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The title compound, [RhCl(C8H12)(C6H13NO)], which is of inter­est from the point of view of catalysis, crystallizes with two independent molecules in the asymmetric unit, which is the complete unit cell. Neither the Rh—Cl nor the Rh—N bond lengths deviate significantly from the corresponding dimensions observed for closely related chloride–rhodium complexes in the literature. Individual mol­ecules are inter­linked through N—H...Cl hydrogen-bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052920/bg3061sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052920/bg3061Isup2.hkl
Contains datablock I

CCDC reference: 667247

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.016
  • wR factor = 0.035
  • Data-to-parameter ratio = 22.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Rh1 - Cl1 .. 5.13 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Rh1 - N1 .. 5.43 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Rh2 - Cl2 .. 8.03 su
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.70 From the CIF: _reflns_number_total 7489 Count of symmetry unique reflns 3809 Completeness (_total/calc) 196.61% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3680 Fraction of Friedel pairs measured 0.966 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of N1 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of N2 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18 = . S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 4 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 1 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

Comment top

Chlorido(η4-1,5-cyclooctadiene)[κN-(S)-2-methoxymethylpyrrolidine]rhodium(I), [Rh(Cl)(η4-C8H12){(S)-C6H13NO}] (I), represents the O-methylated analogue of the previously described prolinol complexes [Rh(Cl)(η4-C8H12){(R)-C5H11NO}] and [Rh(Cl)(η4-C8H12){(S)-C5H11NO}] which themselves belong to a family of catalytically attractive rhodium compounds containing β-amino alcohol ligands (Dahlenburg et al., 2007). Complex (I) crystallizes from CDCl3 in the triclinic space group P1 with two independent moieties per cell.

Not unexpectedly, neither the Rh—Cl distances nor the Rh—N bond lengths deviate significantly from the corresponding dimensions observed fo closely related chlorido rhodium complexes in the literature possessing N-bonded ethanolamine, valinol, prolinol, and norephedrine ligands [Rh—Cl = 2.381 2.398 Å and Rh—N = 2.127 2.137 Å] (Dahlenburg et al., 2007).

In the solid state the individual complexes of (I) are assembled through N—H···Cl hydrogen bonds (Table 2). The (R)-enantiomer of the parent prolinol compound [Rh(Cl)(η4-C8H12)(C5H11NO)] shows similar N—H···Cl (and O—H···Cl) hydrogen-bonding between two crystallographically independent molecules (Dahlenburg et al., 2007).

Related literature top

For structurally related rhodium complexes with various chiral and achiral β-amino alcohol ligands, see Dahlenburg et al. (2007).

Experimental top

Compound (I) was prepared by the bridge-opening reaction of [{Rh(η4-C8H12)}2(µ-Cl)2] with (S)-2-methoxymethylpyrrolidine, similar to the procedure previously communicated for the syntheses of a number of chlorido(η4-1,5-cyclooctadiene)rhodium(I) derivatives bearing diverse N-bonded β-amino alcohol ligands (Dahlenburg et al., 2007). The specimen used for the X-ray diffraction study was collected from a partially evaporated NMR sample in CDCl3 solution.

Refinement top

Carbon-and nitrogen-bound H atoms were positioned geometrically (C—H = 0.95–0.99 Å; N—H = 0.93 Å) and refined using appropriate riding models. All hydrogen Uiso values were fixed at 1.2 times Ueq of the preceding carrier atom.

Structure description top

Chlorido(η4-1,5-cyclooctadiene)[κN-(S)-2-methoxymethylpyrrolidine]rhodium(I), [Rh(Cl)(η4-C8H12){(S)-C6H13NO}] (I), represents the O-methylated analogue of the previously described prolinol complexes [Rh(Cl)(η4-C8H12){(R)-C5H11NO}] and [Rh(Cl)(η4-C8H12){(S)-C5H11NO}] which themselves belong to a family of catalytically attractive rhodium compounds containing β-amino alcohol ligands (Dahlenburg et al., 2007). Complex (I) crystallizes from CDCl3 in the triclinic space group P1 with two independent moieties per cell.

