Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049239/bt2529sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049239/bt2529Isup2.hkl |
CCDC reference: 667147
Key indicators
- Single-crystal X-ray study
- T = 183 K
- Mean (C-C) = 0.010 Å
- Disorder in main residue
- R factor = 0.066
- wR factor = 0.169
- Data-to-parameter ratio = 18.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 3
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.120 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.32 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.25 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.23 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O2A PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C1M PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 5 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 23.60 Deg. O1 -C2 -O1A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.10 Deg. O2 -C2 -O2A 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 6 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
Trans-2,2'-bipyridinedichloromethyl-1-(phenylimino)-1-(phenylhydrazono)-acetate ruthenium(II) was prepared according to literature procedure (Al-Noaimi et al.,2007) and recrystallized by slowly evaporating a solution of dichloromethane.
The methylyester group has a 0.591 (18):0.409 (18) occupancy disorder over two positions. The disordered atoms were refined isotropically. The O2A—C3A distance was restrained to 1.433 (9) Å. All hydrogen atoms were set to idealized positions and were refined with 1.2 times (1.5 for the methyl group) the isotropic displacement parameter of the corresponding carbon atom.
Ruthenium (II) complexes containing the azoimine (N=N—C=N) functional unit are light-sensitive, redox-active, and efficient colorant materials (Kaim, 2001). This function is π-acidic and has successfully been used to stabilize the low-valent metal redox state. The importance of azoimine chemistry encourages us to develop a new ligand containing an azoimine unit. The new unsymmetrical bidentate ligand, methyl-1-(phenylimino)-1-(phenylhydrazono)-acetate (L), lacks a twofold symmetry axis and on complexation with ruthenium (II), affords a pseudo-octahedral, trans-[Ru(bpy)LCl2] complex. The five membered rings formed by the coordination of azoimine and bpy are planar and have almost equivalent coordination bite-angles N1—Ru—N2 = 75.9 (2)°, and N4—Ru—N5 = 76.6 (2)°, respectively, whereas Cl2—Ru—Cl1 angle is 169.52 (6)°. However, it is interesting to note that the bond lengths of Ru(II) and azoimine N atoms, (Ru—N1) = 2.009 (5) Å and (Ru—N2) = 1.953 (5) (4) Å are significantly shorter than those of Ru(II) and the bpy N atoms, (Ru—N4) = 2.145 (5) Å and (Ru—N5) = 2.123 (5) Å indicated preferential π-bonding of Ru(II) with the azo group.
