (9)
C8	0.0272 (12)	0.0303 (13)	0.0269 (11)	0.0000 (10)	0.0001 (9)	−0.0064 (10)
C18	0.0297 (13)	0.0474 (15)	0.0325 (13)	−0.0005 (11)	−0.0077 (10)	−0.0054 (11)
C17	0.0371 (15)	0.0541 (18)	0.0465 (16)	−0.0165 (13)	−0.0054 (13)	0.0020 (14)
C9	0.0311 (13)	0.0375 (13)	0.0265 (12)	−0.0047 (11)	0.0033 (10)	−0.0103 (10)
C10	0.055 (2)	0.063 (2)	0.0378 (15)	0.0074 (16)	0.0089 (13)	0.0044 (14)
C11	0.090 (3)	0.072 (3)	0.0439 (18)	0.000 (2)	0.0190 (18)	0.0109 (17)
C12	0.071 (2)	0.069 (2)	0.0434 (18)	−0.0280 (19)	0.0284 (17)	−0.0162 (16)
C13	0.0360 (17)	0.086 (3)	0.055 (2)	−0.0121 (17)	0.0139 (13)	−0.0219 (19)
C14	0.0331 (15)	0.065 (2)	0.0445 (15)	0.0003 (14)	0.0061 (12)	−0.0093 (15)
C15	0.0346 (14)	0.0381 (15)	0.0319 (12)	0.0091 (11)	0.0035 (11)	0.0016 (11)
C16	0.0276 (12)	0.0384 (14)	0.0348 (12)	0.0010 (11)	0.0108 (10)	−0.0016 (11)

Geometric parameters (Å, º)

Ru1—N2	2.0890 (19)	C6—C7	1.371 (3)
Ru1—N1	2.1714 (18)	C7—H7	0.9500
Ru1—S2	2.2440 (6)	C8—C9	1.515 (3)
Ru1—S1	2.2814 (6)	C8—H8A	0.9900
Ru1—Cl1	2.3835 (6)	C8—H8AB	0.9900
Ru1—Cl2	2.4157 (6)	C18—H18A	0.9800
S1—O1	1.4814 (18)	C18—H18B	0.9800
S1—C15	1.784 (3)	C18—H18C	0.9800
S1—C16	1.789 (2)	C17—H17A	0.9800
S2—O2	1.4786 (19)	C17—H17B	0.9800
S2—C17	1.779 (3)	C17—H17C	0.9800
S2—C18	1.784 (3)	C9—C10	1.370 (4)
N1—C1	1.336 (3)	C9—C14	1.387 (4)
N1—C5	1.360 (3)	C10—C11	1.386 (5)
N2—N3	1.317 (3)	C10—H10	0.9500
N2—C6	1.360 (3)	C11—C12	1.396 (6)
N3—N4	1.339 (3)	C11—H11	0.9500
N4—C7	1.344 (3)	C12—C13	1.374 (6)
N4—C8	1.473 (3)	C12—H12	0.9500
C1—C2	1.384 (4)	C13—C14	1.397 (4)
C1—H1	0.9500	C13—H13	0.9500
C2—C3	1.385 (4)	C14—H14	0.9500
C2—H2	0.9500	C15—H15A	0.9800
C3—C4	1.376 (4)	C15—H15B	0.9800
C3—H3	0.9500	C15—H15C	0.9800
C4—C5	1.386 (3)	C16—H16A	0.9800
C4—H4	0.9500	C16—H16B	0.9800
C5—C6	1.449 (3)	C16—H16C	0.9800
N2—Ru1—N1	77.10 (7)	N2—C6—C5	118.1 (2)
N2—Ru1—S2	93.13 (5)	C7—C6—C5	134.5 (2)
N1—Ru1—S2	170.10 (5)	N4—C7—C6	104.79 (19)
N2—Ru1—S1	175.11 (5)	N4—C7—H7	127.6
N1—Ru1—S1	98.55 (5)	C6—C7—H7	127.6
S2—Ru1—S1	91.27 (2)	N4—C8—C9	110.5 (2)
N2—Ru1—Cl1	88.98 (5)	N4—C8—H8A	109.6