Not unexpectedly, neither the Rh—Cl distances nor the Rh—N bond lengths deviate significantly from the corresponding dimensions observed fo closely related chlorido rhodium complexes in the literature possessing N-bonded ethanolamine, valinol, prolinol, and norephedrine ligands [Rh—Cl = 2.381 2.398 Å and Rh—N = 2.127 2.137 Å] (Dahlenburg et al., 2007).

In the solid state the individual complexes of (I) are assembled through N—H···Cl hydrogen bonds (Table 2). The (R)-enantiomer of the parent prolinol compound [Rh(Cl)(η4-C8H12)(C5H11NO)] shows similar N—H···Cl (and O—H···Cl) hydrogen-bonding between two crystallographically independent molecules (Dahlenburg et al., 2007).

For structurally related rhodium complexes with various chiral and achiral β-amino alcohol ligands, see Dahlenburg et al. (2007).

Computing details top

Data collection: COLLECT (Bruker, 2002); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXTL-NT (Bruker, 2002); 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).

Figures top
[Figure 1] Fig. 1. Structures of the two crystallographically independent molecules of (I). Displacement ellipsoids are drawn at the 50% probability level.
Chlorido(η4-cycloocta-1,5-diene)[(S)-2-(methoxymethyl)pyrrolidine- κN]rhodium(I) top
Crystal data top
[RhCl(C8H12)(C6H13NO)]Z = 2
Mr = 361.71F(000) = 372
Triclinic, P1Dx = 1.622 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.5499 (2) ÅCell parameters from 98 reflections
b = 6.6563 (2) Åθ = 6.0–20.0°
c = 18.8540 (7) ŵ = 1.32 mm1
α = 92.253 (3)°T = 150 K
β = 95.026 (3)°Plate, yellow
γ = 114.841 (2)°0.25 × 0.18 × 0.10 mm
V = 740.44 (4) Å3
Data collection top
Bruker–Nonius KappaCCD
diffractometer
7489 independent reflections
Radiation source: fine-focus sealed tube7246 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 9 pixels mm-1θmax = 28.7°, θmin = 3.3°
ω–rotations with 1.70 ° and 76 sec per frame scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
k = 88
Tmin = 0.730, Tmax = 0.880l = 2525
19576 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)] = 0.016H-atom parameters constrained
wR(F2) = 0.035 w = 1/[σ2(Fo2) + (0.0125P)2 + 0.1842P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.002
7489 reflectionsΔρmax = 0.37 e Å3
327 parametersΔρmin = 0.35 e Å3
3 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.013 (13)
Crystal data top
[RhCl(C8H12)(C6H13NO)]γ = 114.841 (2)°
Mr = 361.71V = 740.44 (4) Å3
Triclinic, P1Z = 2
a = 6.5499 (2) ÅMo Kα radiation
b = 6.6563 (2) ŵ = 1.32 mm1
c = 18.8540 (7) ÅT = 150 K
α = 92.253 (3)°0.25 × 0.18 × 0.10 mm
β = 95.026 (3)°
Data collection top
Bruker–Nonius KappaCCD
diffractometer
7489 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
7246 reflections with I > 2σ(I)
Tmin = 0.730, Tmax = 0.880Rint = 0.019
19576 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.016H-atom parameters constrained
wR(F2) = 0.035Δρmax = 0.37 e Å3
S = 1.06Δρmin = 0.35 e Å3
7489 reflectionsAbsolute structure: Flack (1983)
327 parametersAbsolute structure parameter: 0.013 (13)
3 restraints
Special details top

