4-Bromo­benzoyl­methyl­ene–triphenyl­phospho­rane ylide

Sabounchei, S.J.; Dadras, A.; Jafarzadeh, M.; Khavasi, H.R.

doi:10.1107/S1600536807022623

4-Bromobenzoylmethylene-triphenylphosphorane ylide

S. J. Sabounchei, A. Dadras, M. Jafarzadeh and H. R. Khavasi

In the molecule of the title compound, (4-bromobenzoyl)(triphenylphosphonio)methanide, C₂₆H₂₀BrOP, the geometry around the P atom is nearly tetrahedral and the O atom is oriented cis to the P atom. The bromophenyl ring of the benzoyl group is twisted with respect to the plane of the carbonyl group through an angle of 3.83 (3)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022623/hk2238sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022623/hk2238Isup2.hkl Contains datablock I

CCDC reference: 632047

checkCIF report

Key indicators

Single-crystal X-ray study
T = 128 K
Mean (C-C) = 0.003 Å
R factor = 0.027
wR factor = 0.059
Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Br1    ..  Br1     ..       3.35 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C26 H20 Br O P

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Phosphoranes of the type (C₆H₅)₃PCHCOC₆H₄Br (BBPPY) can coordinate to metals through either C or O atoms. The crystal and molecular structure of this ylide with space group P2₁/c, was determined successfully (Bart, 1969). The structural investigation with metrical parameters for the title compound, (I), show that how they vary with a change in delocalization in the metal derivatives, as well as in other resonance-stabilized ylides.

In the molecule of the title compound, (I), (Fig. 1), the bond lengths and angles (Table 1) are generally within normal ranges (Allen et al., 1987).

The P1—C8 [1.719 (17) Å] bond is shorter than the other P—C bonds (Table 1) and longer than the equivalent bond lengths of 1.66 Å reported for methylenetriphenylphosphorane (Bart, 1969), which shows partial double-bond character for these two bonds. The C7—O1 [1.256 (2) A°] double bond is shorter than the C=O bonds in ketons (1.331 Å; Allen et al., 1987). These bond distances suggest resonance decolization in the molecule (Fig. 2). The resonance formulation is supported by the near planarity of P1, C8, O1 and C7 in (I). The torsion angle O1—C7—C8—P1 [2.8 (3)°] also indicates the resonance.

The bromophenyl ring of the benzoyl group is twisted with respect to the plane of the carbonyl group through an angle of 3.83 (3)°. The C7—C8—P1 [120.37 (13)°] bond angle indicates a distorted trigonal arrangement about C8. The P1···O1 [2.990 (3) Å] distance is significantly shorter than the sum of the van der Waals radii of P and O (3.3 Å; Dunitz, 1979), indicating a strong intramolecular interaction between P⁺ and O^- charge centers, which leads to the cis orientation.

Related literature top

For general background, see: Allen et al. (1987); Dunitz (1979). For related literature, see: Bart (1969).

Experimental top

The title compound was prepared by addition of 2,4-Bromophenyl acetophenone (278 mg, 1 mmol) in chloroform (20 ml) to a solution of triphenylphosphine (262 mg, 1 mmol) in the same solvent (5 ml). The resulting pale yellow solution was stirred for 10 h, and then concentrated under reduced pressure to 5 ml, and diethyl ether (20 ml) was added. The yellow solid formed was filtered off, washed with petroleum benzene (10 ml), and then dried under reduced pressure. In order to get the final product, all of the crude solid, was transferred to an alkaline solution of NaOH (5%) and stirred at 310 K for about 14 h, yielding the white precipitate. The product was washed several times with distilled water and air dried. The resulting solid was recrystallized from an acetonitrile-diethyl ether mixture (5:15) (yield; 436 mg, 95%, m.p. 465–467 K).

Structure description top

In the molecule of the title compound, (I), (Fig. 1), the bond lengths and angles (Table 1) are generally within normal ranges (Allen et al., 1987).

For general background, see: Allen et al. (1987); Dunitz (1979). For related literature, see: Bart (1969).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at 30% probability level.
	Fig. 2. Resonance in the BBPPY.

