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The title organometallic complex, trans-[Rh(C12H8NO)Cl2(C12H9NO)], which was obtained from the reaction of rhodium(III) chloride and 2-benzoyl­pyridine, features an RhIII atom coordinated by two N, one O, one C and two Cl atoms in a distorted octa­hedral environment.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805034926/ng6227sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805034926/ng6227Isup2.hkl
Contains datablock I

CCDC reference: 289823

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.030
  • wR factor = 0.090
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 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 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: COLLECT (Nonius, 2000); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

trans-(2-Benzoylpyridine-κ2N,O)dichloro[2-(pyridine-2-carbonyl)phenyl- κ2C1,N]rhodium(III) top
Crystal data top
[Rh(C12H8NO)Cl2(C12H9NO)]F(000) = 1080
Mr = 539.21Dx = 1.677 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.5492 (2) ÅCell parameters from 18110 reflections
b = 8.2515 (1) Åθ = 2.0–25.4°
c = 19.2229 (3) ŵ = 1.08 mm1
β = 96.521 (1)°T = 200 K
V = 2135.24 (5) Å3Prism, orange
Z = 40.45 × 0.24 × 0.08 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
3894 independent reflections
Radiation source: fine-focus sealed tube3560 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 9 pixels mm-1θmax = 25.3°, θmin = 2.1°
CCD rotation images, thick slices scansh = 1616
Absorption correction: multi-scan
(Blessing, 1995)
k = 99
Tmin = 0.729, Tmax = 0.918l = 2323
20293 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0556P)2 + 0.8456P]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.002
3894 reflectionsΔρmax = 0.90 e Å3
281 parametersΔρmin = 1.18 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0129 (7)
Special details top

Experimental. Rhodium(III) chloride trihydrate (0.132 g, 0.5 mmol) and 2-pyridyl phenone (0.549 g, 3.0 mmol) were placed in a ceramic boat (10 cm, 1.3 cm in length and in width, respectively) and heated in an oven at 150 °C for 15 h. After cooling, the resulting reaction mixture was washed with 20 ml of methanol and orange single crystals, (I), were isolated by suction filtration (yield 78%). Spectroscopic analysis: IR (KBr, cm-1): ν(CO) 1677, 1612; 1H NMR (400 MHz, [(CD3)2SO], δ, p.p.m.): 9.53 (d, 1H, H(C24), J = 5.7 Hz), 8.77 (d, 1H, H(C1), J = 5.4 Hz), 8.42 (d, 1H, H(C4), J = 8.5 Hz), 8.35 (t, 1H, H(C3), J = 7.6 Hz), 8.31 (t, 1H, H(C22), J = 7.5 Hz), 8.24 (d, 1H, H(C21), J = 7.7 Hz), 8.15 (d, 2H, H(C8) + H(C12), J = 7.7 Hz), 8.05 (t, 1H, H(C2), J = 6.6 Hz), 7.94–7.89 (m, 2H, H(C23) + H(C10)), 7.80–7.75 (m, 4H, H(C17) + H(C9) + H(C11) + H(C14)), 7.46 (t, 1H, H(C16), J = 7.7 Hz), 7.29 (t, 1H, H(C15), J = 7.3 Hz); 13C NMR (500 MHz, [(CD3)2SO], δ, p.p.m.): 201.5, 187.7, 156.8, 156.5, 155.4, 155.3, 153.7, 153.5, 140.2, 140.0, 139.3, 135.1, 135.1, 133.6, 131.1, 130.8, 130.8, 130.7, 129.6, 128.4, 128.0, 127.5, 125.9, 124.1; analysis, calculated for C24H17Cl2N2O2Rh: C 53.46, H 3.18, Cl 13.15, N 5.20%; found: C 53.41, H 3.32, Cl 13.29, N 5.35%.