N1—Ru1—Cl1	86.60 (5)	C9—C8—H8A	109.6
S2—Ru1—Cl1	94.93 (2)	N4—C8—H8AB	109.6
S1—Ru1—Cl1	88.52 (2)	C9—C8—H8AB	109.6
N2—Ru1—Cl2	89.92 (5)	H8A—C8—H8AB	108.1
N1—Ru1—Cl2	88.09 (5)	S2—C18—H18A	109.5
S2—Ru1—Cl2	90.32 (2)	S2—C18—H18B	109.5
S1—Ru1—Cl2	92.19 (2)	H18A—C18—H18B	109.5
Cl1—Ru1—Cl2	174.69 (2)	S2—C18—H18C	109.5
O1—S1—C15	105.23 (12)	H18A—C18—H18C	109.5
O1—S1—C16	105.50 (11)	H18B—C18—H18C	109.5
C15—S1—C16	99.46 (13)	S2—C17—H17A	109.5
O1—S1—Ru1	118.17 (7)	S2—C17—H17B	109.5
C15—S1—Ru1	113.87 (9)	H17A—C17—H17B	109.5
C16—S1—Ru1	112.62 (9)	S2—C17—H17C	109.5
O2—S2—C17	106.05 (14)	H17A—C17—H17C	109.5
O2—S2—C18	104.33 (12)	H17B—C17—H17C	109.5
C17—S2—C18	100.13 (14)	C10—C9—C14	120.5 (3)
O2—S2—Ru1	120.08 (8)	C10—C9—C8	119.5 (2)
C17—S2—Ru1	112.19 (10)	C14—C9—C8	120.1 (3)
C18—S2—Ru1	111.94 (9)	C9—C10—C11	120.0 (3)
C1—N1—C5	117.23 (19)	C9—C10—H10	120.0
C1—N1—Ru1	128.13 (16)	C11—C10—H10	120.0
C5—N1—Ru1	114.63 (15)	C10—C11—C12	120.2 (4)
N3—N2—C6	110.02 (18)	C10—C11—H11	119.9
N3—N2—Ru1	134.47 (14)	C12—C11—H11	119.9
C6—N2—Ru1	115.51 (15)	C13—C12—C11	119.5 (3)
N2—N3—N4	105.96 (17)	C13—C12—H12	120.3
N3—N4—C7	111.83 (18)	C11—C12—H12	120.3
N3—N4—C8	120.44 (18)	C12—C13—C14	120.3 (3)
C7—N4—C8	127.72 (19)	C12—C13—H13	119.9
N1—C1—C2	122.6 (2)	C14—C13—H13	119.9
N1—C1—H1	118.7	C9—C14—C13	119.5 (3)
C2—C1—H1	118.7	C9—C14—H14	120.3
C1—C2—C3	119.8 (2)	C13—C14—H14	120.3
C1—C2—H2	120.1	S1—C15—H15A	109.5
C3—C2—H2	120.1	S1—C15—H15B	109.5
C4—C3—C2	118.3 (2)	H15A—C15—H15B	109.5
C4—C3—H3	120.8	S1—C15—H15C	109.5
C2—C3—H3	120.8	H15A—C15—H15C	109.5
C3—C4—C5	119.0 (2)	H15B—C15—H15C	109.5
C3—C4—H4	120.5	S1—C16—H16A	109.5
C5—C4—H4	120.5	S1—C16—H16B	109.5
N1—C5—C4	123.0 (2)	H16A—C16—H16B	109.5
N1—C5—C6	114.6 (2)	S1—C16—H16C	109.5
C4—C5—C6	122.4 (2)	H16A—C16—H16C	109.5
N2—C6—C7	107.39 (19)	H16B—C16—H16C	109.5
C6—N2—N3—N4	−0.8 (2)	C4—C5—C6—N2	177.9 (2)
Ru1—N2—N3—N4	179.26 (15)	N1—C5—C6—C7	−178.5 (2)
N2—N3—N4—C7	0.4 (2)	C4—C5—C6—C7	0.5 (4)
N2—N3—N4—C8	−178.75 (19)	N3—N4—C7—C6	0.1 (2)
C5—N1—C1—C2	1.7 (3)	C8—N4—C7—C6	179.2 (2)
Ru1—N1—C1—C2	−179.42 (18)	N2—C6—C7—N4	−0.6 (2)