(4-bromobenzoyl)(triphenylphosphonio)methanide top

Crystal data top

C₂₆H₂₀BrOP	Z = 8
M_r = 459.3	F(000) = 1872
Monoclinic, C2/c	D_x = 1.425 Mg m⁻³
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 16.6819 (17) Å	θ = 1.7–26.8°
b = 10.9590 (8) Å	µ = 2.01 mm⁻¹
c = 23.718 (2) Å	T = 128 K
β = 98.983 (8)°	Plate, colorless
V = 4282.8 (7) Å³	0.3 × 0.2 × 0.05 mm

Data collection top

Stoe IPDS II diffractometer	4025 reflections with I > 2σ(I)
rotation method scans	R_int = 0.027
Absorption correction: numerical shape of crystal determined optically	θ_max = 26.8°, θ_min = 1.7°
T_min = 0.62, T_max = 0.91	h = −21→21
16156 measured reflections	k = −13→13
4447 independent reflections	l = −29→30

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.028	w = 1/[σ²(F_o²) + (0.0207P)² + 5.8973P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.059	(Δ/σ)_max = 0.015
S = 1.12	Δρ_max = 0.39 e Å⁻³
4447 reflections	Δρ_min = −0.24 e Å⁻³
262 parameters

Crystal data top

C₂₆H₂₀BrOP	V = 4282.8 (7) Å³
M_r = 459.3	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 16.6819 (17) Å	µ = 2.01 mm⁻¹
b = 10.9590 (8) Å	T = 128 K
c = 23.718 (2) Å	0.3 × 0.2 × 0.05 mm
β = 98.983 (8)°

