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The crystal structure of the title compound, [RuCl2(C12H8N2O4)2]·H2O, which is a precursor of the dye for dye-sensitized solar cells, is composed of a ruthenium(II) complex mol­ecule containing 2,2′-bi­pyridine-4,4′-di­carboxyl­ic acid (H2dcbpy) as a ligand and an uncoordinated water mol­ecule. The overlapped arrangement and the separation of 3.34 (7) Å suggest π–π stacking between parallel H2dcbpy ligands in neighboring complex mol­ecules. A three-dimensional network is formed by intermolecular O—H...O and O—H...Cl hydrogen bonds and π–π stacking between neighboring complex mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804017507/lh6249sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804017507/lh6249Isup2.hkl
Contains datablock I

CCDC reference: 248752

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • H-atom completeness 89%
  • Disorder in solvent or counterion
  • R factor = 0.026
  • wR factor = 0.073
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... >O10A PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) ..... <O10B PLAT432_ALERT_2_C Short Inter X...Y Contact Cl1 .. C7 .. 3.22 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C11 .. 2.98 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C22 .. O10B .. 3.00 Ang.
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C24 H18 Cl2 N4 O9 Ru1 Atom count from the _atom_site data: C24 H16 Cl2 N4 O9 Ru1 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C24 H18 Cl2 N4 O9 Ru TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 96.00 96.00 0.00 H 72.00 64.00 8.00 Cl 8.00 8.00 0.00 N 16.00 16.00 0.00 O 36.00 36.00 0.00 Ru 4.00 4.00 0.00
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART-W2K/NT (Bruker, 2003); cell refinement: SAINT-W2K/NT (Bruker, 2003); data reduction: SAINT-W2K/NT; program(s) used to solve structure: SHELXTL-NT (Bruker, 2003); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT.

cis-Bis(2,2'-bipyridine-4,4'-dicarboxylic acid\-κ2N,N')dichlororuthenium(II) monohydrate top
Crystal data top
[RuCl2(C12H8N2O4)2]·H2OF(000) = 1360
Mr = 678.39Dx = 1.795 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5415 reflections
a = 12.2172 (7) Åθ = 2.3–27.9°
b = 11.0152 (7) ŵ = 0.90 mm1
c = 19.5064 (12) ÅT = 173 K
β = 106.999 (1)°Plate, black
V = 2510.4 (3) Å30.26 × 0.23 × 0.21 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5983 independent reflections
Radiation source: fine-focus sealed tube5466 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 8.366 pixels mm-1θmax = 27.9°, θmin = 1.8°
φ and ω scansh = 1615
Absorption correction: multi-scan
(SADABS; Scheldrick, 1996)
k = 1414
Tmin = 0.800, Tmax = 0.833l = 1925
17958 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0407P)2 + 1.3308P]
where P = (Fo2 + 2Fc2)/3
5983 reflections(Δ/σ)max = 0.001
387 parametersΔρmax = 0.68 e Å3
0 restraintsΔρmin = 0.43 e Å3
Special details top

Experimental. none

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.0552 (0.0133) x + 9.0634 (0.0185) y + 4.9075 (0.0474) z = 6.4469 (0.0287)

* 0.0000 (0.0000) C11 * 0.0000 (0.0000) O1 * 0.0000 (0.0000) O2

Rms deviation of fitted atoms = 0.0000

4.4379 (0.0082) x + 8.9784 (0.0043) y + 6.3473 (0.0127) z = 6.7378 (0.0035)

Angle to previous plane (with approximate e.s.d.) = 4.59 (0.26)

* 0.0093 (0.0011) N1 * -0.0043 (0.0012) C1 * -0.0046 (0.0013) C2 * 0.0084 (0.0012) C3 * -0.0035 (0.0012) C4 * -0.0053 (0.0011) C5

Rms deviation of fitted atoms = 0.0063

3.1503 (0.0078) x + 9.3619 (0.0042) y + 7.1016 (0.0123) z = 6.7018 (0.0023)

Angle to previous plane (with approximate e.s.d.) = 6.38 (0.09)

