Carbon­yl(8-hydroxy­quinolinato)[tris­(2-methyl­phen­yl) phosphite]rhodium(I)

The mol­ecules of the title compound, [Rh(C₉H₆NO)(C₂₁H₂₁O₃P)(CO)], pack in a `tail-to-tail' fashion, with a π-stacking distance of 3.500 (1) Å. The effective cone angle (Θ_E) for the phosphite ligand is 168°. The bidentate oxine ligand has a bite angle of 81.27 (11)° and the Rh—P bond distance is 2.189 (1) Å.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.042
• wR factor = 0.094
• Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.51 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Rh     -   C10     ..       5.18 su
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      35.00 A   3  

   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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Carbonyl(8-hydroxyquinolinato)[tris(2-methylphenyl) phosphite]rhodium(I)

Crystal data

[Rh(C9H6NO)(C21H21OP)(CO)]	F(000) = 1280
Mr = 627.42	Dx = 1.502 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 3375 reflections
a = 7.652 (5) Å	θ = 2.3–28.2°
b = 20.370 (5) Å	µ = 0.71 mm^−1
c = 18.173 (5) Å	T = 100 K
β = 101.546 (5)°	Needle, yellow
V = 2775 (2) Å^3	0.22 × 0.13 × 0.13 mm
Z = 4

Data collection

Bruker X8 Apex 4K Kappa CCD diffractometer	4794 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.046
ω and ψ scans	θmax = 28.3°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→10
Tmin = 0.858, Tmax = 0.915	k = −27→27
15688 measured reflections	l = −19→24
6869 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.0334P)^2 + 2.2331P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.094	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.55 e Å^−3
6869 reflections	Δρmin = −0.95 e Å^−3
356 parameters

