Bis[(4-bromo­benzoyl­meth­yl)triphenyl­phospho­nium] di-μ-bromido-bis­[di­bromido­mercurate(IV)]

Sabounchei, S.J.; Dadras, A.; Jodaian, V.; Nemattalab, H.; Khavasi, H.R.

doi:10.1107/S1600536808001220

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page m833

doi:10.1107/S1600536808001220

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Bis[(4-bromobenzoylmethyl)triphenylphosphonium] di-μ-bromido-bis[dibromidomercurate(IV)]

Seyyed Javad Sabounchei,^a ^* Alireza Dadras,^a Vida Jodaian,^a Hassan Nemattalab ^a and Hamid Reza Khavasi ^b

^aFaculty of Chemistry, Bu-Ali Sina University, Hamadan 65174, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: jsabounchei@yahoo.co.uk

(Received 1 August 2007; accepted 11 January 2008; online 21 May 2008)

Colourless needle-shaped crystals of the title compound, (C₂₆H₂₁BrOP)₂[Hg₂Br₆], have been prepared by addition of a solution of HgBr₂ in methanol to a solution of (4-bromobenzoylmethyl)triphenylphosphorane in dry methanol. The compound features Hg₂Br₆²⁻ dianions, whose site symmetry is $[\overline{1}]$ .

Related literature

For other hexabromodimercurates, see: Bell et al. (2002 ); Fábry & Maximov (1991 ); Pickardt & Wischlinski (1999 ). For related literature, see: Hu et al. (2003 ); Nockemann & Meyer (2002 ); Sabounchei et al. (2007 ); Thiel et al. (1994 ).

Experimental

Crystal data

(C₂₆H₂₁BrOP)₂[Hg₂Br₆]
M_r = 1801.18
Monoclinic, P 2₁ /n
a = 9.4146 (6) Å
b = 21.8848 (14) Å
c = 13.2675 (9) Å
β = 100.785 (5)°
V = 2685.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 11.76 mm⁻¹
T = 120 (2) K
0.5 × 0.12 × 0.1 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: numerical [shape of crystal determined optically (X-SHAPE; Stoe & Cie, 2005) T_min = 0.200, T_max = 0.300
19321 measured reflections
6386 independent reflections
5929 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.076
S = 1.17
6386 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 1.64 e Å⁻³
Δρ_min = −1.32 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2005 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001220/fi2042sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808001220/fi2042Isup2.hkl

checkCIF report

Comment top

Colourless, needle-shaped crystals of C₂₆H₂₁HgBr₃OP were obtained from a mixture of methanol, dmso and diethyl ether. The crystal structure consists of discrete [BrC₆H₄COCH₂PPh₃]⁺ cations and [Hg₂Br₆]^2- anions (Fig. 1). The crystals are air-stable and resistant to moisture. All atoms occupy general position in the monoclinic space group, P2₁/n. The site symmetry of the anion is -1, with the inversion centre halfway between the two Hg atoms. Comparison of the bond lengths and bond angles within the above crystal show that the phosphonium as a ligand is electrostatically under the influence of an anionic part of an bromomercurate in the unit cells (for instance the bond lengths C6—C7, O1—C7, C8—P1 and P1—C9 and bond angles C8—P1—C9, O1—C7—C8 are 1.489 (5), 1.213 (5), 1.804 (4) and 1.800 (4) A° and 106.7 (2) and 120.4 (4)° for title compound and 1.514 (2), 1.256 (2), 1.719 (2) and 1.805 (2) A° and 105.3 (1) and 123.2 (2)° for the phosphorane molecule (Sabounchei et al., 2007)). The bridging Hg—Br bond lengths in the crystal are 2.6693 (4) A° and 2.7920 (4) A°, the terminal Hg—Br distances are 2.5192 (5) A° and 2.5433 (5) A°. These values are well within the reported bond distances (2.703—-2.787 A° for bridging bromide and 2.479–2.532 A° for terminal bromide) in [Hg₂Br₆]^-2 anions (Nockemann & Meyer, 2002; Thiel et al., 1994; Hu et al., 2003).

Related literature top

For other hexabromodimercurates, see: Bell et al. (2002); Fábry & Maximov (1991); Pickardt & Wischlinski (1999).

For related literature, see: Hu et al. (2003); Nockemann & Meyer (2002); Sabounchei et al. (2007); Thiel et al. (1994).