Data collection top

Stoe IPDS II diffractometer	4447 independent reflections
Absorption correction: numerical shape of crystal determined optically	4025 reflections with I > 2σ(I)
T_min = 0.62, T_max = 0.91	R_int = 0.027
16156 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.059	H-atom parameters constrained
S = 1.12	Δρ_max = 0.39 e Å⁻³
4447 reflections	Δρ_min = −0.24 e Å⁻³
262 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.16258 (10)	−0.03950 (17)	0.14125 (7)	0.0192 (3)
C2	−0.21774 (11)	0.05592 (17)	0.13165 (8)	0.0218 (4)
H2	−0.223	0.1118	0.1604	0.026*
C3	−0.26484 (10)	0.06607 (16)	0.07828 (8)	0.0205 (4)
H3	−0.3019	0.1298	0.0712	0.025*
C4	−0.25771 (10)	−0.01771 (15)	0.03477 (7)	0.0170 (3)
C5	−0.20215 (10)	−0.11313 (16)	0.04636 (8)	0.0206 (4)
H5	−0.197	−0.1697	0.0179	0.025*
C6	−0.15460 (11)	−0.12498 (16)	0.09947 (8)	0.0212 (4)
H6	−0.118	−0.1892	0.1069	0.025*
C7	−0.30930 (10)	−0.01368 (16)	−0.02367 (7)	0.0186 (3)
C8	−0.36518 (11)	0.08152 (16)	−0.03652 (7)	0.0197 (4)
H8	−0.3671	0.1443	−0.0104	0.024*
C9	−0.48997 (10)	−0.05477 (16)	−0.11460 (7)	0.0188 (3)
C10	−0.49752 (11)	−0.13549 (16)	−0.07044 (8)	0.0217 (4)
H10	−0.4711	−0.1196	−0.0337	0.026*
C11	−0.54467 (12)	−0.23993 (17)	−0.08151 (9)	0.0266 (4)
H11	−0.5495	−0.2943	−0.0521	0.032*
C12	−0.58459 (13)	−0.26341 (18)	−0.13623 (10)	0.0308 (5)
H12	−0.6158	−0.3337	−0.1434	0.037*
C13	−0.57818 (13)	−0.18271 (19)	−0.18017 (9)	0.0319 (5)
H13	−0.6056	−0.1981	−0.2167	0.038*
C14	−0.53068 (12)	−0.07852 (17)	−0.16958 (8)	0.0255 (4)
H14	−0.526	−0.0245	−0.1991	0.031*
C15	−0.38403 (11)	0.10728 (17)	−0.16402 (7)	0.0199 (4)
C16	−0.32349 (13)	0.0264 (2)	−0.17531 (9)	0.0333 (5)
H16	−0.3085	−0.0391	−0.151	0.04*
C17	−0.28599 (14)	0.0444 (2)	−0.22271 (9)	0.0386 (5)
H17	−0.2455	−0.0091	−0.23	0.046*
C18	−0.30800 (12)	0.1410 (2)	−0.25940 (8)	0.0306 (4)
H18	−0.2821	0.1528	−0.2909	0.037*
C19	−0.36853 (12)	0.21988 (18)	−0.24907 (8)	0.0264 (4)
H19	−0.384	0.2841	−0.274	0.032*
C20	−0.40652 (11)	0.20340 (17)	−0.20119 (8)	0.0229 (4)
H20	−0.447	0.257	−0.1942	0.027*
C21	−0.49912 (10)	0.20790 (15)	−0.09477 (7)	0.0162 (3)
C22	−0.58242 (11)	0.18995 (16)	−0.09849 (7)	0.0195 (4)
H22	−0.6044	0.1126	−0.1062	0.023*
C23	−0.63283 (11)	0.28770 (17)	−0.09072 (8)	0.0231 (4)
H23	−0.6884	0.2754	−0.0929	0.028*
C24	−0.60041 (12)	0.40320 (17)	−0.07974 (9)	0.0269 (4)
H24	−0.6343	0.4684	−0.0749	0.032*
C25	−0.51717 (12)	0.42187 (17)	−0.07595 (9)	0.0274 (4)
H25	−0.4955	0.4995	−0.0685	0.033*
C26	−0.46648 (11)	0.32434 (17)	−0.08331 (8)	0.0225 (4)
H26	−0.4108	0.3366	−0.0806	0.027*
O1	−0.30126 (8)	−0.09884 (12)	−0.05778 (5)	0.0239 (3)
P1	−0.43030 (3)	0.08289 (4)	−0.100322 (18)	0.01607 (9)
Br1	−0.094213 (11)	−0.053119 (18)	0.213126 (8)	0.02670 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0132 (8)	0.0252 (9)	0.0184 (8)	−0.0027 (7)	−0.0002 (7)	0.0059 (7)
C2	0.0185 (8)	0.0251 (9)	0.0217 (9)	0.0012 (7)	0.0029 (7)	−0.0032 (7)
C3	0.0168 (8)	0.0206 (9)	0.0238 (9)	0.0041 (7)	0.0019 (7)	−0.0009 (7)
C4	0.0128 (8)	0.0178 (8)	0.0206 (8)	0.0005 (6)	0.0030 (7)	0.0013 (7)
C5	0.0191 (8)	0.0189 (9)	0.0239 (9)	0.0019 (7)	0.0038 (7)	−0.0013 (7)
C6	0.0166 (8)	0.0196 (9)	0.0270 (9)	0.0029 (7)	0.0018 (7)	0.0036 (7)
C7	0.0172 (8)	0.0192 (8)	0.0196 (8)	0.0024 (7)	0.0035 (7)	0.0003 (7)
C8	0.0201 (8)	0.0209 (9)	0.0173 (8)	0.0048 (7)	0.0007 (7)	−0.0029 (7)
C9	0.0188 (8)	0.0165 (8)	0.0218 (8)	0.0050 (7)	0.0059 (7)	−0.0024 (7)
C10	0.0217 (9)	0.0220 (9)	0.0227 (9)	0.0069 (7)	0.0071 (7)	0.0001 (7)
C11	0.0280 (10)	0.0193 (9)	0.0353 (11)	0.0059 (7)	0.0134 (9)	0.0034 (8)
C12	0.0335 (11)	0.0168 (9)	0.0437 (12)	−0.0006 (8)	0.0109 (10)	−0.0078 (8)
C13	0.0382 (11)	0.0265 (10)	0.0297 (10)	−0.0024 (9)	0.0013 (9)	−0.0098 (8)
C14	0.0339 (10)	0.0207 (9)	0.0219 (9)	0.0009 (8)	0.0042 (8)	−0.0016 (7)
C15	0.0182 (8)	0.0250 (9)	0.0166 (8)	−0.0006 (7)	0.0035 (7)	−0.0023 (7)
C16	0.0340 (11)	0.0404 (12)	0.0278 (10)	0.0145 (9)	0.0120 (9)	0.0065 (9)
C17	0.0334 (11)	0.0527 (14)	0.0335 (11)	0.0175 (10)	0.0175 (10)	0.0046 (10)
C18	0.0278 (10)	0.0449 (12)	0.0210 (9)	−0.0017 (9)	0.0098 (8)	−0.0014 (9)
C19	0.0305 (10)	0.0293 (10)	0.0198 (9)	−0.0027 (8)	0.0050 (8)	0.0007 (8)
C20	0.0233 (9)	0.0257 (9)	0.0199 (9)	0.0020 (7)	0.0047 (8)	−0.0028 (7)
C21	0.0179 (8)	0.0181 (8)	0.0131 (7)	0.0045 (6)	0.0037 (6)	0.0017 (6)
C22	0.0196 (8)	0.0194 (9)	0.0200 (8)	0.0002 (7)	0.0045 (7)	0.0012 (7)
C23	0.0164 (8)	0.0270 (10)	0.0270 (9)	0.0030 (7)	0.0073 (8)	0.0025 (7)
C24	0.0270 (10)	0.0214 (9)	0.0350 (10)	0.0096 (8)	0.0134 (9)	0.0042 (8)
C25	0.0271 (10)	0.0168 (9)	0.0404 (11)	0.0004 (7)	0.0117 (9)	−0.0003 (8)
C26	0.0178 (8)	0.0226 (9)	0.0282 (9)	0.0008 (7)	0.0069 (8)	0.0020 (7)
O1	0.0240 (7)	0.0242 (7)	0.0228 (6)	0.0074 (5)	0.0010 (5)	−0.0053 (5)
P1	0.0158 (2)	0.0174 (2)	0.0152 (2)	0.00392 (16)	0.00301 (17)	−0.00050 (16)
Br1	0.02069 (10)	0.03603 (11)	0.02137 (9)	0.00387 (8)	−0.00301 (7)	0.00497 (8)

