fac-Tri­carbonyl(2,9-di­methyl-1,10-phenanthroline)(2,6-di­methyl­phenyl isocyanide)­rhenium(I) hexa­fluoro­phosphate

In the title compound, [Re(C₉H₉N)(C₁₄H₁₂N₂)(CO)₃]PF₆, the complex cation adopts a distorted octahedral geometry, with the Re atom at the center and a facial disposition of the three carbonyl ligands.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.021
• wR factor = 0.051
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.97 Deg.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.91 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   C3      ..       6.65 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Re1    -   C2      ..       6.20 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Re1    -   C3      ..       8.87 su

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 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
   4 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR2002 (Burla et al., 2003); 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).

fac-Tricarbonyl(2,9-dimethyl-1,10-phenanthroline)(2,6-dimethylphenyl isocyanide)rhenium(I) hexafluorophosphate

Crystal data

[Re(C9H9N)(C14H12N2)(CO)3]PF6	F(000) = 1464
Mr = 754.63	Dx = 1.877 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 24 reflections
a = 14.510 (4) Å	θ = 1–25°
b = 11.223 (4) Å	µ = 4.69 mm^−1
c = 17.887 (5) Å	T = 100 K
β = 113.53 (2)°	Prism, yellow
V = 2670.6 (14) Å^3	0.5 × 0.3 × 0.3 mm
Z = 4

Data collection

Enraf Nonius CAD4 diffractometer	Rint = 0.026
non–profiled ω/2θ scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: empirical (using intensity measurements) (refined from ΔF; Walker & Stuart, 1983)	h = 0→17
Tmin = 0.198, Tmax = 0.245	k = 0→13
4871 measured reflections	l = −21→19
4682 independent reflections	3 standard reflections every 60 min
3991 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	396 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.021	w = 1/[σ^2(Fo^2) + (0.0226P)^2 + 4.1906P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.051	(Δ/σ)max = 0.002
S = 1.09	Δρmax = 0.57 e Å^−3
4682 reflections	Δρmin = −0.60 e Å^−3
365 parameters

