Bis­[μ-bis(2,6-di-1-naphthyl­phenyl)­phosphanido]­bis­[(tetra­hydro­furan)­sodium(I)]

The molecular structure of the tetra­hydro­furan (THF) adduct of the sodium salt of the primary phosphane DnpPH₂ (Dnp is 2,6-di-1-naphthyl­phenyl), of composition [Na(THF){P(H)Dnp}(THF)]₂ or [Na₂(C₂₆H₁₈P)₂(C₄H₈O)₂], is reported. The dimeric and centrosymmetric complex features a three-coordinate Na atom in a slightly pyramidal coordination environment, with a sum of angles around sodium of 348.9°, and a P atom in a highly distorted tetrahedral coordination environment.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.053
• wR factor = 0.154
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.22 Ratio

   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
   1 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

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Bis[µ-bis(2,6-di-1-naphthylphenyl)phosphanido]bis[(tetrahydrofuran)sodium(I)]

Crystal data

[Na2(C26H18P)2(C4H8O)2]	Z = 1
Mr = 912.94	F(000) = 480
Triclinic, P1	Dx = 1.263 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.5408 (9) Å	Cell parameters from 750 reflections
b = 11.5054 (10) Å	θ = 2.0–25.0°
c = 11.6538 (10) Å	µ = 0.15 mm^−1
α = 61.951 (1)°	T = 173 K
β = 75.180 (1)°	Block, red
γ = 87.642 (1)°	0.40 × 0.30 × 0.20 mm
V = 1200.64 (18) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	4213 independent reflections
Radiation source: fine-focus sealed tube	3354 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
Tmin = 0.913, Tmax = 0.970	k = −13→13
11571 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2^(Fo2) + (0.0886P)2^+ 0.5175P] where P = (Fo2 + 2Fc2^)/3
4213 reflections	(Δ/^σ)max < 0.001
312 parameters	Δ^ρmax = 0.51 e Å−3
0 restraints	Δ^ρmin =^−0.35 e Å−3

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.