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 (Å2) top
xyzUiso*/Ueq
Rh10.740042 (14)0.23604 (2)0.461802 (10)0.01895 (12)
Cl10.61174 (5)0.33261 (9)0.38202 (3)0.02823 (18)
Cl20.86288 (5)0.15031 (9)0.54994 (3)0.02630 (18)
O10.68117 (13)0.3691 (2)0.55273 (9)0.0247 (4)
O20.60440 (16)0.0616 (3)0.28719 (11)0.0434 (6)
N10.80511 (15)0.4591 (3)0.46074 (11)0.0220 (5)
N20.66528 (15)0.0243 (3)0.46712 (11)0.0224 (5)
C10.8453 (2)0.5235 (4)0.40658 (15)0.0285 (6)
H10.84680.46330.36400.034*
C20.8867 (2)0.6774 (4)0.40994 (16)0.0312 (7)
H20.91640.71970.37070.037*
C30.8846 (2)0.7694 (3)0.46909 (18)0.0304 (7)
H30.91340.87580.47090.037*
C40.8397 (2)0.7052 (4)0.52485 (15)0.0257 (6)
H40.83640.76790.56660.031*
C50.80109 (18)0.5504 (3)0.51934 (13)0.0222 (6)
C60.74022 (18)0.4777 (3)0.57159 (14)0.0229 (6)
C70.74851 (19)0.5413 (3)0.64403 (13)0.0239 (6)
C80.8423 (2)0.5700 (4)0.68034 (15)0.0325 (7)
H80.90040.55230.65700.039*
C90.8499 (2)0.6200 (4)0.74959 (16)0.0406 (8)
H90.91440.63820.77450.049*
C100.7648 (3)0.6459 (4)0.78144 (16)0.0407 (8)
H100.76980.68420.82890.049*
C110.6722 (2)0.6177 (4)0.74587 (16)0.0376 (7)
H110.61330.63520.76830.045*
C120.6638 (2)0.5620 (4)0.67766 (15)0.0293 (6)
H120.59980.53710.65320.035*
C130.81116 (19)0.1367 (3)0.38797 (13)0.0230 (6)
C140.9120 (2)0.1688 (4)0.38579 (14)0.0260 (6)
H140.94770.23340.42180.031*
C150.9612 (2)0.1098 (4)0.33145 (14)0.0312 (7)
H151.03090.13000.33150.037*
C160.9104 (2)0.0217 (4)0.27779 (15)0.0366 (7)
H160.94420.01650.23970.044*
C170.8110 (2)0.0148 (4)0.27968 (14)0.0328 (7)
H170.77550.07510.24210.039*
C180.76169 (19)0.0406 (4)0.33535 (14)0.0261 (6)
C190.6599 (2)0.0225 (4)0.33873 (15)0.0297 (6)
C200.63119 (19)0.0646 (3)0.40995 (15)0.0266 (6)
C210.5744 (2)0.2037 (4)0.41660 (18)0.0352 (7)
H210.55400.26820.37590.042*
C220.5500 (2)0.2497 (4)0.4815 (2)0.0384 (8)
H220.50940.34380.48570.046*
C230.5835 (2)0.1564 (4)0.53900 (17)0.0348 (7)
H230.56750.18500.58480.042*
C240.64091 (19)0.0209 (4)0.53022 (15)0.0280 (6)
H240.66380.04230.57080.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Rh10.02154 (16)0.01741 (16)0.01798 (16)0.00318 (7)0.00263 (10)0.00000 (7)
Cl10.0271 (3)0.0305 (4)0.0264 (4)0.0003 (3)0.0001 (3)0.0074 (3)