Refinement. 3690 Friedel pairs were used in the refinement of the Flack parameter.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Rh10.084451 (15)0.914650 (14)0.609209 (7)0.01109 (4)
Cl10.20120 (12)0.67363 (10)0.67548 (3)0.02427 (14)
N10.2502 (3)1.1749 (3)0.69167 (8)0.0131 (3)
H10.20921.28870.68030.016*
O10.0795 (3)1.0168 (3)0.84488 (8)0.0287 (4)
C10.5026 (3)1.2725 (3)0.69824 (10)0.0180 (4)
H1A0.55991.35370.65610.022*
H1B0.55701.15490.70260.022*
C20.5807 (3)1.4316 (3)0.76628 (11)0.0217 (4)
H2A0.60921.58440.75490.026*
H2B0.72091.43400.79160.026*
C30.3818 (3)1.3363 (3)0.81205 (10)0.0210 (4)
H3A0.43121.29430.85800.025*
H3B0.32091.44650.82200.025*
C40.2023 (3)1.1302 (4)0.76651 (10)0.0142 (4)
H4A0.22760.99700.77880.017*
C50.0394 (3)1.0849 (4)0.77490 (10)0.0178 (4)
H5A0.06331.22070.76860.021*
H5B0.14420.96630.73870.021*
C60.2952 (4)0.9857 (4)0.86247 (12)0.0254 (4)
H6A0.32080.91890.90810.038*
H6B0.41160.88710.82500.038*
H6C0.30291.12950.86650.038*
C70.0141 (3)0.7171 (3)0.50952 (10)0.0179 (4)
H7A0.13780.68410.52490.021*
C80.1764 (3)0.6376 (3)0.54673 (10)0.0177 (4)
H8A0.17530.54690.58430.021*
C90.3832 (3)0.6819 (3)0.53303 (12)0.0229 (4)
H9A0.47470.63430.57350.028*
H9B0.47640.59030.48940.028*
C100.3300 (3)0.9254 (3)0.52363 (12)0.0219 (4)
H10A0.32160.95140.47240.026*
H10B0.45370.95840.53940.026*
C110.1070 (3)1.0805 (3)0.56654 (11)0.0165 (4)
H11A0.11151.12580.61460.020*
C120.1055 (3)1.1619 (3)0.54041 (10)0.0155 (4)
H12A0.23111.26440.57170.019*
C130.1534 (4)1.1028 (3)0.46791 (10)0.0213 (4)
H13A0.31871.15210.46820.026*
H13B0.10491.18380.43220.026*
C140.0326 (4)0.8540 (3)0.44560 (11)0.0238 (4)
H14A0.12110.81790.42190.029*
H14B0.11700.81440.41070.029*
Rh20.094539 (15)0.761289 (15)0.114302 (7)0.01106 (4)
Cl20.21538 (8)0.68239 (9)0.18309 (3)0.02146 (10)
N20.2549 (3)0.6455 (3)0.19530 (9)0.0143 (3)
H20.39520.66730.18150.017*
O20.5079 (2)1.0692 (2)0.34836 (7)0.0215 (3)
C150.1275 (3)0.4022 (3)0.20168 (11)0.0198 (4)
H15A0.13700.31470.15940.024*
H15B0.03390.36330.20630.024*
C160.2431 (4)0.3587 (4)0.26888 (11)0.0248 (4)
H16A0.37380.32970.25800.030*
H16B0.13600.22970.29120.030*
C170.3211 (4)0.5724 (3)0.31814 (11)0.0235 (4)
H17A0.48060.62200.33880.028*
H17B0.22540.54830.35760.028*
C180.2969 (3)0.7465 (3)0.27071 (9)0.0149 (3)
H18A0.16070.76820.28190.018*
C190.4995 (3)0.9695 (3)0.27987 (10)0.0183 (4)
H19A0.64000.95020.27580.022*
H19B0.48471.06440.24250.022*
C200.7024 (4)1.2750 (4)0.36377 (12)0.0264 (4)
H20A0.69661.34460.40990.040*
H20B0.70551.37350.32620.040*
