Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The asymmetric unit of the title triphenyl­phospho­nium salt, C23H24O2P+·Br, contains two cations and two anions. In the crystal structure, O—H...Br, C—H...O and C—H...Br hydrogen bonds link the ions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053548/hk2349sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053548/hk2349Isup2.hkl
Contains datablock I

CCDC reference: 672808

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.013 Å
  • R factor = 0.084
  • wR factor = 0.196
  • Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C46 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.36 Ang. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 13 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C23 H24 O2 P PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C23 H24 O2 P
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 121
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Triphenylphosphoniums are an important class of isoaromatic compounds and have widespread applications in pharmaceuticals (Mashraqui et al., 2004; Ishikawa & Manabe, 2006). As part of our ongoing studies in this area, we report herein the synthesis and crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The asymmetric unit contains two independent molecules. Rings A (C1–C6), B (C7–C12), C (C13–C18), D (C24–C29), E (C30–C35) and F (C36–C41) are, of course, planar and the dihedral angles between them are A/B = 79.30 (3)°, A/C = 87.03 (3)°, B/C = 63.74 (2)°, D/E = 61.30 (2)°, D/F = 70.17 (3)° and E/F = 84.32 (3)°.

In the crystal structure, O—H···Br, C—H···O and C—H···Br hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they seem to be effective in the stabilization of the structure.

Related literature top

For related literature, see: Mashraqui et al. (2004); Ishikawa & Manabe (2006). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title copound, (I), a mixture of 5-bromovaleric acid (2.4613 g, 9 mmol) and triphenylphosphine (3.6076 g, 9 mmol) was heated under reflux in acetonitrile (100 ml) for 24 h. The resulting salt was recrystallized from acetonitrile, washed with ether, and dried in vacuum to give the title compound (yield; 2.5994 g). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.

Refinement top

H atoms were positioned geometrically, with O—H = 0.82 Å (for OH) and C—H = 0.93 and 0.97 Å for aromatic and methylene H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.5 for OH H, and x = 1.2 for all other H atoms.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: X-CAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.
(4-Carboxybutyl)triphenylphosphonium bromide top
Crystal data top
C23H24O2P+·BrZ = 4
Mr = 443.29F(000) = 912
Triclinic, P1Dx = 1.379 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2690 (19) ÅCell parameters from 25 reflections
