(2,4-Di­chloro­benzoyl­methyl)­tri­phenyl­phospho­nium chloride

Zhang, X.; Zhong, P.; Hu, M.-; Lin, D.; Lin, J.

doi:10.1107/S1600536804013996

(2,4-Dichlorobenzoylmethyl)triphenylphosphonium chloride

X. Zhang, P. Zhong, M. - Hu, D. Lin and J. Lin

In the crystal structure of the title compound, C₂₆H₂₀Cl₂OP⁺·Cl⁻, there are intermolecular C—H

O hydrogen bonds, and both intramolecular and intermolecular C—H

Cl hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804013996/cf6357sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804013996/cf6357Isup2.hkl Contains datablock I

CCDC reference: 245301

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.039
wR factor = 0.097
Data-to-parameter ratio = 14.8

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

(I) top

Crystal data top

C₂₆H₂₀Cl₂OP⁺·Cl⁻	F(000) = 1000
M_r = 485.74	D_x = 1.403 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4946 reflections
a = 12.5615 (4) Å	θ = 2.5–25.2°
b = 10.9659 (4) Å	µ = 0.49 mm⁻¹
c = 17.2638 (5) Å	T = 298 K
β = 104.805 (1)°	Block, colorless
V = 2299.11 (13) Å³	0.26 × 0.21 × 0.19 mm
Z = 4

Data collection top

Bruker APEX area-detector diffractometer	4131 independent reflections
Radiation source: fine-focus sealed tube	3694 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 25.2°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −15→13
T_min = 0.884, T_max = 0.914	k = −13→13
11818 measured reflections	l = −20→19