H20C0.83921.24880.36590.040*
C210.1169 (3)0.7272 (3)0.01827 (10)0.0168 (4)
H21A0.24170.63060.04080.020*
C220.0168 (4)0.9508 (4)0.04382 (14)0.0185 (5)
H22A0.07440.99370.08340.022*
C230.1775 (4)1.1297 (3)0.01277 (11)0.0234 (4)
H23A0.16191.27110.01730.028*
H23B0.16971.08810.03870.028*
C240.4096 (4)1.1644 (3)0.05044 (12)0.0244 (4)
H24A0.52351.21680.01610.029*
H24B0.45561.28180.09020.029*
C250.4086 (3)0.9560 (3)0.07954 (10)0.0181 (4)
H25A0.47510.96780.12730.022*
C260.3173 (3)0.7468 (3)0.04160 (10)0.0169 (4)
H26A0.32070.62510.06560.020*
C270.2129 (3)0.7032 (4)0.03583 (11)0.0210 (4)
H27A0.24770.58850.06010.025*
H27B0.28140.84110.06030.025*
C280.0445 (4)0.6248 (4)0.04210 (11)0.0195 (4)
H28A0.09590.66440.08820.023*
H28B0.11850.46100.04200.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Rh10.01358 (9)0.00928 (8)0.01085 (8)0.00528 (7)0.00132 (6)0.00121 (6)
Cl10.0390 (3)0.0184 (3)0.0208 (3)0.0188 (3)0.0037 (2)0.0012 (2)
N10.0149 (7)0.0133 (7)0.0125 (7)0.0072 (6)0.0014 (6)0.0026 (6)
O10.0225 (8)0.0499 (10)0.0204 (7)0.0196 (7)0.0088 (6)0.0144 (7)
C10.0147 (8)0.0203 (9)0.0174 (9)0.0060 (7)0.0018 (7)0.0006 (7)
C20.0181 (9)0.0188 (10)0.0235 (10)0.0044 (8)0.0007 (8)0.0036 (8)
C30.0201 (9)0.0253 (10)0.0161 (9)0.0092 (8)0.0008 (7)0.0040 (8)
C40.0168 (9)0.0160 (10)0.0114 (9)0.0085 (8)0.0006 (7)0.0031 (7)
C50.0171 (9)0.0231 (10)0.0140 (9)0.0091 (8)0.0021 (7)0.0032 (8)
C60.0226 (10)0.0322 (12)0.0246 (10)0.0129 (9)0.0106 (8)0.0070 (9)
C70.0212 (9)0.0145 (9)0.0152 (9)0.0053 (8)0.0021 (7)0.0023 (7)
C80.0193 (9)0.0110 (8)0.0175 (9)0.0021 (7)0.0009 (7)0.0004 (7)
C90.0152 (9)0.0183 (10)0.0287 (11)0.0009 (8)0.0009 (8)0.0019 (8)
C100.0167 (9)0.0228 (10)0.0259 (10)0.0089 (8)0.0022 (8)0.0030 (8)
C110.0172 (9)0.0145 (9)0.0202 (10)0.0092 (8)0.0008 (8)0.0052 (8)
C120.0192 (9)0.0125 (8)0.0137 (8)0.0059 (7)0.0001 (7)0.0041 (7)
C130.0228 (10)0.0235 (10)0.0165 (9)0.0077 (8)0.0055 (8)0.0073 (8)
C140.0297 (11)0.0233 (10)0.0146 (9)0.0070 (9)0.0061 (8)0.0008 (8)
Rh20.00948 (8)0.01340 (8)0.01073 (8)0.00511 (7)0.00209 (6)0.00113 (6)
Cl20.0144 (2)0.0360 (3)0.0181 (2)0.0139 (2)0.00577 (17)0.00443 (19)
N20.0146 (8)0.0178 (8)0.0128 (8)0.0088 (7)0.0032 (6)0.0012 (6)
O20.0210 (7)0.0207 (7)0.0169 (7)0.0040 (6)0.0009 (5)0.0041 (5)
C150.0245 (10)0.0155 (9)0.0197 (9)0.0097 (8)0.0005 (8)0.0005 (7)
C160.0330 (12)0.0209 (10)0.0244 (10)0.0152 (9)0.0014 (9)0.0052 (8)
C170.0299 (11)0.0212 (10)0.0183 (9)0.0105 (9)0.0015 (8)0.0035 (8)
C180.0146 (8)0.0192 (9)0.0123 (8)0.0084 (7)0.0018 (7)0.0001 (7)