* 0.0099 (0.0010) N2 * -0.0127 (0.0011) C6 * 0.0047 (0.0011) C7 * 0.0059 (0.0012) C8 * -0.0088 (0.0012) C9 * 0.0010 (0.0012) C10

Rms deviation of fitted atoms = 0.0081

3.4444 (0.0419) x + 9.3708 (0.0073) y + 6.6675 (0.0589) z = 6.5628 (0.0231)

Angle to previous plane (with approximate e.s.d.) = 1.65 (0.26)

* 0.0000 (0.0000) C12 * 0.0000 (0.0000) O3 * 0.0000 (0.0000) O4

Rms deviation of fitted atoms = 0.0000

3.7624 (0.0134) x - 9.2224 (0.0203) y + 6.6730 (0.0538) z = 0.0459 (0.0030)

Angle to previous plane (with approximate e.s.d.) = 64.85 (0.17)

* 0.0000 (0.0000) C23 * 0.0000 (0.0000) O5 * 0.0000 (0.0000) O6

Rms deviation of fitted atoms = 0.0000

3.5180 (0.0081) x - 8.7665 (0.0043) y + 8.2936 (0.0117) z = 0.0896 (0.0030)

Angle to previous plane (with approximate e.s.d.) = 5.33 (0.30)

* -0.0251 (0.0011) N3 * 0.0077 (0.0011) C13 * 0.0160 (0.0012) C14 * -0.0225 (0.0012) C15 * 0.0055 (0.0012) C16 * 0.0183 (0.0011) C17

Rms deviation of fitted atoms = 0.0174

- 1.3653 (0.0088) x + 8.6389 (0.0054) y - 10.7468 (0.0122) z = 0.5754 (0.0064)

Angle to previous plane (with approximate e.s.d.) = 11.07 (0.10)

* 0.0027 (0.0012) N4 * -0.0053 (0.0012) C18 * 0.0019 (0.0013) C19 * 0.0039 (0.0013) C20 * -0.0064 (0.0014) C21 * 0.0032 (0.0013) C22

Rms deviation of fitted atoms = 0.0042

- 1.7697 (0.0391) x + 8.7386 (0.0079) y - 10.2045 (0.0453) z = 0.3661 (0.0280)

Angle to previous plane (with approximate e.s.d.) = 2.25 (0.24)

* 0.0000 (0.0000) C24 * 0.0000 (0.0000) O7 * 0.0000 (0.0000) O8

Rms deviation of fitted atoms = 0.0000

3.7550 (0.0028) x + 9.1500 (0.0016) y + 6.9072 (0.0067) z = 6.6526 (0.0015)

Angle to previous plane (with approximate e.s.d.) = 70.13 (0.10)

* 0.0004 (0.0013) N1 * -0.0842 (0.0015) C1 * -0.0922 (0.0016) C2 * -0.0105 (0.0015) C3 * 0.0514 (0.0016) C4 * 0.0535 (0.0015) C5 * 0.0349 (0.0013) C11 * 0.0863 (0.0012) N2 * 0.0763 (0.0015) C6 * 0.0385 (0.0015) C7 * -0.0301 (0.0015) C8 * -0.0574 (0.0016) C9 * 0.0095 (0.0015) C10 * -0.0765 (0.0013) C12 3.0730 (0.0020) N3_$3 3.1214 (0.0022) C13_$3 3.2294 (0.0020) C14_$3 3.2794 (0.0019) C15_$3 3.2920 (0.0020) C16_$3 3.2026 (0.0021) C17_$3 3.2956 (0.0019) C23_$3 3.0390 (0.0023) N4_$3 3.2656 (0.0023) C18_$3 3.5969 (0.0024) C19_$3 3.7131 (0.0026) C20_$3 3.4984 (0.0029) C21_$3 3.1562 (0.0029) C22_$3 4.0469 (0.0027) C24_$3

Rms deviation of fitted atoms = 0.0581

[$3 = symmetry transformation (x + 1/2,-y + 1/2, z + 1/2)]

