1-(4-Chloro­phenyl)-2-[tris­(4-methyl­phenyl)-λ5-phosphanyl­idene]butane-1,3-dione

Sabounchei, S.J.; Shahriary, P.; Hosseini Fashami, F.; Morales-Morales, D.; Hernandez-Ortega, S.

doi:10.1107/S1600536812051689

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o183

doi:10.1107/S1600536812051689

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1-(4-Chlorophenyl)-2-[tris(4-methylphenyl)-λ⁵-phosphanylidene]butane-1,3-dione

Seyyed Javad Sabounchei,^a ^* Parisa Shahriary,^a Faegheh Hosseini Fashami,^a David Morales-Morales ^b and Simon Hernandez-Ortega ^b

^aFaculty of Chemistry, Bu-Ali Sina University, Hamedan 65174, Iran, and ^bInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México 04510, Mexico
^*Correspondence e-mail: jsabounchei@yahoo.co.uk

(Received 7 November 2012; accepted 22 December 2012; online 4 January 2013)

In the title ylide, C₃₁H₂₈ClO₂P [common name α-acetyl-α-p-chlorobenzoylmethylenetri(p-tolyl)phosphorane], the dihedral angle between the 4-chlorophenyl ring and that of the ylide moiety is 66.15 (10)°. The geometry around the P atom is slightly distorted tetrahedral [angle range = 105.22 (8)–115.52 (9)°] and the carbonyl O atoms are syn-oriented with respect to the P atom. The ylide group is close to planar [maximum deviation from the least-squares plane = 0.006 (2) Å] and the P—C, C—C and C=O bond lengths are consistent with electron delocalization involving the O atoms.

Related literature

For a general background to organophosphorus compounds and a review of stabilized phosphonium ylides, see: Bachrach & Nitsche (1994 ). For other related literature on ylides, see: Wilson & Tebby (1972 ); Sabounchei et al. (2010 ). For analogous structures, see: Bart (1969 ); Kalyanasundari et al. (1994 ); Sabounchei et al. (2007 ); Castañeda et al. (2001 , 2003 ). For bond distance and angle data, see: Dunitz (1979 ); Allen et al. (1987 ).

Experimental

Crystal data

C₃₁H₂₈ClO₂P
M_r = 498.95
Monoclinic, C 2/c
a = 20.327 (2) Å
b = 14.7560 (15) Å
c = 18.9759 (19) Å
β = 113.140 (2)°
V = 5233.8 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 K
0.35 × 0.27 × 0.25 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
21296 measured reflections
4780 independent reflections
3380 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.099
S = 1.00
4780 reflections
320 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812051689/zs2244sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812051689/zs2244Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812051689/zs2244Isup3.cml

checkCIF report

Comment top

X-ray structures of stabilized phosphonium ylides possessing a substituent that conjugates with the P═C double bond have been reviewed (Bachrach & Nitsche, 1994). Ylidic resonance is important in phosphonium ylides stabilized by electron-withdrawing substituents due to electronic delocalization between the P—C bond, the ylidic bond, and an acyl group (Castañeda et al., 2001, 2003). In the title compound, C₃₁H₂₈ClO₂P (Fig. 1), the dihedral angle between the 4-chlorophenyl ring and the plane of the planar ylide moiety (defined by atoms P, C2, C3, O2, C4) is 66.15 (10)°. The geometry around the P atom is slightly distorted tetrahedral [angle range, 105.22 (8)–115.52 (9)Å]. The P–C2 bond [1.7540 (18) Å] is comparable with analogous distances (Kalyanasundari et al., 1994; Sabounchei et al., 2007) and is longer than the typical P═C double bond in methylenetriphenylphosphorane, Ph₃P═CH₂ (Bart, 1969), where there is no opportunity for conjugation with another group. For a similar reason, the C═O bonds are longer than the C═O bonds in ketones (Allen et al., 1987). In the title compound the difference between the C–O bond lengths in the C1–O1–Ph group compared to the C3–O2–CH₃ group (0.016 Å) may be due to the presence of the extended resonance between the COCH₃ group and the carbanion. The ylide C-atom is clearly sp²-hybridized, the sum of the bond angles [359 (4)°] being essentially 360°. The distortions from planarity of the extended ylide group (as induced by non-bonding interactions) are not extreme; the P—C2—C3═O2 torsion angle [2.3 (2)°] suggests a degree of coplanarity and concomitance, but the P—C2—C1—O1 angle [-37.1 (3)°] indicates some rotation of the second carbonyl group out of the plane. In ylides stabilized by a single keto or ester group, there is a strong interaction between cationoid phosphorus and the syn acyl O atom (Wilson & Tebby, 1972). The P···O2 [2.853 (1) Å] and P···O1 [3.088 (2) Å] distances are significantly shorter than the sum of the van der Waals radii of P and O (Dunitz, 1979), indicating a strong intramolecular interaction between the P⁺ and O^- charge centers, which leads to the cis orientation.