N1—C1—C2—C3	−1.1 (4)	C5—C6—C7—N4	177.1 (2)
C1—C2—C3—C4	−0.2 (4)	N3—N4—C8—C9	123.2 (2)
C2—C3—C4—C5	0.9 (4)	C7—N4—C8—C9	−55.9 (3)
C1—N1—C5—C4	−1.0 (3)	N4—C8—C9—C10	−82.9 (3)
Ru1—N1—C5—C4	179.97 (17)	N4—C8—C9—C14	96.9 (3)
C1—N1—C5—C6	177.95 (19)	C14—C9—C10—C11	−2.3 (5)
Ru1—N1—C5—C6	−1.1 (2)	C8—C9—C10—C11	177.5 (3)
C3—C4—C5—N1	−0.3 (3)	C9—C10—C11—C12	0.0 (6)
C3—C4—C5—C6	−179.2 (2)	C10—C11—C12—C13	3.2 (6)
N3—N2—C6—C7	0.9 (2)	C11—C12—C13—C14	−4.1 (5)
Ru1—N2—C6—C7	−179.16 (14)	C10—C9—C14—C13	1.4 (5)
N3—N2—C6—C5	−177.21 (18)	C8—C9—C14—C13	−178.4 (3)
Ru1—N2—C6—C5	2.7 (2)	C12—C13—C14—C9	1.9 (5)
N1—C5—C6—N2	−1.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cl2^i	0.95	2.49	3.438 (2)	172

Symmetry code: (i) −x+1/2, y−1/2, z.

(OC-6-32)-[1-Benzyl-4-(pyridin-2-yl-κN)-1H-1,2,3-triazole-κN³]dichloridobis(dimethyl sulfoxide-κS)ruthenium(II) (3)

Crystal data

[RuCl2(C14H12N4)(C2H6OS)2]	Z = 2
Mr = 564.50	F(000) = 572
Triclinic, P1	Dx = 1.710 Mg m^−3
a = 9.3535 (14) Å	Cu Kα radiation, λ = 1.54184 Å
b = 9.4900 (15) Å	Cell parameters from 7943 reflections
c = 13.904 (2) Å	θ = 3.4–66.9°
α = 98.893 (5)°	µ = 10.01 mm^−1
β = 106.772 (5)°	T = 90 K
γ = 106.276 (5)°	Cubic, yellow
V = 1096.4 (3) Å^3	0.67 × 0.63 × 0.45 mm

Data collection

Bruker Kappa APEXII CCD DUO diffractometer	3704 independent reflections
Radiation source: IµS microfocus	3657 reflections with I > 2σ(I)
QUAZAR multilayer optics monochromator	Rint = 0.026
φ and ω scans	θmax = 66.9°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −10→11
Tmin = 0.062, Tmax = 0.094	k = −10→11
9693 measured reflections	l = −16→11

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0546P)^2 + 2.1529P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 0.001
3704 reflections	Δρmax = 2.21 e Å^−3
266 parameters	Δρmin = −0.63 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
Ru1	0.34993 (3)	0.83627 (3)	0.70658 (2)	0.01710 (13)
Cl1	0.47441 (11)	0.82110 (10)	0.88125 (7)	0.0249 (2)
C1	0.4322 (5)	0.5485 (4)	0.6392 (3)	0.0251 (8)
H1	0.326454	0.492417	0.631964	0.030*
C3	0.6834 (5)	0.5504 (4)	0.6309 (3)	0.0249 (8)