Special details

Experimental. The intensity data was collected on a Bruker X8 Apex 4 K CCD diffractometer using an exposure time of 10 s/frame. A total of 567 frames were collected with a frame width of 0.5° covering up to θ = 28.28° with 99.8% completeness accomplished.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Rh	0.05678 (3)	0.067539 (13)	0.326437 (13)	0.01445 (7)
P	−0.00499 (11)	0.06430 (4)	0.20356 (4)	0.01362 (17)
N	0.1378 (3)	0.05940 (13)	0.44269 (13)	0.0147 (6)
O1	−0.1307 (3)	0.12303 (11)	0.16663 (11)	0.0155 (5)
O2	−0.0890 (3)	−0.00198 (11)	0.16393 (11)	0.0159 (5)
O3	0.1552 (3)	0.06341 (11)	0.15795 (11)	0.0157 (4)
O4	0.1849 (3)	−0.02005 (11)	0.33090 (11)	0.0177 (5)
O5	−0.1252 (4)	0.19580 (13)	0.32860 (13)	0.0315 (6)
C1	0.1149 (4)	0.09986 (18)	0.49657 (17)	0.0193 (7)
H1	0.0574	0.1397	0.4836	0.023*
C2	0.1748 (5)	0.08479 (18)	0.57323 (17)	0.0234 (8)
H2	0.1559	0.1143	0.6099	0.028*
C3	0.2600 (4)	0.02715 (19)	0.59320 (17)	0.0225 (8)
H3	0.2978	0.0168	0.6437	0.027*
C4	0.2914 (4)	−0.01726 (17)	0.53755 (17)	0.0177 (7)
C5	0.3786 (5)	−0.07805 (18)	0.55240 (18)	0.0229 (8)
H5	0.4222	−0.0913	0.6016	0.027*
C6	0.3987 (5)	−0.11744 (18)	0.49374 (19)	0.0238 (8)
H6	0.4558	−0.1577	0.5039	0.029*
C7	0.3357 (4)	−0.09897 (17)	0.41837 (18)	0.0196 (7)
H7	0.3531	−0.1269	0.38	0.024*
C8	0.2481 (4)	−0.03985 (16)	0.40065 (17)	0.0158 (7)
C9	0.2252 (4)	0.00100 (16)	0.46175 (16)	0.0151 (6)
C10	−0.0562 (5)	0.14565 (17)	0.32612 (17)	0.0195 (7)
C11	−0.1745 (4)	0.13945 (16)	0.08956 (16)	0.0136 (6)
C12	−0.1348 (4)	0.20310 (16)	0.07077 (17)	0.0157 (6)
C13	−0.1887 (5)	0.22094 (18)	−0.00451 (18)	0.0218 (8)
H13	−0.165	0.2631	−0.0194	0.026*
C14	−0.2765 (5)	0.17738 (18)	−0.05743 (17)	0.0215 (8)
H14	−0.3096	0.1903	−0.1074	0.026*
C15	−0.3154 (5)	0.11482 (18)	−0.03664 (17)	0.0210 (7)
H15	−0.3762	0.0858	−0.0723	0.025*
C16	−0.2633 (4)	0.09524 (17)	0.03796 (17)	0.0169 (7)
H16	−0.2881	0.0531	0.0527	0.02*
C21	−0.2194 (4)	−0.03825 (16)	0.19084 (16)	0.0137 (6)
C22	−0.1789 (4)	−0.10423 (16)	0.20556 (17)	0.0157 (7)
C23	−0.3114 (4)	−0.14183 (18)	0.22786 (17)	0.0198 (7)
H23	−0.2912	−0.1863	0.2374	0.024*