Related literature top

For a general background to organophosphorus compounds and a review of stabilized phosphonium ylides, see: Bachrach & Nitsche (1994). For other related literature on ylides, see: Wilson & Tebby (1972); Sabounchei et al. (2010). For analogous structures, see: Bart (1969); Kalyanasundari et al. (1994); Sabounchei et al. (2007); Castañeda et al. (2001, 2003). For bond distance and angle data, see: Dunitz (1979); Allen et al. (1987).

Experimental top

A mixture of parachlorobenzoyltri(paratolyl)phosphorane (0.03 mol) and acetic anhydride (0.3 mol) in dry chloroform (10–20 ml) was stirred at 60°C. The reaction was monitored by TLC. The resulting dark solution was evaporated at 80 °C (12 ml) to give a glue which was triturated with ether and the precipitated product was filtered and recrystallized using a solvent diffusion technique (yield; 65%: m.p. 459–458).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at 30% probability level.

1-(4-Chlorophenyl)-2-[tris(4-methylphenyl)-λ⁵-phosphanylidene]butane- 1,3-dione top

Crystal data top

C₃₁H₂₈ClO₂P	F(000) = 2096
M_r = 498.95	D_x = 1.266 Mg m⁻³
Monoclinic, C2/c	Melting point = 458–459 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 20.327 (2) Å	Cell parameters from 7723 reflections
b = 14.7560 (15) Å	θ = 2.3–25.3°
c = 18.9759 (19) Å	µ = 0.23 mm⁻¹
β = 113.140 (2)°	T = 298 K
V = 5233.8 (9) Å³	Prism, yellow
Z = 8	0.35 × 0.27 × 0.25 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3380 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.045
Graphite monochromator	θ_max = 25.4°, θ_min = 1.8°
Detector resolution: 0.83 pixels mm^-1	h = −24→24
ω scans	k = −17→17
21296 measured reflections	l = −22→22
4780 independent reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0456P)²] where P = (F_o² + 2F_c²)/3
4780 reflections	(Δ/σ)_max < 0.001
320 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₃₁H₂₈ClO₂P	V = 5233.8 (9) Å³
M_r = 498.95	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.327 (2) Å	µ = 0.23 mm⁻¹
b = 14.7560 (15) Å	T = 298 K
c = 18.9759 (19) Å	0.35 × 0.27 × 0.25 mm
β = 113.140 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3380 reflections with I > 2σ(I)
21296 measured reflections	R_int = 0.045
4780 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.00	Δρ_max = 0.23 e Å⁻³
4780 reflections	Δρ_min = −0.21 e Å⁻³
320 parameters

