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The title compound, [Rh(C7H3Cl2O2)(C18H15P)(CO)], is a rhodium(I) derivative of chlorinated tropolonate. It crystallizes with a nearly square-planar geometry about the rhodium(I) metal centre. The most important bond distances and angles include: Rh-O(trans P) = 2.086 (2) Å, Rh-O(trans carbon­yl) = 2.056 (2) Å, Rh-P = 2.2377 (8) Å, Rh-C(carbon­yl) = 1.809 (2) Å, O-Rh-O = 76.60 (6)° and O-C-C-O = -3.0 (3)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050392/cv2156sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050392/cv2156Isup2.hkl
Contains datablock I

CCDC reference: 633667

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.027
  • wR factor = 0.061
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 500 Ang. PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Rh - C01 .. 7.63 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2004); software used to prepare material for publication: SHELXL97.

Carbonyl(3,7-dichlorotropolonato)(triphenylphosphine)rhodium(I) top
Crystal data top
[Rh(C7H3Cl2O2)(C18H15P)(CO)]F(000) = 1168
Mr = 583.18Dx = 1.665 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ynCell parameters from 7376 reflections
a = 8.823 (5) Åθ = 2.3–28.2°
b = 17.662 (5) ŵ = 1.06 mm1
c = 15.563 (5) ÅT = 100 K
β = 106.450 (5)°Plate, yellow
V = 2325.9 (17) Å30.18 × 0.10 × 0.03 mm
Z = 4
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
5065 independent reflections
Radiation source: fine-focus sealed tube4322 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 512 x 512 pixels mm-1θmax = 27.0°, θmin = 2.7°
φ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
k = 2212
Tmin = 0.882, Tmax = 0.97l = 1918
16578 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)] = 0.027Hydrogen site location: calc
wR(F2) = 0.061H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0234P)2 + 1.6672P]
where P = (Fo2 + 2Fc2)/3
5065 reflections(Δ/σ)max = 0.001
298 parametersΔρmax = 0.71 e Å3
0 restraintsΔρmin = 0.45 e Å3
Special details top

Experimental. First 80 frames repeated after data collection to control a crystal stability

1H NMR (CDCl3, 300 MHz): δ 7.85 (m, 2H), 7.71 (m, 7H), 7.41 (m, 9H); 31P NMR (CDCl3, 242.6 MHz): δ 48.12 (d, 1JRh–P 174.4 Hz); 13C NMR (CDCl3, 242.6 MHz): δ 176.5 (s, CO), 136.9 (s), 134.4 (s), 132.2 (s), 130.6 (s), 128.4 (s), 127.7 (d), 120.3 (s).