Experimental top

Starting materials were purchased from commercial sources and used without further purification.The title compound was prepared by addition of solution of HgBr₂ (0.18 g, 0.5 mmol) in methanol (15 ml) to a solution of the 4-bromobenzoylmethylenetriphenylphosphorane (0.229?g, 0.5?mmol) in dry methanol (15 ml) and stirring for 12 h. A white product formed upon slow evaporation ofthe solvent. It was washed several times with dry diethylether and dried invacuo. The product was then washed with benzene and dried in vacuo. Yield 83%, m.p=290 K. It was recrystallized from a mixture of methanol, dimethylsulfoxide and diethyl ether (1:1:3).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. View of (I) (30% probability displacement ellipsoids), symmetry code (i)1 - x,-y,2 - z.

Bis[(4-bromobenzoylmethyl)triphenylphosphonium] di-µ-bromido-bis[dibromidomercurate(IV)] top

Crystal data top

(C₂₆H₂₁BrOP)₂[Hg₂Br₆]	F(000) = 1680
M_r = 1801.18	D_x = 2.228 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2500 reflections
a = 9.4146 (6) Å	θ = 1.8–28.0°
b = 21.8848 (14) Å	µ = 11.76 mm⁻¹
c = 13.2675 (9) Å	T = 120 K
β = 100.785 (5)°	Needle, colourless
V = 2685.3 (3) Å³	0.5 × 0.12 × 0.1 mm
Z = 2

Data collection top

Stoe IPDSII diffractometer	5929 reflections with I > 2σ(I)
ω scan	R_int = 0.063
Absorption correction: numerical (shape of crystal determined optically)	θ_max = 28.0°, θ_min = 1.8°
T_min = 0.200, T_max = 0.300	h = −12→12
19321 measured reflections	k = −27→28
6386 independent reflections	l = −17→17

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.0312P)² + 4.7097P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.076	(Δ/σ)_max = 0.018
S = 1.17	Δρ_max = 1.64 e Å⁻³
6386 reflections	Δρ_min = −1.32 e Å⁻³
298 parameters

Crystal data top

(C₂₆H₂₁BrOP)₂[Hg₂Br₆]	V = 2685.3 (3) Å³
M_r = 1801.18	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.4146 (6) Å	µ = 11.76 mm⁻¹
b = 21.8848 (14) Å	T = 120 K
c = 13.2675 (9) Å	0.5 × 0.12 × 0.1 mm
β = 100.785 (5)°