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0488P)² + 0.8375P] where P = (F_o² + 2F_c²)/3
4131 reflections	(Δ/σ)_max = 0.001
280 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.27 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	U_iso*/U_eq
Cl1	0.24361 (5)	0.02437 (6)	0.46942 (3)	0.05385 (17)
Cl2	0.61549 (6)	0.25228 (6)	0.60973 (3)	0.0655 (2)
Cl3	0.41717 (5)	0.40538 (5)	0.23792 (3)	0.04786 (16)
P1	0.22962 (4)	0.05283 (4)	0.14703 (3)	0.02852 (13)
O1	0.22501 (12)	0.01602 (15)	0.30247 (9)	0.0481 (4)
C1	0.34476 (19)	0.0414 (2)	0.03147 (14)	0.0477 (5)
H1	0.3975	−0.0016	0.0692	0.057*
C2	0.3552 (2)	0.0554 (2)	−0.04595 (17)	0.0589 (7)
H2	0.4158	0.0222	−0.0600	0.071*
C3	0.2771 (2)	0.1178 (2)	−0.10228 (14)	0.0561 (7)
H3	0.2841	0.1249	−0.1544	0.067*
C4	0.1891 (2)	0.1693 (2)	−0.08173 (13)	0.0530 (6)
H4	0.1370	0.2126	−0.1197	0.064*
C5	0.17726 (18)	0.1571 (2)	−0.00459 (12)	0.0419 (5)
H5	0.1173	0.1924	0.0092	0.050*
C6	0.25464 (16)	0.09251 (17)	0.05215 (11)	0.0327 (4)
C7	0.12457 (19)	0.26426 (19)	0.16885 (14)	0.0452 (5)
H7	0.1916	0.3016	0.1704	0.054*
C8	0.0359 (2)	0.3323 (2)	0.17779 (16)	0.0581 (6)
H8	0.0437	0.4160	0.1860	0.070*
C9	−0.0634 (2)	0.2784 (2)	0.17482 (18)	0.0636 (7)
H9	−0.1227	0.3256	0.1802	0.076*
C10	−0.0754 (2)	0.1548 (2)	0.16394 (19)	0.0647 (7)
H10	−0.1428	0.1182	0.1621	0.078*
C11	0.01225 (18)	0.0843 (2)	0.15565 (15)	0.0479 (5)
H11	0.0041	0.0003	0.1489	0.058*
C12	0.11185 (15)	0.13869 (17)	0.15738 (11)	0.0322 (4)
C13	0.12664 (19)	−0.1564 (2)	0.07666 (15)	0.0497 (6)
H13	0.0826	−0.1040	0.0396	0.060*
C14	0.1120 (2)	−0.2811 (2)	0.06840 (17)	0.0612 (7)
H14	0.0573	−0.3126	0.0263	0.073*
C15	0.1787 (2)	−0.3588 (2)	0.12276 (16)	0.0547 (6)
H15	0.1682	−0.4427	0.1176	0.066*
C16	0.2606 (2)	−0.3126 (2)	0.18443 (14)	0.0484 (6)
H16	0.3061	−0.3654	0.2203	0.058*
C17	0.27572 (18)	−0.18827 (19)	0.19343 (12)	0.0410 (5)
H17	0.3317	−0.1574	0.2349	0.049*
C18	0.20702 (15)	−0.10935 (16)	0.14031 (11)	0.0316 (4)
C19	0.34558 (15)	0.09112 (17)	0.22925 (11)	0.0317 (4)
H19A	0.4089	0.0418	0.2271	0.038*
H19B	0.3649	0.1763	0.2262	0.038*
C20	0.31270 (16)	0.06657 (17)	0.30704 (11)	0.0331 (4)
C21	0.38759 (16)	0.10597 (16)	0.38370 (11)	0.0312 (4)
C22	0.36295 (17)	0.09391 (17)	0.45809 (12)	0.0353 (4)
C23	0.43275 (18)	0.13783 (18)	0.52769 (12)	0.0397 (5)
H23	0.4153	0.1296	0.5766	0.048*
C24	0.52900 (18)	0.19413 (18)	0.52286 (12)	0.0403 (5)
C25	0.55827 (17)	0.20601 (19)	0.45163 (12)	0.0409 (5)
H25	0.6243	0.2430	0.4500	0.049*
C26	0.48749 (16)	0.16186 (18)	0.38302 (12)	0.0366 (4)
H26	0.5066	0.1694	0.3346	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0564 (4)	0.0627 (4)	0.0486 (3)	−0.0152 (3)	0.0248 (3)	0.0026 (3)
Cl2	0.0780 (5)	0.0699 (4)	0.0363 (3)	−0.0185 (3)	−0.0080 (3)	0.0006 (3)
Cl3	0.0527 (3)	0.0405 (3)	0.0540 (3)	−0.0029 (2)	0.0203 (3)	0.0055 (2)
P1	0.0272 (3)	0.0283 (2)	0.0303 (3)	0.00074 (19)	0.0076 (2)	0.00056 (19)
O1	0.0445 (9)	0.0586 (10)	0.0410 (9)	−0.0183 (8)	0.0104 (7)	0.0010 (7)
C1	0.0475 (13)	0.0468 (12)	0.0552 (14)	0.0060 (11)	0.0246 (11)	0.0041 (11)
C2	0.0664 (16)	0.0559 (14)	0.0701 (17)	−0.0088 (13)	0.0460 (15)	−0.0116 (13)
C3	0.0777 (18)	0.0571 (14)	0.0398 (13)	−0.0274 (14)	0.0268 (13)	−0.0083 (11)
C4	0.0603 (15)	0.0608 (15)	0.0343 (12)	−0.0147 (12)	0.0052 (11)	0.0063 (11)
C5	0.0398 (12)	0.0482 (12)	0.0378 (11)	−0.0018 (10)	0.0101 (9)	0.0032 (9)
C6	0.0340 (10)	0.0311 (9)	0.0342 (10)	−0.0038 (8)	0.0110 (8)	−0.0021 (8)
C7	0.0446 (12)	0.0368 (11)	0.0577 (14)	−0.0003 (10)	0.0195 (11)	−0.0046 (10)
C8	0.0660 (16)	0.0380 (12)	0.0762 (17)	0.0104 (12)	0.0292 (14)	−0.0054 (12)
C9	0.0492 (15)	0.0614 (16)	0.087 (2)	0.0197 (13)	0.0298 (14)	−0.0030 (14)
C10	0.0382 (13)	0.0620 (16)	0.101 (2)	0.0024 (12)	0.0301 (14)	−0.0066 (15)
C11	0.0381 (12)	0.0423 (12)	0.0666 (15)	0.0004 (10)	0.0192 (11)	−0.0030 (11)
C12	0.0305 (10)	0.0342 (10)	0.0329 (10)	0.0046 (8)	0.0097 (8)	0.0011 (8)
C13	0.0448 (13)	0.0386 (12)	0.0573 (14)	0.0041 (10)	−0.0025 (11)	−0.0049 (10)
C14	0.0546 (15)	0.0456 (13)	0.0761 (18)	−0.0077 (12)	0.0035 (13)	−0.0196 (13)
C15	0.0711 (17)	0.0301 (11)	0.0712 (17)	−0.0032 (11)	0.0337 (14)	−0.0061 (11)
C16	0.0670 (15)	0.0363 (11)	0.0471 (13)	0.0116 (11)	0.0243 (12)	0.0082 (10)
C17	0.0485 (12)	0.0384 (11)	0.0365 (11)	0.0058 (10)	0.0115 (10)	0.0022 (9)
C18	0.0317 (10)	0.0289 (9)	0.0358 (10)	0.0013 (8)	0.0113 (8)	0.0002 (8)
C19	0.0295 (10)	0.0327 (10)	0.0317 (10)	−0.0011 (8)	0.0056 (8)	−0.0012 (8)
C20	0.0361 (11)	0.0280 (9)	0.0352 (10)	0.0009 (8)	0.0091 (8)	0.0029 (8)
C21	0.0347 (10)	0.0275 (9)	0.0315 (10)	0.0031 (8)	0.0085 (8)	0.0030 (8)
C22	0.0405 (11)	0.0294 (9)	0.0376 (11)	0.0022 (8)	0.0129 (9)	0.0046 (8)
C23	0.0545 (13)	0.0356 (10)	0.0293 (10)	0.0042 (10)	0.0111 (9)	0.0042 (8)
C24	0.0494 (13)	0.0346 (10)	0.0313 (11)	0.0007 (10)	0.0000 (9)	0.0017 (8)
C25	0.0367 (11)	0.0424 (11)	0.0402 (12)	−0.0042 (9)	0.0038 (9)	0.0042 (9)
C26	0.0374 (11)	0.0409 (11)	0.0317 (10)	0.0006 (9)	0.0090 (9)	0.0024 (9)

