1,2-Bis­(di­tolyl­phosphino)­ethane

In the solid state, the title compound, 1,2-{(p-CH₃-C₆H₄)₂P}₂C₂H₄ or C₃₀H₃₂P₂, exhibits trans geometry. There is an inversion center at the mid-point of the central C-C bond.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.123
• Data-to-parameter ratio = 21.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.62 mm
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.14 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.81 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART for WNT/2000 (Bruker 1997-2000); cell refinement: SAINT-Plus (Bruker, 1997-1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

1,2-Bis(ditolylphosphino)ethane

Crystal data

C30H32P2	F(000) = 484
Mr = 454.50	Dx = 1.190 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.5469 (5) Å	Cell parameters from 9472 reflections
b = 11.8565 (6) Å	θ = 2.2–28.3°
c = 14.3645 (7) Å	µ = 0.19 mm^−1
β = 128.731 (1)°	T = 90 K
V = 1268.40 (11) Å^3	Block, colourless
Z = 2	0.62 × 0.52 × 0.25 mm

Data collection

Bruker AXS SMART APEX CCD diffractometer	2920 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Graphite monochromator	θmax = 28.3°, θmin = 2.5°
ω scans	h = −12→12
12864 measured reflections	k = −15→15
3137 independent reflections	l = −19→18

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0698P)^2 + 0.6662P] where P = (Fo^2 + 2Fc^2)/3
3137 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.38 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
P1	0.24214 (6)	0.91172 (3)	0.42721 (3)	0.03399 (14)
C11	0.35232 (17)	0.78303 (12)	0.51218 (11)	0.0280 (3)
C21	0.10568 (16)	0.86330 (10)	0.27282 (11)	0.0250 (2)
C22	0.07017 (16)	0.75011 (11)	0.23957 (11)	0.0262 (3)
H22	0.1189	0.6935	0.2993	0.031*
C16	0.30200 (17)	0.73993 (12)	0.57746 (11)	0.0278 (3)
H16	0.2124	0.7776	0.5755	0.033*
C12	0.4862 (2)	0.72661 (15)	0.51881 (13)	0.0382 (3)
H12	0.5232	0.7544	0.4752	0.046*
C25	−0.07493 (19)	0.91217 (16)	0.06423 (15)	0.0451 (4)
H25	−0.1250	0.9685	0.0042	0.054*
C23	−0.03533 (17)	0.71911 (13)	0.12051 (12)	0.0333 (3)
H23	−0.0591	0.6415	0.0996	0.040*
C14	0.5148 (2)	0.58766 (15)	0.65240 (12)	0.0414 (4)
C15	0.38061 (18)	0.64299 (14)	0.64521 (11)	0.0339 (3)
H15	0.3419	0.6140	0.6874	0.041*
C26	0.02831 (19)	0.94389 (12)	0.18260 (14)	0.0355 (3)
H26	0.0468	1.0217	0.2028	0.043*
C1	0.4234 (3)	0.98155 (15)	0.43614 (14)	0.0480 (5)
H1A	0.4704	0.9289	0.4081	0.058*
H1B	0.3742	1.0483	0.3831	0.058*
C24	−0.10667 (18)	0.79954 (17)	0.03162 (12)	0.0426 (4)
C13	0.5657 (2)	0.63115 (18)	0.58762 (14)	0.0458 (4)
H13	0.6570	0.5943	0.5909	0.055*
C17	0.6051 (3)	0.4843 (2)	0.72847 (17)	0.0649 (6)
H17A	0.5626	0.4706	0.7743	0.097*
H17B	0.7354	0.4959	0.7834	0.097*
H17C	0.5763	0.4191	0.6773	0.097*
C27	−0.2118 (3)	0.7640 (3)	−0.09684 (15)	0.0788 (8)
H27A	−0.1285	0.7436	−0.1123	0.118*
H27B	−0.2883	0.8265	−0.1492	0.118*
H27C	−0.2869	0.6987	−0.1125	0.118*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.0532 (3)	0.0247 (2)	0.0370 (2)	−0.01477 (14)	0.0345 (2)	−0.01136 (13)
C11	0.0265 (6)	0.0360 (7)	0.0213 (5)	−0.0129 (5)	0.0149 (5)	−0.0090 (5)
C21	0.0278 (6)	0.0225 (6)	0.0284 (6)	−0.0008 (4)	0.0193 (5)	0.0001 (4)
C22	0.0265 (6)	0.0238 (6)	0.0251 (6)	−0.0022 (4)	0.0146 (5)	−0.0011 (4)
C16	0.0242 (6)	0.0384 (7)	0.0215 (6)	−0.0090 (5)	0.0146 (5)	−0.0074 (5)
C12	0.0311 (7)	0.0593 (10)	0.0320 (7)	−0.0083 (6)	0.0235 (6)	−0.0037 (6)
C25	0.0244 (6)	0.0669 (11)	0.0395 (8)	0.0118 (6)	0.0178 (6)	0.0292 (8)
C23	0.0244 (6)	0.0430 (8)	0.0292 (7)	−0.0062 (5)	0.0152 (5)	−0.0097 (5)
C14	0.0323 (7)	0.0636 (11)	0.0198 (6)	0.0086 (7)	0.0122 (6)	0.0061 (6)
C15	0.0318 (6)	0.0497 (8)	0.0204 (6)	−0.0036 (6)	0.0164 (5)	0.0005 (5)
C26	0.0333 (7)	0.0293 (6)	0.0507 (8)	0.0086 (5)	0.0296 (7)	0.0138 (6)
C1	0.0728 (11)	0.0461 (9)	0.0395 (8)	−0.0416 (8)	0.0422 (9)	−0.0247 (7)
C24	0.0185 (6)	0.0801 (12)	0.0232 (6)	−0.0015 (6)	0.0101 (5)	0.0044 (7)
C13	0.0284 (7)	0.0776 (12)	0.0315 (7)	0.0086 (7)	0.0189 (6)	0.0034 (7)
C17	0.0647 (12)	0.0898 (16)	0.0366 (9)	0.0371 (11)	0.0300 (9)	0.0258 (10)
C27	0.0328 (9)	0.165 (3)	0.0220 (8)	−0.0215 (12)	0.0091 (7)	−0.0057 (11)