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. 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 > 2sigma(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
Rh0.43393 (2)0.363881 (9)0.306253 (11)0.01063 (6)
Cl30.37593 (8)0.26276 (3)0.58760 (4)0.02242 (14)
Cl70.24575 (8)0.59751 (3)0.40212 (4)0.02535 (15)
P0.47114 (7)0.41700 (3)0.18327 (4)0.01033 (12)
O10.36047 (19)0.45985 (8)0.35770 (10)0.0145 (3)
O010.5251 (2)0.21800 (9)0.24117 (11)0.0229 (4)
O20.39171 (19)0.32583 (8)0.42427 (10)0.0147 (3)
C40.2400 (3)0.39295 (14)0.60655 (16)0.0194 (5)
H40.22580.36540.65460.023*
C310.3594 (3)0.50448 (12)0.15024 (15)0.0122 (4)
C360.3846 (3)0.56448 (12)0.21184 (15)0.0145 (5)
H360.45910.55960.26740.017*
C50.1862 (3)0.46688 (14)0.60004 (16)0.0215 (5)
H50.13670.48190.64270.026*
C210.6756 (3)0.44363 (12)0.19273 (14)0.0118 (4)
C120.2706 (3)0.31800 (12)0.06505 (15)0.0153 (5)
H120.20480.32450.10180.018*
C20.3395 (3)0.37555 (12)0.46925 (15)0.0136 (5)
C110.4150 (3)0.35694 (12)0.08383 (14)0.0122 (4)
C220.7962 (3)0.39152 (13)0.22996 (15)0.0160 (5)
H220.77090.34430.24850.019*
C010.4902 (3)0.27504 (13)0.26616 (15)0.0150 (5)
C240.9920 (3)0.48082 (14)0.21319 (16)0.0185 (5)
H241.09730.49370.22110.022*
C350.2989 (3)0.63096 (13)0.19002 (16)0.0182 (5)
H350.31680.67070.23080.022*
C330.1604 (3)0.57952 (13)0.04618 (16)0.0179 (5)
H330.08510.58460.00910.022*
C30.3122 (3)0.35419 (13)0.55158 (15)0.0159 (5)
C320.2471 (3)0.51232 (13)0.06723 (15)0.0145 (5)
H320.23000.47300.02590.017*
C70.2562 (3)0.51520 (13)0.46462 (16)0.0166 (5)
C340.1862 (3)0.63849 (13)0.10737 (17)0.0195 (5)
H340.12830.68300.09320.023*
C150.4695 (3)0.29597 (14)0.04314 (17)0.0222 (5)
H150.53650.28770.07880.027*
C60.1969 (3)0.52145 (14)0.53770 (16)0.0205 (5)
H60.15870.56910.54630.025*
C250.8729 (3)0.53252 (13)0.17516 (16)0.0172 (5)
H250.89880.57970.15680.021*
C260.7157 (3)0.51403 (12)0.16439 (15)0.0149 (5)
H260.63670.54860.13820.018*
C140.3260 (3)0.25846 (13)0.06107 (16)0.0213 (5)
H140.29670.22520.10930.026*
C160.5127 (3)0.34618 (13)0.02881 (16)0.0164 (5)
H160.60750.37260.04000.020*
C10.3178 (3)0.45172 (12)0.42981 (15)0.0133 (5)
C230.9532 (3)0.40986 (14)0.23935 (16)0.0184 (5)
H231.03240.37470.26310.022*
C130.2259 (3)0.26984 (13)0.00815 (16)0.0178 (5)
H130.12880.24520.02160.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Rh0.01193 (10)0.01076 (9)0.00965 (9)0.00044 (7)0.00377 (7)0.00048 (6)
Cl30.0320 (4)0.0196 (3)0.0180 (3)0.0016 (2)0.0108 (3)0.0045 (2)
Cl70.0396 (4)0.0141 (3)0.0245 (3)0.0055 (3)0.0126 (3)0.0004 (2)
P0.0095 (3)0.0111 (3)0.0105 (3)0.0004 (2)0.0030 (2)0.0002 (2)
O10.0181 (9)0.0129 (8)0.0133 (8)0.0018 (6)0.0060 (7)0.0001 (6)
O010.0342 (11)0.0149 (8)0.0209 (9)0.0053 (7)0.0101 (8)0.0002 (7)
O20.0199 (9)0.0127 (8)0.0131 (8)0.0032 (6)0.0074 (7)0.0015 (6)
C40.0189 (13)0.0280 (13)0.0118 (12)0.0004 (10)0.0053 (10)0.0006 (10)
C310.0093 (11)0.0139 (11)0.0148 (12)0.0002 (9)0.0057 (9)0.0028 (9)
C360.0146 (12)0.0161 (11)0.0139 (12)0.0013 (9)0.0059 (9)0.0015 (9)