b = 13.674 (3) Åθ = 9–13°
c = 17.075 (3) ŵ = 2.02 mm1
α = 88.91 (3)°T = 294 K
β = 87.15 (3)°Block, colourless
γ = 81.07 (3)°0.30 × 0.20 × 0.10 mm
V = 2135.1 (8) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
3700 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 26.0°, θmin = 1.2°
ω/2θ scansh = 1111
Absorption correction: ψ scan
(North et al., 1968)
k = 1616
Tmin = 0.583, Tmax = 0.824l = 021
8913 measured reflections3 standard reflections every 120 min
8367 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.084Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.05P)2 + 8P]
where P = (Fo2 + 2Fc2)/3
8367 reflections(Δ/σ)max < 0.001
475 parametersΔρmax = 0.72 e Å3
121 restraintsΔρmin = 0.60 e Å3
Crystal data top
C23H24O2P+·Brγ = 81.07 (3)°
Mr = 443.29V = 2135.1 (8) Å3
Triclinic, P1Z = 4
a = 9.2690 (19) ÅMo Kα radiation
b = 13.674 (3) ŵ = 2.02 mm1
c = 17.075 (3) ÅT = 294 K
α = 88.91 (3)°0.30 × 0.20 × 0.10 mm
β = 87.15 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
3700 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.055
Tmin = 0.583, Tmax = 0.8243 standard reflections every 120 min
8913 measured reflections intensity decay: none
8367 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.084121 restraints
wR(F2) = 0.196H-atom parameters constrained
S = 0.99Δρmax = 0.72 e Å3
8367 reflectionsΔρmin = 0.60 e Å3
475 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
xyzUiso*/Ueq
Br10.75038 (14)0.91104 (8)0.16509 (6)0.0872 (4)
P11.2962 (2)1.04654 (14)0.31701 (12)0.0425 (5)
O11.0624 (8)1.0797 (4)0.6324 (4)0.080 (2)
O21.1257 (8)1.2101 (4)0.6878 (4)0.086 (2)
H2B1.15201.16930.72210.129*
C11.3356 (12)1.0358 (8)0.0821 (6)0.091 (3)
H1A1.40951.04160.04420.110*
C21.3601 (11)1.0448 (7)0.1601 (6)0.077 (3)
H2A1.45071.05830.17400.093*
C31.2581 (9)1.0349 (6)0.2169 (5)0.048 (2)
C41.1218 (9)1.0171 (6)0.1935 (5)0.055 (2)
H4A1.04661.01270.23090.066*
C51.0996 (11)1.0062 (7)0.1173 (6)0.077 (3)
H5A1.01050.98990.10360.092*
C61.2000 (12)1.0179 (7)0.0602 (6)0.080 (3)
H6A1.17951.01420.00760.096*
C71.3757 (12)0.7501 (7)0.3593 (6)0.084 (3)
H7A1.36150.69250.33460.101*
C81.3386 (10)0.8424 (7)0.3196 (6)0.071
H8A1.30860.84530.26830.085*
C91.3489 (8)0.9279 (5)0.3602 (5)0.0442 (19)
C101.4013 (10)0.9180 (6)0.4333 (5)0.063 (2)
H10A1.41050.97490.46050.075*
C111.4414 (10)0.8272 (7)0.4686 (5)0.067 (2)
H11A1.47640.82370.51890.080*
C121.4300 (10)0.7428 (7)0.4303 (6)0.069 (3)
H12A1.45950.68120.45320.083*
C131.6691 (9)1.2263 (6)0.3333 (5)0.053 (2)
H13A1.74521.26270.33740.063*
C141.6956 (9)1.1236 (6)0.3317 (5)0.055 (2)
H14A1.79121.09090.33320.066*
C151.5840 (9)1.0697 (6)0.3279 (5)0.048 (2)
H15A1.60441.00090.32770.057*
C161.4439 (8)1.1154 (5)0.3244 (4)0.0404 (19)
C171.4149 (8)1.2191 (5)0.3242 (5)0.048 (2)
H17A1.31941.25150.32090.058*
C181.5273 (9)1.2726 (6)0.3287 (5)0.052 (2)
H18A1.50721.34140.32870.062*