Data collection top

Stoe IPDSII diffractometer	6386 independent reflections
Absorption correction: numerical (shape of crystal determined optically)	5929 reflections with I > 2σ(I)
T_min = 0.200, T_max = 0.300	R_int = 0.063
19321 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.17	Δρ_max = 1.64 e Å⁻³
6386 reflections	Δρ_min = −1.32 e Å⁻³
298 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
Hg1	0.459203 (16)	0.045660 (7)	0.872826 (12)	0.02046 (6)
Br1	−0.20000 (5)	0.01733 (2)	0.54508 (3)	0.02701 (10)
Br2	0.41038 (4)	0.160021 (18)	0.86866 (3)	0.02001 (9)
Br3	0.70223 (4)	0.011883 (18)	0.99824 (3)	0.01917 (9)
Br4	0.39811 (5)	−0.00959 (2)	0.70367 (3)	0.02576 (10)
C1	0.0365 (4)	0.0819 (2)	0.8196 (3)	0.0216 (8)
H1	0.1321	0.0808	0.854	0.026*
C2	−0.0011 (4)	0.0538 (2)	0.7241 (3)	0.0230 (8)
H2	0.0686	0.035	0.6936	0.028*
C3	−0.1454 (4)	0.05466 (19)	0.6753 (3)	0.0196 (8)
C4	−0.2511 (4)	0.08368 (19)	0.7184 (3)	0.0196 (8)
H4	−0.3469	0.0839	0.6845	0.024*
C5	−0.2114 (4)	0.11225 (18)	0.8126 (3)	0.0176 (7)
H5	−0.2812	0.1321	0.8417	0.021*
C6	−0.0678 (4)	0.11159 (17)	0.8644 (3)	0.0146 (7)
C7	−0.0321 (4)	0.14202 (18)	0.9665 (3)	0.0176 (7)
C8	0.1241 (4)	0.13891 (19)	1.0237 (3)	0.0175 (7)
H8A	0.1881	0.1431	0.9746	0.021*
H8B	0.1413	0.0991	1.0556	0.021*
C9	0.3623 (4)	0.20382 (18)	1.1473 (3)	0.0150 (7)
C10	0.4485 (4)	0.15232 (18)	1.1426 (3)	0.0183 (7)
H10	0.4062	0.1142	1.1275	0.022*
C11	0.5986 (4)	0.1587 (2)	1.1606 (3)	0.0207 (8)
H11	0.6567	0.1248	1.156	0.025*
C12	0.6615 (4)	0.2155 (2)	1.1854 (3)	0.0234 (8)
H12	0.7617	0.2194	1.1983	0.028*
C13	0.5753 (4)	0.2667 (2)	1.1912 (3)	0.0228 (8)
H13	0.6177	0.3045	1.2087	0.027*
C14	0.4254 (4)	0.26093 (19)	1.1708 (3)	0.0205 (8)
H14	0.3675	0.2951	1.1729	0.025*
C15	0.1055 (4)	0.17780 (19)	1.2365 (3)	0.0172 (7)
C16	0.0059 (4)	0.1308 (2)	1.2391 (3)	0.0233 (8)
H16	−0.0286	0.1079	1.1805	0.028*
C17	−0.0408 (5)	0.1186 (2)	1.3301 (4)	0.0300 (10)
H17	−0.1067	0.0873	1.3326	0.036*
C18	0.0096 (5)	0.1526 (2)	1.4175 (4)	0.0303 (10)
H18	−0.0234	0.1442	1.4778	0.036*
C19	0.1093 (5)	0.1993 (2)	1.4156 (3)	0.0266 (9)
H19	0.1429	0.2221	1.4743	0.032*
C20	0.1586 (5)	0.21153 (19)	1.3246 (3)	0.0213 (8)
H20	0.2267	0.2421	1.3229	0.026*
C21	0.0937 (4)	0.26785 (17)	1.0688 (3)	0.0153 (7)
C22	−0.0084 (4)	0.29971 (18)	1.1122 (3)	0.0175 (7)
H22	−0.0356	0.2855	1.1718	0.021*
C23	−0.0689 (4)	0.3527 (2)	1.0657 (3)	0.0223 (8)
H23	−0.1374	0.3739	1.0942	0.027*
C24	−0.0282 (5)	0.3743 (2)	0.9772 (4)	0.0261 (9)
H24	−0.0693	0.41	0.9467	0.031*
C25	0.0741 (5)	0.3429 (2)	0.9334 (4)	0.0285 (9)
H25	0.1011	0.3575	0.874	0.034*
C26	0.1351 (5)	0.2896 (2)	0.9792 (3)	0.0241 (8)
H26	0.2033	0.2684	0.9505	0.029*
P1	0.16840 (10)	0.19701 (4)	1.12096 (7)	0.01362 (18)
O1	−0.1233 (3)	0.16804 (15)	1.0042 (2)	0.0243 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.02434 (9)	0.01809 (8)	0.01816 (9)	0.00154 (5)	0.00193 (6)	0.00013 (5)
Br1	0.0272 (2)	0.0325 (2)	0.0190 (2)	−0.00427 (17)	−0.00171 (15)	−0.00519 (16)
Br2	0.02090 (18)	0.01773 (18)	0.0232 (2)	0.00194 (14)	0.00861 (14)	0.00331 (14)
Br3	0.01555 (16)	0.01933 (19)	0.02263 (19)	0.00089 (13)	0.00359 (14)	0.00510 (14)
Br4	0.0335 (2)	0.0234 (2)	0.01901 (19)	−0.00529 (16)	0.00126 (16)	−0.00361 (15)
C1	0.0133 (16)	0.027 (2)	0.023 (2)	0.0043 (15)	−0.0005 (14)	−0.0037 (16)
C2	0.0169 (17)	0.026 (2)	0.025 (2)	0.0005 (15)	0.0016 (15)	−0.0049 (17)
C3	0.0219 (18)	0.0197 (19)	0.0151 (18)	−0.0015 (15)	−0.0020 (14)	0.0027 (14)
C4	0.0138 (16)	0.0213 (19)	0.0213 (19)	−0.0041 (14)	−0.0027 (14)	0.0033 (15)
C5	0.0136 (15)	0.0174 (18)	0.0217 (19)	0.0001 (14)	0.0031 (14)	0.0062 (15)
C6	0.0091 (14)	0.0137 (17)	0.0203 (19)	0.0008 (12)	0.0008 (13)	0.0006 (14)
C7	0.0155 (16)	0.0161 (17)	0.0212 (19)	−0.0022 (13)	0.0035 (14)	−0.0011 (14)
C8	0.0168 (17)	0.0197 (18)	0.0160 (17)	0.0009 (14)	0.0030 (13)	−0.0059 (15)
C9	0.0123 (15)	0.0192 (18)	0.0135 (17)	−0.0002 (13)	0.0019 (12)	−0.0010 (14)
C10	0.0176 (17)	0.0163 (18)	0.0195 (19)	−0.0009 (14)	−0.0007 (14)	−0.0006 (14)
C11	0.0154 (17)	0.021 (2)	0.025 (2)	0.0031 (14)	0.0026 (15)	−0.0004 (16)
C12	0.0136 (16)	0.027 (2)	0.029 (2)	−0.0018 (15)	0.0026 (15)	0.0024 (17)
C13	0.0189 (18)	0.020 (2)	0.028 (2)	−0.0063 (15)	0.0030 (15)	−0.0041 (16)
C14	0.0195 (18)	0.0180 (19)	0.024 (2)	0.0000 (15)	0.0036 (15)	−0.0033 (15)
C15	0.0137 (16)	0.0192 (18)	0.0195 (18)	0.0022 (14)	0.0055 (13)	0.0012 (14)
C16	0.0206 (18)	0.024 (2)	0.025 (2)	−0.0014 (15)	0.0035 (16)	0.0023 (16)
C17	0.024 (2)	0.029 (2)	0.039 (3)	−0.0019 (17)	0.0095 (18)	0.013 (2)
C18	0.032 (2)	0.036 (3)	0.026 (2)	0.0083 (19)	0.0124 (18)	0.0119 (19)
C19	0.033 (2)	0.030 (2)	0.018 (2)	0.0100 (18)	0.0087 (17)	0.0020 (17)
C20	0.0246 (19)	0.0178 (18)	0.021 (2)	0.0005 (15)	0.0045 (15)	0.0012 (15)
C21	0.0146 (15)	0.0132 (16)	0.0176 (18)	−0.0013 (13)	0.0022 (13)	−0.0003 (14)
C22	0.0163 (16)	0.0171 (18)	0.0190 (18)	−0.0015 (14)	0.0031 (14)	−0.0011 (14)
C23	0.0180 (17)	0.021 (2)	0.027 (2)	0.0036 (15)	0.0021 (15)	−0.0024 (17)
C24	0.026 (2)	0.022 (2)	0.027 (2)	0.0052 (16)	−0.0022 (17)	0.0054 (17)
C25	0.035 (2)	0.028 (2)	0.024 (2)	0.0027 (19)	0.0077 (18)	0.0090 (18)
C26	0.030 (2)	0.021 (2)	0.023 (2)	0.0024 (17)	0.0095 (17)	0.0018 (16)
P1	0.0123 (4)	0.0141 (4)	0.0147 (4)	0.0004 (3)	0.0032 (3)	−0.0015 (3)
O1	0.0159 (13)	0.0271 (16)	0.0300 (16)	0.0008 (11)	0.0050 (11)	−0.0085 (13)