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
xyzUiso*/UeqOcc. (<1)
Ru10.411752 (11)0.412693 (12)0.233999 (7)0.01680 (6)
Cl10.33489 (4)0.56866 (4)0.14632 (2)0.02382 (9)
Cl20.49439 (4)0.57685 (4)0.31602 (2)0.02208 (9)
N10.47078 (12)0.29585 (13)0.31534 (7)0.0192 (3)
N20.27878 (12)0.41250 (12)0.27763 (8)0.0182 (3)
N30.35091 (12)0.28330 (12)0.15838 (7)0.0176 (3)
N40.54696 (12)0.39383 (13)0.19329 (8)0.0198 (3)
C10.57049 (15)0.23567 (16)0.32862 (9)0.0241 (3)
C20.61569 (15)0.16976 (16)0.39020 (9)0.0239 (3)
C30.55563 (14)0.16486 (15)0.44117 (9)0.0204 (3)
C40.45128 (14)0.22490 (15)0.42732 (9)0.0209 (3)
C50.41002 (14)0.28988 (15)0.36398 (9)0.0189 (3)
C60.29984 (14)0.35426 (14)0.34188 (8)0.0183 (3)
C70.22075 (14)0.35352 (15)0.38039 (9)0.0202 (3)
C80.11605 (15)0.41078 (15)0.35153 (9)0.0207 (3)
C90.09364 (14)0.46723 (16)0.28498 (10)0.0232 (3)
C100.17668 (15)0.46692 (16)0.24993 (9)0.0222 (3)
C110.60507 (15)0.09795 (15)0.50950 (9)0.0205 (3)
C120.03060 (16)0.40952 (16)0.39293 (10)0.0255 (4)
C130.24909 (14)0.22645 (15)0.14544 (9)0.0199 (3)
C140.20595 (14)0.15249 (15)0.08656 (9)0.0203 (3)
C150.26901 (14)0.13625 (15)0.03800 (9)0.0199 (3)
C160.37642 (14)0.19000 (15)0.05262 (9)0.0212 (3)
C170.41588 (14)0.26176 (15)0.11328 (9)0.0192 (3)
C180.52974 (14)0.31851 (15)0.13568 (9)0.0203 (3)
C190.61579 (15)0.29394 (16)0.10433 (9)0.0229 (3)
C200.72256 (14)0.34668 (16)0.13298 (9)0.0228 (3)
C210.74029 (16)0.42238 (17)0.19254 (10)0.0274 (4)
C220.65110 (16)0.44446 (18)0.22072 (10)0.0263 (4)
C230.22296 (15)0.06469 (16)0.02942 (10)0.0219 (3)
C240.81493 (15)0.32232 (16)0.09881 (9)0.0233 (3)
O10.70141 (11)0.04331 (13)0.51116 (7)0.0285 (3)
O20.56231 (11)0.09528 (11)0.55848 (7)0.0253 (3)
O30.06527 (12)0.46813 (17)0.36008 (8)0.0406 (4)
O40.04845 (13)0.36221 (18)0.45021 (9)0.0482 (4)
O50.12117 (11)0.01857 (13)0.03576 (7)0.0281 (3)
O60.27282 (12)0.05265 (15)0.07417 (8)0.0354 (3)
O70.91114 (11)0.38004 (13)0.13156 (7)0.0276 (3)
O80.80164 (11)0.25868 (13)0.04662 (7)0.0319 (3)
H10.61140.23880.29400.029*
H20.68650.12830.39800.029*
H40.40860.22150.46090.025*
H70.23790.31450.42570.024*
H90.02200.50550.26400.028*
H100.16140.50640.20480.027*
H130.20540.23770.17800.024*
H140.13420.11310.07920.024*
H160.42230.17770.02140.025*