C190.0208 (9)0.0179 (9)0.0173 (9)0.0094 (8)0.0028 (7)0.0002 (7)
C200.0235 (10)0.0200 (10)0.0290 (11)0.0050 (8)0.0063 (9)0.0043 (8)
C210.0163 (9)0.0189 (9)0.0136 (8)0.0063 (7)0.0011 (7)0.0025 (7)
C220.0223 (11)0.0187 (12)0.0160 (10)0.0106 (10)0.0004 (8)0.0016 (9)
C230.0339 (11)0.0130 (9)0.0204 (10)0.0075 (8)0.0003 (8)0.0038 (7)
C240.0234 (10)0.0158 (9)0.0250 (10)0.0009 (8)0.0049 (8)0.0022 (8)
C250.0128 (8)0.0214 (10)0.0159 (9)0.0027 (7)0.0045 (7)0.0021 (7)
C260.0158 (9)0.0207 (9)0.0170 (9)0.0088 (8)0.0087 (7)0.0054 (7)
C270.0261 (11)0.0213 (10)0.0163 (9)0.0098 (9)0.0082 (8)0.0003 (8)
C280.0250 (11)0.0172 (11)0.0124 (9)0.0059 (9)0.0014 (8)0.0003 (8)
Geometric parameters (Å, º) top
Rh1—N12.1236 (15)Rh2—N22.1263 (15)
Rh1—Cl12.3960 (6)Rh2—Cl22.3870 (5)
Rh1—C112.1199 (17)Rh2—C252.0985 (18)
Rh1—C122.1021 (17)Rh2—C262.1154 (18)
Rh1—C72.1491 (19)Rh2—C212.1242 (18)
Rh1—C82.1300 (19)Rh2—C222.150 (2)
N1—C41.487 (2)N2—C151.494 (2)
N1—C11.492 (2)N2—C181.500 (2)
N1—H10.9300N2—H20.9300
O1—C61.411 (2)O2—C191.415 (2)
O1—C51.422 (2)O2—C201.422 (3)
C1—C21.534 (3)C15—C161.519 (3)
C1—H1A0.9900C15—H15A0.9900
C1—H1B0.9900C15—H15B0.9900
C2—C31.546 (3)C16—C171.533 (3)
C2—H2A0.9900C16—H16A0.9900
C2—H2B0.9900C16—H16B0.9900
C3—C41.542 (3)C17—C181.542 (3)
C3—H3A0.9900C17—H17A0.9900
C3—H3B0.9900C17—H17B0.9900
C4—C51.506 (3)C18—C191.510 (3)
C4—H4A1.0000C18—H18A1.0000
C5—H5A0.9900C19—H19A0.9900
C5—H5B0.9900C19—H19B0.9900
C6—H6A0.9800C20—H20A0.9800
C6—H6B0.9800C20—H20B0.9800
C6—H6C0.9800C20—H20C0.9800
C7—C81.399 (3)C21—C221.395 (3)
C7—C141.522 (3)C21—C281.514 (3)
C7—H7A0.9500C21—H21A0.9500
C8—C91.506 (3)C22—C231.514 (3)
C8—H8A0.9500C22—H22A0.9500
C9—C101.529 (3)C23—C241.540 (3)
C9—H9A0.9900C23—H23A0.9900
C9—H9B0.9900C23—H23B0.9900
C10—C111.521 (3)C24—C251.510 (3)
C10—H10A0.9900C24—H24A0.9900
C10—H10B0.9900C24—H24B0.9900
C11—C121.407 (3)C25—C261.398 (3)
C11—H11A0.9500C25—H25A0.9500
C12—C131.503 (3)C26—C271.519 (3)
C12—H12A0.9500C26—H26A0.9500
C13—C141.527 (3)C27—C281.533 (3)
C13—H13A0.9900C27—H27A0.9900
C13—H13B0.9900C27—H27B0.9900
C14—H14A0.9900C28—H28A0.9900
C14—H14B0.9900C28—H28B0.9900
C12—Rh1—C1138.94 (7)C25—Rh2—C2638.76 (8)
C12—Rh1—N187.10 (7)C25—Rh2—C2198.69 (7)
C11—Rh1—N190.70 (7)C26—Rh2—C2182.18 (7)
C12—Rh1—C898.37 (7)C25—Rh2—N290.73 (7)
C11—Rh1—C882.13 (8)C26—Rh2—N290.97 (7)
N1—Rh1—C8160.31 (7)C21—Rh2—N2154.68 (7)
C12—Rh1—C781.99 (7)C25—Rh2—C2282.24 (9)
C11—Rh1—C790.51 (8)C26—Rh2—C2290.28 (9)
N1—Rh1—C7161.01 (7)C21—Rh2—C2238.08 (8)
C8—Rh1—C738.17 (7)N2—Rh2—C22167.08 (8)