For related literature, see: Al-Noaimi et al. (2007); Kaim (2001).
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Siemens, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
[RuCl2(C15H13N3O2)(C10H8N2)]·CH2Cl2 | F(000) = 1368 |
Mr = 680.36 | Dx = 1.635 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 18205 reflections |
a = 12.1073 (7) Å | θ = 2.5–27.5° |
b = 11.4851 (5) Å | µ = 0.99 mm−1 |
c = 20.2336 (9) Å | T = 183 K |
β = 100.858 (3)° | Prism, red-brown |
V = 2763.2 (2) Å3 | 0.05 × 0.05 × 0.04 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 3610 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.120 |
Graphite monochromator | θmax = 27.5°, θmin = 2.5° |
φ and ω scans | h = −15→15 |
18205 measured reflections | k = −14→14 |
6319 independent reflections | l = −26→24 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0705P)2 + 2.7651P] where P = (Fo2 + 2Fc2)/3 |
6319 reflections | (Δ/σ)max = 0.002 |
341 parameters | Δρmax = 2.18 e Å−3 |
1 restraint | Δρmin = −0.94 e Å−3 |
[RuCl2(C15H13N3O2)(C10H8N2)]·CH2Cl2 | V = 2763.2 (2) Å3 |
Mr = 680.36 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.1073 (7) Å | µ = 0.99 mm−1 |
b = 11.4851 (5) Å | T = 183 K |
c = 20.2336 (9) Å | 0.05 × 0.05 × 0.04 mm |
β = 100.858 (3)° |
Nonius KappaCCD diffractometer | 3610 reflections with I > 2σ(I) |
18205 measured reflections | Rint = 0.120 |
6319 independent reflections |
R[F2 > 2σ(F2)] = 0.066 | 1 restraint |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 1.02 | Δρmax = 2.18 e Å−3 |
6319 reflections | Δρmin = −0.94 e Å−3 |
341 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ru1 | 0.80699 (4) | 0.05555 (4) | 0.84888 (3) | 0.02344 (17) | |
Cl1 | 0.79947 (13) | 0.00091 (14) | 0.73396 (8) | 0.0302 (4) | |
Cl2 | 0.81852 (13) | 0.14379 (14) | 0.95461 (8) | 0.0314 (4) | |
O1 | 0.4366 (8) | −0.0154 (8) | 0.9012 (6) | 0.031 (3)* | 0.591 (18) |
O2 | 0.5162 (8) | −0.1884 (7) | 0.9350 (5) | 0.028 (2)* | 0.591 (18) |
C3 | 0.4083 (9) | −0.2204 (9) | 0.9550 (6) | 0.026 (3)* | 0.591 (18) |
H3A | 0.4151 | −0.2980 | 0.9756 | 0.039* | 0.591 (18) |
H3B | 0.3481 | −0.2209 | 0.9152 | 0.039* | 0.591 (18) |
H3C | 0.3906 | −0.1635 | 0.9876 | 0.039* | 0.591 (18) |