H190.60180.24180.06390.028*
H210.81310.45840.21350.033*
H220.66340.49710.26080.032*
H510.732 (2)0.007 (2)0.5529 (15)0.053 (8)*
H520.114 (2)0.460 (3)0.3843 (14)0.052 (8)*
H530.098 (2)0.018 (2)0.0756 (13)0.039 (7)*
H540.957 (2)0.378 (2)0.1070 (13)0.039 (7)*
O10A0.5347 (4)0.5949 (3)0.0574 (2)0.0933 (16)0.710 (5)
O10B0.6317 (11)0.7128 (7)0.1944 (5)0.120 (5)0.290 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.01690 (8)0.01976 (8)0.01514 (8)0.00012 (4)0.00689 (6)0.00008 (4)
Cl10.0273 (2)0.02253 (19)0.0197 (2)0.00075 (15)0.00396 (16)0.00264 (14)
Cl20.0228 (2)0.0242 (2)0.01894 (19)0.00024 (14)0.00568 (16)0.00272 (14)
N10.0196 (6)0.0234 (7)0.0162 (6)0.0006 (5)0.0075 (5)0.0000 (5)
N20.0186 (7)0.0200 (7)0.0171 (7)0.0009 (5)0.0066 (5)0.0010 (5)
N30.0177 (6)0.0191 (6)0.0174 (6)0.0013 (5)0.0074 (5)0.0023 (5)
N40.0200 (7)0.0241 (7)0.0169 (7)0.0012 (5)0.0080 (6)0.0013 (5)
C10.0241 (8)0.0282 (9)0.0238 (8)0.0033 (7)0.0129 (7)0.0012 (7)
C20.0219 (8)0.0253 (8)0.0262 (9)0.0046 (6)0.0096 (7)0.0019 (7)
C30.0205 (8)0.0207 (8)0.0202 (8)0.0002 (6)0.0063 (6)0.0003 (6)
C40.0209 (8)0.0232 (8)0.0203 (8)0.0013 (6)0.0087 (6)0.0006 (6)
C50.0190 (7)0.0201 (7)0.0190 (7)0.0016 (6)0.0081 (6)0.0015 (6)
C60.0193 (7)0.0183 (7)0.0178 (7)0.0008 (6)0.0060 (6)0.0005 (6)
C70.0222 (8)0.0206 (8)0.0186 (7)0.0005 (6)0.0072 (6)0.0008 (6)
C80.0191 (8)0.0226 (8)0.0218 (8)0.0016 (6)0.0083 (7)0.0010 (6)
C90.0179 (8)0.0275 (9)0.0240 (8)0.0022 (6)0.0057 (6)0.0013 (7)
C100.0230 (8)0.0250 (8)0.0190 (8)0.0020 (7)0.0068 (6)0.0023 (6)
C110.0183 (8)0.0204 (8)0.0226 (8)0.0017 (6)0.0058 (6)0.0001 (6)
C120.0220 (8)0.0304 (9)0.0264 (9)0.0001 (7)0.0105 (7)0.0008 (7)
C130.0192 (7)0.0226 (8)0.0205 (8)0.0002 (6)0.0097 (6)0.0021 (6)
C140.0192 (7)0.0202 (8)0.0220 (8)0.0013 (6)0.0070 (6)0.0013 (6)
C150.0197 (8)0.0204 (8)0.0204 (8)0.0005 (6)0.0071 (6)0.0006 (6)
C160.0198 (8)0.0246 (8)0.0210 (8)0.0008 (6)0.0090 (6)0.0013 (6)
C170.0166 (7)0.0225 (8)0.0204 (8)0.0006 (6)0.0082 (6)0.0006 (6)
C180.0198 (8)0.0240 (8)0.0178 (7)0.0029 (6)0.0064 (6)0.0017 (6)
C190.0228 (8)0.0276 (8)0.0203 (8)0.0028 (7)0.0093 (7)0.0050 (7)
C200.0208 (8)0.0287 (9)0.0208 (8)0.0019 (7)0.0092 (7)0.0010 (7)
C210.0216 (9)0.0377 (10)0.0244 (9)0.0078 (7)0.0090 (7)0.0073 (7)