C191.1305 (8)1.1083 (5)0.3668 (5)0.046 (2)
H19A1.09381.16700.33670.055*
H19B1.05741.06460.36720.055*
C201.1476 (8)1.1391 (6)0.4518 (5)0.053 (2)
H20A1.18551.08130.48260.064*
H20B1.21691.18540.45220.064*
C211.0021 (9)1.1868 (6)0.4880 (5)0.061 (2)
H21A0.93931.13670.49690.073*
H21B0.95531.23580.45180.073*
C221.0196 (10)1.2365 (6)0.5659 (5)0.061 (2)
H22A1.08891.28250.55730.073*
H22B0.92631.27460.58260.073*
C231.0709 (9)1.1661 (6)0.6308 (5)0.052 (2)
Br20.05878 (11)0.37271 (7)0.29062 (6)0.0675 (3)
P20.3584 (2)0.53719 (15)0.15327 (12)0.0433 (5)
O30.3181 (9)0.4922 (6)0.5941 (4)0.106 (3)
O40.1554 (8)0.5727 (5)0.5404 (4)0.090 (2)
H4B0.15040.58910.58600.135*
C240.8304 (12)0.6946 (9)0.1678 (7)0.083 (3)
H24A0.92530.72880.17200.100*
C250.7298 (13)0.7270 (8)0.1165 (6)0.087 (3)
H25A0.75840.78240.08520.105*
C260.5902 (11)0.6808 (7)0.1098 (5)0.070 (3)
H26A0.52420.70370.07370.083*
C270.5446 (9)0.5969 (6)0.1581 (5)0.046 (2)
C280.6490 (10)0.5632 (6)0.2094 (5)0.057 (2)
H28A0.62250.50780.24100.068*
C290.7921 (11)0.6120 (8)0.2133 (6)0.070 (3)
H29A0.86170.58870.24670.084*
C300.4604 (11)0.2666 (7)0.1041 (6)0.076 (3)
H30A0.53960.24070.08620.091*
C310.4702 (10)0.3675 (6)0.1175 (5)0.062 (2)
H31A0.55680.40950.10810.074*
C320.3532 (8)0.4058 (5)0.1444 (4)0.0377 (18)
C330.2246 (9)0.3432 (6)0.1582 (5)0.051 (2)
H33A0.14510.36840.17650.061*
C340.2146 (10)0.2429 (6)0.1447 (6)0.065 (3)
H34A0.12830.20070.15400.078*
C350.3312 (11)0.2059 (6)0.1178 (5)0.065 (3)
H35A0.32310.13840.10860.078*
C360.1545 (11)0.7136 (7)0.0082 (6)0.073 (3)
H36A0.12830.77640.00990.088*
C370.2211 (10)0.6756 (6)0.0734 (5)0.061 (2)
H37A0.23980.71290.11880.074*
C380.2603 (8)0.5817 (5)0.0716 (4)0.044 (2)
C390.2274 (8)0.5262 (6)0.0050 (5)0.052 (2)
H39A0.25160.46280.00320.062*
C400.1573 (9)0.5654 (7)0.0604 (5)0.061 (2)
H40A0.13170.52710.10480.074*
C410.1266 (10)0.6601 (8)0.0586 (6)0.070 (3)
H41A0.08650.68790.10310.084*
C420.2689 (9)0.5638 (6)0.2411 (4)0.047 (2)
H42A0.16440.54340.23230.056*
H42B0.28550.63490.24850.056*
C430.3169 (8)0.5153 (5)0.3154 (4)0.038
H43A0.29110.44410.31060.045*
H43B0.42240.53040.32220.045*
C440.2487 (9)0.5481 (5)0.3879 (4)0.046 (2)
H44A0.14390.54380.37830.055*
H44B0.28870.61650.39920.055*
C450.2796 (10)0.4834 (6)0.4574 (4)0.054 (2)
H45A0.38090.47360.45630.065*
H45B0.21990.41920.44980.065*
C460.2555 (11)0.5170 (7)0.5363 (5)0.062 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1248 (10)0.0621 (7)0.0723 (7)0.0051 (6)0.0086 (7)0.0098 (5)
P10.0439 (13)0.0341 (11)0.0534 (13)0.0164 (9)0.0077 (10)0.0008 (10)
O10.118 (6)0.041 (4)0.091 (5)0.040 (4)0.014 (4)0.011 (3)
O20.144 (7)0.047 (4)0.072 (5)0.026 (4)0.016 (4)0.005 (3)
C10.105 (6)0.107 (7)0.066 (5)0.033 (6)0.006 (5)0.000 (5)
C20.073 (5)0.096 (6)0.069 (5)0.032 (5)0.000 (4)0.017 (5)
C30.051 (4)0.047 (4)0.051 (4)0.022 (4)0.002 (3)0.000 (4)
C40.047 (4)0.061 (5)0.057 (4)0.007 (4)0.003 (4)0.011 (4)