O1A | 0.4517 (12) | 0.0003 (12) | 0.9250 (9) | 0.035 (4)* | 0.409 (18) |
O2A | 0.4811 (12) | −0.1968 (10) | 0.9050 (9) | 0.035 (4)* | 0.409 (18) |
C3A | 0.3700 (15) | −0.244 (2) | 0.9125 (15) | 0.075 (8)* | 0.409 (18) |
H3AA | 0.3713 | −0.3289 | 0.9097 | 0.113* | 0.409 (18) |
H3AB | 0.3117 | −0.2130 | 0.8765 | 0.113* | 0.409 (18) |
H3AC | 0.3538 | −0.2203 | 0.9563 | 0.113* | 0.409 (18) |
N1 | 0.6430 (4) | 0.0329 (4) | 0.8503 (3) | 0.0234 (11) | |
N2 | 0.7989 (4) | −0.1010 (4) | 0.8852 (3) | 0.0253 (12) | |
N3 | 0.7061 (4) | −0.1351 (4) | 0.9053 (3) | 0.0300 (13) | |
N4 | 0.8169 (4) | 0.2264 (4) | 0.8076 (3) | 0.0267 (12) | |
N5 | 0.9826 (4) | 0.0887 (4) | 0.8655 (3) | 0.0258 (12) | |
C1 | 0.6232 (5) | −0.0568 (6) | 0.8861 (3) | 0.0286 (14) | |
C2 | 0.5114 (5) | −0.0823 (6) | 0.9070 (4) | 0.0332 (16) | |
C4 | 0.5537 (5) | 0.1105 (5) | 0.8210 (3) | 0.0230 (14) | |
C5 | 0.4923 (6) | 0.0882 (6) | 0.7574 (4) | 0.0384 (18) | |
H5A | 0.5069 | 0.0200 | 0.7338 | 0.046* | |
C6 | 0.4104 (6) | 0.1649 (7) | 0.7284 (4) | 0.050 (2) | |
H6A | 0.3679 | 0.1490 | 0.6849 | 0.060* | |
C7 | 0.3891 (6) | 0.2648 (6) | 0.7615 (4) | 0.0382 (17) | |
H7A | 0.3316 | 0.3171 | 0.7415 | 0.046* | |
C8 | 0.4516 (6) | 0.2874 (6) | 0.8234 (4) | 0.0383 (18) | |
H8A | 0.4374 | 0.3563 | 0.8464 | 0.046* | |
C9 | 0.5349 (6) | 0.2124 (5) | 0.8534 (4) | 0.0344 (16) | |
H9A | 0.5791 | 0.2306 | 0.8961 | 0.041* | |
C10 | 0.8811 (5) | −0.1937 (5) | 0.8949 (3) | 0.0248 (14) | |
C11 | 0.9375 (6) | −0.2197 (6) | 0.8435 (4) | 0.0342 (16) | |
H11A | 0.9222 | −0.1771 | 0.8026 | 0.041* | |
C12 | 1.0165 (6) | −0.3083 (6) | 0.8520 (4) | 0.0415 (18) | |
H12A | 1.0540 | −0.3284 | 0.8163 | 0.050* | |
C13 | 1.0405 (6) | −0.3671 (6) | 0.9123 (4) | 0.0419 (19) | |
H13A | 1.0970 | −0.4256 | 0.9189 | 0.050* | |
C14 | 0.9829 (6) | −0.3416 (6) | 0.9634 (4) | 0.0363 (17) | |
H14A | 0.9979 | −0.3848 | 1.0041 | 0.044* | |
C15 | 0.9035 (5) | −0.2534 (6) | 0.9554 (3) | 0.0331 (16) | |
H15A | 0.8651 | −0.2343 | 0.9908 | 0.040* | |
C16 | 0.7321 (5) | 0.2876 (6) | 0.7724 (3) | 0.0345 (16) | |
H16A | 0.6594 | 0.2534 | 0.7630 | 0.041* | |
C17 | 0.7458 (6) | 0.3988 (6) | 0.7490 (4) | 0.0386 (18) | |
H17A | 0.6835 | 0.4396 | 0.7239 | 0.046* | |
C18 | 0.8492 (6) | 0.4493 (6) | 0.7624 (3) | 0.0337 (16) | |
H18A | 0.8598 | 0.5271 | 0.7490 | 0.040* | |
C19 | 0.9369 (5) | 0.3855 (5) | 0.7953 (3) | 0.0298 (15) | |
H19A | 1.0100 | 0.4186 | 0.8041 | 0.036* | |
C20 | 0.9216 (5) | 0.2729 (5) | 0.8164 (3) | 0.0270 (14) | |