C220.0252 (9)0.0336 (9)0.0217 (8)0.0073 (7)0.0094 (7)0.0083 (7)
C230.0186 (8)0.0238 (8)0.0232 (8)0.0009 (6)0.0061 (7)0.0016 (6)
C240.0222 (8)0.0275 (8)0.0219 (8)0.0015 (7)0.0094 (7)0.0003 (7)
O10.0249 (7)0.0382 (7)0.0238 (6)0.0111 (6)0.0091 (5)0.0075 (6)
O20.0223 (6)0.0317 (7)0.0236 (6)0.0016 (5)0.0096 (5)0.0033 (5)
O30.0227 (7)0.0685 (11)0.0357 (8)0.0135 (7)0.0163 (6)0.0170 (8)
O40.0355 (8)0.0784 (12)0.0388 (9)0.0213 (8)0.0237 (7)0.0291 (9)
O50.0231 (6)0.0363 (7)0.0268 (7)0.0101 (5)0.0105 (5)0.0099 (6)
O60.0250 (7)0.0558 (9)0.0300 (7)0.0125 (6)0.0151 (6)0.0163 (7)
O70.0203 (6)0.0384 (7)0.0271 (7)0.0053 (5)0.0117 (5)0.0072 (6)
O80.0274 (7)0.0422 (8)0.0302 (7)0.0072 (6)0.0150 (6)0.0121 (6)
O10A0.147 (4)0.072 (2)0.076 (2)0.035 (2)0.056 (3)0.0312 (17)
O10B0.183 (12)0.046 (5)0.100 (7)0.016 (6)0.007 (7)0.016 (5)
Geometric parameters (Å, º) top
Cl2—Ru12.4299 (4)C2—C31.399 (2)
Cl1—Ru12.4123 (4)C2—H20.9500
N1—Ru12.0063 (14)C8—C71.389 (2)
N2—Ru12.0426 (14)C8—C91.393 (2)
N3—Ru12.0295 (14)C8—C121.495 (2)
N4—Ru12.0419 (14)C21—C221.378 (3)
O1—C111.314 (2)C21—C201.394 (2)
O2—C111.216 (2)C21—H210.9500
O3—C121.327 (2)C14—C151.396 (2)
O4—C121.194 (2)C14—H140.9500
O5—C231.315 (2)C16—C171.387 (2)
O6—C231.209 (2)C16—C151.391 (2)
O7—C241.325 (2)C16—H160.9500
O8—C241.207 (2)C23—C151.495 (2)
N4—C221.348 (2)C10—C91.379 (2)
N4—C181.363 (2)C10—H100.9500
N3—C131.349 (2)C1—H10.9500
N3—C171.367 (2)C6—C71.387 (2)
N2—C101.347 (2)C6—C51.470 (2)
N2—C61.364 (2)C7—H70.9500
N1—C11.344 (2)C17—C181.470 (2)
N1—C51.366 (2)C3—C41.391 (2)
O7—H540.84 (3)C18—C191.389 (2)
O5—H530.85 (3)C5—C41.389 (2)
O3—H520.87 (3)C24—C201.493 (2)
O1—H510.89 (3)C22—H220.9500
C13—C141.381 (2)C4—H40.9500
C13—H130.9500C19—C201.387 (2)
C11—C31.488 (2)C19—H190.9500
C2—C11.374 (2)C9—H90.9500
C22—N4—C18118.64 (15)N3—C17—C16121.70 (15)
C22—N4—Ru1125.48 (12)N3—C17—C18114.33 (14)
C18—N4—Ru1115.80 (11)C16—C17—C18123.96 (14)
C13—N3—C17118.44 (14)C16—C15—C14118.75 (15)
C13—N3—Ru1125.72 (11)C16—C15—C23119.65 (15)
C17—N3—Ru1115.56 (11)C14—C15—C23121.60 (15)
C10—N2—C6118.82 (14)C4—C3—C2119.02 (15)
C10—N2—Ru1126.06 (12)C4—C3—C11121.23 (15)
C6—N2—Ru1115.09 (11)C2—C3—C11119.73 (15)
C1—N1—C5119.23 (14)O4—C12—O3123.94 (18)