H3	0.751793	0.498296	0.617920	0.030*
N3	0.6204 (4)	1.1465 (4)	0.7637 (3)	0.0211 (6)
C5	0.6319 (4)	0.7785 (4)	0.6771 (3)	0.0201 (7)
S1	0.22838 (10)	0.98237 (10)	0.76998 (7)	0.0195 (2)
S2	0.25606 (10)	0.85272 (10)	0.54247 (7)	0.0201 (2)
Cl2	0.11642 (10)	0.61922 (10)	0.67424 (7)	0.0240 (2)
C2	0.5301 (5)	0.4707 (4)	0.6218 (3)	0.0281 (8)
H2	0.492296	0.362796	0.603645	0.034*
N2	0.5625 (4)	0.9976 (3)	0.7295 (2)	0.0197 (6)
O1	0.0918 (3)	1.0056 (3)	0.6943 (2)	0.0237 (6)
O2	0.3217 (3)	0.7874 (3)	0.4691 (2)	0.0248 (6)
N1	0.4805 (4)	0.7007 (3)	0.6660 (2)	0.0197 (6)
N4	0.7735 (4)	1.1863 (3)	0.7691 (2)	0.0198 (6)
C4	0.7360 (5)	0.7070 (4)	0.6590 (3)	0.0227 (8)
H4	0.841005	0.764702	0.665853	0.027*
C6	0.6756 (4)	0.9424 (4)	0.7130 (3)	0.0186 (7)
C7	0.8119 (4)	1.0644 (4)	0.7384 (3)	0.0193 (7)
H7	0.911618	1.063422	0.735085	0.023*
C8	0.8771 (4)	1.3460 (4)	0.8080 (3)	0.0227 (8)
H8A	0.818548	1.408213	0.831416	0.027*
H8B	0.907011	1.381665	0.750905	0.027*
C9	1.0257 (4)	1.3673 (4)	0.8971 (3)	0.0197 (7)
C10	1.1666 (5)	1.4801 (4)	0.9085 (3)	0.0231 (8)
H10	1.168318	1.539792	0.859658	0.028*
C13	1.1646 (5)	1.3045 (5)	1.0502 (3)	0.0282 (9)
H13	1.163861	1.242858	1.097911	0.034*
C11	1.3043 (5)	1.5055 (4)	0.9911 (3)	0.0254 (8)
H11	1.399325	1.583829	0.999096	0.030*
C12	1.3051 (5)	1.4179 (5)	1.0621 (3)	0.0272 (8)
H12	1.400003	1.435062	1.118164	0.033*
C15	0.1582 (5)	0.9144 (5)	0.8671 (3)	0.0285 (8)
H15A	0.104786	0.979669	0.892022	0.043*
H15B	0.248383	0.916245	0.925322	0.043*
H15C	0.083077	0.810137	0.837040	0.043*
C14	1.0261 (5)	1.2809 (4)	0.9692 (3)	0.0244 (8)
H14	0.930278	1.204961	0.962791	0.029*
C16	0.3581 (5)	1.1661 (4)	0.8480 (3)	0.0254 (8)
H16A	0.403859	1.224247	0.805103	0.038*
H16B	0.443670	1.156519	0.904175	0.038*
H16C	0.298350	1.218801	0.877788	0.038*
C17	0.0452 (5)	0.7802 (4)	0.4819 (3)	0.0255 (8)
H17A	0.015495	0.804549	0.414508	0.038*
H17B	−0.002664	0.826346	0.526319	0.038*
H17C	0.006768	0.669736	0.471409	0.038*
C18	0.2932 (5)	1.0468 (4)	0.5377 (3)	0.0250 (8)
H18A	0.238266	1.050697	0.467030	0.037*
H18B	0.407723	1.098936	0.557126	0.037*