C21 | 1.0138 (5) | 0.1957 (5) | 0.8469 (3) | 0.0231 (14) | |
C22 | 1.1254 (5) | 0.2272 (5) | 0.8559 (3) | 0.0292 (15) | |
H22A | 1.1456 | 0.3011 | 0.8408 | 0.035* | |
C23 | 1.2088 (5) | 0.1510 (6) | 0.8871 (3) | 0.0323 (16) | |
H23A | 1.2861 | 0.1708 | 0.8920 | 0.039* | |
C24 | 1.1769 (5) | 0.0480 (6) | 0.9100 (3) | 0.0292 (14) | |
H24A | 1.2317 | −0.0042 | 0.9333 | 0.035* | |
C25 | 1.0633 (5) | 0.0189 (6) | 0.8993 (3) | 0.0314 (15) | |
H25A | 1.0419 | −0.0529 | 0.9166 | 0.038* | |
C1M | 0.6506 (8) | −0.0735 (7) | 0.4544 (5) | 0.060 (2) | |
H1MA | 0.6835 | −0.1467 | 0.4409 | 0.072* | |
H1MB | 0.5703 | −0.0711 | 0.4324 | 0.072* | |
Cl1M | 0.7200 (2) | 0.0438 (2) | 0.42859 (13) | 0.0728 (7) | |
Cl2M | 0.6616 (3) | −0.0711 (2) | 0.54335 (14) | 0.0908 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru1 | 0.0180 (3) | 0.0213 (3) | 0.0314 (3) | 0.0000 (2) | 0.0057 (2) | 0.0029 (2) |
Cl1 | 0.0284 (8) | 0.0302 (8) | 0.0333 (9) | 0.0007 (7) | 0.0092 (7) | −0.0002 (7) |
Cl2 | 0.0279 (8) | 0.0333 (9) | 0.0321 (9) | −0.0002 (7) | 0.0035 (7) | −0.0009 (7) |
N1 | 0.019 (3) | 0.025 (3) | 0.026 (3) | 0.000 (2) | 0.003 (2) | 0.004 (2) |
N2 | 0.024 (3) | 0.017 (2) | 0.037 (3) | 0.000 (2) | 0.010 (3) | 0.002 (2) |
N3 | 0.025 (3) | 0.030 (3) | 0.037 (3) | 0.004 (2) | 0.010 (3) | 0.006 (3) |
N4 | 0.021 (3) | 0.026 (3) | 0.032 (3) | 0.000 (2) | 0.002 (2) | −0.001 (2) |
N5 | 0.019 (3) | 0.026 (3) | 0.032 (3) | 0.006 (2) | 0.005 (2) | 0.005 (2) |
C1 | 0.022 (3) | 0.033 (4) | 0.032 (4) | −0.004 (3) | 0.008 (3) | 0.003 (3) |
C2 | 0.018 (3) | 0.040 (4) | 0.042 (4) | 0.005 (3) | 0.007 (3) | 0.007 (3) |
C4 | 0.017 (3) | 0.018 (3) | 0.035 (4) | −0.004 (2) | 0.007 (3) | −0.003 (3) |
C5 | 0.028 (4) | 0.032 (4) | 0.051 (5) | 0.007 (3) | −0.003 (3) | −0.003 (3) |
C6 | 0.039 (4) | 0.057 (5) | 0.045 (5) | 0.012 (4) | −0.012 (4) | −0.005 (4) |
C7 | 0.036 (4) | 0.030 (4) | 0.050 (5) | 0.009 (3) | 0.011 (4) | 0.008 (4) |
C8 | 0.048 (4) | 0.028 (4) | 0.044 (5) | 0.012 (3) | 0.022 (4) | 0.000 (3) |
C9 | 0.040 (4) | 0.025 (3) | 0.035 (4) | 0.008 (3) | 0.000 (3) | 0.002 (3) |
C10 | 0.015 (3) | 0.020 (3) | 0.039 (4) | 0.002 (2) | 0.005 (3) | 0.004 (3) |
C11 | 0.040 (4) | 0.030 (4) | 0.035 (4) | 0.007 (3) | 0.010 (3) | 0.003 (3) |
C12 | 0.036 (4) | 0.039 (4) | 0.050 (5) | 0.014 (3) | 0.011 (4) | 0.003 (4) |
C13 | 0.033 (4) | 0.028 (4) | 0.063 (5) | 0.008 (3) | 0.005 (4) | −0.001 (4) |
C14 | 0.038 (4) | 0.025 (3) | 0.041 (4) | 0.006 (3) | −0.006 (3) | 0.002 (3) |