Cl20.0264 (3)0.0292 (4)0.0226 (3)0.0007 (3)0.0003 (3)0.0003 (3)
O10.0254 (9)0.0233 (11)0.0260 (10)0.0048 (8)0.0049 (8)0.0036 (8)
O20.0361 (11)0.0561 (16)0.0355 (12)0.0110 (11)0.0062 (9)0.0131 (11)
N10.0220 (10)0.0217 (12)0.0224 (11)0.0028 (9)0.0026 (9)0.0009 (9)
N20.0190 (10)0.0202 (12)0.0279 (12)0.0016 (9)0.0028 (9)0.0018 (9)
C10.0311 (14)0.0287 (16)0.0264 (14)0.0021 (12)0.0061 (12)0.0036 (12)
C20.0318 (15)0.0258 (17)0.0370 (16)0.0031 (13)0.0080 (12)0.0061 (13)
C30.0285 (16)0.0201 (16)0.0422 (18)0.0036 (11)0.0021 (14)0.0057 (12)
C40.0251 (14)0.0213 (14)0.0302 (15)0.0016 (11)0.0004 (11)0.0036 (12)
C50.0222 (13)0.0200 (14)0.0239 (13)0.0011 (11)0.0007 (10)0.0010 (11)
C60.0208 (12)0.0213 (14)0.0265 (14)0.0026 (11)0.0026 (10)0.0002 (11)
C70.0285 (14)0.0186 (14)0.0248 (13)0.0002 (11)0.0038 (11)0.0010 (11)
C80.0309 (15)0.0337 (18)0.0325 (15)0.0020 (13)0.0020 (12)0.0027 (13)
C90.0444 (18)0.044 (2)0.0304 (16)0.0053 (15)0.0065 (14)0.0053 (14)
C100.064 (2)0.0352 (19)0.0225 (15)0.0033 (16)0.0035 (14)0.0030 (13)
C110.0485 (18)0.0351 (19)0.0322 (16)0.0023 (15)0.0170 (14)0.0019 (13)
C120.0313 (14)0.0262 (16)0.0312 (15)0.0011 (12)0.0070 (12)0.0003 (12)
C130.0263 (13)0.0245 (15)0.0179 (13)0.0004 (11)0.0012 (10)0.0018 (11)
C140.0301 (14)0.0247 (16)0.0232 (13)0.0033 (12)0.0028 (11)0.0006 (11)
C150.0277 (14)0.0377 (18)0.0291 (15)0.0018 (13)0.0082 (12)0.0006 (13)
C160.0380 (16)0.048 (2)0.0245 (15)0.0028 (14)0.0085 (12)0.0082 (14)
C170.0368 (16)0.0365 (18)0.0248 (14)0.0006 (13)0.0019 (12)0.0089 (13)
C180.0273 (14)0.0274 (16)0.0229 (13)0.0016 (12)0.0009 (11)0.0021 (11)
C190.0286 (14)0.0277 (16)0.0315 (15)0.0020 (12)0.0019 (12)0.0066 (12)
C200.0203 (12)0.0215 (15)0.0370 (15)0.0006 (11)0.0011 (11)0.0023 (12)
C210.0283 (15)0.0233 (16)0.053 (2)0.0046 (13)0.0011 (14)0.0061 (15)
C220.0247 (16)0.0250 (18)0.065 (2)0.0072 (11)0.0016 (16)0.0094 (14)
C230.0277 (14)0.0305 (18)0.0471 (18)0.0024 (13)0.0078 (13)0.0169 (14)
C240.0248 (13)0.0265 (16)0.0327 (15)0.0011 (11)0.0039 (11)0.0051 (12)
Geometric parameters (Å, º) top
Rh1—Cl12.3246 (7)C9—H90.9601
Rh1—Cl22.3454 (6)C10—C111.378 (5)
Rh1—O12.2831 (18)C10—H100.9599
Rh1—N12.042 (2)C11—C121.382 (4)
Rh1—N22.028 (2)C11—H110.9601