Geometric parameters (Å, º) top

Cl1—C22	1.737 (2)	C11—C12	1.380 (3)
Cl2—C24	1.733 (2)	C11—H11	0.930
P1—C6	1.7984 (19)	C13—C14	1.382 (3)
P1—C18	1.8000 (19)	C13—C18	1.388 (3)
P1—C12	1.8006 (18)	C13—H13	0.930
P1—C19	1.8044 (19)	C14—C15	1.381 (4)
O1—C20	1.218 (2)	C14—H14	0.930
C1—C2	1.384 (3)	C15—C16	1.374 (3)
C1—C6	1.389 (3)	C15—H15	0.930
C1—H1	0.930	C16—C17	1.380 (3)
C2—C3	1.374 (4)	C16—H16	0.930
C2—H2	0.930	C17—C18	1.389 (3)
C3—C4	1.366 (4)	C17—H17	0.930
C3—H3	0.930	C19—C20	1.526 (3)
C4—C5	1.384 (3)	C19—H19A	0.970
C4—H4	0.930	C19—H19B	0.970
C5—C6	1.385 (3)	C20—C21	1.479 (3)
C5—H5	0.930	C21—C26	1.399 (3)
C7—C8	1.382 (3)	C21—C22	1.402 (3)
C7—C12	1.395 (3)	C22—C23	1.381 (3)
C7—H7	0.930	C23—C24	1.379 (3)
C8—C9	1.369 (4)	C23—H23	0.930
C8—H8	0.930	C24—C25	1.377 (3)
C9—C10	1.372 (4)	C25—C26	1.375 (3)
C9—H9	0.930	C25—H25	0.930
C10—C11	1.382 (3)	C26—H26	0.930
C10—H10	0.930