C50.078 (6)0.081 (6)0.073 (5)0.010 (5)0.021 (4)0.017 (5)
C60.108 (6)0.076 (6)0.058 (5)0.017 (5)0.014 (4)0.005 (5)
C70.116 (7)0.050 (4)0.089 (6)0.013 (5)0.019 (5)0.013 (4)
C80.0710.0710.0710.0110.0030.001
C90.045 (4)0.038 (4)0.052 (4)0.009 (3)0.009 (4)0.003 (3)
C100.083 (6)0.049 (4)0.058 (5)0.010 (4)0.018 (4)0.001 (4)
C110.084 (6)0.063 (5)0.052 (5)0.008 (5)0.005 (4)0.006 (4)
C120.080 (6)0.050 (4)0.079 (5)0.013 (4)0.004 (5)0.010 (4)
C130.042 (5)0.058 (6)0.064 (6)0.024 (4)0.012 (4)0.010 (4)
C140.040 (5)0.047 (5)0.080 (6)0.010 (4)0.011 (4)0.005 (5)
C150.047 (5)0.032 (4)0.068 (6)0.014 (4)0.003 (4)0.004 (4)
C160.043 (5)0.035 (4)0.050 (5)0.024 (4)0.007 (4)0.001 (4)
C170.033 (5)0.037 (5)0.077 (6)0.014 (4)0.003 (4)0.000 (4)
C180.059 (6)0.044 (5)0.060 (6)0.031 (4)0.010 (4)0.005 (4)
C190.049 (5)0.026 (4)0.068 (6)0.017 (4)0.014 (4)0.000 (4)
C200.042 (5)0.054 (5)0.066 (6)0.018 (4)0.010 (4)0.003 (4)
C210.057 (6)0.059 (6)0.064 (6)0.004 (5)0.002 (5)0.000 (5)
C220.073 (7)0.051 (6)0.060 (6)0.010 (5)0.004 (5)0.005 (5)
C230.063 (6)0.045 (5)0.048 (5)0.009 (4)0.002 (4)0.007 (4)
Br20.0661 (7)0.0614 (6)0.0733 (7)0.0044 (5)0.0272 (5)0.0093 (5)
P20.0507 (14)0.0355 (12)0.0465 (13)0.0130 (10)0.0120 (10)0.0004 (9)
O30.145 (6)0.117 (6)0.068 (4)0.063 (5)0.000 (4)0.001 (4)
O40.109 (5)0.115 (5)0.059 (4)0.059 (4)0.008 (4)0.004 (4)
C240.074 (8)0.087 (9)0.087 (8)0.001 (7)0.018 (7)0.025 (7)
C250.083 (9)0.075 (8)0.098 (9)0.003 (7)0.000 (7)0.010 (7)
C260.071 (7)0.064 (6)0.069 (7)0.003 (5)0.009 (5)0.018 (5)
C270.058 (5)0.040 (5)0.045 (5)0.019 (4)0.011 (4)0.001 (4)
C280.059 (6)0.055 (6)0.061 (6)0.017 (5)0.021 (5)0.000 (5)
C290.055 (7)0.074 (7)0.085 (8)0.023 (5)0.006 (5)0.019 (6)
C300.063 (7)0.057 (6)0.114 (9)0.024 (5)0.019 (6)0.013 (6)
C310.058 (6)0.045 (5)0.084 (7)0.007 (4)0.022 (5)0.002 (5)
C320.043 (5)0.028 (4)0.042 (4)0.008 (3)0.007 (4)0.004 (3)
C330.041 (5)0.041 (5)0.073 (6)0.013 (4)0.008 (4)0.005 (4)
C340.057 (6)0.041 (5)0.097 (8)0.005 (4)0.003 (5)0.002 (5)
C350.084 (7)0.038 (5)0.076 (7)0.017 (5)0.001 (6)0.002 (5)
C360.089 (8)0.049 (6)0.083 (8)0.022 (5)0.005 (6)0.009 (6)
C370.093 (7)0.045 (5)0.049 (5)0.018 (5)0.011 (5)0.001 (4)
C380.057 (5)0.033 (4)0.043 (5)0.006 (4)0.012 (4)0.002 (4)
C390.045 (5)0.056 (6)0.056 (6)0.014 (4)0.004 (4)0.004 (5)
C400.054 (6)0.080 (7)0.048 (5)0.007 (5)0.004 (4)0.014 (5)
C410.067 (7)0.072 (7)0.076 (7)0.031 (6)0.002 (5)0.019 (6)
C420.052 (5)0.039 (5)0.052 (5)0.011 (4)0.007 (4)0.001 (4)
C430.0380.0380.0380.0060.0020.000
C440.052 (5)0.033 (4)0.053 (5)0.005 (4)0.010 (4)0.011 (4)
C450.070 (6)0.047 (5)0.046 (5)0.011 (4)0.007 (4)0.005 (4)
C460.076 (6)0.066 (5)0.048 (5)0.022 (4)0.001 (4)0.002 (4)
Geometric parameters (Å, º) top
P1—C91.777 (8)P2—C381.776 (8)
P1—C31.778 (8)P2—C271.789 (8)
P1—C161.788 (7)P2—C321.798 (7)
P1—C191.814 (8)P2—C421.818 (7)
O1—C231.196 (9)O3—C461.191 (10)
O2—C231.317 (9)O4—C461.294 (10)