C24	−0.4719 (5)	−0.11478 (18)	0.23614 (17)	0.0211 (7)
H24	−0.5573	−0.141	0.2516	0.025*
C25	−0.5064 (5)	−0.04890 (18)	0.22164 (17)	0.0210 (8)
H25	−0.614	−0.0307	0.2278	0.025*
C26	−0.3794 (4)	−0.01007 (17)	0.19775 (16)	0.0181 (7)
H26	−0.4017	0.0341	0.1866	0.022*
C31	0.2679 (4)	0.11718 (16)	0.15672 (18)	0.0174 (7)
C32	0.2959 (5)	0.13632 (17)	0.08543 (19)	0.0213 (7)
C33	0.4075 (5)	0.18971 (19)	0.0843 (2)	0.0301 (9)
H33	0.4281	0.2044	0.0383	0.036*
C34	0.4892 (5)	0.22190 (19)	0.1488 (3)	0.0339 (10)
H34	0.5613	0.2582	0.1458	0.041*
C35	0.4639 (5)	0.20031 (19)	0.2177 (2)	0.0295 (9)
H35	0.5215	0.2212	0.2613	0.035*
C36	0.3531 (4)	0.14754 (18)	0.2220 (2)	0.0222 (8)
H36	0.336	0.1326	0.2684	0.027*
C121	−0.0418 (5)	0.25081 (16)	0.12883 (18)	0.0208 (7)
H12A	−0.0823	0.2443	0.175	0.031*
H12B	−0.0683	0.2949	0.1114	0.031*
H12C	0.0847	0.2437	0.1372	0.031*
C221	−0.0026 (5)	−0.13218 (17)	0.19848 (19)	0.0213 (7)
H22A	0.0886	−0.1154	0.2381	0.032*
H22B	0.0236	−0.1199	0.1508	0.032*
H22C	−0.0065	−0.1792	0.2019	0.032*
C321	0.2116 (5)	0.09979 (19)	0.01527 (19)	0.0278 (9)
H32A	0.2708	0.1113	−0.0247	0.042*
H32B	0.0877	0.1114	0.0015	0.042*
H32C	0.2224	0.0534	0.0244	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rh	0.01875 (13)	0.01625 (12)	0.00808 (11)	0.00222 (13)	0.00208 (8)	−0.00032 (11)
P	0.0179 (4)	0.0143 (4)	0.0087 (3)	0.0012 (4)	0.0027 (3)	0.0000 (3)
N	0.0144 (13)	0.0202 (15)	0.0089 (11)	−0.0013 (12)	0.0009 (10)	−0.0011 (11)
O1	0.0210 (12)	0.0183 (11)	0.0070 (10)	0.0019 (10)	0.0024 (9)	−0.0005 (9)
O2	0.0208 (13)	0.0164 (11)	0.0118 (10)	−0.0022 (10)	0.0061 (9)	−0.0002 (9)
O3	0.0178 (11)	0.0162 (11)	0.0136 (10)	−0.0014 (10)	0.0039 (8)	−0.0001 (10)
O4	0.0219 (12)	0.0216 (12)	0.0097 (10)	0.0038 (10)	0.0031 (9)	0.0014 (9)
O5	0.0427 (17)	0.0272 (14)	0.0224 (13)	0.0132 (13)	0.0015 (12)	−0.0049 (12)
C1	0.0195 (17)	0.0262 (18)	0.0118 (15)	0.0017 (15)	0.0019 (13)	−0.0032 (14)
C2	0.0244 (19)	0.036 (2)	0.0092 (14)	−0.0019 (16)	0.0018 (13)	−0.0084 (14)
C3	0.0205 (18)	0.036 (2)	0.0088 (14)	−0.0059 (16)	−0.0019 (13)	0.0019 (15)
C4	0.0142 (16)	0.0263 (18)	0.0121 (14)	−0.0054 (14)	0.0015 (12)	0.0046 (14)