H18C	0.253771	1.096943	0.586229	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ru1	0.01527 (18)	0.01563 (18)	0.01954 (18)	0.00614 (12)	0.00501 (12)	0.00265 (12)
Cl1	0.0253 (5)	0.0278 (5)	0.0212 (4)	0.0119 (4)	0.0045 (4)	0.0065 (4)
C1	0.026 (2)	0.0198 (19)	0.0272 (19)	0.0087 (16)	0.0064 (16)	0.0024 (15)
C3	0.030 (2)	0.0251 (19)	0.0220 (18)	0.0183 (17)	0.0048 (16)	0.0033 (15)
N3	0.0177 (15)	0.0198 (16)	0.0245 (15)	0.0066 (12)	0.0062 (12)	0.0042 (12)
C5	0.0216 (18)	0.0227 (19)	0.0171 (17)	0.0106 (15)	0.0055 (14)	0.0055 (14)
S1	0.0180 (4)	0.0210 (4)	0.0202 (4)	0.0082 (3)	0.0070 (3)	0.0037 (3)
S2	0.0211 (4)	0.0185 (4)	0.0203 (4)	0.0076 (3)	0.0063 (3)	0.0036 (3)
Cl2	0.0215 (4)	0.0200 (4)	0.0269 (4)	0.0035 (3)	0.0074 (4)	0.0050 (3)
C2	0.033 (2)	0.0187 (18)	0.029 (2)	0.0088 (16)	0.0065 (17)	0.0027 (15)
N2	0.0198 (15)	0.0174 (15)	0.0207 (15)	0.0066 (12)	0.0061 (12)	0.0028 (12)
O1	0.0199 (13)	0.0305 (14)	0.0233 (13)	0.0134 (11)	0.0072 (11)	0.0055 (11)
O2	0.0282 (14)	0.0210 (13)	0.0255 (13)	0.0094 (11)	0.0106 (11)	0.0030 (11)
N1	0.0196 (15)	0.0180 (15)	0.0192 (15)	0.0071 (12)	0.0041 (12)	0.0025 (12)
N4	0.0139 (14)	0.0192 (15)	0.0237 (15)	0.0044 (12)	0.0052 (12)	0.0034 (12)
C4	0.0232 (19)	0.027 (2)	0.0197 (17)	0.0120 (16)	0.0070 (15)	0.0048 (15)
C6	0.0184 (17)	0.0201 (18)	0.0183 (16)	0.0099 (14)	0.0057 (14)	0.0029 (14)
C7	0.0150 (17)	0.0234 (18)	0.0221 (17)	0.0101 (14)	0.0070 (14)	0.0055 (14)
C8	0.0204 (18)	0.0178 (18)	0.0292 (19)	0.0069 (15)	0.0072 (16)	0.0062 (15)
C9	0.0175 (17)	0.0180 (17)	0.0232 (18)	0.0084 (14)	0.0064 (15)	0.0014 (14)
C10	0.0242 (19)	0.0185 (18)	0.0268 (19)	0.0060 (15)	0.0106 (16)	0.0052 (15)
C13	0.035 (2)	0.028 (2)	0.0224 (19)	0.0129 (18)	0.0102 (17)	0.0073 (16)
C11	0.0207 (19)	0.0211 (19)	0.029 (2)	0.0053 (15)	0.0064 (16)	−0.0007 (15)
C12	0.024 (2)	0.028 (2)	0.0235 (19)	0.0101 (16)	0.0021 (16)	−0.0026 (16)
C15	0.029 (2)	0.033 (2)	0.029 (2)	0.0115 (18)	0.0154 (17)	0.0117 (17)
C14	0.0238 (19)	0.0244 (19)	0.0242 (19)	0.0054 (16)	0.0114 (16)	0.0037 (15)
C16	0.025 (2)	0.0235 (19)	0.0262 (19)	0.0094 (16)	0.0094 (16)	−0.0014 (15)