Geometric parameters (Å, º)

P1—C11	1.8215 (15)	C23—H23	0.9500
P1—C21	1.8247 (13)	C14—C15	1.385 (2)
P1—C1	1.8489 (15)	C14—C13	1.390 (2)
C11—C16	1.3911 (17)	C14—C17	1.503 (2)
C11—C12	1.392 (2)	C15—H15	0.9500
C21—C26	1.3929 (18)	C26—H26	0.9500
C21—C22	1.3933 (17)	C1—C1^i	1.529 (3)
C22—C23	1.3853 (18)	C1—H1A	0.9900
C22—H22	0.9500	C1—H1B	0.9900
C16—C15	1.385 (2)	C24—C27	1.508 (2)
C16—H16	0.9500	C13—H13	0.9500
C12—C13	1.377 (3)	C17—H17A	0.9800
C12—H12	0.9500	C17—H17B	0.9800
C25—C26	1.381 (2)	C17—H17C	0.9800
C25—C24	1.385 (3)	C27—H27A	0.9800
C25—H25	0.9500	C27—H27B	0.9800
C23—C24	1.384 (2)	C27—H27C	0.9800
C11—P1—C21	102.99 (6)	C14—C15—H15	119.5
C11—P1—C1	101.86 (8)	C25—C26—C21	120.88 (14)
C21—P1—C1	98.67 (6)	C25—C26—H26	119.6
C16—C11—C12	117.83 (14)	C21—C26—H26	119.6
C16—C11—P1	117.47 (11)	C1^i—C1—P1	111.25 (13)
C12—C11—P1	124.68 (10)	C1^i—C1—H1A	109.4
C26—C21—C22	117.92 (13)	P1—C1—H1A	109.4
C26—C21—P1	118.34 (11)	C1^i—C1—H1B	109.4
C22—C21—P1	123.72 (10)	P1—C1—H1B	109.4
C23—C22—C21	120.78 (12)	H1A—C1—H1B	108.0
C23—C22—H22	119.6	C23—C24—C25	118.37 (14)
C21—C22—H22	119.6	C23—C24—C27	120.20 (19)
C15—C16—C11	120.98 (13)	C25—C24—C27	121.40 (18)
C15—C16—H16	119.5	C12—C13—C14	121.26 (14)
C11—C16—H16	119.5	C12—C13—H13	119.4
C13—C12—C11	120.96 (13)	C14—C13—H13	119.4
C13—C12—H12	119.5	C14—C17—H17A	109.5
C11—C12—H12	119.5	C14—C17—H17B	109.5
C26—C25—C24	121.04 (13)	H17A—C17—H17B	109.5
C26—C25—H25	119.5	C14—C17—H17C	109.5
C24—C25—H25	119.5	H17A—C17—H17C	109.5
C24—C23—C22	120.95 (14)	H17B—C17—H17C	109.5
C24—C23—H23	119.5	C24—C27—H27A	109.5
C22—C23—H23	119.5	C24—C27—H27B	109.5
C15—C14—C13	117.96 (15)	H27A—C27—H27B	109.5
C15—C14—C17	121.57 (15)	C24—C27—H27C	109.5
C13—C14—C17	120.47 (16)	H27A—C27—H27C	109.5
C16—C15—C14	121.00 (13)	H27B—C27—H27C	109.5
C16—C15—H15	119.5
C21—P1—C11—C16	−111.37 (10)	C11—C16—C15—C14	1.6 (2)
C1—P1—C11—C16	146.71 (10)	C13—C14—C15—C16	−1.3 (2)
C21—P1—C11—C12	70.37 (13)	C17—C14—C15—C16	178.16 (16)
C1—P1—C11—C12	−31.55 (13)	C24—C25—C26—C21	0.9 (2)
C11—P1—C21—C26	−168.09 (10)	C22—C21—C26—C25	−2.32 (19)
C1—P1—C21—C26	−63.69 (12)	P1—C21—C26—C25	179.41 (11)
C11—P1—C21—C22	13.75 (12)	C11—P1—C1—C1^i	−67.0 (2)
C1—P1—C21—C22	118.15 (12)	C21—P1—C1—C1^i	−172.30 (19)
C26—C21—C22—C23	1.53 (19)	C22—C23—C24—C25	−2.1 (2)
P1—C21—C22—C23	179.70 (10)	C22—C23—C24—C27	176.29 (14)
C12—C11—C16—C15	−1.04 (19)	C26—C25—C24—C23	1.3 (2)
P1—C11—C16—C15	−179.42 (10)	C26—C25—C24—C27	−177.06 (14)
C16—C11—C12—C13	0.1 (2)	C11—C12—C13—C14	0.2 (3)
P1—C11—C12—C13	178.38 (12)	C15—C14—C13—C12	0.3 (3)
C21—C22—C23—C24	0.7 (2)	C17—C14—C13—C12	−179.08 (17)

Symmetry code: (i) −x+1, −y+2, −z+1.