Geometric parameters (Å, º) top

C1—C6	1.385 (3)	C13—H13	0.93
C1—C2	1.388 (2)	C14—H14	0.93
C1—Br1	1.9032 (17)	C15—C20	1.387 (3)
C2—C3	1.386 (2)	C15—C16	1.401 (3)
C2—H2	0.93	C15—P1	1.8204 (18)
C3—C4	1.400 (2)	C16—C17	1.383 (3)
C3—H3	0.93	C16—H16	0.93
C4—C5	1.396 (2)	C17—C18	1.383 (3)
C4—C7	1.514 (2)	C17—H17	0.93
C5—C6	1.386 (2)	C18—C19	1.380 (3)
C5—H5	0.93	C18—H18	0.93
C6—H6	0.93	C19—C20	1.396 (3)
C7—O1	1.256 (2)	C19—H19	0.93
C7—C8	1.401 (2)	C20—H20	0.93
C8—P1	1.7194 (17)	C21—C22	1.393 (2)
C8—H8	0.93	C21—C26	1.397 (3)
C9—C10	1.392 (3)	C21—P1	1.8054 (17)
C9—C14	1.397 (3)	C22—C23	1.392 (2)
C9—P1	1.8101 (18)	C22—H22	0.93
C10—C11	1.390 (3)	C23—C24	1.385 (3)
C10—H10	0.93	C23—H23	0.93
C11—C12	1.387 (3)	C24—C25	1.393 (3)
C11—H11	0.93	C24—H24	0.93
C12—C13	1.384 (3)	C25—C26	1.391 (3)
C12—H12	0.93	C25—H25	0.93
C13—C14	1.390 (3)	C26—H26	0.93

