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.
Supporting information
CCDC reference: 226982
Key indicators
- Single-crystal X-ray study
- T = 90 K
- Mean (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
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
top
Crystal data top
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) Å3 | Block, colourless |
Z = 2 | 0.62 × 0.52 × 0.25 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0698P)2 + 0.6662P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C1i | 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) | C1i—C1—P1 | 111.25 (13) |
C12—C11—P1 | 124.68 (10) | C1i—C1—H1A | 109.4 |
C26—C21—C22 | 117.92 (13) | P1—C1—H1A | 109.4 |
C26—C21—P1 | 118.34 (11) | C1i—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—C1i | −67.0 (2) |
C1—P1—C21—C22 | 118.15 (12) | C21—P1—C1—C1i | −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. |