C6—P1—C18	103.99 (9)	C18—C13—H13	120.0
C6—P1—C12	107.65 (9)	C15—C14—C13	119.9 (2)
C18—P1—C12	113.76 (9)	C15—C14—H14	120.0
C6—P1—C19	111.49 (9)	C13—C14—H14	120.0
C18—P1—C19	111.28 (9)	C16—C15—C14	120.2 (2)
C12—P1—C19	108.59 (9)	C16—C15—H15	119.9
C2—C1—C6	119.2 (2)	C14—C15—H15	119.9
C2—C1—H1	120.4	C15—C16—C17	120.4 (2)
C6—C1—H1	120.4	C15—C16—H16	119.8
C3—C2—C1	120.8 (2)	C17—C16—H16	119.8
C3—C2—H2	119.6	C16—C17—C18	119.8 (2)
C1—C2—H2	119.6	C16—C17—H17	120.1
C4—C3—C2	120.0 (2)	C18—C17—H17	120.1
C4—C3—H3	120.0	C13—C18—C17	119.65 (18)
C2—C3—H3	120.0	C13—C18—P1	119.27 (15)
C3—C4—C5	120.2 (2)	C17—C18—P1	120.78 (15)
C3—C4—H4	119.9	C20—C19—P1	107.79 (13)
C5—C4—H4	119.9	C20—C19—H19A	110.1
C4—C5—C6	120.1 (2)	P1—C19—H19A	110.1
C4—C5—H5	120.0	C20—C19—H19B	110.1
C6—C5—H5	120.0	P1—C19—H19B	110.1
C5—C6—C1	119.67 (19)	H19A—C19—H19B	108.5
C5—C6—P1	120.89 (15)	O1—C20—C21	123.30 (17)
C1—C6—P1	118.70 (16)	O1—C20—C19	117.84 (17)
C8—C7—C12	118.8 (2)	C21—C20—C19	118.85 (16)
C8—C7—H7	120.6	C26—C21—C22	117.21 (18)
C12—C7—H7	120.6	C26—C21—C20	119.16 (17)
C9—C8—C7	121.1 (2)	C22—C21—C20	123.60 (17)
C9—C8—H8	119.5	C23—C22—C21	121.64 (19)
C7—C8—H8	119.5	C23—C22—Cl1	115.44 (15)
C8—C9—C10	119.9 (2)	C21—C22—Cl1	122.91 (16)
C8—C9—H9	120.1	C24—C23—C22	118.37 (18)
C10—C9—H9	120.1	C24—C23—H23	120.8
C9—C10—C11	120.3 (2)	C22—C23—H23	120.8
C9—C10—H10	119.8	C25—C24—C23	122.33 (19)
C11—C10—H10	119.8	C25—C24—Cl2	119.12 (17)
C12—C11—C10	119.9 (2)	C23—C24—Cl2	118.55 (16)
C12—C11—H11	120.1	C26—C25—C24	118.34 (19)
C10—C11—H11	120.1	C26—C25—H25	120.8
C11—C12—C7	120.04 (18)	C24—C25—H25	120.8
C11—C12—P1	122.36 (15)	C25—C26—C21	122.08 (18)
C7—C12—P1	117.59 (15)	C25—C26—H26	119.0
C14—C13—C18	120.0 (2)	C21—C26—H26	119.0
C14—C13—H13	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl3ⁱ	0.93	2.82	3.640 (2)	148
C9—H9···O1ⁱⁱ	0.93	2.51	3.386 (3)	157
C17—H17···Cl2ⁱⁱⁱ	0.93	2.79	3.396 (2)	123
C19—H19A···Cl3^iv	0.97	2.59	3.534 (2)	165
C19—H19B···Cl3	0.97	2.59	3.555 (2)	173
C23—H23···Cl3^v	0.93	2.80	3.715 (2)	166

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x+1, −y, −z+1; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2.

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(2,4-Di­chloro­benzoyl­methyl)­tri­phenyl­phospho­nium chloride

Supporting information

Key indicators

checkCIF/PLATON results

(2,4-Dichlorobenzoylmethyl)triphenylphosphonium chloride