Special details

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
Re1	0.123071 (10)	0.894497 (12)	0.291446 (8)	0.00968 (5)
P1	0.65276 (7)	0.06428 (9)	0.16381 (6)	0.0156 (2)
F3	0.73794 (18)	−0.0364 (2)	0.19099 (14)	0.0291 (6)
F5	0.73090 (17)	0.1576 (2)	0.22299 (14)	0.0259 (5)
N1	0.1352 (2)	0.8233 (3)	0.40936 (17)	0.0107 (6)
C12	0.2961 (3)	1.2494 (4)	0.4683 (3)	0.0308 (10)
H12A	0.2441	1.2488	0.4142	0.046*
H12B	0.2995	1.3269	0.492	0.046*
H12C	0.2814	1.1909	0.5011	0.046*
F2	0.57434 (18)	−0.0283 (2)	0.10403 (14)	0.0282 (6)
F1	0.68484 (16)	0.1031 (2)	0.09122 (13)	0.0217 (5)
N2	0.0591 (2)	1.0354 (3)	0.34206 (17)	0.0115 (6)
C8	0.5786 (3)	1.1632 (4)	0.4574 (2)	0.0222 (9)
H8	0.6407	1.1448	0.4565	0.027*
F4	0.61992 (19)	0.0254 (2)	0.23578 (14)	0.0301 (6)
C11	0.3956 (3)	1.2207 (3)	0.4643 (2)	0.0178 (8)
F6	0.56676 (15)	0.1647 (2)	0.13602 (14)	0.0220 (5)
C10	0.4793 (3)	1.2925 (4)	0.5008 (2)	0.0217 (9)
H10	0.4741	1.3614	0.5278	0.026*
C15	−0.0340 (3)	1.1452 (4)	0.2158 (2)	0.0230 (9)
H15A	0.0157	1.1749	0.1978	0.034*
H15B	−0.0902	1.1989	0.199	0.034*
H15C	−0.0563	1.0681	0.1923	0.034*
O3	0.1147 (2)	1.0077 (2)	0.13274 (15)	0.0200 (6)
O1	−0.0857 (2)	0.7758 (3)	0.19786 (17)	0.0266 (7)
C14	0.0931 (2)	1.0246 (3)	0.4254 (2)	0.0116 (7)
N3	0.3247 (2)	1.0444 (3)	0.38721 (18)	0.0147 (7)
C6	0.5047 (3)	0.9827 (4)	0.3695 (3)	0.0270 (10)
H6A	0.4616	0.9944	0.3132	0.041*
H6B	0.484	0.9126	0.3894	0.041*
H6C	0.5728	0.9732	0.375	0.041*
C13	0.1322 (2)	0.9121 (3)	0.4608 (2)	0.0106 (7)
C3	0.1158 (3)	0.9684 (3)	0.1926 (2)	0.0161 (8)
O2	0.2505 (2)	0.7087 (2)	0.25044 (18)	0.0244 (6)
C24	0.1861 (3)	0.6898 (3)	0.5226 (2)	0.0151 (8)
H24	0.2018	0.6123	0.5419	0.018*
C4	0.2542 (3)	0.9870 (3)	0.3544 (2)	0.0122 (7)
C23	0.1910 (3)	0.7788 (3)	0.5753 (2)	0.0148 (8)
H23	0.2132	0.7634	0.6309	0.018*
C19	0.0849 (2)	1.1169 (3)	0.4752 (2)	0.0137 (7)
C7	0.4977 (3)	1.0891 (3)	0.4182 (2)	0.0175 (8)
C22	0.1622 (2)	0.8947 (3)	0.5451 (2)	0.0130 (7)
