1,2-Bis­(di-4-pyridyl­phosphino)­ethane (d4pype)

The title compound (d4pype), C₂₂H₂₀N₄P₂, crystallizes as a discrete molecular species disposed about a crystallographic inversion centre at the mid-point of the central C-C bond.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.052
• wR factor = 0.182
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.10
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C6
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

   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
   2 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: MSC/AFC7 Diffractometer Control Software for Windows (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software for Windows; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 1980-2001).

1,2-bis(di-4-pyridylphosphino)ethane

Crystal data

C22H20N4P2	F(000) = 420
Mr = 402.37	Dx = 1.321 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 16 reflections
a = 14.073 (6) Å	θ = 10.4–17.1°
b = 8.228 (2) Å	µ = 0.23 mm^−1
c = 9.200 (2) Å	T = 295 K
β = 108.33 (3)°	Prism, colorless
V = 1011.2 (6) Å^3	0.15 × 0.10 × 0.05 mm
Z = 2

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.038
Radiation source: Rigaku rotating anode	θmax = 27.5°, θmin = 2.9°
Graphite monochromator	h = −7→18
ω–2θ scans	k = 0→10
2552 measured reflections	l = −11→11
2323 independent reflections	3 standard reflections every 150 reflections
1170 reflections with I > 2σ(I)	intensity decay: 0.9%

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.182	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0879P)^2] where P = (Fo^2 + 2Fc^2)/3
2323 reflections	(Δ/σ)max = 0.016
128 parameters	Δρmax = 0.80 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. The scan width was (1.73 + 0.30tanθ)° with an ω scan speed of 16° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
P1	1.01084 (7)	0.39633 (12)	0.77915 (11)	0.0356 (3)
N1	0.8656 (2)	−0.1085 (4)	0.7997 (4)	0.0483 (11)
N2	1.3113 (3)	0.2467 (5)	0.7066 (6)	0.0670 (16)
C1	0.9591 (2)	0.1935 (4)	0.7933 (4)	0.0313 (10)
C2	0.8618 (3)	0.1833 (5)	0.7985 (4)	0.0405 (11)
C3	0.8193 (3)	0.0325 (5)	0.8040 (5)	0.0486 (14)
C4	0.9583 (3)	−0.0976 (5)	0.7932 (5)	0.0482 (13)
C5	1.0072 (3)	0.0479 (4)	0.7903 (5)	0.0419 (11)
C6	1.1325 (3)	0.3388 (4)	0.7601 (4)	0.0339 (10)
C7	1.1374 (3)	0.3166 (6)	0.6132 (5)	0.0546 (16)
C8	1.2270 (4)	0.2687 (7)	0.5945 (6)	0.071 (2)
C9	1.3050 (3)	0.2681 (7)	0.8453 (6)	0.0700 (19)
C10	1.2190 (3)	0.3133 (7)	0.8778 (5)	0.0593 (16)
C11	1.0454 (3)	0.4717 (4)	0.9783 (4)	0.0335 (11)
H2	0.82440	0.27940	0.79800	0.0490*
H3	0.75360	0.02910	0.81160	0.0580*
H4	0.99330	−0.19570	0.79060	0.0580*
H5	1.07380	0.04740	0.78610	0.0500*
H7	1.07990	0.33390	0.52660	0.0660*
H8	1.22780	0.25030	0.49290	0.0850*
H9	1.36400	0.25130	0.92940	0.0840*
H10	1.22010	0.32640	0.98090	0.0710*
H11A	1.08860	0.56010	0.97380	0.0370*
H11B	1.08950	0.39520	1.05190	0.0370*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0407 (5)	0.0300 (5)	0.0386 (5)	0.0031 (5)	0.0161 (4)	−0.0010 (5)
N1	0.0458 (19)	0.0400 (18)	0.061 (2)	−0.0036 (17)	0.0196 (16)	−0.0071 (17)
N2	0.059 (2)	0.066 (3)	0.094 (3)	−0.008 (2)	0.050 (2)	−0.010 (2)
C1	0.0316 (17)	0.0303 (19)	0.0313 (18)	0.0008 (15)	0.0087 (14)	−0.0023 (14)
C2	0.0347 (19)	0.032 (2)	0.051 (2)	0.0063 (17)	0.0079 (17)	−0.0037 (17)
C3	0.040 (2)	0.046 (2)	0.060 (3)	−0.0070 (19)	0.016 (2)	−0.015 (2)
C4	0.048 (2)	0.0317 (18)	0.067 (3)	0.006 (2)	0.021 (2)	−0.003 (2)
C5	0.0376 (19)	0.0312 (18)	0.062 (2)	0.0018 (17)	0.0229 (18)	−0.0002 (18)
C6	0.0400 (19)	0.0270 (16)	0.0392 (19)	−0.0032 (16)	0.0191 (16)	−0.0007 (15)
C7	0.058 (3)	0.069 (3)	0.045 (2)	0.000 (2)	0.028 (2)	0.001 (2)
C8	0.084 (4)	0.085 (4)	0.065 (3)	−0.003 (3)	0.053 (3)	−0.004 (3)
C9	0.046 (3)	0.088 (4)	0.076 (3)	0.006 (2)	0.019 (2)	−0.012 (3)
C10	0.049 (2)	0.085 (4)	0.046 (2)	0.016 (3)	0.018 (2)	−0.010 (2)
C11	0.0380 (19)	0.0266 (17)	0.0374 (19)	−0.0011 (15)	0.0142 (15)	−0.0040 (15)

