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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Oct 5;67(Pt 11):m1498. doi: 10.1107/S1600536811040074

(SP-4-2)-Chlorido{N-[2-(diphenyl­phosphan­yl)benzyl­idene]benzyl­amine-κ2 P,N}(meth­yl)palladium(II)

Haleden Chiririwa a,*, Reinout Meijboom a
PMCID: PMC3246930  PMID: 22219750

Abstract

In the title PdII complex, [Pd(CH3)Cl(C26H22NP)], the PdII atom is coordinated in a slightly distorted square-planar geometry by the imino N and phosphane P atoms of the ligand, by one chloride ion and by a methyl ligand. The methyl group is trans to the N atom of the ligand.

Related literature

For structures with related ligands, see: Coleman et al. (2001 ▶); Ghilardi et al. (1992 ▶); Sanchez et al. (1998 ▶, 1999 ▶, 2001 ▶); Chiririwa et al. (2011 ▶). graphic file with name e-67-m1498-scheme1.jpg

Experimental

Crystal data

  • [Pd(CH3)Cl(C26H22NP)]

  • M r = 536.30

  • Monoclinic, Inline graphic

  • a = 10.0147 (8) Å

  • b = 21.8935 (18) Å

  • c = 10.7478 (8) Å

  • β = 94.192 (2)°

  • V = 2350.2 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.99 mm−1

  • T = 173 K

  • 0.13 × 0.12 × 0.03 mm

Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.883, T max = 0.971

  • 32545 measured reflections

  • 5809 independent reflections

  • 4857 reflections with I > 2σ(I)

  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034

  • wR(F 2) = 0.091

  • S = 1.03

  • 5809 reflections

  • 281 parameters

  • H-atom parameters constrained

  • Δρmax = 1.21 e Å−3

  • Δρmin = −0.62 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040074/im2317sup1.cif

e-67-m1498-sup1.cif (31.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040074/im2317Isup2.hkl

e-67-m1498-Isup2.hkl (284.4KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

Financial assistance from the South African National Research Foundation (SA NRF) and the Research Fund of the University of Johannesburg is gratefully acknowledged.

supplementary crystallographic information

Comment

In recent years, palladium complexes with iminophosphane ligands of the type N-[(2-diphenylphosphanyl)benzylidene]amine type have been used as catalyst precursors for a range of organic reactions. Our group is interested in these types of complexes and we recently reported one such type of complex (Chiririwa et al., 2011). The molecular structure of the title compound revealed a slightly distorted square planar geometry around the palladium metal center. The Pd—P distance of 2.1939 (7) Å is within the expected range and close to the values determined for the dihalide complexes of the same ligand (2.1925 (9) Å, Coleman et al., 2001).

Experimental

To a solution of the precursor [PdClMe(COD)] (0.07 g, 0.27 mmol) in anhydrous CH2Cl2 (10 ml) was added the calculated amount of iminophosphane ligand in CH2Cl2 solution, and the reaction wmixture as stirred at room temperature for 1 h. The yellow solution was then concentrated under reduced pressure to half volume and the addition of hexane caused precipitation of complex, which was filtered off, washed with Et2O and dried under vacuum for 4 h. Orange crystals of the title compound were obtained in 50% yield. Crystals suitable for X-ray diffraction studies were obtained by slow evaporation of a DMSO-d6/CH2Cl2 solution of the title compound at room temperature.

Refinement

The aromatic, methylene, and methyl H atoms were placed in geometrically idealized positions (C—H = 0.95–0.98) and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C) for aromatic and methylene H atoms, and Uiso(H) = 1.5Ueq(C) for methyl H atoms respectively.

Figures

Fig. 1.

Fig. 1.

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The structure of the title compound, showing 50% probability displacement ellipsoids.