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	U_iso*/U_eq
Cl	0.00240 (4)	0.88102 (4)	0.03610 (4)	0.0896 (3)
P	0.17486 (3)	0.37797 (3)	0.21740 (3)	0.03935 (15)
O1	0.16378 (8)	0.56120 (10)	0.29060 (8)	0.0645 (4)
O2	0.02681 (7)	0.33829 (10)	0.13545 (8)	0.0579 (4)
C1	0.12109 (10)	0.54772 (13)	0.22438 (11)	0.0454 (5)
C2	0.10499 (9)	0.45716 (12)	0.19188 (10)	0.0419 (5)
C3	0.03535 (10)	0.42100 (14)	0.14970 (11)	0.0467 (5)
C4	−0.03122 (10)	0.47932 (15)	0.12414 (13)	0.0653 (6)
H4A	−0.0364	0.5109	0.0780	0.098*
H4B	−0.0271	0.5224	0.1636	0.098*
H4C	−0.0723	0.4416	0.1146	0.098*
C5	0.08882 (10)	0.62939 (13)	0.17585 (11)	0.0433 (5)
C6	0.07281 (10)	0.63087 (14)	0.09771 (12)	0.0507 (5)
H6	0.0796	0.5788	0.0738	0.061*
C7	0.04699 (11)	0.70818 (16)	0.05475 (12)	0.0593 (6)
H7	0.0364	0.7084	0.0024	0.071*
C8	0.03717 (11)	0.78467 (14)	0.09061 (13)	0.0576 (6)
C9	0.05338 (12)	0.78600 (15)	0.16758 (13)	0.0644 (6)
H9	0.0468	0.8385	0.1911	0.077*
C10	0.07965 (11)	0.70826 (14)	0.21011 (12)	0.0571 (6)
H10	0.0913	0.7091	0.2627	0.069*
C11	0.17988 (10)	0.30004 (12)	0.29265 (10)	0.0410 (5)
C12	0.12272 (11)	0.29172 (13)	0.31441 (11)	0.0492 (5)
H12	0.0813	0.3251	0.2890	0.059*
C13	0.12636 (12)	0.23438 (14)	0.37351 (12)	0.0556 (6)
H13	0.0874	0.2301	0.3874	0.067*
C14	0.18664 (13)	0.18355 (14)	0.41202 (12)	0.0545 (6)
C15	0.24374 (12)	0.19226 (14)	0.39040 (12)	0.0570 (6)
H15	0.2849	0.1584	0.4157	0.068*
C16	0.24135 (11)	0.24988 (13)	0.33223 (12)	0.0512 (5)
H16	0.2809	0.2552	0.3194	0.061*
C17	0.19077 (14)	0.11954 (16)	0.47598 (13)	0.0811 (8)
H17A	0.1538	0.1343	0.4936	0.122*
H17B	0.2366	0.1254	0.5176	0.122*
H17C	0.1845	0.0583	0.4573	0.122*
C18	0.25965 (9)	0.43610 (12)	0.25043 (10)	0.0389 (4)
C19	0.28960 (10)	0.46131 (13)	0.19951 (11)	0.0475 (5)
H19	0.2670	0.4455	0.1481	0.057*
C20	0.35285 (11)	0.50983 (14)	0.22410 (12)	0.0551 (6)
H20	0.3723	0.5255	0.1889	0.066*
C21	0.38777 (10)	0.53554 (13)	0.29975 (12)	0.0497 (5)
C22	0.35801 (10)	0.50872 (13)	0.35062 (11)	0.0479 (5)
H22	0.3809	0.5240	0.4021	0.058*
C23	0.29551 (10)	0.46009 (13)	0.32700 (11)	0.0458 (5)
H23	0.2769	0.4429	0.3626	0.055*
C24	0.45494 (12)	0.59149 (17)	0.32627 (14)	0.0790 (8)
H24A	0.4514	0.6396	0.3586	0.118*
H24B	0.4611	0.6167	0.2826	0.118*
H24C	0.4953	0.5539	0.3545	0.118*
C25	0.16994 (10)	0.31556 (12)	0.13338 (10)	0.0414 (5)
C26	0.20041 (11)	0.23050 (13)	0.13922 (12)	0.0510 (5)
H26	0.2223	0.2032	0.1870	0.061*
C27	0.19849 (12)	0.18588 (14)	0.07444 (13)	0.0571 (6)
H27	0.2197	0.1291	0.0796	0.069*
C28	0.16629 (11)	0.22285 (15)	0.00284 (12)	0.0524 (5)
C29	0.13751 (11)	0.30865 (15)	−0.00266 (11)	0.0587 (6)
H29	0.1167	0.3362	−0.0505	0.070*
C30	0.13905 (11)	0.35433 (14)	0.06151 (11)	0.0529 (5)
H30	0.1190	0.4119	0.0563	0.063*
C31	0.16111 (13)	0.17156 (16)	−0.06824 (13)	0.0760 (7)
H31A	0.1908	0.1186	−0.0536	0.114*