Geometric parameters (Å, º) top

Hg1—Br4	2.5192 (5)	C12—C13	1.394 (6)
Hg1—Br2	2.5433 (5)	C12—H12	0.93
Hg1—Br3	2.6693 (4)	C13—C14	1.391 (5)
Hg1—Br3ⁱ	2.7919 (4)	C13—H13	0.93
Br1—C3	1.893 (4)	C14—H14	0.93
Br3—Hg1ⁱ	2.7919 (4)	C15—C20	1.394 (6)
C1—C2	1.392 (6)	C15—C16	1.396 (6)
C1—C6	1.400 (5)	C15—P1	1.794 (4)
C1—H1	0.93	C16—C17	1.386 (6)
C2—C3	1.391 (6)	C16—H16	0.93
C2—H2	0.93	C17—C18	1.384 (8)
C3—C4	1.391 (6)	C17—H17	0.93
C4—C5	1.385 (6)	C18—C19	1.389 (7)
C4—H4	0.93	C18—H18	0.93
C5—C6	1.398 (5)	C19—C20	1.397 (6)
C5—H5	0.93	C19—H19	0.93
C6—C7	1.489 (5)	C20—H20	0.93
C7—O1	1.213 (5)	C21—C22	1.395 (5)
C7—C8	1.526 (5)	C21—C26	1.403 (6)
C8—P1	1.804 (4)	C21—P1	1.787 (4)
C8—H8A	0.97	C22—C23	1.384 (6)
C8—H8B	0.97	C22—H22	0.93
C9—C14	1.394 (6)	C23—C24	1.386 (6)
C9—C10	1.397 (5)	C23—H23	0.93
C9—P1	1.800 (4)	C24—C25	1.395 (7)
C10—C11	1.396 (5)	C24—H24	0.93
C10—H10	0.93	C25—C26	1.388 (6)
C11—C12	1.391 (6)	C25—H25	0.93
C11—H11	0.93	C26—H26	0.93