C6—C1—C2	121.84 (16)	C16—C15—P1	118.53 (14)
C6—C1—Br1	118.47 (13)	C17—C16—C15	119.76 (19)
C2—C1—Br1	119.68 (14)	C17—C16—H16	120.1
C3—C2—C1	118.49 (17)	C15—C16—H16	120.1
C3—C2—H2	120.8	C16—C17—C18	120.7 (2)
C1—C2—H2	120.8	C16—C17—H17	119.6
C2—C3—C4	121.27 (16)	C18—C17—H17	119.6
C2—C3—H3	119.4	C19—C18—C17	119.83 (19)
C4—C3—H3	119.4	C19—C18—H18	120.1
C5—C4—C3	118.45 (16)	C17—C18—H18	120.1
C5—C4—C7	117.86 (15)	C18—C19—C20	120.08 (18)
C3—C4—C7	123.65 (15)	C18—C19—H19	120
C6—C5—C4	121.16 (17)	C20—C19—H19	120
C6—C5—H5	119.4	C15—C20—C19	120.21 (18)
C4—C5—H5	119.4	C15—C20—H20	119.9
C1—C6—C5	118.79 (16)	C19—C20—H20	119.9
C1—C6—H6	120.6	C22—C21—C26	119.74 (16)
C5—C6—H6	120.6	C22—C21—P1	121.86 (13)
O1—C7—C8	123.21 (16)	C26—C21—P1	118.31 (13)
O1—C7—C4	117.75 (15)	C23—C22—C21	120.03 (17)
C8—C7—C4	119.01 (15)	C23—C22—H22	120
C7—C8—P1	120.37 (13)	C21—C22—H22	120
C7—C8—H8	119.8	C24—C23—C22	120.13 (17)
P1—C8—H8	119.8	C24—C23—H23	119.9
C10—C9—C14	119.74 (17)	C22—C23—H23	119.9
C10—C9—P1	120.05 (14)	C23—C24—C25	120.17 (17)
C14—C9—P1	120.18 (14)	C23—C24—H24	119.9
C11—C10—C9	119.75 (18)	C25—C24—H24	119.9
C11—C10—H10	120.1	C26—C25—C24	119.92 (17)
C9—C10—H10	120.1	C26—C25—H25	120
C12—C11—C10	120.27 (18)	C24—C25—H25	120
C12—C11—H11	119.9	C25—C26—C21	120.01 (17)
C10—C11—H11	119.9	C25—C26—H26	120
C13—C12—C11	120.26 (18)	C21—C26—H26	120
C13—C12—H12	119.9	C8—P1—C21	105.31 (8)
C11—C12—H12	119.9	C8—P1—C9	114.25 (9)
C12—C13—C14	119.86 (19)	C21—P1—C9	107.98 (8)
C12—C13—H13	120.1	C8—P1—C15	116.12 (9)
C14—C13—H13	120.1	C21—P1—C15	107.81 (8)
C13—C14—C9	120.11 (18)	C9—P1—C15	105.02 (8)
C13—C14—H14	119.9	P1—C8—C7	120.37 (13)
C9—C14—H14	119.9	O1—C7—C8	123.21 (16)
C20—C15—C16	119.38 (17)	C4—C7—C8	119.01 (15)
C20—C15—P1	122.09 (14)	O1—C7—C4	117.75 (15)