H31B	0.1768	0.2098	−0.0995	0.114*
H31C	0.1124	0.1538	−0.0967	0.114*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0792 (4)	0.0604 (4)	0.0944 (5)	−0.0098 (3)	−0.0035 (4)	0.0274 (3)
P	0.0384 (3)	0.0401 (3)	0.0382 (3)	0.0009 (2)	0.0137 (2)	−0.0008 (2)
O1	0.0648 (10)	0.0623 (10)	0.0484 (9)	0.0131 (8)	0.0030 (8)	−0.0117 (7)
O2	0.0500 (9)	0.0525 (9)	0.0657 (10)	−0.0059 (7)	0.0169 (7)	−0.0046 (8)
C1	0.0406 (11)	0.0503 (12)	0.0442 (12)	0.0052 (10)	0.0157 (10)	−0.0035 (10)
C2	0.0394 (11)	0.0410 (11)	0.0427 (11)	0.0043 (9)	0.0133 (9)	−0.0001 (9)
C3	0.0446 (12)	0.0486 (13)	0.0450 (12)	0.0018 (10)	0.0156 (10)	0.0029 (10)
C4	0.0407 (12)	0.0631 (14)	0.0856 (17)	0.0021 (11)	0.0179 (12)	0.0124 (13)
C5	0.0392 (11)	0.0422 (11)	0.0464 (12)	−0.0025 (9)	0.0144 (9)	−0.0029 (9)
C6	0.0528 (13)	0.0481 (13)	0.0508 (13)	−0.0071 (10)	0.0199 (11)	−0.0037 (10)
C7	0.0577 (14)	0.0663 (16)	0.0462 (13)	−0.0176 (12)	0.0123 (11)	0.0040 (12)
C8	0.0496 (13)	0.0459 (13)	0.0617 (15)	−0.0097 (10)	0.0051 (11)	0.0094 (11)
C9	0.0725 (16)	0.0437 (13)	0.0666 (16)	0.0046 (12)	0.0162 (13)	−0.0033 (12)
C10	0.0655 (15)	0.0526 (13)	0.0489 (13)	0.0047 (11)	0.0177 (11)	−0.0042 (11)
C11	0.0421 (11)	0.0395 (11)	0.0414 (11)	−0.0013 (9)	0.0163 (9)	−0.0020 (9)
C12	0.0454 (12)	0.0541 (13)	0.0497 (12)	0.0013 (10)	0.0204 (10)	−0.0020 (10)
C13	0.0598 (14)	0.0600 (14)	0.0555 (14)	−0.0097 (12)	0.0317 (12)	−0.0015 (11)
C14	0.0718 (15)	0.0478 (13)	0.0447 (12)	−0.0104 (11)	0.0237 (12)	−0.0004 (10)
C15	0.0588 (14)	0.0524 (13)	0.0566 (14)	0.0074 (11)	0.0191 (12)	0.0109 (11)
C16	0.0465 (12)	0.0535 (13)	0.0555 (13)	0.0044 (10)	0.0221 (11)	0.0072 (10)
C17	0.115 (2)	0.0694 (16)	0.0632 (16)	−0.0135 (15)	0.0399 (16)	0.0115 (13)
C18	0.0393 (11)	0.0383 (11)	0.0376 (11)	0.0040 (8)	0.0136 (9)	0.0014 (8)
C19	0.0509 (12)	0.0535 (12)	0.0371 (11)	−0.0043 (10)	0.0161 (10)	0.0000 (9)
C20	0.0568 (13)	0.0627 (14)	0.0513 (13)	−0.0084 (11)	0.0271 (11)	0.0050 (11)
C21	0.0444 (12)	0.0471 (12)	0.0547 (13)	−0.0018 (10)	0.0163 (11)	0.0025 (10)
C22	0.0424 (12)	0.0524 (13)	0.0428 (12)	−0.0006 (10)	0.0101 (10)	−0.0044 (10)
C23	0.0446 (12)	0.0538 (12)	0.0396 (11)	0.0001 (10)	0.0173 (9)	0.0039 (9)
C24	0.0662 (16)	0.0871 (18)	0.0793 (18)	−0.0277 (14)	0.0238 (14)	−0.0006 (14)
C25	0.0390 (11)	0.0425 (11)	0.0419 (11)	−0.0026 (9)	0.0151 (9)	−0.0032 (9)
C26	0.0624 (14)	0.0430 (12)	0.0512 (13)	0.0019 (10)	0.0263 (11)	0.0014 (10)
C27	0.0722 (15)	0.0414 (12)	0.0666 (15)	0.0004 (11)	0.0367 (13)	−0.0055 (11)
C28	0.0480 (12)	0.0570 (14)	0.0564 (14)	−0.0082 (11)	0.0250 (11)	−0.0144 (11)
C29	0.0563 (14)	0.0719 (16)	0.0402 (12)	0.0089 (12)	0.0106 (10)	−0.0035 (11)
C30	0.0534 (13)	0.0547 (13)	0.0457 (13)	0.0134 (10)	0.0142 (10)	−0.0024 (10)
C31	0.0838 (18)	0.0818 (17)	0.0694 (16)	−0.0112 (15)	0.0376 (14)	−0.0299 (14)