Rh1—C131.981 (3)C12—H120.9600
O1—C61.229 (3)C13—C141.397 (4)
O2—C191.217 (3)C13—C181.396 (4)
N1—C11.339 (3)C14—C151.389 (4)
N1—C51.361 (3)C14—H140.9599
N2—C241.346 (4)C15—C161.380 (4)
N2—C201.358 (3)C15—H150.9600
C1—C21.387 (4)C16—C171.385 (4)
C1—H10.9600C16—H160.9600
C2—C31.370 (4)C17—C181.401 (4)
C2—H20.9600C17—H170.9600
C3—C41.396 (4)C18—C191.482 (4)
C3—H30.9600C19—C201.506 (4)
C4—C51.380 (4)C20—C211.396 (4)
C4—H40.9600C21—C221.380 (5)
C5—C61.496 (4)C21—H210.9600
C6—C71.481 (4)C22—C231.381 (5)
C7—C121.391 (4)C22—H220.9600
C7—C81.399 (4)C23—C241.383 (4)
C8—C91.387 (4)C23—H230.9600
C8—H80.9600C24—H240.9600
C9—C101.381 (5)
Cl1—Rh1—Cl2175.00 (2)C10—C11—H11120.5
O1—Rh1—Cl192.30 (5)C11—C10—C9120.8 (3)
O1—Rh1—Cl282.70 (5)C11—C10—H10119.2
O1—C6—C7120.9 (2)C11—C12—C7119.9 (3)
O1—C6—C5119.0 (2)C11—C12—H12120.6
O2—C19—C18123.3 (3)C12—C7—C6120.1 (2)
O2—C19—C20118.7 (3)C12—C7—C8119.9 (2)
N1—Rh1—Cl188.61 (6)C12—C11—H11119.5
N1—Rh1—Cl290.42 (6)C13—Rh1—Cl193.29 (7)
N1—Rh1—O176.29 (7)C13—Rh1—Cl291.70 (7)
N1—C1—C2121.7 (3)C13—Rh1—O1171.09 (8)
N1—C1—H1120.5C13—Rh1—N196.90 (10)
N1—C5—C4121.7 (2)C13—Rh1—N288.05 (10)
N1—C5—C6114.2 (2)C13—C14—H14119.9
N2—Rh1—Cl189.32 (6)C13—C18—C19122.7 (2)
N2—Rh1—Cl291.22 (6)C14—C13—C18118.5 (2)
N2—Rh1—O198.96 (8)C14—C13—Rh1120.0 (2)
N2—Rh1—N1174.74 (8)C14—C15—H15119.7
N2—C20—C19120.8 (2)C15—C14—C13120.7 (3)
N2—C20—C21120.7 (3)C15—C14—H14119.4
N2—C24—C23122.2 (3)C15—C16—C17119.9 (3)
N2—C24—H24119.5C15—C16—H16120.3
C1—N1—C5118.8 (2)C16—C15—C14120.4 (3)
C1—N1—Rh1125.45 (19)C16—C15—H15119.9
C1—C2—H2120.0C16—C17—C18119.9 (3)
C2—C1—H1117.8C16—C17—H17119.9
C2—C3—C4118.6 (3)C17—C16—H16119.8
C2—C3—H3119.4C17—C18—C13120.5 (2)
C3—C2—C1119.9 (3)C17—C18—C19116.5 (2)
C3—C2—H2120.0C18—C17—H17120.1
C3—C4—H4120.2C18—C13—Rh1121.45 (19)
C4—C3—H3122.0C18—C19—C20117.3 (2)
C4—C5—C6123.6 (2)C20—N2—Rh1123.41 (18)
C5—N1—Rh1115.64 (17)C20—C21—H21119.5
C5—C4—C3119.1 (3)C21—C20—C19118.3 (3)
C5—C4—H4120.6C21—C22—H22119.8
C6—O1—Rh1107.72 (16)C22—C21—C20120.0 (3)
C7—C6—C5120.0 (2)C22—C21—H21120.5
C7—C8—H8119.2C22—C23—H23120.6
C7—C12—H12119.6C22—C23—C24119.4 (3)
C8—C7—C6119.8 (2)C23—C22—C21118.6 (3)
C8—C9—C10119.8 (3)C23—C22—H22121.5
C8—C9—H9119.3C23—C24—H24118.3