C16	0.0107 (3)	1.1352 (3)	0.3069 (2)	0.0154 (8)
C20	0.1222 (3)	1.0989 (4)	0.5618 (2)	0.0170 (8)
H20	0.1208	1.1615	0.5953	0.02*
C2	0.1992 (3)	0.7738 (3)	0.2652 (2)	0.0164 (8)
C25	0.1575 (2)	0.7132 (3)	0.4388 (2)	0.0120 (7)
C26	0.1501 (3)	0.6103 (3)	0.3829 (2)	0.0173 (8)
H26A	0.0938	0.6221	0.332	0.026*
H26B	0.1411	0.5377	0.4076	0.026*
H26C	0.2106	0.6054	0.3735	0.026*
C17	0.0003 (3)	1.2308 (3)	0.3541 (2)	0.0180 (8)
H17	−0.0336	1.2993	0.3284	0.022*
C1	−0.0101 (3)	0.8170 (3)	0.2325 (2)	0.0168 (8)
C21	0.1590 (3)	0.9929 (3)	0.5948 (2)	0.0163 (8)
H21	0.1828	0.9831	0.651	0.02*
C18	0.0396 (3)	1.2238 (3)	0.4373 (2)	0.0177 (8)
H18	0.0364	1.2889	0.4684	0.021*
C9	0.5692 (3)	1.2639 (4)	0.4979 (2)	0.0234 (9)
H9	0.6246	1.3129	0.5235	0.028*
C5	0.4075 (3)	1.1197 (3)	0.4241 (2)	0.0147 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.00960 (7)	0.00964 (7)	0.00964 (7)	−0.00029 (6)	0.00369 (5)	−0.00098 (6)
P1	0.0205 (5)	0.0131 (5)	0.0147 (5)	0.0011 (4)	0.0086 (4)	0.0006 (4)
F3	0.0390 (14)	0.0240 (14)	0.0233 (13)	0.0153 (11)	0.0116 (11)	0.0050 (10)
F5	0.0239 (12)	0.0289 (13)	0.0228 (12)	−0.0040 (10)	0.0073 (10)	−0.0105 (10)
N1	0.0063 (13)	0.0126 (16)	0.0134 (15)	−0.0017 (12)	0.0040 (12)	−0.0017 (13)
C12	0.024 (2)	0.033 (3)	0.039 (3)	−0.0040 (19)	0.017 (2)	−0.016 (2)
F2	0.0348 (14)	0.0182 (13)	0.0307 (13)	−0.0093 (11)	0.0119 (11)	−0.0048 (11)
F1	0.0251 (12)	0.0259 (12)	0.0179 (11)	0.0009 (11)	0.0126 (9)	0.0031 (10)
N2	0.0105 (14)	0.0118 (16)	0.0127 (15)	0.0002 (12)	0.0051 (12)	−0.0001 (12)
C8	0.0133 (18)	0.030 (2)	0.025 (2)	0.0002 (17)	0.0101 (17)	0.0071 (18)
F4	0.0465 (15)	0.0281 (14)	0.0260 (13)	0.0032 (12)	0.0253 (12)	0.0083 (11)
C11	0.0175 (19)	0.018 (2)	0.0174 (19)	−0.0043 (16)	0.0067 (16)	−0.0012 (16)
F6	0.0180 (11)	0.0183 (12)	0.0321 (13)	0.0042 (10)	0.0123 (10)	0.0051 (10)
C10	0.020 (2)	0.021 (2)	0.022 (2)	−0.0062 (17)	0.0065 (17)	−0.0009 (17)