Geometric parameters (Å, º) top

Cl—C8	1.737 (2)	C15—H15	0.9300
P—C2	1.7540 (18)	C16—H16	0.9300
P—C18	1.8028 (18)	C17—H17A	0.9600
P—C11	1.8048 (19)	C17—H17B	0.9600
P—C25	1.8097 (19)	C17—H17C	0.9600
O1—C1	1.231 (2)	C18—C19	1.380 (2)
O2—C3	1.247 (2)	C18—C23	1.391 (2)
C1—C2	1.454 (3)	C19—C20	1.383 (3)
C1—C5	1.502 (3)	C19—H19	0.9300
C2—C3	1.428 (3)	C20—C21	1.381 (3)
C3—C4	1.514 (3)	C20—H20	0.9300
C4—H4A	0.9600	C21—C22	1.383 (3)
C4—H4B	0.9600	C21—C24	1.503 (3)
C4—H4C	0.9600	C22—C23	1.372 (2)
C5—C10	1.381 (3)	C22—H22	0.9300
C5—C6	1.388 (3)	C23—H23	0.9300
C6—C7	1.380 (3)	C24—H24A	0.9600
C6—H6	0.9300	C24—H24B	0.9600
C7—C8	1.373 (3)	C24—H24C	0.9600
C7—H7	0.9300	C25—C30	1.381 (3)
C8—C9	1.365 (3)	C25—C26	1.385 (3)
C9—C10	1.383 (3)	C26—C27	1.382 (3)
C9—H9	0.9300	C26—H26	0.9300
C10—H10	0.9300	C27—C28	1.368 (3)
C11—C12	1.383 (2)	C27—H27	0.9300
C11—C16	1.391 (3)	C28—C29	1.381 (3)
C12—C13	1.383 (3)	C28—C31	1.514 (3)
C12—H12	0.9300	C29—C30	1.381 (3)
C13—C14	1.376 (3)	C29—H29	0.9300
C13—H13	0.9300	C30—H30	0.9300
C14—C15	1.380 (3)	C31—H31A	0.9600
C14—C17	1.514 (3)	C31—H31B	0.9600
C15—C16	1.379 (3)	C31—H31C	0.9600