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1	0.64121 (7)	0.38479 (6)	0.45661 (6)	0.0430 (2)
Na1	0.36953 (12)	0.38854 (11)	0.50390 (13)	0.0602 (3)
O1	0.1865 (2)	0.2522 (2)	0.6150 (2)	0.0748 (7)
C1	0.6952 (2)	0.2281 (2)	0.5622 (2)	0.0328 (5)
C2	0.6505 (2)	0.1729 (2)	0.7050 (2)	0.0327 (5)
C3	0.6892 (2)	0.0539 (2)	0.7895 (2)	0.0370 (6)
H3A	0.6572	0.0191	0.8845	0.044*
C4	0.7743 (2)	−0.0157 (2)	0.7379 (2)	0.0383 (6)
H4A	0.8019	−0.0967	0.7967	0.046*
C5	0.8183 (2)	0.0349 (2)	0.5997 (2)	0.0358 (5)
H5A	0.8759	−0.0129	0.5639	0.043*
C6	0.7802 (2)	0.1539 (2)	0.5116 (2)	0.0315 (5)
C7	0.8321 (2)	0.2033 (2)	0.3627 (2)	0.0335 (5)
C8	0.7493 (2)	0.1947 (2)	0.2869 (2)	0.0333 (5)
C9	0.6188 (2)	0.1340 (2)	0.3479 (2)	0.0351 (5)
H9A	0.5825	0.1005	0.4423	0.042*
C10	0.5440 (3)	0.1228 (2)	0.2725 (3)	0.0421 (6)
H10A	0.4573	0.0794	0.3156	0.050*
C11	0.5936 (3)	0.1744 (3)	0.1330 (3)	0.0470 (7)
H11A	0.5409	0.1664	0.0816	0.056*
C12	0.7172 (3)	0.2357 (2)	0.0714 (3)	0.0451 (6)
H12A	0.7495	0.2714	−0.0237	0.054*
C13	0.7998 (2)	0.2485 (2)	0.1437 (2)	0.0369 (6)
C14	0.9297 (3)	0.3105 (3)	0.0817 (3)	0.0473 (7)
H14A	0.9631	0.3498	−0.0136	0.057*
C15	1.0077 (3)	0.3148 (3)	0.1568 (3)	0.0471 (7)
H15A	1.0955	0.3551	0.1139	0.057*
C16	0.9587 (2)	0.2599 (2)	0.2972 (3)	0.0398 (6)
H16A	1.0150	0.2620	0.3482	0.048*
C17	0.5561 (2)	0.2421 (2)	0.7672 (2)	0.0338 (5)
C18	0.5999 (2)	0.3575 (2)	0.7682 (2)	0.0351 (5)
C19	0.7334 (2)	0.4119 (2)	0.7112 (2)	0.0371 (5)
H19A	0.7966	0.3708	0.6715	0.044*
C20	0.7713 (3)	0.5232 (3)	0.7132 (3)	0.0512 (7)
H20A	0.8611	0.5580	0.6759	0.061*
C21	0.6797 (3)	0.5863 (3)	0.7693 (3)	0.0575 (8)
H21A	0.7074	0.6641	0.7689	0.069*
C22	0.5515 (3)	0.5370 (3)	0.8243 (3)	0.0503 (7)
H22A	0.4903	0.5814	0.8615	0.060*
C23	0.5067 (3)	0.4205 (2)	0.8276 (2)	0.0387 (6)
C24	0.3739 (3)	0.3677 (3)	0.8862 (2)	0.0466 (7)
H24A	0.3117	0.4099	0.9254	0.056*
C25	0.3346 (3)	0.2554 (3)	0.8866 (3)	0.0481 (7)
H25A	0.2454	0.2190	0.9273	0.058*
C26	0.4267 (2)	0.1936 (2)	0.8264 (2)	0.0386 (6)
H26A	0.3977	0.1161	0.8272	0.046*
C27	0.1654 (4)	0.1111 (3)	0.6722 (4)	0.0798 (11)
H27A	0.2503	0.0711	0.6744	0.096*
H27B	0.1227	0.0883	0.6181	0.096*
C28	0.0797 (4)	0.0625 (3)	0.8095 (4)	0.0745 (10)
H28A	0.1323	0.0343	0.8760	0.089*
H28B	0.0176	−0.0129	0.8341	0.089*
C29	0.0066 (3)	0.1810 (3)	0.8032 (4)	0.0694 (9)
H29A	−0.0828	0.1713	0.7945	0.083*
H29B	−0.0024	0.1860	0.8874	0.083*
C30	0.079 (2)	0.3008 (16)	0.688 (2)	0.061 (4)	0.38 (3)
H30A	0.1155	0.3565	0.7183	0.073*	0.38 (3)
H30B	0.0213	0.3528	0.6306	0.073*	0.38 (3)
C30A	0.0538 (12)	0.2813 (12)	0.6548 (13)	0.062 (3)	0.62 (3)
H30C	−0.0011	0.2701	0.6027	0.075*	0.62 (3)
H30D	0.0516	0.3727	0.6417	0.075*	0.62 (3)