C15	0.024 (2)	0.022 (2)	0.020 (2)	0.0090 (17)	0.0062 (17)	0.0048 (17)
O3	0.0255 (15)	0.0222 (15)	0.0138 (14)	−0.0008 (12)	0.0094 (11)	0.0028 (12)
O1	0.0181 (15)	0.0377 (18)	0.0200 (15)	−0.0111 (14)	0.0036 (12)	−0.0042 (13)
C14	0.0036 (15)	0.0159 (19)	0.0156 (18)	−0.0017 (14)	0.0041 (14)	−0.0005 (15)
N3	0.0140 (16)	0.0163 (17)	0.0131 (15)	−0.0019 (14)	0.0047 (13)	0.0023 (13)
C6	0.028 (2)	0.029 (2)	0.030 (2)	0.0017 (19)	0.0171 (19)	0.0005 (19)
C13	0.0051 (15)	0.0128 (19)	0.0147 (17)	−0.0011 (14)	0.0050 (13)	−0.0022 (14)
C3	0.0125 (18)	0.0111 (19)	0.025 (2)	−0.0014 (14)	0.0073 (16)	−0.0059 (16)
O2	0.0294 (15)	0.0224 (16)	0.0246 (15)	0.0088 (13)	0.0140 (13)	−0.0047 (13)
C24	0.0120 (17)	0.0145 (18)	0.021 (2)	0.0015 (15)	0.0092 (15)	0.0051 (16)
C4	0.0140 (18)	0.0123 (18)	0.0120 (18)	0.0028 (16)	0.0070 (15)	0.0006 (15)
C23	0.0093 (17)	0.023 (2)	0.0145 (19)	0.0003 (15)	0.0071 (15)	0.0056 (16)
C19	0.0081 (16)	0.0158 (19)	0.0197 (19)	−0.0050 (15)	0.0082 (14)	−0.0057 (16)
C7	0.0165 (18)	0.021 (2)	0.0160 (19)	0.0003 (16)	0.0076 (15)	0.0078 (16)
C22	0.0073 (15)	0.0183 (18)	0.0157 (18)	0.0001 (16)	0.0069 (14)	0.0016 (16)
C16	0.0128 (18)	0.0136 (19)	0.020 (2)	0.0006 (14)	0.0068 (16)	0.0025 (15)
C20	0.0133 (17)	0.021 (2)	0.0198 (19)	−0.0022 (16)	0.0099 (15)	−0.0083 (17)
C2	0.021 (2)	0.0131 (19)	0.0147 (19)	−0.0053 (16)	0.0072 (16)	−0.0009 (15)
C25	0.0069 (16)	0.0132 (19)	0.0174 (19)	0.0002 (14)	0.0064 (14)	0.0030 (15)
C26	0.0199 (19)	0.0101 (18)	0.023 (2)	−0.0006 (16)	0.0093 (16)	0.0007 (16)
C17	0.0145 (18)	0.016 (2)	0.024 (2)	0.0028 (16)	0.0086 (16)	−0.0014 (16)
C1	0.020 (2)	0.0150 (19)	0.0157 (19)	−0.0002 (17)	0.0078 (16)	−0.0006 (16)
C21	0.0138 (18)	0.024 (2)	0.0142 (18)	−0.0035 (16)	0.0084 (15)	−0.0032 (16)
C18	0.0137 (18)	0.016 (2)	0.026 (2)	0.0001 (15)	0.0109 (17)	−0.0044 (16)
C9	0.018 (2)	0.024 (2)	0.023 (2)	−0.0091 (17)	0.0025 (17)	0.0025 (18)
C5	0.0143 (17)	0.017 (2)	0.0104 (17)	−0.0034 (15)	0.0024 (14)	0.0046 (15)