Crystal data

[Pd(CH3)Cl(C26H22NP)] F(000) = 1088
Mr = 536.30 Dx = 1.516 Mg m−3
Monoclinic, P21/n Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn Cell parameters from 7032 reflections
a = 10.0147 (8) Å θ = 1.9–30.7°
b = 21.8935 (18) Å µ = 0.99 mm−1
c = 10.7478 (8) Å T = 173 K
β = 94.192 (2)° Needle, orange
V = 2350.2 (3) Å3 0.13 × 0.12 × 0.03 mm
Z = 4
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Data collection

Bruker SMART APEX diffractometer 5809 independent reflections
Radiation source: fine-focus sealed tube 4857 reflections with I > 2σ(I)
graphite Rint = 0.043
Detector resolution: 0 pixels mm-1 θmax = 28.3°, θmin = 2.1°
n/a scans h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) k = −29→29
Tmin = 0.883, Tmax = 0.971 l = −14→13
32545 measured reflections
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Refinement

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)] = 0.034 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091 H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0424P)2 + 2.9231P] where P = (Fo2 + 2Fc2)/3
5809 reflections (Δ/σ)max < 0.001
281 parameters Δρmax = 1.21 e Å−3
0 restraints Δρmin = −0.62 e Å−3
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Pd1 0.14680 (2) 0.803769 (10) 0.037830 (19) 0.02303 (7)
Cl2 0.00399 (7) 0.71581 (4) 0.04518 (7) 0.03620 (17)
C3 0.03775 (19) 0.84358 (9) 0.17933 (18) 0.0076 (4)
H3A 0.0318 0.8878 0.1664 0.011*
H3B 0.0837 0.8351 0.2612 0.011*
H3C −0.0526 0.8261 0.1757 0.011*
P4 0.27908 (6) 0.88365 (3) 0.03775 (6) 0.02086 (14)
C5 0.2990 (3) 0.93431 (13) 0.1722 (2) 0.0244 (5)
C6 0.3269 (3) 0.90852 (15) 0.2906 (3) 0.0320 (6)
H6 0.3298 0.8654 0.2999 0.038*
C7 0.3503 (3) 0.94591 (17) 0.3946 (3) 0.0378 (7)
H7 0.3684 0.9283 0.4749 0.045*
C8 0.3470 (3) 1.00886 (17) 0.3808 (3) 0.0383 (7)
H8 0.3635 1.0344 0.4517 0.046*
C9 0.3199 (3) 1.03468 (15) 0.2641 (3) 0.0359 (7)
H9 0.3178 1.0778 0.2552 0.043*
C10 0.2958 (3) 0.99750 (14) 0.1599 (3) 0.0289 (6)
H10 0.2770 1.0154 0.0800 0.035*
C11 0.2327 (3) 0.93237 (12) −0.0962 (2) 0.0230 (5)