C15 | 0.027 (4) | 0.037 (4) | 0.034 (4) | −0.001 (3) | 0.001 (3) | 0.001 (3) |
C16 | 0.024 (4) | 0.040 (4) | 0.040 (4) | 0.001 (3) | 0.007 (3) | 0.009 (3) |
C17 | 0.033 (4) | 0.037 (4) | 0.046 (5) | 0.004 (3) | 0.008 (3) | 0.022 (4) |
C18 | 0.039 (4) | 0.026 (3) | 0.038 (4) | −0.002 (3) | 0.013 (3) | 0.008 (3) |
C19 | 0.028 (4) | 0.028 (3) | 0.033 (4) | −0.005 (3) | 0.004 (3) | 0.002 (3) |
C20 | 0.022 (3) | 0.028 (3) | 0.031 (4) | 0.000 (3) | 0.006 (3) | 0.002 (3) |
C21 | 0.018 (3) | 0.024 (3) | 0.029 (4) | 0.002 (3) | 0.009 (3) | 0.008 (3) |
C22 | 0.029 (4) | 0.020 (3) | 0.038 (4) | −0.003 (3) | 0.006 (3) | 0.007 (3) |
C23 | 0.022 (3) | 0.037 (4) | 0.038 (4) | −0.005 (3) | 0.005 (3) | 0.007 (3) |
C24 | 0.024 (3) | 0.029 (3) | 0.034 (4) | 0.005 (3) | 0.004 (3) | 0.002 (3) |
C25 | 0.019 (3) | 0.031 (4) | 0.041 (4) | 0.002 (3) | −0.002 (3) | 0.007 (3) |
C1M | 0.068 (6) | 0.047 (5) | 0.064 (6) | 0.000 (4) | 0.010 (5) | 0.000 (4) |
Cl1M | 0.0828 (17) | 0.0619 (14) | 0.0747 (17) | −0.0055 (13) | 0.0173 (14) | 0.0212 (13) |
Cl2M | 0.129 (3) | 0.0800 (19) | 0.0746 (18) | 0.0223 (17) | 0.0474 (18) | 0.0275 (14) |
Ru1—N2 | 1.951 (5) | C8—C9 | 1.377 (9) |
Ru1—N1 | 2.007 (5) | C8—H8A | 0.9500 |
Ru1—N5 | 2.123 (5) | C9—H9A | 0.9500 |
Ru1—N4 | 2.144 (5) | C10—C11 | 1.379 (8) |
Ru1—Cl2 | 2.3475 (17) | C10—C15 | 1.385 (9) |
Ru1—Cl1 | 2.3935 (17) | C11—C12 | 1.385 (9) |
O1—C2 | 1.176 (10) | C11—H11A | 0.9500 |
O2—C2 | 1.341 (10) | C12—C13 | 1.378 (10) |
O2—C3 | 1.485 (12) | C12—H12A | 0.9500 |
C3—H3A | 0.9800 | C13—C14 | 1.382 (10) |
C3—H3B | 0.9800 | C13—H13A | 0.9500 |
C3—H3C | 0.9800 | C14—C15 | 1.385 (9) |
O1A—C2 | 1.286 (15) | C14—H14A | 0.9500 |
O2A—C2 | 1.364 (13) | C15—H15A | 0.9500 |
O2A—C3A | 1.483 (9) | C16—C17 | 1.383 (9) |
C3A—H3AA | 0.9800 | C16—H16A | 0.9500 |
C3A—H3AB | 0.9800 | C17—C18 | 1.360 (9) |
C3A—H3AC | 0.9800 | C17—H17A | 0.9500 |
N1—C1 | 1.307 (8) | C18—C19 | 1.357 (9) |
N1—C4 | 1.440 (8) | C18—H18A | 0.9500 |
N2—N3 | 1.325 (6) | C19—C20 | 1.384 (9) |
N2—C10 | 1.446 (7) | C19—H19A | 0.9500 |
N3—C1 | 1.350 (8) | C20—C21 | 1.468 (8) |
N4—C16 | 1.335 (8) | C21—C22 | 1.377 (8) |
N4—C20 | 1.356 (7) | C22—C23 | 1.394 (9) |
N5—C25 | 1.347 (8) | C22—H22A | 0.9500 |
N5—C21 | 1.361 (7) | C23—C24 | 1.354 (9) |
C1—C2 | 1.520 (8) | C23—H23A | 0.9500 |
C4—C5 | 1.384 (9) | C24—C25 | 1.392 (8) |
C4—C9 | 1.381 (9) | C24—H24A | 0.9500 |
C5—C6 | 1.374 (10) | C25—H25A | 0.9500 |
C5—H5A | 0.9500 | C1M—Cl1M | 1.721 (8) |
C6—C7 | 1.378 (10) | C1M—Cl2M | 1.779 (9) |