Geometric parameters (Å, º)

Re1—C3	1.918 (4)	O1—C1	1.122 (5)
Re1—C2	1.920 (4)	C14—C19	1.401 (5)
Re1—C1	1.994 (4)	C14—C13	1.426 (5)
Re1—C4	2.063 (4)	N3—C4	1.152 (5)
Re1—N1	2.196 (3)	N3—C5	1.401 (5)
Re1—N2	2.203 (3)	C6—C7	1.504 (6)
P1—F2	1.595 (2)	C6—H6A	0.96
P1—F5	1.595 (2)	C6—H6B	0.96
P1—F3	1.600 (2)	C6—H6C	0.96
P1—F4	1.601 (2)	C13—C22	1.406 (5)
P1—F1	1.605 (2)	O2—C2	1.147 (5)
P1—F6	1.606 (2)	C24—C23	1.356 (5)
N1—C25	1.332 (5)	C24—C25	1.411 (5)
N1—C13	1.368 (4)	C24—H24	0.93
C12—C11	1.509 (5)	C23—C22	1.407 (5)
C12—H12A	0.96	C23—H23	0.93
C12—H12B	0.96	C19—C18	1.405 (5)
C12—H12C	0.96	C19—C20	1.435 (5)
N2—C16	1.338 (5)	C7—C5	1.397 (5)
N2—C14	1.376 (4)	C22—C21	1.428 (5)
C8—C9	1.379 (6)	C16—C17	1.410 (5)
C8—C7	1.380 (6)	C20—C21	1.341 (6)
C8—H8	0.93	C20—H20	0.93
C11—C10	1.384 (5)	C25—C26	1.503 (5)
C11—C5	1.389 (5)	C26—H26A	0.96
C10—C9	1.364 (6)	C26—H26B	0.96
C10—H10	0.93	C26—H26C	0.96
C15—C16	1.498 (5)	C17—C18	1.367 (5)
C15—H15A	0.96	C17—H17	0.93
C15—H15B	0.96	C21—H21	0.93
C15—H15C	0.96	C18—H18	0.93
O3—C3	1.151 (5)	C9—H9	0.93
C3—Re1—C2	84.56 (15)	C4—N3—C5	176.7 (4)
C3—Re1—C1	90.93 (15)	C7—C6—H6A	109.5
C2—Re1—C1	95.39 (16)	C7—C6—H6B	109.5
C3—Re1—C4	89.12 (15)	H6A—C6—H6B	109.5
C2—Re1—C4	89.59 (15)	C7—C6—H6C	109.5
C1—Re1—C4	175.01 (14)	H6A—C6—H6C	109.5
C3—Re1—N1	175.53 (13)	H6B—C6—H6C	109.5
C2—Re1—N1	98.32 (13)	N1—C13—C22	122.7 (3)
C1—Re1—N1	92.21 (13)	N1—C13—C14	117.5 (3)
C4—Re1—N1	87.48 (12)	C22—C13—C14	119.7 (3)
C3—Re1—N2	101.03 (13)	O3—C3—Re1	176.2 (3)
C2—Re1—N2	169.88 (13)	C23—C24—C25	120.9 (4)
C1—Re1—N2	92.98 (13)	C23—C24—H24	119.6
C4—Re1—N2	82.12 (12)	C25—C24—H24	119.6
N1—Re1—N2	75.63 (11)	N3—C4—Re1	176.1 (3)
F2—P1—F5	179.51 (14)	C24—C23—C22	119.2 (3)
F2—P1—F3	90.10 (14)	C24—C23—H23	120.4
F5—P1—F3	90.23 (14)	C22—C23—H23	120.4
F2—P1—F4	90.00 (14)	C14—C19—C18	117.8 (3)
F5—P1—F4	90.36 (14)	C14—C19—C20	119.3 (3)
F3—P1—F4	90.29 (13)	C18—C19—C20	122.9 (3)
F2—P1—F1	89.65 (13)	C8—C7—C5	116.4 (4)
F5—P1—F1	89.98 (13)	C8—C7—C6	122.2 (4)
F3—P1—F1	89.95 (13)	C5—C7—C6	121.3 (3)
F4—P1—F1	179.58 (15)	C13—C22—C23	117.2 (3)
F2—P1—F6	89.50 (13)	C13—C22—C21	119.2 (3)
F5—P1—F6	90.16 (13)	C23—C22—C21	123.6 (3)
F3—P1—F6	179.60 (16)	N2—C16—C17	121.1 (3)
F4—P1—F6	89.79 (13)	N2—C16—C15	119.5 (3)
F1—P1—F6	89.97 (12)	C17—C16—C15	119.4 (3)
C25—N1—C13	118.5 (3)	C21—C20—C19	120.8 (3)
C25—N1—Re1	129.1 (2)	C21—C20—H20	119.6
C13—N1—Re1	111.7 (2)	C19—C20—H20	119.6
C11—C12—H12A	109.5	O2—C2—Re1	174.4 (3)
C11—C12—H12B	109.5	N1—C25—C24	121.0 (3)
H12A—C12—H12B	109.5	N1—C25—C26	120.5 (3)
C11—C12—H12C	109.5	C24—C25—C26	118.4 (3)
H12A—C12—H12C	109.5	C25—C26—H26A	109.5
H12B—C12—H12C	109.5	C25—C26—H26B	109.5
C16—N2—C14	118.5 (3)	H26A—C26—H26B	109.5
C16—N2—Re1	129.5 (2)	C25—C26—H26C	109.5
C14—N2—Re1	110.8 (2)	H26A—C26—H26C	109.5
C9—C8—C7	121.2 (4)	H26B—C26—H26C	109.5
C9—C8—H8	119.4	C18—C17—C16	120.7 (4)
C7—C8—H8	119.4	C18—C17—H17	119.6
C10—C11—C5	116.9 (4)	C16—C17—H17	119.6
C10—C11—C12	121.9 (4)	O1—C1—Re1	178.1 (4)
C5—C11—C12	121.2 (3)	C20—C21—C22	121.1 (3)
C9—C10—C11	121.1 (4)	C20—C21—H21	119.4
C9—C10—H10	119.5	C22—C21—H21	119.4
C11—C10—H10	119.5	C17—C18—C19	119.1 (3)
C16—C15—H15A	109.5	C17—C18—H18	120.5
C16—C15—H15B	109.5	C19—C18—H18	120.5
H15A—C15—H15B	109.5	C10—C9—C8	120.7 (4)
C16—C15—H15C	109.5	C10—C9—H9	119.7
H15A—C15—H15C	109.5	C8—C9—H9	119.7
H15B—C15—H15C	109.5	C11—C5—C7	123.6 (3)
N2—C14—C19	122.6 (3)	C11—C5—N3	118.4 (3)
N2—C14—C13	117.7 (3)	C7—C5—N3	118.0 (3)
C19—C14—C13	119.5 (3)