C5	0.0212 (18)	0.028 (2)	0.0175 (15)	−0.0047 (16)	−0.0019 (13)	0.0101 (15)
C6	0.0211 (19)	0.0204 (18)	0.0276 (19)	−0.0011 (15)	−0.0003 (15)	0.0065 (15)
C7	0.0189 (18)	0.0207 (17)	0.0194 (16)	0.0004 (15)	0.0039 (13)	0.0004 (14)
C8	0.0130 (16)	0.0201 (16)	0.0144 (15)	−0.0024 (14)	0.0027 (12)	0.0011 (13)
C9	0.0140 (16)	0.0211 (17)	0.0104 (14)	−0.0029 (14)	0.0027 (12)	0.0009 (13)
C10	0.0230 (18)	0.0248 (18)	0.0089 (14)	0.0008 (16)	−0.0012 (13)	−0.0023 (14)
C11	0.0150 (16)	0.0176 (16)	0.0085 (13)	0.0051 (13)	0.0035 (12)	0.0015 (12)
C12	0.0132 (16)	0.0190 (16)	0.0152 (14)	0.0033 (14)	0.0037 (12)	0.0023 (13)
C13	0.0245 (19)	0.0215 (18)	0.0214 (17)	0.0021 (15)	0.0096 (14)	0.0069 (15)
C14	0.0241 (19)	0.032 (2)	0.0080 (14)	0.0053 (16)	0.0022 (13)	0.0047 (14)
C15	0.0255 (19)	0.0275 (19)	0.0088 (14)	0.0000 (16)	0.0005 (13)	−0.0041 (14)
C16	0.0205 (17)	0.0174 (16)	0.0130 (14)	−0.0001 (14)	0.0036 (13)	−0.0009 (13)
C21	0.0163 (16)	0.0166 (15)	0.0076 (13)	−0.0054 (14)	0.0009 (12)	−0.0004 (12)
C22	0.0197 (17)	0.0173 (16)	0.0101 (14)	−0.0016 (14)	0.0029 (12)	−0.0007 (13)
C23	0.0228 (18)	0.0231 (18)	0.0123 (15)	−0.0054 (15)	0.0011 (13)	0.0031 (14)
C24	0.0224 (18)	0.031 (2)	0.0095 (14)	−0.0081 (16)	0.0026 (13)	0.0004 (14)
C25	0.0192 (18)	0.032 (2)	0.0112 (14)	0.0017 (15)	0.0021 (13)	−0.0036 (14)
C26	0.0215 (18)	0.0221 (17)	0.0096 (14)	0.0051 (15)	0.0005 (12)	−0.0007 (13)
C31	0.0148 (16)	0.0148 (16)	0.0232 (17)	0.0014 (14)	0.0055 (13)	0.0024 (14)
C32	0.0189 (18)	0.0228 (18)	0.0256 (17)	0.0055 (15)	0.0127 (14)	0.0009 (15)
C33	0.030 (2)	0.025 (2)	0.042 (2)	−0.0011 (17)	0.0229 (18)	0.0018 (18)
C34	0.026 (2)	0.0190 (18)	0.063 (3)	−0.0067 (17)	0.024 (2)	−0.0079 (19)
C35	0.0157 (18)	0.0274 (19)	0.045 (2)	−0.0014 (17)	0.0050 (16)	−0.0160 (19)
C36	0.0163 (17)	0.0255 (19)	0.0247 (17)	0.0042 (15)	0.0037 (14)	−0.0053 (15)
C121	0.0231 (18)	0.0165 (17)	0.0217 (17)	−0.0001 (15)	0.0017 (14)	0.0028 (14)
C221	0.0268 (19)	0.0163 (16)	0.0217 (17)	0.0058 (15)	0.0071 (14)	0.0042 (14)
C321	0.033 (2)	0.035 (2)	0.0188 (17)	0.0020 (18)	0.0145 (16)	0.0019 (16)