C12—Rh1—Cl1158.38 (6)C25—Rh2—Cl2156.03 (6)
C11—Rh1—Cl1162.67 (6)C26—Rh2—Cl2165.20 (6)
N1—Rh1—Cl190.47 (4)C21—Rh2—Cl291.21 (5)
C8—Rh1—Cl191.09 (5)N2—Rh2—Cl289.43 (5)
C7—Rh1—Cl193.97 (6)C22—Rh2—Cl292.63 (7)
C4—N1—C1102.50 (14)C15—N2—C18103.84 (14)
C4—N1—Rh1119.03 (12)C15—N2—Rh2112.21 (12)
C1—N1—Rh1114.78 (11)C18—N2—Rh2119.48 (12)
C4—N1—H1106.6C15—N2—H2106.9
C1—N1—H1106.6C18—N2—H2106.9
Rh1—N1—H1106.6Rh2—N2—H2106.9
C6—O1—C5113.45 (15)C19—O2—C20111.74 (16)
N1—C1—C2104.90 (15)N2—C15—C16104.54 (16)
N1—C1—H1A110.8N2—C15—H15A110.8
C2—C1—H1A110.8C16—C15—H15A110.8
N1—C1—H1B110.8N2—C15—H15B110.8
C2—C1—H1B110.8C16—C15—H15B110.8
H1A—C1—H1B108.8H15A—C15—H15B108.9
C1—C2—C3104.37 (16)C15—C16—C17104.50 (16)
C1—C2—H2A110.9C15—C16—H16A110.9
C3—C2—H2A110.9C17—C16—H16A110.9
C1—C2—H2B110.9C15—C16—H16B110.9
C3—C2—H2B110.9C17—C16—H16B110.9
H2A—C2—H2B108.9H16A—C16—H16B108.9
C4—C3—C2104.89 (16)C16—C17—C18105.80 (16)
C4—C3—H3A110.8C16—C17—H17A110.6
C2—C3—H3A110.8C18—C17—H17A110.6
C4—C3—H3B110.8C16—C17—H17B110.6
C2—C3—H3B110.8C18—C17—H17B110.6
H3A—C3—H3B108.8H17A—C17—H17B108.7
N1—C4—C5110.67 (15)N2—C18—C19110.83 (15)
N1—C4—C3104.52 (15)N2—C18—C17105.67 (15)
C5—C4—C3114.78 (18)C19—C18—C17114.30 (16)
N1—C4—H4A108.9N2—C18—H18A108.6
C5—C4—H4A108.9C19—C18—H18A108.6
C3—C4—H4A108.9C17—C18—H18A108.6
O1—C5—C4107.16 (15)O2—C19—C18107.61 (15)
O1—C5—H5A110.3O2—C19—H19A110.2
C4—C5—H5A110.3C18—C19—H19A110.2
O1—C5—H5B110.3O2—C19—H19B110.2
C4—C5—H5B110.3C18—C19—H19B110.2
H5A—C5—H5B108.5H19A—C19—H19B108.5
O1—C6—H6A109.5O2—C20—H20A109.5
O1—C6—H6B109.5O2—C20—H20B109.5
H6A—C6—H6B109.5H20A—C20—H20B109.5
O1—C6—H6C109.5O2—C20—H20C109.5
H6A—C6—H6C109.5H20A—C20—H20C109.5
H6B—C6—H6C109.5H20B—C20—H20C109.5
C8—C7—C14123.11 (18)C22—C21—C28125.83 (19)
C8—C7—Rh170.17 (11)C22—C21—Rh271.97 (13)
C14—C7—Rh1112.11 (13)C28—C21—Rh2109.72 (13)
C8—C7—H7A118.4C22—C21—H21A117.1
C14—C7—H7A118.4C28—C21—H21A117.1
Rh1—C7—H7A87.8Rh2—C21—H21A88.2
C7—C8—C9126.34 (17)C21—C22—C23124.4 (2)
C7—C8—Rh171.66 (11)C21—C22—Rh269.95 (12)
C9—C8—Rh1109.19 (13)C23—C22—Rh2112.47 (16)
C7—C8—H8A116.8C21—C22—H22A117.8
C9—C8—H8A116.8C23—C22—H22A117.8
Rh1—C8—H8A89.1Rh2—C22—H22A87.6
C8—C9—C10113.95 (16)C22—C23—C24112.19 (17)
C8—C9—H9A108.8C22—C23—H23A109.2
C10—C9—H9A108.8C24—C23—H23A109.2
C8—C9—H9B108.8C22—C23—H23B109.2
C10—C9—H9B108.8C24—C23—H23B109.2
H9A—C9—H9B107.7H23A—C23—H23B107.9
C11—C10—C9111.37 (16)C25—C24—C23112.97 (16)
C11—C10—H10A109.4C25—C24—H24A109.0
C9—C10—H10A109.4C23—C24—H24A109.0
C11—C10—H10B109.4C25—C24—H24B109.0
C9—C10—H10B109.4C23—C24—H24B109.0