H1	0.702 (3)	0.406 (3)	0.333 (3)	0.050 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0661 (5)	0.0335 (4)	0.0322 (4)	0.0210 (3)	−0.0170 (3)	−0.0172 (3)
Na1	0.0622 (8)	0.0484 (7)	0.0717 (8)	0.0122 (5)	−0.0202 (6)	−0.0293 (6)
O1	0.0679 (14)	0.0550 (13)	0.0800 (16)	0.0217 (11)	−0.0020 (12)	−0.0252 (12)
C1	0.0407 (13)	0.0283 (11)	0.0323 (12)	0.0053 (10)	−0.0127 (10)	−0.0154 (10)
C2	0.0387 (13)	0.0298 (12)	0.0334 (12)	0.0039 (10)	−0.0120 (10)	−0.0170 (10)
C3	0.0467 (14)	0.0337 (13)	0.0316 (13)	0.0051 (10)	−0.0140 (11)	−0.0147 (10)
C4	0.0488 (15)	0.0294 (12)	0.0405 (14)	0.0116 (11)	−0.0213 (11)	−0.0155 (11)
C5	0.0364 (13)	0.0315 (12)	0.0440 (14)	0.0084 (10)	−0.0124 (11)	−0.0212 (11)
C6	0.0345 (12)	0.0286 (11)	0.0352 (12)	0.0033 (9)	−0.0103 (10)	−0.0178 (10)
C7	0.0399 (13)	0.0263 (11)	0.0364 (13)	0.0074 (10)	−0.0097 (10)	−0.0171 (10)
C8	0.0434 (14)	0.0243 (11)	0.0364 (13)	0.0080 (10)	−0.0131 (10)	−0.0170 (10)
C9	0.0414 (13)	0.0311 (12)	0.0312 (12)	0.0038 (10)	−0.0088 (10)	−0.0139 (10)
C10	0.0482 (15)	0.0350 (13)	0.0453 (15)	0.0050 (11)	−0.0186 (12)	−0.0181 (11)
C11	0.0653 (19)	0.0379 (14)	0.0476 (16)	0.0101 (13)	−0.0271 (14)	−0.0225 (12)
C12	0.0692 (19)	0.0369 (14)	0.0329 (13)	0.0111 (13)	−0.0170 (13)	−0.0184 (11)
C13	0.0485 (15)	0.0282 (12)	0.0337 (13)	0.0076 (10)	−0.0083 (11)	−0.0160 (10)
C14	0.0577 (17)	0.0378 (14)	0.0365 (14)	0.0014 (12)	0.0014 (12)	−0.0166 (11)
C15	0.0408 (15)	0.0424 (15)	0.0511 (16)	−0.0020 (11)	−0.0013 (12)	−0.0215 (13)
C16	0.0381 (14)	0.0339 (13)	0.0485 (15)	0.0007 (10)	−0.0085 (11)	−0.0218 (12)
C17	0.0422 (14)	0.0327 (12)	0.0274 (12)	0.0061 (10)	−0.0137 (10)	−0.0131 (10)
C18	0.0489 (15)	0.0319 (12)	0.0252 (11)	0.0085 (10)	−0.0141 (10)	−0.0125 (10)
C19	0.0425 (14)	0.0362 (13)	0.0366 (13)	0.0073 (10)	−0.0138 (11)	−0.0192 (11)
C20	0.0653 (19)	0.0421 (15)	0.0528 (17)	−0.0010 (13)	−0.0215 (14)	−0.0245 (13)
C21	0.089 (2)	0.0402 (15)	0.0562 (18)	0.0071 (15)	−0.0280 (17)	−0.0291 (14)
C22	0.075 (2)	0.0414 (15)	0.0403 (15)	0.0167 (14)	−0.0197 (14)	−0.0231 (12)
C23	0.0539 (16)	0.0372 (13)	0.0277 (12)	0.0162 (11)	−0.0149 (11)	−0.0166 (10)
C24	0.0554 (17)	0.0477 (15)	0.0330 (13)	0.0188 (13)	−0.0099 (12)	−0.0183 (12)
C25	0.0407 (15)	0.0555 (17)	0.0364 (14)	0.0071 (12)	−0.0063 (11)	−0.0147 (12)
C26	0.0408 (14)	0.0379 (13)	0.0345 (13)	0.0036 (11)	−0.0095 (10)	−0.0155 (11)
C27	0.093 (3)	0.060 (2)	0.115 (3)	0.0248 (19)	−0.036 (2)	−0.062 (2)
C28	0.067 (2)	0.0514 (19)	0.098 (3)	0.0043 (16)	−0.028 (2)	−0.0273 (19)
C29	0.062 (2)	0.072 (2)	0.083 (2)	0.0117 (17)	−0.0225 (18)	−0.043 (2)
C30	0.061 (8)	0.049 (7)	0.092 (10)	0.024 (5)	−0.021 (6)	−0.049 (6)
C30A	0.062 (5)	0.046 (4)	0.083 (6)	0.019 (3)	−0.014 (4)	−0.038 (3)