C12 0.0979 (3) 0.94571 (15) −0.1249 (3) 0.0342 (7)
H12 0.0322 0.9300 −0.0741 0.041*
C13 0.0595 (3) 0.98184 (17) −0.2272 (3) 0.0432 (8)
H13 −0.0324 0.9912 −0.2457 0.052*
C14 0.1539 (3) 1.00428 (16) −0.3024 (3) 0.0399 (8)
H14 0.1270 1.0289 −0.3726 0.048*
C15 0.2879 (3) 0.99095 (15) −0.2756 (3) 0.0354 (7)
H15 0.3528 1.0063 −0.3277 0.042*
C16 0.3278 (3) 0.95514 (14) −0.1728 (3) 0.0282 (6)
H16 0.4200 0.9461 −0.1546 0.034*
C17 0.4509 (3) 0.86061 (13) 0.0161 (2) 0.0226 (5)
C18 0.5588 (3) 0.89176 (13) 0.0761 (3) 0.0261 (6)
H18 0.5423 0.9237 0.1330 0.031*
C19 0.6903 (3) 0.87685 (14) 0.0541 (3) 0.0292 (6)
H19 0.7625 0.8981 0.0968 0.035*
C20 0.7159 (3) 0.83128 (15) −0.0296 (3) 0.0308 (6)
H20 0.8055 0.8209 −0.0444 0.037*
C21 0.6097 (3) 0.80071 (14) −0.0920 (3) 0.0297 (6)
H21 0.6273 0.7703 −0.1517 0.036*
C22 0.4772 (3) 0.81369 (13) −0.0687 (3) 0.0250 (6)
C23 0.3733 (3) 0.77818 (14) −0.1409 (3) 0.0281 (6)
H23 0.3998 0.7590 −0.2144 0.034*
N24 0.2515 (2) 0.77023 (11) −0.1160 (2) 0.0268 (5)
C25 0.1677 (3) 0.73599 (14) −0.2122 (3) 0.0320 (6)
H25A 0.1118 0.7058 −0.1712 0.038*
H25B 0.2261 0.7135 −0.2668 0.038*
C26 0.0787 (3) 0.77936 (14) −0.2899 (3) 0.0298 (6)
C27 0.1329 (3) 0.81835 (16) −0.3762 (3) 0.0382 (7)
H27 0.2268 0.8186 −0.3838 0.046*
C28 0.0509 (4) 0.85650 (18) −0.4506 (3) 0.0459 (8)
H28 0.0885 0.8829 −0.5089 0.055*
C29 −0.0870 (4) 0.85608 (18) −0.4398 (3) 0.0471 (8)
H29 −0.1435 0.8819 −0.4916 0.057*
C30 −0.1421 (3) 0.81823 (17) −0.3541 (3) 0.0407 (8)
H30 −0.2360 0.8182 −0.3467 0.049*
C31 −0.0594 (3) 0.78024 (15) −0.2789 (3) 0.0338 (7)
H31 −0.0972 0.7546 −0.2194 0.041*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Pd1 0.02098 (11) 0.02433 (12) 0.02424 (11) −0.00327 (8) 0.00494 (7) 0.00132 (8)
Cl2 0.0312 (4) 0.0368 (4) 0.0411 (4) −0.0125 (3) 0.0065 (3) 0.0015 (3)
C3 0.0080 (8) 0.0087 (9) 0.0069 (9) −0.0025 (7) 0.0057 (7) −0.0015 (7)
P4 0.0200 (3) 0.0219 (3) 0.0212 (3) −0.0011 (2) 0.0052 (2) 0.0004 (3)
C5 0.0223 (12) 0.0276 (14) 0.0243 (13) −0.0017 (10) 0.0077 (10) −0.0030 (11)