H10A—C10—H10B108.0H24A—C24—H24B107.8
C12—C11—C10124.88 (19)C26—C25—C24124.98 (18)
C12—C11—Rh169.85 (10)C26—C25—Rh271.28 (10)
C10—C11—Rh1113.50 (13)C24—C25—Rh2110.91 (13)
C12—C11—H11A117.6C26—C25—H25A117.5
C10—C11—H11A117.6C24—C25—H25A117.5
Rh1—C11—H11A86.6Rh2—C25—H25A87.8
C11—C12—C13126.47 (18)C25—C26—C27123.65 (18)
C11—C12—Rh171.21 (10)C25—C26—Rh269.96 (10)
C13—C12—Rh1110.29 (13)C27—C26—Rh2113.19 (13)
C11—C12—H12A116.8C25—C26—H26A118.2
C13—C12—H12A116.8C27—C26—H26A118.2
Rh1—C12—H12A88.4Rh2—C26—H26A86.9
C12—C13—C14112.74 (16)C26—C27—C28111.86 (16)
C12—C13—H13A109.0C26—C27—H27A109.2
C14—C13—H13A109.0C28—C27—H27A109.2
C12—C13—H13B109.0C26—C27—H27B109.2
C14—C13—H13B109.0C28—C27—H27B109.2
H13A—C13—H13B107.8H27A—C27—H27B107.9
C7—C14—C13111.54 (16)C21—C28—C27112.25 (17)
C7—C14—H14A109.3C21—C28—H28A109.2
C13—C14—H14A109.3C27—C28—H28A109.2
C7—C14—H14B109.3C21—C28—H28B109.2
C13—C14—H14B109.3C27—C28—H28B109.2
H14A—C14—H14B108.0H28A—C28—H28B107.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl1i0.932.593.4888 (16)163
N2—H2···Cl2ii0.932.513.4028 (16)162
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula[RhCl(C8H12)(C6H13NO)]
Mr361.71
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)6.5499 (2), 6.6563 (2), 18.8540 (7)
α, β, γ (°)92.253 (3), 95.026 (3), 114.841 (2)
V3)740.44 (4)
Z2
Radiation typeMo Kα
µ (mm1)1.32
Crystal size (mm)0.25 × 0.18 × 0.10
Data collection
DiffractometerBruker–Nonius KappaCCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.730, 0.880
No. of measured, independent and
observed [I > 2σ(I)] reflections
19576, 7489, 7246
Rint0.019
(sin θ/λ)max1)0.676
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.016, 0.035, 1.06
No. of reflections7489
No. of parameters327
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.35
Absolute structureFlack (1983)
Absolute structure parameter0.013 (13)

Computer programs: COLLECT (Bruker, 2002), EVALCCD (Duisenberg et al., 2003), SHELXTL-NT (Bruker, 2002), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
Rh1—N12.1236 (15)Rh2—N22.1263 (15)
Rh1—Cl12.3960 (6)Rh2—Cl22.3870 (5)
Rh1—C112.1199 (17)Rh2—C252.0985 (18)
Rh1—C122.1021 (17)Rh2—C262.1154 (18)
Rh1—C72.1491 (19)Rh2—C212.1242 (18)
Rh1—C82.1300 (19)Rh2—C222.150 (2)
N1—Rh1—Cl190.47 (4)N2—Rh2—Cl289.43 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl1i0.932.593.4888 (16)162.8
N2—H2···Cl2ii0.932.513.4028 (16)161.5
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.
 

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