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The molecule of the title compound, C
32H
30N
2O
2P
2, an oxidative derivative of
N,
N′-bis[(diphenylphosphino)methyl]-1,4-phenylenediamine, occupies a special position on an inversion center. The crystal structure contains N—H
O=P hydrogen bonds, connecting the molecules to form an infinite chain along [100].
Supporting information
CCDC reference: 610690
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.007 Å
- R factor = 0.078
- wR factor = 0.251
- Data-to-parameter ratio = 19.2
checkCIF/PLATON results
No syntax errors found
Alert level C
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.251
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.28 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.09 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C7 -C12 1.36 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
10 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
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
N,
N'-Bis[(diphenylphosphinoyl)methyl]-1,4-phenylenediamine
top
Crystal data top
C32H30N2O2P2 | Z = 2 |
Mr = 536.52 | F(000) = 564 |
Monoclinic, P21/c | Dx = 1.286 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 6.0688 (7) Å | θ = 2.7–22.0° |
b = 11.0033 (13) Å | µ = 0.19 mm−1 |
c = 20.759 (2) Å | T = 292 K |
β = 91.284 (2)° | Prism, brown |
V = 1385.9 (3) Å3 | 0.30 × 0.20 × 0.10 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3301 independent reflections |
Radiation source: fine-focus sealed tube | 2043 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.072 |
ω scans | θmax = 28.3°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −8→7 |
Tmin = 0.956, Tmax = 0.981 | k = −14→14 |
9412 measured reflections | l = −23→27 |
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)] = 0.078 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.251 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.1492P)2] where P = (Fo2 + 2Fc2)/3 |
3301 reflections | (Δ/σ)max = 0.004 |
172 parameters | Δρmax = 0.62 e Å−3 |
36 restraints | Δρmin = −0.36 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 | 0.21496 (15) | 0.69778 (9) | 0.14094 (5) | 0.0380 (4) | |
O1 | 0.0314 (4) | 0.7388 (3) | 0.09785 (15) | 0.0545 (8) | |
N1 | 0.5739 (5) | 0.8217 (3) | 0.09475 (16) | 0.0463 (9) | |
H1A | 0.6845 | 0.7738 | 0.0904 | 0.056* | |
C1 | 0.3389 (6) | 0.5596 (4) | 0.11406 (18) | 0.0397 (9) | |
C2 | 0.5457 (8) | 0.5183 (4) | 0.1357 (2) | 0.0611 (13) | |
H2A | 0.6260 | 0.5632 | 0.1660 | 0.073* | |
C3 | 0.6302 (8) | 0.4127 (5) | 0.1124 (3) | 0.0733 (15) | |
H3A | 0.7659 | 0.3850 | 0.1280 | 0.088* | |