Geometric parameters (Å, º)

P1—C1	1.810 (2)	C14—H14A	0.9500
P1—Na1	2.7769 (14)	C15—C16	1.401 (4)
P1—Na1^i	2.8468 (13)	C15—H15A	0.9500
P1—H1	1.32 (3)	C16—H16A	0.9500
P1—P1^i	4.153 (1)	C17—C26	1.366 (3)
Na1—O1	2.218 (3)	C17—C18	1.429 (3)
Na1—P1^i	2.8468 (13)	C18—C19	1.420 (3)
Na1—C19^i	2.917 (3)	C18—C23	1.426 (3)
Na1—C20^i	3.003 (3)	C18—Na1^i	3.088 (2)
Na1—C18^i	3.088 (2)	C19—C20	1.370 (4)
Na1—Na1^i	3.793 (2)	C19—Na1^i	2.917 (3)
O1—C30A	1.435 (10)	C19—H19A	0.9500
O1—C27	1.437 (4)	C20—C21	1.398 (4)
O1—C30	1.495 (17)	C20—Na1^i	3.003 (3)
C1—C6	1.420 (3)	C20—H20A	0.9500
C1—C2	1.422 (3)	C21—C22	1.355 (4)
C2—C3	1.379 (3)	C21—H21A	0.9500
C2—C17	1.503 (3)	C22—C23	1.421 (4)
C3—C4	1.388 (3)	C22—H22A	0.9500
C3—H3A	0.9500	C23—C24	1.409 (4)
C4—C5	1.381 (3)	C24—C25	1.371 (4)
C4—H4A	0.9500	C24—H24A	0.9500
C5—C6	1.391 (3)	C25—C26	1.415 (4)
C5—H5A	0.9500	C25—H25A	0.9500
C6—C7	1.499 (3)	C26—H26A	0.9500
C7—C16	1.367 (3)	C27—C28	1.466 (5)
C7—C8	1.427 (3)	C27—H27A	0.9900
C8—C9	1.413 (3)	C27—H27B	0.9900
C8—C13	1.433 (3)	C28—C29	1.519 (5)
C9—C10	1.372 (3)	C28—H28A	0.9900
C9—H9A	0.9500	C28—H28B	0.9900
C10—C11	1.397 (4)	C29—C30	1.448 (19)
C10—H10A	0.9500	C29—C30A	1.517 (12)
C11—C12	1.353 (4)	C29—H29A	0.9900
C11—H11A	0.9500	C29—H29B	0.9900
C12—C13	1.412 (4)	C30—H30A	0.9900
C12—H12A	0.9500	C30—H30B	0.9900
C13—C14	1.413 (4)	C30A—H30C	0.9900
C14—C15	1.363 (4)	C30A—H30D	0.9900
C1—P1—Na1	114.44 (8)	C16—C15—H15A	119.9
C1—P1—Na1^i	125.33 (8)	C7—C16—C15	121.9 (2)
Na1—P1—Na1^i	84.81 (4)	C7—C16—H16A	119.0
C1—P1—H1	103.1 (12)	C15—C16—H16A	119.0
Na1—P1—H1	113.3 (11)	C26—C17—C18	118.8 (2)
Na1^i—P1—H1	115.4 (12)	C26—C17—C2	120.1 (2)
O1—Na1—P1	140.49 (7)	C18—C17—C2	121.1 (2)
O1—Na1—P1^i	113.25 (8)	C19—C18—C23	118.9 (2)
P1—Na1—P1^i	95.19 (4)	C19—C18—C17	122.0 (2)
O1—Na1—C19^i	96.58 (9)	C23—C18—C17	119.1 (2)
P1—Na1—C19^i	117.82 (7)	C19—C18—Na1^i	69.67 (13)
P1^i—Na1—C19^i	74.64 (6)	C23—C18—Na1^i	87.11 (14)
O1—Na1—C20^i	79.16 (10)	C17—C18—Na1^i	113.05 (14)
P1—Na1—C20^i	123.77 (8)	C20—C19—C18	120.3 (2)
P1^i—Na1—C20^i	100.07 (6)	C20—C19—Na1^i	80.16 (16)
C19^i—Na1—C20^i	26.70 (7)	C18—C19—Na1^i	83.17 (13)
O1—Na1—C18^i	123.43 (9)	C20—C19—H19A	119.9
P1—Na1—C18^i	91.15 (6)	C18—C19—H19A	119.9
P1^i—Na1—C18^i	69.92 (5)	Na1^i—C19—H19A	106.9
C19^i—Na1—C18^i	27.17 (7)	C19—C20—C21	120.9 (3)