C6—H6A | 0.9500 | C1M—H1MA | 0.9900 |
C7—C8 | 1.360 (10) | C1M—H1MB | 0.9900 |
C7—H7A | 0.9500 | ||
N2—Ru1—N1 | 75.9 (2) | C8—C7—C6 | 119.0 (7) |
N2—Ru1—N5 | 103.0 (2) | C8—C7—H7A | 120.5 |
N1—Ru1—N5 | 169.8 (2) | C6—C7—H7A | 120.5 |
N2—Ru1—N4 | 179.1 (2) | C7—C8—C9 | 121.3 (7) |
N1—Ru1—N4 | 104.60 (19) | C7—C8—H8A | 119.3 |
N5—Ru1—N4 | 76.70 (19) | C9—C8—H8A | 119.3 |
N2—Ru1—Cl2 | 93.06 (16) | C8—C9—C4 | 119.6 (7) |
N1—Ru1—Cl2 | 86.11 (15) | C8—C9—H9A | 120.2 |
N5—Ru1—Cl2 | 83.84 (15) | C4—C9—H9A | 120.2 |
N4—Ru1—Cl2 | 87.81 (14) | C11—C10—C15 | 121.1 (6) |
N2—Ru1—Cl1 | 97.39 (16) | C11—C10—N2 | 118.9 (6) |
N1—Ru1—Cl1 | 97.07 (15) | C15—C10—N2 | 120.0 (5) |
N5—Ru1—Cl1 | 93.11 (15) | C10—C11—C12 | 119.7 (7) |
N4—Ru1—Cl1 | 81.74 (14) | C10—C11—H11A | 120.2 |
Cl2—Ru1—Cl1 | 169.53 (6) | C12—C11—H11A | 120.2 |
C2—O2—C3 | 111.7 (7) | C13—C12—C11 | 119.7 (7) |
O2—C3—H3A | 109.5 | C13—C12—H12A | 120.2 |
O2—C3—H3B | 109.5 | C11—C12—H12A | 120.2 |
H3A—C3—H3B | 109.5 | C12—C13—C14 | 120.5 (6) |
O2—C3—H3C | 109.5 | C12—C13—H13A | 119.8 |
H3A—C3—H3C | 109.5 | C14—C13—H13A | 119.8 |
H3B—C3—H3C | 109.5 | C15—C14—C13 | 120.3 (7) |
C2—O2A—C3A | 126.3 (14) | C15—C14—H14A | 119.9 |
O2A—C3A—H3AA | 109.5 | C13—C14—H14A | 119.9 |
O2A—C3A—H3AB | 109.5 | C14—C15—C10 | 118.8 (6) |
H3AA—C3A—H3AB | 109.5 | C14—C15—H15A | 120.6 |
O2A—C3A—H3AC | 109.5 | C10—C15—H15A | 120.6 |
H3AA—C3A—H3AC | 109.5 | N4—C16—C17 | 122.6 (6) |
H3AB—C3A—H3AC | 109.5 | N4—C16—H16A | 118.7 |
C1—N1—C4 | 120.9 (5) | C17—C16—H16A | 118.7 |
C1—N1—Ru1 | 113.3 (4) | C18—C17—C16 | 119.4 (7) |
C4—N1—Ru1 | 125.6 (4) | C18—C17—H17A | 120.3 |
N3—N2—C10 | 110.0 (5) | C16—C17—H17A | 120.3 |
N3—N2—Ru1 | 119.6 (4) | C19—C18—C17 | 118.2 (6) |
C10—N2—Ru1 | 130.4 (4) | C19—C18—H18A | 120.9 |
N2—N3—C1 | 110.0 (5) | C17—C18—H18A | 120.9 |
C16—N4—C20 | 117.9 (5) | C18—C19—C20 | 121.2 (6) |
C16—N4—Ru1 | 126.6 (4) | C18—C19—H19A | 119.4 |
C20—N4—Ru1 | 115.4 (4) | C20—C19—H19A | 119.4 |
C25—N5—C21 | 117.7 (5) | N4—C20—C19 | 120.2 (6) |
C25—N5—Ru1 | 125.6 (4) | N4—C20—C21 | 115.8 (5) |
C21—N5—Ru1 | 116.1 (4) | C19—C20—C21 | 123.9 (6) |
N1—C1—N3 | 118.7 (5) | N5—C21—C22 | 121.2 (5) |
N1—C1—C2 | 124.9 (6) | N5—C21—C20 | 115.7 (5) |
N3—C1—C2 | 116.4 (5) | C22—C21—C20 | 123.2 (5) |
O1—C2—O1A | 23.6 (7) | C21—C22—C23 | 120.3 (6) |
O1—C2—O2 | 127.4 (7) | C21—C22—H22A | 119.9 |
O1A—C2—O2 | 122.2 (8) | C23—C22—H22A | 119.9 |
O1—C2—O2A | 115.4 (8) | C24—C23—C22 | 118.3 (6) |
O1A—C2—O2A | 123.9 (9) | C24—C23—H23A | 120.8 |
O2—C2—O2A | 29.1 (6) | C22—C23—H23A | 120.8 |