C4 | 0.5173 (12) | 0.3467 (5) | 0.0661 (3) | 0.0792 (17) | |
H4A | 0.5777 | 0.2755 | 0.0501 | 0.095* | |
C5 | 0.3147 (10) | 0.3861 (5) | 0.0436 (2) | 0.0698 (14) | |
H5A | 0.2383 | 0.3416 | 0.0123 | 0.084* | |
C6 | 0.2251 (8) | 0.4916 (4) | 0.0673 (2) | 0.0543 (11) | |
H6A | 0.0878 | 0.5177 | 0.0521 | 0.065* | |
C7 | 0.1224 (8) | 0.6772 (4) | 0.2222 (2) | 0.0506 (10) | |
C8 | 0.2030 (13) | 0.5946 (6) | 0.2644 (3) | 0.1009 (16) | |
H8A | 0.3130 | 0.5413 | 0.2519 | 0.121* | |
C9 | 0.1210 (15) | 0.5884 (7) | 0.3280 (3) | 0.1134 (18) | |
H9A | 0.1806 | 0.5334 | 0.3576 | 0.136* | |
C10 | −0.0415 (12) | 0.6620 (6) | 0.3446 (3) | 0.0932 (16) | |
H10A | −0.1024 | 0.6543 | 0.3851 | 0.112* | |
C11 | −0.1194 (10) | 0.7473 (6) | 0.3039 (3) | 0.0827 (14) | |
H11A | −0.2275 | 0.8012 | 0.3170 | 0.099* | |
C12 | −0.0391 (8) | 0.7543 (6) | 0.2433 (2) | 0.0661 (12) | |
H12A | −0.0953 | 0.8132 | 0.2152 | 0.079* | |
C13 | 0.4367 (7) | 0.8078 (4) | 0.15031 (19) | 0.0431 (9) | |
H13A | 0.3729 | 0.8861 | 0.1604 | 0.052* | |
H13B | 0.5294 | 0.7837 | 0.1868 | 0.052* | |
C14 | 0.5325 (6) | 0.9108 (3) | 0.04783 (17) | 0.0346 (8) | |
C15 | 0.3301 (6) | 0.9671 (3) | 0.03903 (17) | 0.0367 (8) | |
H15A | 0.2141 | 0.9457 | 0.0653 | 0.044* | |
C16 | 0.7026 (6) | 0.9458 (3) | 0.00783 (18) | 0.0388 (9) | |
H16A | 0.8404 | 0.9096 | 0.0129 | 0.047* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0321 (6) | 0.0435 (6) | 0.0387 (6) | 0.0031 (4) | 0.0050 (4) | 0.0082 (4) |
O1 | 0.0364 (16) | 0.0635 (19) | 0.0633 (19) | 0.0042 (14) | −0.0036 (13) | 0.0143 (15) |
N1 | 0.0364 (18) | 0.050 (2) | 0.053 (2) | 0.0090 (14) | 0.0127 (14) | 0.0187 (15) |
C1 | 0.0349 (19) | 0.047 (2) | 0.038 (2) | 0.0000 (16) | 0.0078 (15) | 0.0042 (16) |
C2 | 0.047 (3) | 0.053 (3) | 0.083 (3) | 0.006 (2) | −0.007 (2) | −0.008 (2) |
C3 | 0.047 (3) | 0.067 (3) | 0.106 (4) | 0.015 (2) | 0.010 (3) | −0.001 (3) |
C4 | 0.108 (5) | 0.054 (3) | 0.077 (4) | 0.009 (3) | 0.039 (3) | −0.006 (3) |
C5 | 0.094 (4) | 0.067 (3) | 0.049 (3) | −0.006 (3) | 0.005 (3) | −0.012 (2) |
C6 | 0.065 (3) | 0.057 (3) | 0.041 (2) | −0.003 (2) | 0.000 (2) | −0.001 (2) |
C7 | 0.059 (2) | 0.049 (2) | 0.044 (2) | 0.0005 (18) | 0.0178 (18) | 0.0052 (17) |
C8 | 0.162 (4) | 0.078 (3) | 0.065 (3) | 0.038 (3) | 0.043 (3) | 0.023 (2) |
C9 | 0.177 (4) | 0.086 (3) | 0.079 (3) | 0.024 (3) | 0.042 (3) | 0.031 (3) |
C10 | 0.132 (4) | 0.080 (3) | 0.070 (3) | −0.004 (3) | 0.053 (3) | 0.002 (3) |
C11 | 0.084 (3) | 0.100 (3) | 0.065 (3) | 0.002 (3) | 0.028 (2) | −0.017 (3) |
C12 | 0.059 (3) | 0.088 (3) | 0.052 (2) | 0.008 (2) | 0.011 (2) | −0.007 (2) |
C13 | 0.043 (2) | 0.047 (2) | 0.040 (2) | −0.0011 (17) | 0.0007 (16) | 0.0084 (17) |