C9—C8—C7119.5 (3)C24—N2—C20118.9 (2)
C9—C8—H8121.2C24—N2—C20118.9 (2)
C9—C10—H10120.0C24—N2—Rh1117.35 (19)
C10—C9—H9120.9C24—C23—H23119.9
C10—C11—C12120.0 (3)
Rh1—O1—C6—C528.0 (3)C1—N1—C5—C41.8 (4)
Rh1—O1—C6—C7154.6 (2)C1—N1—C5—C6170.4 (2)
Rh1—N1—C1—C2179.0 (2)C3—C4—C5—N10.4 (4)
Rh1—N1—C5—C4178.2 (2)C3—C4—C5—C6171.9 (3)
Rh1—N1—C5—C66.0 (3)N1—C5—C6—O117.4 (3)
Rh1—N2—C20—C21175.6 (2)C4—C5—C6—O1154.7 (3)
Rh1—N2—C20—C198.8 (3)N1—C5—C6—C7165.2 (2)
Rh1—N2—C24—C23175.0 (2)C4—C5—C6—C722.8 (4)
Rh1—C13—C14—C15175.2 (2)O1—C6—C7—C1239.1 (4)
Rh1—C13—C18—C17173.4 (2)C5—C6—C7—C12138.3 (3)
Rh1—C13—C18—C1913.3 (4)O1—C6—C7—C8136.5 (3)
O1—Rh1—N1—C1161.4 (2)C5—C6—C7—C846.2 (4)
O1—Rh1—N1—C514.67 (17)C12—C7—C8—C90.5 (5)
O1—Rh1—N2—C20145.2 (2)C6—C7—C8—C9176.0 (3)
O1—Rh1—N2—C2428.5 (2)C7—C8—C9—C101.9 (5)
N1—Rh1—O1—C623.28 (17)C8—C9—C10—C112.0 (5)
N1—Rh1—C13—C1440.3 (2)C9—C10—C11—C120.4 (5)
N1—Rh1—C13—C18136.5 (2)C10—C11—C12—C72.9 (5)
N2—Rh1—O1—C6159.03 (17)C8—C7—C12—C112.9 (4)
N2—Rh1—C13—C14141.5 (2)C6—C7—C12—C11178.4 (3)
N2—Rh1—C13—C1841.7 (2)C18—C13—C14—C151.7 (4)
Cl1—Rh1—N1—C168.7 (2)C13—C14—C15—C161.6 (5)
Cl1—Rh1—N1—C5107.38 (17)C14—C15—C16—C173.0 (5)
Cl1—Rh1—N2—C2053.0 (2)C15—C16—C17—C181.3 (5)
Cl1—Rh1—N2—C24120.70 (19)C14—C13—C18—C173.4 (4)
Cl1—Rh1—O1—C6111.29 (17)C14—C13—C18—C19169.9 (3)
Cl1—Rh1—C13—C14129.3 (2)C16—C17—C18—C132.0 (5)
Cl1—Rh1—C13—C1847.5 (2)C16—C17—C18—C19171.7 (3)
Cl2—Rh1—N2—C20132.0 (2)C13—C18—C19—O2156.5 (3)
Cl2—Rh1—N2—C2454.32 (19)C17—C18—C19—O229.9 (4)
Cl2—Rh1—N1—C1116.2 (2)C13—C18—C19—C2033.5 (4)
Cl2—Rh1—N1—C567.71 (17)C17—C18—C19—C20140.1 (3)
Cl2—Rh1—O1—C668.94 (16)C24—N2—C20—C212.0 (4)
Cl2—Rh1—C13—C1450.4 (2)C24—N2—C20—C19177.5 (2)
Cl2—Rh1—C13—C18132.8 (2)O2—C19—C20—N2154.1 (3)
C13—Rh1—N1—C124.4 (2)C18—C19—C20—N235.5 (4)
C13—Rh1—N1—C5159.48 (18)O2—C19—C20—C2130.3 (4)
C13—Rh1—N2—C2040.3 (2)C18—C19—C20—C21140.1 (3)
C13—Rh1—N2—C24146.0 (2)N2—C20—C21—C221.9 (4)
C1—N1—C13—C1453.9 (2)C19—C20—C21—C22177.5 (3)
C5—N1—C1—C23.0 (4)C20—C21—C22—C230.6 (5)
N1—C1—C2—C31.9 (4)C21—C22—C23—C240.5 (4)
C1—C2—C3—C40.4 (4)C20—N2—C24—C231.0 (4)
C2—C3—C4—C51.5 (4)C22—C23—C24—N20.3 (4)
 

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