C17	0.0237 (19)	0.025 (2)	0.0231 (18)	0.0073 (16)	0.0039 (15)	0.0036 (15)
C18	0.029 (2)	0.0223 (19)	0.0256 (19)	0.0100 (16)	0.0104 (16)	0.0071 (15)

Geometric parameters (Å, º)

Ru1—N2	2.044 (3)	C6—C7	1.370 (5)
Ru1—N1	2.126 (3)	C7—H7	0.9500
Ru1—S2	2.2434 (9)	C8—C9	1.509 (5)
Ru1—S1	2.2530 (9)	C8—H8A	0.9900
Ru1—Cl2	2.4167 (9)	C8—H8B	0.9900
Ru1—Cl1	2.4175 (9)	C9—C14	1.390 (5)
C1—N1	1.341 (5)	C9—C10	1.394 (5)
C1—C2	1.377 (6)	C10—C11	1.387 (6)
C1—H1	0.9500	C10—H10	0.9500
C3—C4	1.379 (6)	C13—C14	1.384 (6)
C3—C2	1.380 (6)	C13—C12	1.393 (6)
C3—H3	0.9500	C13—H13	0.9500
N3—N2	1.315 (4)	C11—C12	1.385 (6)
N3—N4	1.351 (4)	C11—H11	0.9500
C5—N1	1.351 (5)	C12—H12	0.9500
C5—C4	1.390 (5)	C15—H15A	0.9800
C5—C6	1.456 (5)	C15—H15B	0.9800
S1—O1	1.497 (3)	C15—H15C	0.9800
S1—C16	1.777 (4)	C14—H14	0.9500
S1—C15	1.793 (4)	C16—H16A	0.9800
S2—O2	1.477 (3)	C16—H16B	0.9800
S2—C17	1.782 (4)	C16—H16C	0.9800
S2—C18	1.792 (4)	C17—H17A	0.9800
C2—H2	0.9500	C17—H17B	0.9800
N2—C6	1.364 (5)	C17—H17C	0.9800
N4—C7	1.348 (5)	C18—H18A	0.9800
N4—C8	1.466 (5)	C18—H18B	0.9800
C4—H4	0.9500	C18—H18C	0.9800
N2—Ru1—N1	78.32 (12)	N2—C6—C5	117.9 (3)
N2—Ru1—S2	90.28 (9)	C7—C6—C5	135.0 (3)
N1—Ru1—S2	91.60 (8)	N4—C7—C6	105.0 (3)
N2—Ru1—S1	100.24 (9)	N4—C7—H7	127.5
N1—Ru1—S1	173.01 (8)	C6—C7—H7	127.5
S2—Ru1—S1	95.26 (3)	N4—C8—C9	111.4 (3)
N2—Ru1—Cl2	171.78 (9)	N4—C8—H8A	109.3
N1—Ru1—Cl2	93.49 (9)	C9—C8—H8A	109.3
S2—Ru1—Cl2	90.60 (3)	N4—C8—H8B	109.3
S1—Ru1—Cl2	87.81 (3)	C9—C8—H8B	109.3
N2—Ru1—Cl1	85.57 (9)	H8A—C8—H8B	108.0
N1—Ru1—Cl1	84.32 (8)	C14—C9—C10	119.0 (3)
S2—Ru1—Cl1	174.69 (3)	C14—C9—C8	122.3 (3)
S1—Ru1—Cl1	88.75 (3)	C10—C9—C8	118.7 (3)
Cl2—Ru1—Cl1	93.04 (3)	C11—C10—C9	120.1 (4)
N1—C1—C2	122.5 (4)	C11—C10—H10	119.9
N1—C1—H1	118.8	C9—C10—H10	119.9
C2—C1—H1	118.8	C14—C13—C12	120.4 (4)
C4—C3—C2	119.0 (4)	C14—C13—H13	119.8
C4—C3—H3	120.5	C12—C13—H13	119.8
C2—C3—H3	120.5	C12—C11—C10	120.8 (4)
N2—N3—N4	105.3 (3)	C12—C11—H11	119.6
N1—C5—C4	122.5 (3)	C10—C11—H11	119.6
N1—C5—C6	113.6 (3)	C11—C12—C13	119.0 (4)
C4—C5—C6	123.8 (3)	C11—C12—H12	120.5