Br4—Hg1—Br2	116.277 (15)	C14—C13—H13	120.1
Br4—Hg1—Br3	116.655 (15)	C12—C13—H13	120.1
Br2—Hg1—Br3	114.607 (14)	C13—C14—C9	119.9 (4)
Br4—Hg1—Br3ⁱ	105.642 (15)	C13—C14—H14	120
Br2—Hg1—Br3ⁱ	109.895 (13)	C9—C14—H14	120
Br3—Hg1—Br3ⁱ	89.686 (12)	C20—C15—C16	120.4 (4)
Hg1—Br3—Hg1ⁱ	90.314 (12)	C20—C15—P1	117.9 (3)
C2—C1—C6	120.8 (4)	C16—C15—P1	121.6 (3)
C2—C1—H1	119.6	C17—C16—C15	119.1 (4)
C6—C1—H1	119.6	C17—C16—H16	120.4
C3—C2—C1	118.5 (4)	C15—C16—H16	120.4
C3—C2—H2	120.7	C18—C17—C16	120.8 (4)
C1—C2—H2	120.7	C18—C17—H17	119.6
C4—C3—C2	121.7 (4)	C16—C17—H17	119.6
C4—C3—Br1	118.6 (3)	C17—C18—C19	120.4 (4)
C2—C3—Br1	119.6 (3)	C17—C18—H18	119.8
C5—C4—C3	119.0 (3)	C19—C18—H18	119.8
C5—C4—H4	120.5	C18—C19—C20	119.4 (4)
C3—C4—H4	120.5	C18—C19—H19	120.3
C4—C5—C6	120.8 (4)	C20—C19—H19	120.3
C4—C5—H5	119.6	C15—C20—C19	119.8 (4)
C6—C5—H5	119.6	C15—C20—H20	120.1
C5—C6—C1	119.1 (4)	C19—C20—H20	120.1
C5—C6—C7	118.4 (3)	C22—C21—C26	120.1 (4)
C1—C6—C7	122.5 (3)	C22—C21—P1	121.7 (3)
O1—C7—C6	121.9 (3)	C26—C21—P1	118.1 (3)
O1—C7—C8	120.4 (4)	C23—C22—C21	119.5 (4)
C6—C7—C8	117.7 (3)	C23—C22—H22	120.2
C7—C8—P1	113.4 (3)	C21—C22—H22	120.2
C7—C8—H8A	108.9	C22—C23—C24	120.5 (4)
P1—C8—H8A	108.9	C22—C23—H23	119.8
C7—C8—H8B	108.9	C24—C23—H23	119.8
P1—C8—H8B	108.9	C23—C24—C25	120.5 (4)
H8A—C8—H8B	107.7	C23—C24—H24	119.8
C14—C9—C10	120.4 (3)	C25—C24—H24	119.8
C14—C9—P1	119.5 (3)	C26—C25—C24	119.5 (4)
C10—C9—P1	120.1 (3)	C26—C25—H25	120.2
C11—C10—C9	119.4 (4)	C24—C25—H25	120.2
C11—C10—H10	120.3	C25—C26—C21	119.9 (4)
C9—C10—H10	120.3	C25—C26—H26	120
C12—C11—C10	120.1 (4)	C21—C26—H26	120
C12—C11—H11	119.9	C21—P1—C15	111.40 (18)
C10—C11—H11	119.9	C21—P1—C9	108.34 (18)
C11—C12—C13	120.4 (4)	C15—P1—C9	109.79 (17)
C11—C12—H12	119.8	C21—P1—C8	108.25 (18)
C13—C12—H12	119.8	C15—P1—C8	112.16 (19)
C14—C13—C12	119.8 (4)	C9—P1—C8	106.72 (17)