C14 | 0.0342 (19) | 0.0307 (18) | 0.0389 (19) | −0.0007 (14) | 0.0022 (14) | 0.0047 (15) |
C15 | 0.0293 (18) | 0.039 (2) | 0.043 (2) | 0.0001 (15) | 0.0094 (15) | 0.0073 (15) |
C16 | 0.0300 (18) | 0.042 (2) | 0.045 (2) | 0.0060 (15) | 0.0057 (15) | 0.0060 (16) |
Geometric parameters (Å, º) top
P1—O1 | 1.483 (3) | C7—C12 | 1.375 (6) |
P1—C1 | 1.791 (4) | C8—C9 | 1.422 (8) |
P1—C7 | 1.804 (4) | C8—H8A | 0.9300 |
P1—C13 | 1.817 (4) | C9—C10 | 1.328 (9) |
N1—C14 | 1.401 (5) | C9—H9A | 0.9300 |
N1—C13 | 1.446 (5) | C10—C11 | 1.340 (9) |
N1—H1A | 0.8600 | C10—H10A | 0.9300 |
C1—C6 | 1.396 (6) | C11—C12 | 1.363 (7) |
C1—C2 | 1.399 (6) | C11—H11A | 0.9300 |
C2—C3 | 1.363 (7) | C12—H12A | 0.9300 |
C2—H2A | 0.9300 | C13—H13A | 0.9700 |
C3—C4 | 1.375 (8) | C13—H13B | 0.9700 |
C3—H3A | 0.9300 | C14—C15 | 1.384 (5) |
C4—C5 | 1.376 (8) | C14—C16 | 1.393 (5) |
C4—H4A | 0.9300 | C15—C16i | 1.377 (5) |
C5—C6 | 1.377 (7) | C15—H15A | 0.9300 |
C5—H5A | 0.9300 | C16—C15i | 1.377 (5) |
C6—H6A | 0.9300 | C16—H16A | 0.9300 |
C7—C8 | 1.346 (7) | | |
| | | |
O1—P1—C1 | 112.67 (19) | C7—C8—C9 | 120.4 (6) |
O1—P1—C7 | 110.9 (2) | C7—C8—H8A | 119.8 |
C1—P1—C7 | 109.06 (19) | C9—C8—H8A | 119.8 |
O1—P1—C13 | 113.96 (18) | C10—C9—C8 | 119.3 (6) |
C1—P1—C13 | 106.49 (19) | C10—C9—H9A | 120.4 |
C7—P1—C13 | 103.22 (19) | C8—C9—H9A | 120.4 |
C14—N1—C13 | 122.1 (3) | C9—C10—C11 | 121.1 (6) |
C14—N1—H1A | 119.0 | C9—C10—H10A | 119.4 |
C13—N1—H1A | 119.0 | C11—C10—H10A | 119.4 |
C6—C1—C2 | 118.4 (4) | C10—C11—C12 | 119.6 (6) |
C6—C1—P1 | 117.8 (3) | C10—C11—H11A | 120.2 |
C2—C1—P1 | 123.7 (3) | C12—C11—H11A | 120.2 |
C3—C2—C1 | 120.3 (4) | C11—C12—C7 | 122.1 (5) |
C3—C2—H2A | 119.8 | C11—C12—H12A | 119.0 |
C1—C2—H2A | 119.8 | C7—C12—H12A | 119.0 |
C2—C3—C4 | 120.8 (5) | N1—C13—P1 | 115.1 (3) |
C2—C3—H3A | 119.6 | N1—C13—H13A | 108.5 |
C4—C3—H3A | 119.6 | P1—C13—H13A | 108.5 |
C3—C4—C5 | 119.9 (5) | N1—C13—H13B | 108.5 |
C3—C4—H4A | 120.0 | P1—C13—H13B | 108.5 |
C5—C4—H4A | 120.0 | H13A—C13—H13B | 107.5 |
C4—C5—C6 | 120.1 (5) | C15—C14—C16 | 117.7 (3) |
C4—C5—H5A | 120.0 | C15—C14—N1 | 123.4 (3) |
C6—C5—H5A | 120.0 | C16—C14—N1 | 118.9 (3) |
C5—C6—C1 | 120.5 (4) | C16i—C15—C14 | 121.2 (3) |
C5—C6—H6A | 119.8 | C16i—C15—H15A | 119.4 |
C1—C6—H6A | 119.8 | C14—C15—H15A | 119.4 |
C8—C7—C12 | 117.4 (5) | C15i—C16—C14 | 121.1 (3) |
C8—C7—P1 | 125.2 (4) | C15i—C16—H16A | 119.5 |
C12—C7—P1 | 117.3 (4) | C14—C16—H16A | 119.5 |
Symmetry code: (i) −x+1, −y+2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1ii | 0.86 | 2.15 | 2.922 (4) | 151 |
Symmetry code: (ii) x+1, y, z. |
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