O1—S1—C16	106.23 (18)	C13—C12—H12	120.5
O1—S1—C15	106.64 (18)	S1—C15—H15A	109.5
C16—S1—C15	97.9 (2)	S1—C15—H15B	109.5
O1—S1—Ru1	117.75 (11)	H15A—C15—H15B	109.5
C16—S1—Ru1	114.42 (13)	S1—C15—H15C	109.5
C15—S1—Ru1	111.80 (14)	H15A—C15—H15C	109.5
O2—S2—C17	107.02 (17)	H15B—C15—H15C	109.5
O2—S2—C18	105.76 (17)	C13—C14—C9	120.6 (4)
C17—S2—C18	99.59 (19)	C13—C14—H14	119.7
O2—S2—Ru1	116.22 (12)	C9—C14—H14	119.7
C17—S2—Ru1	115.64 (13)	S1—C16—H16A	109.5
C18—S2—Ru1	110.93 (13)	S1—C16—H16B	109.5
C1—C2—C3	119.5 (4)	H16A—C16—H16B	109.5
C1—C2—H2	120.2	S1—C16—H16C	109.5
C3—C2—H2	120.2	H16A—C16—H16C	109.5
N3—N2—C6	110.8 (3)	H16B—C16—H16C	109.5
N3—N2—Ru1	134.0 (2)	S2—C17—H17A	109.5
C6—N2—Ru1	115.0 (2)	S2—C17—H17B	109.5
C1—N1—C5	117.9 (3)	H17A—C17—H17B	109.5
C1—N1—Ru1	126.7 (3)	S2—C17—H17C	109.5
C5—N1—Ru1	115.1 (2)	H17A—C17—H17C	109.5
C7—N4—N3	111.9 (3)	H17B—C17—H17C	109.5
C7—N4—C8	127.9 (3)	S2—C18—H18A	109.5
N3—N4—C8	120.2 (3)	S2—C18—H18B	109.5
C3—C4—C5	118.5 (4)	H18A—C18—H18B	109.5
C3—C4—H4	120.7	S2—C18—H18C	109.5
C5—C4—H4	120.7	H18A—C18—H18C	109.5
N2—C6—C7	107.1 (3)	H18B—C18—H18C	109.5
N1—C1—C2—C3	−0.7 (6)	C4—C5—C6—N2	−178.9 (3)
C4—C3—C2—C1	1.1 (6)	N1—C5—C6—C7	177.5 (4)
N4—N3—N2—C6	−0.2 (4)	C4—C5—C6—C7	−0.5 (6)
N4—N3—N2—Ru1	174.8 (2)	N3—N4—C7—C6	−0.3 (4)
C2—C1—N1—C5	−0.8 (6)	C8—N4—C7—C6	177.8 (3)
C2—C1—N1—Ru1	−174.9 (3)	N2—C6—C7—N4	0.2 (4)
C4—C5—N1—C1	1.9 (5)	C5—C6—C7—N4	−178.2 (4)
C6—C5—N1—C1	−176.1 (3)	C7—N4—C8—C9	−53.0 (5)
C4—C5—N1—Ru1	176.7 (3)	N3—N4—C8—C9	125.0 (3)
C6—C5—N1—Ru1	−1.3 (4)	N4—C8—C9—C14	−34.4 (5)
N2—N3—N4—C7	0.3 (4)	N4—C8—C9—C10	147.0 (3)
N2—N3—N4—C8	−178.0 (3)	C14—C9—C10—C11	−0.3 (5)
C2—C3—C4—C5	0.0 (5)	C8—C9—C10—C11	178.3 (3)
N1—C5—C4—C3	−1.5 (5)	C9—C10—C11—C12	1.2 (6)
C6—C5—C4—C3	176.3 (3)	C10—C11—C12—C13	−0.7 (6)
N3—N2—C6—C7	0.0 (4)	C14—C13—C12—C11	−0.7 (6)
Ru1—N2—C6—C7	−176.1 (2)	C12—C13—C14—C9	1.6 (6)
N3—N2—C6—C5	178.7 (3)	C10—C9—C14—C13	−1.1 (5)
Ru1—N2—C6—C5	2.7 (4)	C8—C9—C14—C13	−179.6 (4)
N1—C5—C6—N2	−0.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1^i	0.95	2.11	3.031 (4)	164

Symmetry code: (i) x+1, y, z.