C1—N1—Ru1124.39 (11)O4—C12—C8122.97 (17)
C5—N1—Ru1115.93 (11)O3—C12—C8113.08 (16)
C24—O7—H54111.0 (17)N4—C18—C19121.84 (15)
C23—O5—H53109.1 (16)N4—C18—C17114.11 (14)
C12—O3—H52109.8 (18)C19—C18—C17123.96 (15)
C11—O1—H51111.2 (17)N1—C5—C4120.86 (15)
N3—C13—C14122.44 (15)N1—C5—C6114.19 (14)
N3—C13—H13118.8C4—C5—C6124.93 (14)
C14—C13—H13118.8O8—C24—O7124.54 (16)
O2—C11—O1123.86 (16)O8—C24—C20123.22 (16)
O2—C11—C3124.10 (16)O7—C24—C20112.23 (15)
O1—C11—C3112.03 (15)N4—C22—C21122.22 (16)
C1—C2—C3118.79 (16)N4—C22—H22118.9
C1—C2—H2120.6C21—C22—H22118.9
C3—C2—H2120.6C5—C4—C3119.44 (15)
C7—C8—C9119.16 (16)C5—C4—H4120.3
C7—C8—C12118.86 (15)C3—C4—H4120.3
C9—C8—C12121.98 (16)C20—C19—C18118.99 (15)
C22—C21—C20119.31 (17)C20—C19—H19120.5
C22—C21—H21120.3C18—C19—H19120.5
C20—C21—H21120.3C10—C9—C8119.24 (16)
C13—C14—C15119.19 (15)C10—C9—H9120.4
C13—C14—H14120.4C8—C9—H9120.4
C15—C14—H14120.4C19—C20—C21118.99 (16)
C17—C16—C15119.29 (15)C19—C20—C24119.29 (15)
C17—C16—H16120.4C21—C20—C24121.72 (16)
C15—C16—H16120.4N1—Ru1—N395.44 (6)
O6—C23—O5123.49 (17)N1—Ru1—N495.60 (6)
O6—C23—C15123.61 (16)N3—Ru1—N479.16 (6)
O5—C23—C15112.88 (15)N1—Ru1—N279.37 (6)
N2—C10—C9122.10 (16)N3—Ru1—N297.77 (5)
N2—C10—H10118.9N4—Ru1—N2173.90 (6)
C9—C10—H10118.9N1—Ru1—Cl1173.21 (4)
N1—C1—C2122.63 (16)N3—Ru1—Cl190.05 (4)
N1—C1—H1118.7N4—Ru1—Cl189.33 (4)
C2—C1—H1118.7N2—Ru1—Cl195.97 (4)
N2—C6—C7121.76 (15)N1—Ru1—Cl288.43 (4)
N2—C6—C5114.02 (14)N3—Ru1—Cl2174.04 (4)
C7—C6—C5124.17 (15)N4—Ru1—Cl295.98 (4)
C6—C7—C8118.87 (15)N2—Ru1—Cl287.39 (4)
C6—C7—H7120.6Cl1—Ru1—Cl286.420 (16)
C8—C7—H7120.6
C17—N3—C13—C143.3 (2)N2—C6—C5—C4179.42 (15)
Ru1—N3—C13—C14170.29 (12)C7—C6—C5—C43.0 (3)
N3—C13—C14—C150.6 (3)C18—N4—C22—C210.1 (3)
C6—N2—C10—C91.1 (2)Ru1—N4—C22—C21176.43 (15)
Ru1—N2—C10—C9176.67 (13)C20—C21—C22—N41.0 (3)
C5—N1—C1—C21.4 (3)N1—C5—C4—C30.2 (2)
Ru1—N1—C1—C2170.63 (14)C6—C5—C4—C3178.14 (15)
C3—C2—C1—N10.1 (3)C2—C3—C4—C51.1 (3)
C10—N2—C6—C72.4 (2)C11—C3—C4—C5177.75 (15)
Ru1—N2—C6—C7175.58 (12)N4—C18—C19—C200.7 (3)
C10—N2—C6—C5175.25 (14)C17—C18—C19—C20175.70 (16)
Ru1—N2—C6—C56.78 (17)N2—C10—C9—C80.7 (3)
N2—C6—C7—C81.9 (2)C7—C8—C9—C101.2 (3)
C5—C6—C7—C8175.50 (15)C12—C8—C9—C10178.99 (16)
C9—C8—C7—C60.1 (2)C18—C19—C20—C210.2 (3)