O1—C2—C1 | 123.7 (7) | C23—C24—C25 | 119.6 (6) |
O1A—C2—C1 | 120.9 (8) | C23—C24—H24A | 120.2 |
O2—C2—C1 | 108.8 (6) | C25—C24—H24A | 120.2 |
O2A—C2—C1 | 115.2 (7) | N5—C25—C24 | 122.5 (6) |
C5—C4—C9 | 119.4 (6) | N5—C25—H25A | 118.7 |
C5—C4—N1 | 119.9 (5) | C24—C25—H25A | 118.7 |
C9—C4—N1 | 120.5 (6) | Cl1M—C1M—Cl2M | 110.3 (5) |
C6—C5—C4 | 119.7 (7) | Cl1M—C1M—H1MA | 109.6 |
C6—C5—H5A | 120.1 | Cl2M—C1M—H1MA | 109.6 |
C4—C5—H5A | 120.1 | Cl1M—C1M—H1MB | 109.6 |
C5—C6—C7 | 120.9 (7) | Cl2M—C1M—H1MB | 109.6 |
C5—C6—H6A | 119.6 | H1MA—C1M—H1MB | 108.1 |
C7—C6—H6A | 119.6 |
Experimental details
Crystal data | |
Chemical formula | [RuCl2(C15H13N3O2)(C10H8N2)]·CH2Cl2 |
Mr | 680.36 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 183 |
a, b, c (Å) | 12.1073 (7), 11.4851 (5), 20.2336 (9) |
β (°) | 100.858 (3) |
V (Å3) | 2763.2 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.99 |
Crystal size (mm) | 0.05 × 0.05 × 0.04 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18205, 6319, 3610 |
Rint | 0.120 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.169, 1.02 |
No. of reflections | 6319 |
No. of parameters | 341 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 2.18, −0.94 |
Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Siemens, 1990).
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Ruthenium (II) complexes containing the azoimine (N=N—C=N) functional unit are light-sensitive, redox-active, and efficient colorant materials (Kaim, 2001). This function is π-acidic and has successfully been used to stabilize the low-valent metal redox state. The importance of azoimine chemistry encourages us to develop a new ligand containing an azoimine unit. The new unsymmetrical bidentate ligand, methyl-1-(phenylimino)-1-(phenylhydrazono)-acetate (L), lacks a twofold symmetry axis and on complexation with ruthenium (II), affords a pseudo-octahedral, trans-[Ru(bpy)LCl2] complex. The five membered rings formed by the coordination of azoimine and bpy are planar and have almost equivalent coordination bite-angles N1—Ru—N2 = 75.9 (2)°, and N4—Ru—N5 = 76.6 (2)°, respectively, whereas Cl2—Ru—Cl1 angle is 169.52 (6)°. However, it is interesting to note that the bond lengths of Ru(II) and azoimine N atoms, (Ru—N1) = 2.009 (5) Å and (Ru—N2) = 1.953 (5) (4) Å are significantly shorter than those of Ru(II) and the bpy N atoms, (Ru—N4) = 2.145 (5) Å and (Ru—N5) = 2.123 (5) Å indicated preferential π-bonding of Ru(II) with the azo group.