C6 0.0357 (15) 0.0345 (16) 0.0260 (14) −0.0035 (13) 0.0034 (12) 0.0022 (12)
C7 0.0412 (17) 0.049 (2) 0.0231 (14) −0.0068 (15) 0.0023 (12) −0.0017 (13)
C8 0.0374 (16) 0.048 (2) 0.0296 (16) −0.0045 (14) 0.0058 (13) −0.0136 (14)
C9 0.0383 (17) 0.0307 (16) 0.0395 (17) −0.0004 (13) 0.0090 (13) −0.0085 (13)
C10 0.0305 (14) 0.0300 (15) 0.0269 (14) 0.0009 (12) 0.0079 (11) −0.0007 (12)
C11 0.0251 (13) 0.0227 (13) 0.0215 (12) −0.0010 (10) 0.0027 (10) 0.0004 (10)
C12 0.0251 (14) 0.0404 (18) 0.0379 (17) 0.0046 (12) 0.0080 (12) 0.0095 (14)
C13 0.0321 (16) 0.051 (2) 0.046 (2) 0.0076 (15) −0.0019 (14) 0.0114 (16)
C14 0.0482 (19) 0.0397 (19) 0.0306 (16) 0.0012 (15) −0.0047 (14) 0.0118 (14)
C15 0.0402 (17) 0.0419 (18) 0.0245 (14) −0.0071 (14) 0.0053 (12) 0.0054 (13)
C16 0.0254 (13) 0.0342 (16) 0.0251 (13) −0.0027 (11) 0.0030 (11) 0.0029 (12)
C17 0.0210 (12) 0.0263 (14) 0.0209 (12) −0.0002 (10) 0.0038 (9) 0.0040 (10)
C18 0.0261 (13) 0.0257 (14) 0.0266 (14) −0.0003 (11) 0.0026 (11) 0.0007 (11)
C19 0.0213 (12) 0.0338 (16) 0.0321 (15) −0.0018 (11) −0.0007 (11) 0.0060 (12)
C20 0.0214 (13) 0.0379 (17) 0.0335 (15) 0.0044 (12) 0.0051 (11) 0.0044 (13)
C21 0.0258 (13) 0.0339 (16) 0.0301 (14) 0.0046 (12) 0.0066 (11) −0.0029 (12)
C22 0.0250 (13) 0.0261 (14) 0.0244 (13) 0.0022 (10) 0.0043 (10) 0.0017 (11)
C23 0.0294 (14) 0.0287 (15) 0.0269 (14) 0.0036 (12) 0.0072 (11) −0.0040 (12)
N24 0.0276 (11) 0.0248 (12) 0.0283 (12) −0.0005 (9) 0.0032 (9) −0.0044 (10)
C25 0.0322 (15) 0.0324 (16) 0.0319 (15) −0.0031 (12) 0.0053 (12) −0.0130 (13)
C26 0.0294 (14) 0.0338 (16) 0.0265 (14) −0.0056 (12) 0.0039 (11) −0.0134 (12)
C27 0.0343 (16) 0.0465 (19) 0.0346 (16) −0.0073 (14) 0.0087 (13) −0.0080 (14)
C28 0.051 (2) 0.050 (2) 0.0379 (18) −0.0067 (17) 0.0099 (15) 0.0018 (16)
C29 0.048 (2) 0.049 (2) 0.0426 (19) 0.0011 (17) −0.0033 (16) −0.0041 (17)
C30 0.0309 (16) 0.045 (2) 0.0463 (19) −0.0017 (14) 0.0007 (14) −0.0114 (15)
C31 0.0317 (15) 0.0350 (16) 0.0353 (16) −0.0070 (13) 0.0067 (12) −0.0092 (13)
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Geometric parameters (Å, °)