C50.0190 (13)0.0315 (14)0.0131 (12)0.0033 (11)0.0033 (10)0.0055 (10)
C210.0101 (11)0.0159 (11)0.0099 (11)0.0022 (9)0.0036 (9)0.0027 (8)
C120.0149 (12)0.0156 (11)0.0151 (12)0.0014 (9)0.0040 (10)0.0024 (9)
C20.0107 (11)0.0154 (11)0.0133 (11)0.0007 (9)0.0013 (9)0.0009 (9)
C110.0140 (11)0.0112 (10)0.0097 (11)0.0014 (9)0.0003 (9)0.0011 (8)
C220.0172 (12)0.0158 (11)0.0151 (12)0.0001 (9)0.0047 (10)0.0011 (9)
C010.0177 (12)0.0173 (12)0.0105 (11)0.0005 (9)0.0048 (10)0.0043 (9)
C240.0131 (12)0.0295 (13)0.0141 (12)0.0057 (10)0.0060 (10)0.0063 (10)
C350.0215 (13)0.0155 (11)0.0198 (13)0.0023 (10)0.0095 (10)0.0004 (9)
C330.0153 (12)0.0232 (12)0.0157 (12)0.0032 (10)0.0051 (10)0.0092 (9)
C30.0149 (12)0.0169 (11)0.0142 (12)0.0010 (9)0.0015 (9)0.0003 (9)
C320.0140 (12)0.0171 (11)0.0133 (12)0.0014 (9)0.0055 (9)0.0011 (9)
C70.0183 (13)0.0147 (11)0.0144 (12)0.0016 (9)0.0006 (10)0.0013 (9)
C340.0201 (13)0.0150 (11)0.0265 (14)0.0053 (10)0.0118 (11)0.0070 (10)
C150.0256 (14)0.0273 (13)0.0166 (13)0.0018 (11)0.0107 (11)0.0044 (10)
C60.0195 (13)0.0226 (13)0.0180 (13)0.0047 (10)0.0031 (10)0.0065 (10)
C250.0172 (12)0.0212 (12)0.0155 (12)0.0076 (10)0.0083 (10)0.0019 (9)
C260.0159 (12)0.0161 (11)0.0125 (12)0.0003 (9)0.0037 (10)0.0003 (9)
C140.0266 (14)0.0191 (12)0.0152 (13)0.0011 (10)0.0008 (11)0.0059 (9)
C160.0166 (12)0.0163 (11)0.0163 (12)0.0028 (9)0.0047 (10)0.0004 (9)
C10.0100 (11)0.0154 (11)0.0134 (11)0.0018 (9)0.0016 (9)0.0019 (9)
C230.0137 (12)0.0242 (13)0.0168 (12)0.0030 (10)0.0036 (10)0.0028 (10)
C130.0160 (12)0.0157 (11)0.0169 (12)0.0036 (9)0.0029 (10)0.0004 (9)
Geometric parameters (Å, º) top
Rh—C011.809 (2)C11—C161.390 (3)
Rh—O12.0563 (16)C22—C231.390 (3)
Rh—O22.0860 (16)C22—H220.9300
Rh—P2.2377 (8)C24—C231.390 (3)
Cl3—C31.749 (2)C24—C251.391 (3)
Cl7—C71.737 (2)C24—H240.9300
P—C111.825 (2)C35—C341.392 (3)
P—C311.827 (2)C35—H350.9300
P—C211.829 (2)C33—C341.386 (3)
O1—C11.289 (3)C33—C321.400 (3)
O01—C011.153 (3)C33—H330.9300
O2—C21.287 (3)C32—H320.9300
C4—C51.383 (3)C7—C61.384 (3)
C4—C31.383 (3)C7—C11.419 (3)
C4—H40.9300C34—H340.9300
C31—C321.394 (3)C15—C141.385 (4)
C31—C361.404 (3)C15—C161.394 (3)
C36—C351.386 (3)C15—H150.9300
C36—H360.9300C6—H60.9300
C5—C61.390 (4)C25—C261.388 (3)
C5—H50.9300C25—H250.9300
C21—C261.398 (3)C26—H260.9300
C21—C221.402 (3)C14—C131.383 (4)
C12—C131.387 (3)C14—H140.9300
C12—C111.404 (3)C16—H160.9300
C12—H120.9300C23—H230.9300
C2—C31.420 (3)C13—H130.9300
C2—C11.469 (3)
C01—Rh—O1175.37 (8)C36—C35—C34120.3 (2)
C01—Rh—O299.15 (8)C36—C35—H35119.8
O1—Rh—O276.60 (6)C34—C35—H35119.8
C01—Rh—P87.00 (7)C34—C33—C32120.2 (2)
O1—Rh—P97.25 (5)C34—C33—H33119.9
O2—Rh—P173.85 (4)C32—C33—H33119.9
C11—P—C31104.94 (10)C4—C3—C2130.7 (2)
C11—P—C21104.04 (10)C4—C3—Cl3114.91 (19)
C31—P—C21104.28 (10)C2—C3—Cl3114.39 (17)
C11—P—Rh114.27 (8)C31—C32—C33119.9 (2)
C31—P—Rh113.39 (8)C31—C32—H32120.0
C21—P—Rh114.78 (7)C33—C32—H32120.0
C1—O1—Rh116.69 (14)C6—C7—C1130.7 (2)
C2—O2—Rh116.08 (14)C6—C7—Cl7114.88 (18)