C6—C1—C2—C3	−1.1 (3)	C18—C19—C20—C15	−0.5 (3)
Br1—C1—C2—C3	177.82 (13)	C26—C21—C22—C23	−0.1 (3)
C1—C2—C3—C4	0.2 (3)	P1—C21—C22—C23	176.30 (14)
C2—C3—C4—C5	0.4 (3)	C21—C22—C23—C24	0.5 (3)
C2—C3—C4—C7	177.96 (17)	C22—C23—C24—C25	−0.5 (3)
C3—C4—C5—C6	−0.3 (3)	C23—C24—C25—C26	0.1 (3)
C7—C4—C5—C6	−178.00 (16)	C24—C25—C26—C21	0.3 (3)
C2—C1—C6—C5	1.2 (3)	C22—C21—C26—C25	−0.3 (3)
Br1—C1—C6—C5	−177.73 (13)	P1—C21—C26—C25	−176.85 (15)
C4—C5—C6—C1	−0.5 (3)	C7—C8—P1—C21	172.54 (15)
C5—C4—C7—O1	2.5 (2)	C7—C8—P1—C9	54.22 (18)
C3—C4—C7—O1	−175.06 (17)	C7—C8—P1—C15	−68.29 (18)
C5—C4—C7—C8	−179.62 (17)	C22—C21—P1—C8	−119.40 (15)
C3—C4—C7—C8	2.9 (3)	C26—C21—P1—C8	57.05 (16)
O1—C7—C8—P1	2.8 (3)	C22—C21—P1—C9	3.05 (16)
C4—C7—C8—P1	−174.97 (13)	C26—C21—P1—C9	179.50 (14)
C14—C9—C10—C11	0.8 (3)	C22—C21—P1—C15	116.03 (15)
P1—C9—C10—C11	178.81 (14)	C26—C21—P1—C15	−67.52 (16)
C9—C10—C11—C12	−0.5 (3)	C10—C9—P1—C8	17.02 (17)
C10—C11—C12—C13	−0.4 (3)	C14—C9—P1—C8	−164.99 (14)
C11—C12—C13—C14	0.8 (3)	C10—C9—P1—C21	−99.76 (15)
C12—C13—C14—C9	−0.5 (3)	C14—C9—P1—C21	78.22 (16)
C10—C9—C14—C13	−0.3 (3)	C10—C9—P1—C15	145.40 (14)
P1—C9—C14—C13	−178.34 (15)	C14—C9—P1—C15	−36.62 (16)
C20—C15—C16—C17	1.1 (3)	C20—C15—P1—C8	−121.99 (16)
P1—C15—C16—C17	−178.53 (18)	C16—C15—P1—C8	57.58 (18)
C15—C16—C17—C18	−0.4 (4)	C20—C15—P1—C21	−4.19 (18)
C16—C17—C18—C19	−0.6 (4)	C16—C15—P1—C21	175.38 (16)
C17—C18—C19—C20	1.1 (3)	C20—C15—P1—C9	110.76 (16)
C16—C15—C20—C19	−0.6 (3)	C16—C15—P1—C9	−69.66 (17)
P1—C15—C20—C19	178.96 (14)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀BrOP
M_r	459.3
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	128
a, b, c (Å)	16.6819 (17), 10.9590 (8), 23.718 (2)
β (°)	98.983 (8)
V (Å³)	4282.8 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.01
Crystal size (mm)	0.3 × 0.2 × 0.05

Data collection
Diffractometer	Stoe IPDS II
Absorption correction	Numerical shape of crystal determined optically
T_min, T_max	0.62, 0.91
No. of measured, independent and observed [I > 2σ(I)] reflections	16156, 4447, 4025
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.059, 1.12
No. of reflections	4447
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.24

Computer programs: X-AREA (Stoe & Cie, 2005), X-AREA, X-RED (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

C1—Br1	1.9032 (17)	C8—P1	1.7194 (17)
C7—O1	1.256 (2)	C9—P1	1.8101 (18)
C7—C8	1.401 (2)	C15—P1	1.8204 (18)

C8—P1—C21	105.31 (8)	C9—P1—C15	105.02 (8)
C8—P1—C9	114.25 (9)	P1—C8—C7	120.37 (13)
C21—P1—C9	107.98 (8)	O1—C7—C8	123.21 (16)
C8—P1—C15	116.12 (9)	C4—C7—C8	119.01 (15)
C21—P1—C15	107.81 (8)	O1—C7—C4	117.75 (15)

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4-Bromo­benzoyl­methyl­ene-triphenyl­phospho­rane ylide

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4-Bromobenzoylmethylene-triphenylphosphorane ylide