C20^i—Na1—C18^i	46.77 (7)	C19—C20—Na1^i	73.14 (15)
O1—Na1—Na1^i	149.44 (10)	C21—C20—Na1^i	86.49 (18)
P1—Na1—Na1^i	48.37 (3)	C19—C20—H20A	119.5
P1^i—Na1—Na1^i	46.82 (3)	C21—C20—H20A	119.5
C19^i—Na1—Na1^i	98.21 (6)	Na1^i—C20—H20A	110.9
C20^i—Na1—Na1^i	122.56 (7)	C22—C21—C20	120.3 (3)
C18^i—Na1—Na1^i	75.93 (6)	C22—C21—H21A	119.9
C30A—O1—C27	99.7 (6)	C20—C21—H21A	119.9
C27—O1—C30	110.0 (7)	C21—C22—C23	121.5 (3)
C30A—O1—Na1	129.1 (6)	C21—C22—H22A	119.3
C27—O1—Na1	131.2 (2)	C23—C22—H22A	119.3
C30—O1—Na1	114.2 (8)	C24—C23—C22	121.7 (2)
C6—C1—C2	116.7 (2)	C24—C23—C18	120.1 (2)
C6—C1—P1	124.01 (17)	C22—C23—C18	118.2 (2)
C2—C1—P1	119.31 (17)	C25—C24—C23	119.9 (2)
C3—C2—C1	121.4 (2)	C25—C24—H24A	120.1
C3—C2—C17	118.4 (2)	C23—C24—H24A	120.1
C1—C2—C17	120.22 (19)	C24—C25—C26	120.1 (2)
C2—C3—C4	121.0 (2)	C24—C25—H25A	119.9
C2—C3—H3A	119.5	C26—C25—H25A	119.9
C4—C3—H3A	119.5	C17—C26—C25	122.0 (2)
C5—C4—C3	118.9 (2)	C17—C26—H26A	119.0
C5—C4—H4A	120.6	C25—C26—H26A	119.0
C3—C4—H4A	120.6	O1—C27—C28	106.5 (3)
C4—C5—C6	121.6 (2)	O1—C27—H27A	110.4
C4—C5—H5A	119.2	C28—C27—H27A	110.4
C6—C5—H5A	119.2	O1—C27—H27B	110.4
C5—C6—C1	120.5 (2)	C28—C27—H27B	110.4
C5—C6—C7	118.8 (2)	H27A—C27—H27B	108.6
C1—C6—C7	120.76 (19)	C27—C28—C29	103.7 (3)
C16—C7—C8	119.1 (2)	C27—C28—H28A	111.0
C16—C7—C6	120.4 (2)	C29—C28—H28A	111.0
C8—C7—C6	120.5 (2)	C27—C28—H28B	111.0
C9—C8—C7	122.4 (2)	C29—C28—H28B	111.0
C9—C8—C13	118.4 (2)	H28A—C28—H28B	109.0
C7—C8—C13	119.2 (2)	C30—C29—C28	109.5 (7)
C10—C9—C8	120.8 (2)	C30A—C29—C28	102.3 (5)
C10—C9—H9A	119.6	C30—C29—H29A	109.8
C8—C9—H9A	119.6	C30A—C29—H29A	91.1
C9—C10—C11	120.8 (2)	C28—C29—H29A	109.8
C9—C10—H10A	119.6	C30—C29—H29B	109.8
C11—C10—H10A	119.6	C30A—C29—H29B	133.3
C12—C11—C10	119.7 (2)	C28—C29—H29B	109.8
C12—C11—H11A	120.1	H29A—C29—H29B	108.2
C10—C11—H11A	120.1	C29—C30—O1	104.1 (10)
C11—C12—C13	122.2 (2)	C29—C30—H30A	110.9
C11—C12—H12A	118.9	O1—C30—H30A	110.9
C13—C12—H12A	118.9	C29—C30—H30B	110.9
C12—C13—C14	123.1 (2)	O1—C30—H30B	110.9
C12—C13—C8	118.1 (2)	H30A—C30—H30B	109.0
C14—C13—C8	118.8 (2)	O1—C30A—C29	103.7 (7)
C15—C14—C13	120.8 (2)	O1—C30A—H30C	111.0
C15—C14—H14A	119.6	C29—C30A—H30C	111.0
C13—C14—H14A	119.6	O1—C30A—H30D	111.0
C14—C15—C16	120.2 (2)	C29—C30A—H30D	111.0
C14—C15—H15A	119.9	H30C—C30A—H30D	109.0

Symmetry code: (i) −x+1, −y+1, −z+1.