Pd1—C3 2.1233 (19) C15—H15 0.9500
Pd1—N24 2.150 (2) C16—H16 0.9500
Pd1—P4 2.1939 (7) C17—C18 1.395 (4)
Pd1—Cl2 2.4035 (8) C17—C22 1.410 (4)
C3—H3A 0.9800 C18—C19 1.394 (4)
C3—H3B 0.9800 C18—H18 0.9500
C3—H3C 0.9800 C19—C20 1.380 (4)
P4—C5 1.821 (3) C19—H19 0.9500
P4—C17 1.825 (3) C20—C21 1.387 (4)
P4—C11 1.825 (3) C20—H20 0.9500
C5—C10 1.390 (4) C21—C22 1.397 (4)
C5—C6 1.402 (4) C21—H21 0.9500
C6—C7 1.391 (4) C22—C23 1.474 (4)
C6—H6 0.9500 C23—N24 1.279 (4)
C7—C8 1.386 (5) C23—H23 0.9500
C7—H7 0.9500 N24—C25 1.486 (4)
C8—C9 1.384 (5) C25—C26 1.512 (4)
C8—H8 0.9500 C25—H25A 0.9900
C9—C10 1.392 (4) C25—H25B 0.9900
C9—H9 0.9500 C26—C31 1.396 (4)
C10—H10 0.9500 C26—C27 1.399 (4)
C11—C12 1.393 (4) C27—C28 1.384 (5)
C11—C16 1.396 (4) C27—H27 0.9500
C12—C13 1.386 (4) C28—C29 1.395 (5)
C12—H12 0.9500 C28—H28 0.9500
C13—C14 1.378 (5) C29—C30 1.383 (5)
C13—H13 0.9500 C29—H29 0.9500
C14—C15 1.382 (5) C30—C31 1.390 (5)
C14—H14 0.9500 C30—H30 0.9500
C15—C16 1.390 (4) C31—H31 0.9500
C3—Pd1—N24 174.86 (9) C15—C16—C11 120.1 (3)
C3—Pd1—P4 90.87 (6) C15—C16—H16 120.0
N24—Pd1—P4 86.76 (7) C11—C16—H16 120.0
C3—Pd1—Cl2 88.10 (6) C18—C17—C22 118.7 (2)
N24—Pd1—Cl2 94.38 (7) C18—C17—P4 120.8 (2)
P4—Pd1—Cl2 178.09 (3) C22—C17—P4 120.4 (2)
Pd1—C3—H3A 109.5 C19—C18—C17 121.1 (3)
Pd1—C3—H3B 109.5 C19—C18—H18 119.5
H3A—C3—H3B 109.5 C17—C18—H18 119.5
Pd1—C3—H3C 109.5 C20—C19—C18 120.2 (3)
H3A—C3—H3C 109.5 C20—C19—H19 119.9
H3B—C3—H3C 109.5 C18—C19—H19 119.9
C5—P4—C17 102.71 (12) C19—C20—C21 119.4 (3)
C5—P4—C11 106.07 (13) C19—C20—H20 120.3
C17—P4—C11 104.43 (12) C21—C20—H20 120.3
C5—P4—Pd1 121.09 (9) C20—C21—C22 121.3 (3)
C17—P4—Pd1 110.79 (9) C20—C21—H21 119.3
C11—P4—Pd1 110.33 (9) C22—C21—H21 119.3
C10—C5—C6 119.3 (3) C21—C22—C17 119.2 (3)
C10—C5—P4 122.0 (2) C21—C22—C23 116.2 (2)
C6—C5—P4 118.6 (2) C17—C22—C23 124.5 (2)
C7—C6—C5 120.2 (3) N24—C23—C22 127.5 (3)
C7—C6—H6 119.9 N24—C23—H23 116.2
C5—C6—H6 119.9 C22—C23—H23 116.2
C8—C7—C6 119.9 (3) C23—N24—C25 114.9 (2)
C8—C7—H7 120.1 C23—N24—Pd1 129.8 (2)
C6—C7—H7 120.1 C25—N24—Pd1 115.15 (17)
C9—C8—C7 120.3 (3) N24—C25—C26 110.3 (2)
C9—C8—H8 119.9 N24—C25—H25A 109.6
C7—C8—H8 119.9 C26—C25—H25A 109.6
C8—C9—C10 120.1 (3) N24—C25—H25B 109.6
C8—C9—H9 120.0 C26—C25—H25B 109.6
C10—C9—H9 120.0 H25A—C25—H25B 108.1
C5—C10—C9 120.3 (3) C31—C26—C27 118.9 (3)
C5—C10—H10 119.9 C31—C26—C25 120.6 (3)
C9—C10—H10 119.9 C27—C26—C25 120.5 (3)
C12—C11—C16 119.1 (3) C28—C27—C26 120.6 (3)
C12—C11—P4 118.9 (2) C28—C27—H27 119.7
C16—C11—P4 121.9 (2) C26—C27—H27 119.7
C13—C12—C11 120.2 (3) C27—C28—C29 119.8 (3)