Geometric parameters (Å, º)

P1—C1	1.842 (3)	C7—C8	1.383 (7)
P1—C6	1.837 (4)	C9—C10	1.386 (7)
P1—C11	1.849 (4)	C11—C11^i	1.526 (6)
N1—C3	1.337 (5)	C2—H2	0.9491
N1—C4	1.328 (5)	C3—H3	0.9493
N2—C8	1.317 (7)	C4—H4	0.9498
N2—C9	1.318 (7)	C5—H5	0.9501
C1—C2	1.388 (5)	C7—H7	0.9510
C1—C5	1.381 (5)	C8—H8	0.9505
C2—C3	1.385 (6)	C9—H9	0.9503
C4—C5	1.385 (6)	C10—H10	0.9499
C6—C7	1.387 (6)	C11—H11A	0.9572
C6—C10	1.367 (6)	C11—H11B	0.9877
N2···C6^ii	3.440 (6)	H2···C3^ix	2.8484
N1···H8^iii	2.8478	H2···H3^ix	2.3972
N1···H11B^iv	2.6991	H2···C11^i	3.0684
N1···H2^v	2.7012	H2···H11A^i	2.4564
N2···H4^vi	2.7825	H2···H8^viii	2.5800
N2···H5^vi	2.9449	H3···H2^v	2.3972
N2···H11A^ii	2.9269	H3···H8^viii	2.5670
C2···C11^i	3.506 (5)	H4···N2^ii	2.7825
C5···C7	3.575 (6)	H5···C6	2.5715
C5···C10	3.577 (7)	H5···C7	3.0221
C6···N2^vi	3.440 (6)	H5···C10	2.9308
C7···C5	3.575 (6)	H5···N2^ii	2.9449
C10···C5	3.577 (7)	H8···N1^iii	2.8478
C11···C2^i	3.506 (5)	H8···C2^x	3.0290
C2···H10^vii	2.9759	H8···C3^x	3.0463
C2···H8^viii	3.0290	H8···H2^x	2.5800
C2···H11A^i	2.9006	H8···H3^x	2.5670
C3···H10^vii	3.0859	H10···C11	2.7272
C3···H2^v	2.8484	H10···H11B	2.2091
C3···H8^viii	3.0463	H10···C2^xi	2.9759
C4···H11B^iv	3.0137	H10···C3^xi	3.0859
C6···H5	2.5715	H11A···C10	3.0481
C7···H5	3.0221	H11A···N2^vi	2.9269
C10···H5	2.9308	H11A···C2^i	2.9006
C10···H11B	2.8595	H11A···H2^i	2.4564
C10···H11A	3.0481	H11B···C10	2.8595
C11···H10	2.7272	H11B···H10	2.2091
C11···H2^i	3.0684	H11B···N1^iv	2.6991
H2···N1^ix	2.7012	H11B···C4^iv	3.0137
C1—P1—C6	100.04 (15)	C3—C2—H2	120.08
C1—P1—C11	102.74 (16)	N1—C3—H3	118.13