C5—C4—C3129.1 (2)C1—C7—Cl7114.38 (18)
C5—C4—H4115.5C33—C34—C35119.9 (2)
C3—C4—H4115.5C33—C34—H34120.0
C32—C31—C36119.5 (2)C35—C34—H34120.0
C32—C31—P121.99 (17)C14—C15—C16119.5 (2)
C36—C31—P118.53 (17)C14—C15—H15120.3
C35—C36—C31120.1 (2)C16—C15—H15120.3
C35—C36—H36119.9C7—C6—C5129.4 (2)
C31—C36—H36119.9C7—C6—H6115.3
C4—C5—C6128.0 (2)C5—C6—H6115.3
C4—C5—H5116.0C26—C25—C24120.4 (2)
C6—C5—H5116.0C26—C25—H25119.8
C26—C21—C22118.9 (2)C24—C25—H25119.8
C26—C21—P122.37 (17)C25—C26—C21120.3 (2)
C22—C21—P118.69 (17)C25—C26—H26119.8
C13—C12—C11120.1 (2)C21—C26—H26119.8
C13—C12—H12119.9C13—C14—C15120.8 (2)
C11—C12—H12119.9C13—C14—H14119.6
O2—C2—C3119.2 (2)C15—C14—H14119.6
O2—C2—C1115.0 (2)C11—C16—C15120.4 (2)
C3—C2—C1125.8 (2)C11—C16—H16119.8
C16—C11—C12119.3 (2)C15—C16—H16119.8
C16—C11—P122.34 (17)O1—C1—C7118.8 (2)
C12—C11—P118.28 (17)O1—C1—C2115.5 (2)
C23—C22—C21120.5 (2)C7—C1—C2125.7 (2)
C23—C22—H22119.7C22—C23—C24120.0 (2)
C21—C22—H22119.7C22—C23—H23120.0
O01—C01—Rh179.2 (2)C24—C23—H23120.0
C23—C24—C25119.8 (2)C14—C13—C12119.8 (2)
C23—C24—H24120.1C14—C13—H13120.1
C25—C24—H24120.1C12—C13—H13120.1
C01—Rh—P—C1135.65 (11)C31—C36—C35—C340.6 (3)
O1—Rh—P—C11142.51 (9)C5—C4—C3—C26.3 (4)
C01—Rh—P—C31155.85 (11)C5—C4—C3—Cl3175.5 (2)
O1—Rh—P—C3122.31 (9)O2—C2—C3—C4171.3 (2)
C01—Rh—P—C2184.43 (11)C1—C2—C3—C410.6 (4)
O1—Rh—P—C2197.41 (9)O2—C2—C3—Cl36.9 (3)
O2—Rh—O1—C13.49 (15)C1—C2—C3—Cl3171.26 (18)
P—Rh—O1—C1176.47 (15)C36—C31—C32—C330.3 (3)
C01—Rh—O2—C2176.41 (16)P—C31—C32—C33177.71 (17)
O1—Rh—O2—C21.73 (15)C34—C33—C32—C310.4 (3)
C11—P—C31—C325.6 (2)C32—C33—C34—C350.1 (4)
C21—P—C31—C32114.72 (19)C36—C35—C34—C330.6 (4)
Rh—P—C31—C32119.74 (18)C1—C7—C6—C52.5 (5)
C11—P—C31—C36176.33 (18)Cl7—C7—C6—C5179.3 (2)
C21—P—C31—C3667.25 (19)C4—C5—C6—C73.4 (4)
Rh—P—C31—C3658.29 (19)C23—C24—C25—C260.9 (3)
C32—C31—C36—C350.2 (3)C24—C25—C26—C210.8 (3)
P—C31—C36—C35178.28 (18)C22—C21—C26—C251.6 (3)
C3—C4—C5—C62.5 (4)P—C21—C26—C25178.24 (18)
C11—P—C21—C26100.68 (19)C16—C15—C14—C130.5 (4)
C31—P—C21—C269.1 (2)C12—C11—C16—C151.4 (3)
Rh—P—C21—C26133.72 (17)P—C11—C16—C15175.82 (18)
C11—P—C21—C2279.47 (19)C14—C15—C16—C111.9 (4)
C31—P—C21—C22170.79 (18)Rh—O1—C1—C7175.83 (16)
Rh—P—C21—C2246.13 (19)Rh—O1—C1—C24.6 (2)
Rh—O2—C2—C3178.30 (16)C6—C7—C1—O1177.2 (2)
Rh—O2—C2—C10.0 (2)Cl7—C7—C1—O10.4 (3)
C13—C12—C11—C160.5 (3)C6—C7—C1—C23.2 (4)
C13—C12—C11—P177.87 (17)Cl7—C7—C1—C2179.95 (18)
C31—P—C11—C16103.04 (19)O2—C2—C1—O13.0 (3)
C21—P—C11—C166.2 (2)C3—C2—C1—O1175.2 (2)
Rh—P—C11—C16132.14 (17)O2—C2—C1—C7177.4 (2)
C31—P—C11—C1279.70 (19)C3—C2—C1—C74.4 (4)
C21—P—C11—C12171.04 (17)C21—C22—C23—C241.1 (4)
Rh—P—C11—C1245.12 (19)C25—C24—C23—C221.9 (3)
C26—C21—C22—C230.6 (3)C15—C14—C13—C121.5 (4)
P—C21—C22—C23179.22 (18)C11—C12—C13—C142.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O2i0.932.383.301 (3)171
C34—H34···O2ii0.932.543.387 (3)152
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x+1/2, y+1/2, z+1/2.
 

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