Geometric parameters (Å, º)

Rh—C10	1.810 (4)	C14—H14	0.93
Rh—O4	2.030 (2)	C15—C16	1.393 (4)
Rh—N	2.086 (2)	C15—H15	0.93
Rh—P	2.189 (1)	C16—H16	0.93
P—O1	1.596 (2)	C21—C26	1.381 (5)
P—O2	1.603 (2)	C21—C22	1.393 (4)
P—O3	1.611 (2)	C22—C23	1.394 (5)
N—C1	1.318 (4)	C22—C221	1.494 (5)
N—C9	1.375 (4)	C23—C24	1.382 (5)
O1—C11	1.413 (3)	C23—H23	0.93
O2—C21	1.406 (4)	C24—C25	1.383 (5)
O3—C31	1.397 (4)	C24—H24	0.93
O4—C8	1.326 (4)	C25—C26	1.388 (5)
O5—C10	1.155 (4)	C25—H25	0.93
C1—C2	1.410 (4)	C26—H26	0.93
C1—H1	0.93	C31—C36	1.380 (5)
C2—C3	1.357 (5)	C31—C32	1.410 (4)
C2—H2	0.93	C32—C33	1.386 (5)
C3—C4	1.413 (5)	C32—C321	1.506 (5)
C3—H3	0.93	C33—C34	1.379 (6)
C4—C5	1.407 (5)	C33—H33	0.93
C4—C9	1.419 (4)	C34—C35	1.376 (6)
C5—C6	1.367 (5)	C34—H34	0.93
C5—H5	0.93	C35—C36	1.381 (5)
C6—C7	1.409 (5)	C35—H35	0.93
C6—H6	0.93	C36—H36	0.93
C7—C8	1.385 (5)	C121—H12A	0.96
C7—H7	0.93	C121—H12B	0.96
C8—C9	1.426 (4)	C121—H12C	0.96
C11—C16	1.377 (4)	C221—H22A	0.96
C11—C12	1.390 (4)	C221—H22B	0.96
C12—C13	1.396 (4)	C221—H22C	0.96
C12—C121	1.505 (4)	C321—H32A	0.96
C13—C14	1.380 (5)	C321—H32B	0.96
C13—H13	0.93	C321—H32C	0.96
C14—C15	1.378 (5)
C10—Rh—O4	177.93 (11)	C14—C15—H15	120.1
C10—Rh—N	96.78 (12)	C16—C15—H15	120.1
O4—Rh—N	81.16 (9)	C11—C16—C15	118.8 (3)
C10—Rh—P	91.02 (10)	C11—C16—H16	120.6
O4—Rh—P	91.05 (6)	C15—C16—H16	120.6
N—Rh—P	172.11 (8)	C26—C21—C22	123.4 (3)
O1—P—O2	106.78 (12)	C26—C21—O2	121.2 (3)
O1—P—O3	104.40 (12)	C22—C21—O2	115.3 (3)
O2—P—O3	92.13 (12)	C21—C22—C23	116.1 (3)
O1—P—Rh	113.28 (8)	C21—C22—C221	121.4 (3)
O2—P—Rh	117.97 (9)	C23—C22—C221	122.5 (3)
O3—P—Rh	119.60 (9)	C24—C23—C22	121.8 (3)
C1—N—C9	119.0 (3)	C24—C23—H23	119.1
C1—N—Rh	130.2 (2)	C22—C23—H23	119.1
C9—N—Rh	110.79 (19)	C23—C24—C25	120.4 (3)
C11—O1—P	126.67 (19)	C23—C24—H24	119.8
C21—O2—P	122.34 (19)	C25—C24—H24	119.8
C31—O3—P	122.4 (2)	C24—C25—C26	119.6 (3)
C8—O4—Rh	112.7 (2)	C24—C25—H25	120.2
N—C1—C2	122.2 (3)	C26—C25—H25	120.2
N—C1—H1	118.9	C21—C26—C25	118.7 (3)
C2—C1—H1	118.9	C21—C26—H26	120.6
C3—C2—C1	119.7 (3)	C25—C26—H26	120.6
C3—C2—H2	120.1	C36—C31—O3	121.6 (3)
C1—C2—H2	120.1	C36—C31—C32	122.2 (3)
C2—C3—C4	120.3 (3)	O3—C31—C32	116.1 (3)
C2—C3—H3	119.9	C33—C32—C31	116.0 (3)
C4—C3—H3	119.9	C33—C32—C321	122.4 (3)
C5—C4—C3	124.6 (3)	C31—C32—C321	121.6 (3)
C5—C4—C9	118.7 (3)	C34—C33—C32	122.4 (4)
C3—C4—C9	116.6 (3)	C34—C33—H33	118.8
C6—C5—C4	119.3 (3)	C32—C33—H33	118.8
C6—C5—H5	120.3	C35—C34—C33	119.9 (4)
C4—C5—H5	120.3	C35—C34—H34	120
C5—C6—C7	122.1 (3)	C33—C34—H34	120
C5—C6—H6	119	C34—C35—C36	120.0 (4)
C7—C6—H6	119	C34—C35—H35	120
C8—C7—C6	120.9 (3)	C36—C35—H35	120
C8—C7—H7	119.5	C31—C36—C35	119.3 (3)
C6—C7—H7	119.5	C31—C36—H36	120.3
O4—C8—C7	123.6 (3)	C35—C36—H36	120.3
O4—C8—C9	119.3 (3)	C12—C121—H12A	109.5
C7—C8—C9	117.1 (3)	C12—C121—H12B	109.5
N—C9—C4	122.2 (3)	H12A—C121—H12B	109.5
N—C9—C8	116.0 (3)	C12—C121—H12C	109.5
C4—C9—C8	121.8 (3)	H12A—C121—H12C	109.5
O5—C10—Rh	177.5 (3)	H12B—C121—H12C	109.5
C16—C11—C12	123.0 (3)	C22—C221—H22A	109.5
C16—C11—O1	120.4 (3)	C22—C221—H22B	109.5
C12—C11—O1	116.4 (3)	H22A—C221—H22B	109.5
C11—C12—C13	116.6 (3)	C22—C221—H22C	109.5
C11—C12—C121	121.8 (3)	H22A—C221—H22C	109.5
C13—C12—C121	121.7 (3)	H22B—C221—H22C	109.5
C14—C13—C12	121.5 (3)	C32—C321—H32A	109.5
C14—C13—H13	119.2	C32—C321—H32B	109.5
C12—C13—H13	119.2	H32A—C321—H32B	109.5
C15—C14—C13	120.3 (3)	C32—C321—H32C	109.5
C15—C14—H14	119.8	H32A—C321—H32C	109.5
C13—C14—H14	119.8	H32B—C321—H32C	109.5
C14—C15—C16	119.7 (3)
O1—P—Rh—C10	−5.51 (15)	O3—P—Rh—C10	118.24 (15)
O2—P—Rh—C10	−131.27 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2	0.93	2.54	3.118 (4)	121