C6—P1—C11	102.61 (18)	C2—C3—H3	118.09
C3—N1—C4	115.9 (4)	N1—C4—H4	117.93
C8—N2—C9	114.9 (5)	C5—C4—H4	117.99
P1—C1—C2	118.3 (3)	C1—C5—H5	120.05
P1—C1—C5	125.3 (3)	C4—C5—H5	119.96
C2—C1—C5	116.3 (3)	C6—C7—H7	120.45
C1—C2—C3	119.8 (4)	C8—C7—H7	120.50
N1—C3—C2	123.8 (4)	N2—C8—H8	117.51
N1—C4—C5	124.1 (4)	C7—C8—H8	117.46
C1—C5—C4	120.0 (4)	N2—C9—H9	117.46
P1—C6—C7	117.4 (3)	C10—C9—H9	117.53
P1—C6—C10	126.0 (3)	C6—C10—H10	120.28
C7—C6—C10	116.5 (4)	C9—C10—H10	120.32
C6—C7—C8	119.1 (4)	P1—C11—H11A	100.65
N2—C8—C7	125.0 (5)	P1—C11—H11B	112.24
N2—C9—C10	125.0 (5)	H11A—C11—H11B	104.08
C6—C10—C9	119.4 (4)	C11^i—C11—H11A	112.01
P1—C11—C11^i	112.4 (3)	C11^i—C11—H11B	114.35
C1—C2—H2	120.08
C6—P1—C1—C2	−175.5 (3)	P1—C1—C2—C3	177.9 (3)
C6—P1—C1—C5	0.5 (4)	C5—C1—C2—C3	1.5 (5)
C11—P1—C1—C2	79.0 (3)	P1—C1—C5—C4	−176.3 (3)
C11—P1—C1—C5	−105.0 (4)	C2—C1—C5—C4	−0.3 (6)
C1—P1—C6—C7	90.7 (3)	C1—C2—C3—N1	−2.2 (6)
C1—P1—C6—C10	−88.3 (4)	N1—C4—C5—C1	−0.4 (7)
C11—P1—C6—C7	−163.7 (3)	C10—C6—C7—C8	0.9 (7)
C11—P1—C6—C10	17.4 (4)	P1—C6—C10—C9	179.1 (4)
C1—P1—C11—C11^i	−76.7 (3)	C7—C6—C10—C9	0.1 (7)
C6—P1—C11—C11^i	179.8 (2)	P1—C6—C7—C8	−178.2 (4)
C4—N1—C3—C2	1.5 (6)	C6—C7—C8—N2	−2.4 (8)
C3—N1—C4—C5	−0.2 (6)	N2—C9—C10—C6	0.0 (9)
C9—N2—C8—C7	2.4 (8)	P1—C11—C11^i—P1^i	179.98 (16)
C8—N2—C9—C10	−1.2 (8)

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+5/2, y−1/2, −z+3/2; (iii) −x+2, −y, −z+1; (iv) −x+2, −y, −z+2; (v) −x+3/2, y−1/2, −z+3/2; (vi) −x+5/2, y+1/2, −z+3/2; (vii) x−1/2, −y+1/2, z−1/2; (viii) x−1/2, −y+1/2, z+1/2; (ix) −x+3/2, y+1/2, −z+3/2; (x) x+1/2, −y+1/2, z−1/2; (xi) x+1/2, −y+1/2, z+1/2.