C2—P—C18	109.80 (9)	C11—C16—H16	119.9
C2—P—C11	115.52 (9)	C14—C17—H17A	109.5
C18—P—C11	106.20 (8)	C14—C17—H17B	109.5
C2—P—C25	109.72 (9)	H17A—C17—H17B	109.5
C18—P—C25	105.22 (8)	C14—C17—H17C	109.5
C11—P—C25	109.83 (9)	H17A—C17—H17C	109.5
O1—C1—C2	122.17 (18)	H17B—C17—H17C	109.5
O1—C1—C5	117.33 (17)	C19—C18—C23	117.93 (17)
C2—C1—C5	120.40 (17)	C19—C18—P	120.62 (14)
C3—C2—C1	126.13 (17)	C23—C18—P	121.40 (14)
C3—C2—P	114.99 (14)	C18—C19—C20	120.71 (18)
C1—C2—P	118.18 (14)	C18—C19—H19	119.6
O2—C3—C2	120.67 (18)	C20—C19—H19	119.6
O2—C3—C4	117.14 (18)	C21—C20—C19	121.54 (18)
C2—C3—C4	122.11 (18)	C21—C20—H20	119.2
C3—C4—H4A	109.5	C19—C20—H20	119.2
C3—C4—H4B	109.5	C20—C21—C22	117.36 (18)
H4A—C4—H4B	109.5	C20—C21—C24	121.81 (19)
C3—C4—H4C	109.5	C22—C21—C24	120.83 (19)
H4A—C4—H4C	109.5	C23—C22—C21	121.64 (18)
H4B—C4—H4C	109.5	C23—C22—H22	119.2
C10—C5—C6	118.13 (18)	C21—C22—H22	119.2
C10—C5—C1	119.65 (18)	C22—C23—C18	120.80 (18)
C6—C5—C1	122.03 (17)	C22—C23—H23	119.6
C7—C6—C5	121.3 (2)	C18—C23—H23	119.6
C7—C6—H6	119.4	C21—C24—H24A	109.5
C5—C6—H6	119.4	C21—C24—H24B	109.5
C8—C7—C6	118.8 (2)	H24A—C24—H24B	109.5
C8—C7—H7	120.6	C21—C24—H24C	109.5
C6—C7—H7	120.6	H24A—C24—H24C	109.5
C9—C8—C7	121.4 (2)	H24B—C24—H24C	109.5
C9—C8—Cl	119.74 (19)	C30—C25—C26	118.02 (18)
C7—C8—Cl	118.84 (18)	C30—C25—P	120.35 (15)
C8—C9—C10	119.2 (2)	C26—C25—P	121.51 (15)
C8—C9—H9	120.4	C27—C26—C25	120.36 (19)
C10—C9—H9	120.4	C27—C26—H26	119.8
C5—C10—C9	121.1 (2)	C25—C26—H26	119.8
C5—C10—H10	119.4	C28—C27—C26	121.9 (2)
C9—C10—H10	119.4	C28—C27—H27	119.0
C12—C11—C16	118.25 (18)	C26—C27—H27	119.0
C12—C11—P	119.99 (15)	C27—C28—C29	117.62 (19)
C16—C11—P	121.71 (15)	C27—C28—C31	121.6 (2)
C11—C12—C13	120.85 (19)	C29—C28—C31	120.8 (2)
C11—C12—H12	119.6	C30—C29—C28	121.2 (2)
C13—C12—H12	119.6	C30—C29—H29	119.4
C14—C13—C12	121.1 (2)	C28—C29—H29	119.4
C14—C13—H13	119.5	C29—C30—C25	120.82 (19)
C12—C13—H13	119.5	C29—C30—H30	119.6
C13—C14—C15	117.94 (19)	C25—C30—H30	119.6
C13—C14—C17	121.5 (2)	C28—C31—H31A	109.5
C15—C14—C17	120.5 (2)	C28—C31—H31B	109.5
C16—C15—C14	121.7 (2)	H31A—C31—H31B	109.5
C16—C15—H15	119.1	C28—C31—H31C	109.5
C14—C15—H15	119.1	H31A—C31—H31C	109.5
C15—C16—C11	120.1 (2)	H31B—C31—H31C	109.5
C15—C16—H16	119.9