C13—C12—H12 119.9 C27—C28—H28 120.1
C11—C12—H12 119.9 C29—C28—H28 120.1
C14—C13—C12 120.4 (3) C30—C29—C28 120.3 (4)
C14—C13—H13 119.8 C30—C29—H29 119.8
C12—C13—H13 119.8 C28—C29—H29 119.8
C13—C14—C15 120.0 (3) C29—C30—C31 119.7 (3)
C13—C14—H14 120.0 C29—C30—H30 120.1
C15—C14—H14 120.0 C31—C30—H30 120.1
C14—C15—C16 120.2 (3) C30—C31—C26 120.7 (3)
C14—C15—H15 119.9 C30—C31—H31 119.6
C16—C15—H15 119.9 C26—C31—H31 119.6
C3—Pd1—P4—C5 21.97 (12) Pd1—P4—C17—C18 −144.6 (2)
N24—Pd1—P4—C5 −162.59 (13) C5—P4—C17—C22 170.6 (2)
C3—Pd1—P4—C17 142.22 (11) C11—P4—C17—C22 −78.9 (2)
N24—Pd1—P4—C17 −42.35 (11) Pd1—P4—C17—C22 39.9 (2)
C3—Pd1—P4—C11 −102.64 (11) C22—C17—C18—C19 −0.5 (4)
N24—Pd1—P4—C11 72.79 (11) P4—C17—C18—C19 −176.0 (2)
C17—P4—C5—C10 101.3 (2) C17—C18—C19—C20 1.0 (4)
C11—P4—C5—C10 −8.0 (3) C18—C19—C20—C21 0.3 (4)
Pd1—P4—C5—C10 −134.6 (2) C19—C20—C21—C22 −2.2 (5)
C17—P4—C5—C6 −74.6 (2) C20—C21—C22—C17 2.7 (4)
C11—P4—C5—C6 176.1 (2) C20—C21—C22—C23 180.0 (3)
Pd1—P4—C5—C6 49.5 (2) C18—C17—C22—C21 −1.4 (4)
C10—C5—C6—C7 0.4 (4) P4—C17—C22—C21 174.2 (2)
P4—C5—C6—C7 176.3 (2) C18—C17—C22—C23 −178.4 (3)
C5—C6—C7—C8 −0.5 (5) P4—C17—C22—C23 −2.8 (4)
C6—C7—C8—C9 0.3 (5) C21—C22—C23—N24 161.0 (3)
C7—C8—C9—C10 0.0 (5) C17—C22—C23—N24 −21.9 (5)
C6—C5—C10—C9 0.0 (4) C22—C23—N24—C25 175.4 (3)
P4—C5—C10—C9 −175.9 (2) C22—C23—N24—Pd1 −0.2 (5)
C8—C9—C10—C5 −0.1 (4) P4—Pd1—N24—C23 31.1 (3)
C5—P4—C11—C12 −87.4 (3) Cl2—Pd1—N24—C23 −147.4 (3)
C17—P4—C11—C12 164.5 (2) P4—Pd1—N24—C25 −144.5 (2)
Pd1—P4—C11—C12 45.4 (3) Cl2—Pd1—N24—C25 37.0 (2)
C5—P4—C11—C16 94.5 (2) C23—N24—C25—C26 −102.6 (3)
C17—P4—C11—C16 −13.6 (3) Pd1—N24—C25—C26 73.7 (3)
Pd1—P4—C11—C16 −132.7 (2) N24—C25—C26—C31 −109.5 (3)
C16—C11—C12—C13 −0.9 (5) N24—C25—C26—C27 72.0 (3)
P4—C11—C12—C13 −179.0 (3) C31—C26—C27—C28 −0.9 (5)
C11—C12—C13—C14 0.8 (5) C25—C26—C27—C28 177.6 (3)
C12—C13—C14—C15 −0.2 (6) C26—C27—C28—C29 −0.1 (5)
C13—C14—C15—C16 −0.2 (5) C27—C28—C29—C30 0.8 (5)
C14—C15—C16—C11 0.1 (5) C28—C29—C30—C31 −0.3 (5)
C12—C11—C16—C15 0.4 (4) C29—C30—C31—C26 −0.7 (5)
P4—C11—C16—C15 178.5 (2) C27—C26—C31—C30 1.3 (4)
C5—P4—C17—C18 −14.0 (2) C25—C26—C31—C30 −177.2 (3)
C11—P4—C17—C18 96.6 (2)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2317).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040074/im2317sup1.cif

e-67-m1498-sup1.cif (31.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040074/im2317Isup2.hkl

e-67-m1498-Isup2.hkl (284.4KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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