C12—C8—C7—C6179.75 (15)C18—C19—C20—C24178.99 (16)
C13—N3—C17—C164.3 (2)C22—C21—C20—C191.0 (3)
Ru1—N3—C17—C16169.91 (13)C22—C21—C20—C24178.18 (18)
C13—N3—C17—C18174.45 (14)O8—C24—C20—C190.3 (3)
Ru1—N3—C17—C1811.32 (18)O7—C24—C20—C19179.19 (16)
C15—C16—C17—N31.4 (3)O8—C24—C20—C21178.88 (18)
C15—C16—C17—C18177.20 (16)O7—C24—C20—C210.0 (2)
C17—C16—C15—C142.5 (2)C1—N1—Ru1—N380.10 (14)
C17—C16—C15—C23176.48 (15)C5—N1—Ru1—N3107.65 (12)
C13—C14—C15—C163.5 (2)C1—N1—Ru1—N40.50 (15)
C13—C14—C15—C23175.47 (15)C5—N1—Ru1—N4172.75 (12)
O6—C23—C15—C162.0 (3)C1—N1—Ru1—N2177.01 (15)
O5—C23—C15—C16179.51 (16)C5—N1—Ru1—N210.74 (11)
O6—C23—C15—C14176.89 (18)C1—N1—Ru1—Cl295.35 (14)
O5—C23—C15—C141.6 (2)C5—N1—Ru1—Cl276.90 (11)
C1—C2—C3—C41.2 (3)C13—N3—Ru1—N182.42 (14)
C1—C2—C3—C11177.67 (16)C17—N3—Ru1—N1103.82 (12)
O2—C11—C3—C43.5 (3)C13—N3—Ru1—N4177.10 (14)
O1—C11—C3—C4177.37 (16)C17—N3—Ru1—N49.14 (11)
O2—C11—C3—C2175.29 (17)C13—N3—Ru1—N22.44 (14)
O1—C11—C3—C23.8 (2)C17—N3—Ru1—N2176.20 (11)
C7—C8—C12—O40.6 (3)C13—N3—Ru1—Cl193.59 (13)
C9—C8—C12—O4179.6 (2)C17—N3—Ru1—Cl180.16 (11)
C7—C8—C12—O3179.37 (16)C22—N4—Ru1—N176.85 (15)
C9—C8—C12—O30.8 (2)C18—N4—Ru1—N199.78 (12)
C22—N4—C18—C190.7 (3)C22—N4—Ru1—N3171.34 (16)
Ru1—N4—C18—C19177.60 (13)C18—N4—Ru1—N35.29 (12)
C22—N4—C18—C17175.97 (15)C22—N4—Ru1—Cl198.48 (15)
Ru1—N4—C18—C170.90 (19)C18—N4—Ru1—Cl184.89 (12)
N3—C17—C18—N46.8 (2)C22—N4—Ru1—Cl212.15 (15)
C16—C17—C18—N4174.50 (16)C18—N4—Ru1—Cl2171.22 (11)
N3—C17—C18—C19169.85 (16)C10—N2—Ru1—N1172.74 (14)
C16—C17—C18—C198.9 (3)C6—N2—Ru1—N19.47 (11)
C1—N1—C5—C41.5 (2)C10—N2—Ru1—N378.62 (14)
Ru1—N1—C5—C4171.22 (12)C6—N2—Ru1—N3103.59 (11)
C1—N1—C5—C6177.08 (15)C10—N2—Ru1—Cl112.25 (14)
Ru1—N1—C5—C610.24 (18)C6—N2—Ru1—Cl1165.54 (11)
N2—C6—C5—N12.1 (2)C10—N2—Ru1—Cl298.38 (13)
C7—C6—C5—N1175.47 (15)C6—N2—Ru1—Cl279.42 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H52···O6i0.87 (3)1.80 (3)2.6634 (19)174 (3)
O1—H51···Cl1ii0.89 (3)2.06 (3)2.9355 (14)168 (2)
O7—H54···O2iii0.84 (3)1.83 (3)2.6564 (18)168 (3)
O5—H53···Cl2iv0.85 (3)2.22 (3)3.0404 (14)164 (2)
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1/2, y+1/2, z1/2; (iv) x1/2, y+1/2, z1/2.
 

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