O1—C1—C2—C3	132.8 (2)	C12—C13—C14—C17	−179.07 (19)
C5—C1—C2—C3	−50.8 (3)	C13—C14—C15—C16	0.1 (3)
O1—C1—C2—P	−37.1 (3)	C17—C14—C15—C16	179.9 (2)
C5—C1—C2—P	139.25 (15)	C14—C15—C16—C11	−1.1 (3)
C18—P—C2—C3	167.12 (14)	C12—C11—C16—C15	1.4 (3)
C11—P—C2—C3	−72.84 (16)	P—C11—C16—C15	178.76 (15)
C25—P—C2—C3	51.94 (17)	C2—P—C18—C19	−89.06 (16)
C18—P—C2—C1	−21.85 (17)	C11—P—C18—C19	145.38 (15)
C11—P—C2—C1	98.18 (16)	C25—P—C18—C19	28.95 (17)
C25—P—C2—C1	−137.04 (15)	C2—P—C18—C23	88.39 (16)
C1—C2—C3—O2	−167.91 (18)	C11—P—C18—C23	−37.16 (17)
P—C2—C3—O2	2.3 (2)	C25—P—C18—C23	−153.59 (15)
C1—C2—C3—C4	8.8 (3)	C23—C18—C19—C20	−0.8 (3)
P—C2—C3—C4	178.97 (15)	P—C18—C19—C20	176.78 (15)
O1—C1—C5—C10	−29.4 (3)	C18—C19—C20—C21	−0.7 (3)
C2—C1—C5—C10	154.09 (18)	C19—C20—C21—C22	1.7 (3)
O1—C1—C5—C6	145.43 (19)	C19—C20—C21—C24	−177.5 (2)
C2—C1—C5—C6	−31.1 (3)	C20—C21—C22—C23	−1.3 (3)
C10—C5—C6—C7	−1.3 (3)	C24—C21—C22—C23	177.91 (19)
C1—C5—C6—C7	−176.25 (18)	C21—C22—C23—C18	−0.1 (3)
C5—C6—C7—C8	0.0 (3)	C19—C18—C23—C22	1.2 (3)
C6—C7—C8—C9	1.0 (3)	P—C18—C23—C22	−176.35 (14)
C6—C7—C8—Cl	−178.27 (15)	C2—P—C25—C30	27.03 (18)
C7—C8—C9—C10	−0.6 (3)	C18—P—C25—C30	−91.03 (17)
Cl—C8—C9—C10	178.66 (17)	C11—P—C25—C30	155.04 (15)
C6—C5—C10—C9	1.7 (3)	C2—P—C25—C26	−156.82 (16)
C1—C5—C10—C9	176.79 (19)	C18—P—C25—C26	85.11 (17)
C8—C9—C10—C5	−0.8 (3)	C11—P—C25—C26	−28.82 (18)
C2—P—C11—C12	14.15 (18)	C30—C25—C26—C27	−1.1 (3)
C18—P—C11—C12	136.13 (15)	P—C25—C26—C27	−177.29 (16)
C25—P—C11—C12	−110.57 (16)	C25—C26—C27—C28	−0.7 (3)
C2—P—C11—C16	−163.22 (15)	C26—C27—C28—C29	2.2 (3)
C18—P—C11—C16	−41.24 (18)	C26—C27—C28—C31	−176.8 (2)
C25—P—C11—C16	72.06 (18)	C27—C28—C29—C30	−2.1 (3)
C16—C11—C12—C13	−0.6 (3)	C31—C28—C29—C30	177.0 (2)
P—C11—C12—C13	−178.05 (15)	C28—C29—C30—C25	0.4 (3)
C11—C12—C13—C14	−0.4 (3)	C26—C25—C30—C29	1.2 (3)
C12—C13—C14—C15	0.7 (3)	P—C25—C30—C29	177.46 (16)

Experimental details

Crystal data
Chemical formula	C₃₁H₂₈ClO₂P
M_r	498.95
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	20.327 (2), 14.7560 (15), 18.9759 (19)
β (°)	113.140 (2)
V (Å³)	5233.8 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.35 × 0.27 × 0.25

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21296, 4780, 3380
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.099, 1.00
No. of reflections	4780
No. of parameters	320
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.21

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We are grateful to the University of Bu-Ali Sina for financial support. We are also indebted to the Instituto de Química, Universidad Nacional Autónoma de México, for the use of their X-ray diffractometer.

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