Br4—Hg1—Br3—Hg1ⁱ	−107.394 (16)	C16—C15—C20—C19	−1.6 (6)
Br2—Hg1—Br3—Hg1ⁱ	111.825 (14)	P1—C15—C20—C19	178.2 (3)
Br3ⁱ—Hg1—Br3—Hg1ⁱ	0	C18—C19—C20—C15	1.2 (6)
C6—C1—C2—C3	−1.6 (7)	C26—C21—C22—C23	0.3 (6)
C1—C2—C3—C4	1.4 (7)	P1—C21—C22—C23	−176.5 (3)
C1—C2—C3—Br1	179.7 (3)	C21—C22—C23—C24	−0.4 (6)
C2—C3—C4—C5	−0.3 (6)	C22—C23—C24—C25	0.2 (7)
Br1—C3—C4—C5	−178.6 (3)	C23—C24—C25—C26	0.0 (7)
C3—C4—C5—C6	−0.6 (6)	C24—C25—C26—C21	0.0 (7)
C4—C5—C6—C1	0.4 (6)	C22—C21—C26—C25	−0.2 (6)
C4—C5—C6—C7	−178.8 (4)	P1—C21—C26—C25	176.8 (4)
C2—C1—C6—C5	0.7 (6)	C22—C21—P1—C15	−4.3 (4)
C2—C1—C6—C7	179.9 (4)	C26—C21—P1—C15	178.8 (3)
C5—C6—C7—O1	−1.4 (6)	C22—C21—P1—C9	−125.2 (3)
C1—C6—C7—O1	179.4 (4)	C26—C21—P1—C9	57.9 (4)
C5—C6—C7—C8	177.9 (4)	C22—C21—P1—C8	119.5 (3)
C1—C6—C7—C8	−1.3 (6)	C26—C21—P1—C8	−57.4 (4)
O1—C7—C8—P1	−20.7 (5)	C20—C15—P1—C21	−72.1 (3)
C6—C7—C8—P1	160.0 (3)	C16—C15—P1—C21	107.6 (3)
C14—C9—C10—C11	−0.6 (6)	C20—C15—P1—C9	47.9 (4)
P1—C9—C10—C11	178.3 (3)	C16—C15—P1—C9	−132.4 (3)
C9—C10—C11—C12	1.5 (6)	C20—C15—P1—C8	166.4 (3)
C10—C11—C12—C13	−0.8 (7)	C16—C15—P1—C8	−13.9 (4)
C11—C12—C13—C14	−0.8 (7)	C14—C9—P1—C21	28.6 (4)
C12—C13—C14—C9	1.7 (7)	C10—C9—P1—C21	−150.4 (3)
C10—C9—C14—C13	−1.0 (6)	C14—C9—P1—C15	−93.3 (3)
P1—C9—C14—C13	−179.9 (3)	C10—C9—P1—C15	87.7 (4)
C20—C15—C16—C17	0.8 (6)	C14—C9—P1—C8	144.9 (3)
P1—C15—C16—C17	−178.9 (3)	C10—C9—P1—C8	−34.1 (4)
C15—C16—C17—C18	0.3 (7)	C7—C8—P1—C21	−43.9 (3)
C16—C17—C18—C19	−0.7 (7)	C7—C8—P1—C15	79.4 (3)
C17—C18—C19—C20	−0.1 (7)	C7—C8—P1—C9	−160.3 (3)

Symmetry code: (i) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	(C₂₆H₂₁BrOP)₂[Hg₂Br₆]
M_r	1801.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	9.4146 (6), 21.8848 (14), 13.2675 (9)
β (°)	100.785 (5)
V (Å³)	2685.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	11.76
Crystal size (mm)	0.5 × 0.12 × 0.1

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Numerical (shape of crystal determined optically)
T_min, T_max	0.200, 0.300
No. of measured, independent and observed [I > 2σ(I)] reflections	19321, 6386, 5929
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.076, 1.17
No. of reflections	6386
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.64, −1.32

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999).

Acknowledgements

The authors acknowledge Bu-Ali Sina University for financial support.

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