O2—H2B0.8200O4—H4B0.8200
C1—C21.373 (13)C24—C251.366 (14)
C1—C61.388 (11)C24—C291.368 (13)
C1—H1A0.9300C24—H24A0.9300
C2—C31.340 (11)C25—C261.349 (13)
C2—H2A0.9300C25—H25A0.9300
C3—C41.401 (10)C26—C271.423 (11)
C4—C51.342 (11)C26—H26A0.9300
C4—H4A0.9300C27—C281.398 (11)
C5—C61.340 (13)C28—C291.388 (12)
C5—H5A0.9300C28—H28A0.9300
C6—H6A0.9300C29—H29A0.9300
C7—C121.333 (12)C30—C351.374 (12)
C7—C81.423 (12)C30—C311.391 (11)
C7—H7A0.9300C30—H30A0.9300
C8—C91.390 (11)C31—C321.378 (10)
C8—H8A0.9300C31—H31A0.9300
C9—C101.358 (10)C32—C331.384 (10)
C10—C111.376 (11)C33—C341.382 (10)
C10—H10A0.9300C33—H33A0.9300
C11—C121.358 (12)C34—C351.366 (12)
C11—H11A0.9300C34—H34A0.9300
C12—H12A0.9300C35—H35A0.9300
C13—C181.373 (10)C36—C411.358 (13)
C13—C141.388 (10)C36—C371.378 (12)
C13—H13A0.9300C36—H36A0.9300
C14—C151.365 (10)C37—C381.389 (10)
C14—H14A0.9300C37—H37A0.9300
C15—C161.355 (10)C38—C391.375 (10)
C15—H15A0.9300C39—C401.403 (11)
C16—C171.402 (10)C39—H39A0.9300
C17—C181.369 (10)C40—C411.370 (12)
C17—H17A0.9300C40—H40A0.9300
C18—H18A0.9300C41—H41A0.9300
C19—C201.542 (10)C42—C431.501 (10)
C19—H19A0.9700C42—H42A0.9700
C19—H19B0.9700C42—H42B0.9700
C20—C211.512 (10)C43—C441.524 (9)
C20—H20A0.9700C43—H43A0.9700
C20—H20B0.9700C43—H43B0.9700
C21—C221.533 (11)C44—C451.508 (10)
C21—H21A0.9700C44—H44A0.9700
C21—H21B0.9700C44—H44B0.9700
C22—C231.499 (11)C45—C461.470 (11)
C22—H22A0.9700C45—H45A0.9700
C22—H22B0.9700C45—H45B0.9700
C9—P1—C3110.4 (4)C38—P2—C27110.9 (4)
C9—P1—C16107.9 (4)C38—P2—C32109.2 (4)
C3—P1—C16110.0 (4)C27—P2—C32109.4 (3)
C9—P1—C19109.8 (4)C38—P2—C42107.4 (4)
C3—P1—C19107.5 (4)C27—P2—C42109.9 (4)
C16—P1—C19111.3 (3)C32—P2—C42110.1 (3)
C23—O2—H2B109.5C46—O4—H4B109.5
C2—C1—C6119.6 (10)C25—C24—C29120.3 (10)
C2—C1—H1A120.2C25—C24—H24A119.9
C6—C1—H1A120.2C29—C24—H24A119.9
C3—C2—C1122.3 (10)C26—C25—C24121.8 (11)
C3—C2—H2A118.8C26—C25—H25A119.1
C1—C2—H2A118.8C24—C25—H25A119.1
C2—C3—C4117.2 (8)C25—C26—C27119.6 (9)
C2—C3—P1120.4 (7)C25—C26—H26A120.2
C4—C3—P1122.4 (6)C27—C26—H26A120.2
C5—C4—C3120.1 (9)C28—C27—C26118.1 (8)
C5—C4—H4A119.9C28—C27—P2121.3 (6)
C3—C4—H4A119.9C26—C27—P2120.6 (7)
C6—C5—C4122.9 (10)C29—C28—C27120.3 (9)
C6—C5—H5A118.5C29—C28—H28A119.9
C4—C5—H5A118.5C27—C28—H28A119.9
C5—C6—C1117.7 (10)C24—C29—C28119.9 (10)
C5—C6—H6A121.2C24—C29—H29A120.1
C1—C6—H6A121.2C28—C29—H29A120.1
C12—C7—C8122.6 (9)C35—C30—C31118.7 (8)
C12—C7—H7A118.7C35—C30—H30A120.7
C8—C7—H7A118.7C31—C30—H30A120.7
C9—C8—C7117.6 (9)C32—C31—C30120.7 (8)
C9—C8—H8A121.2C32—C31—H31A119.6
C7—C8—H8A121.2C30—C31—H31A119.6
C10—C9—C8118.1 (8)C31—C32—C33119.5 (7)
C10—C9—P1121.3 (6)C31—C32—P2121.2 (6)
C8—C9—P1120.6 (6)C33—C32—P2119.1 (6)
C9—C10—C11122.6 (8)C34—C33—C32119.8 (7)
C9—C10—H10A118.7C34—C33—H33A120.1
C11—C10—H10A118.7C32—C33—H33A120.1
C12—C11—C10120.2 (9)C35—C34—C33120.1 (8)
C12—C11—H11A119.9C35—C34—H34A119.9
C10—C11—H11A119.9C33—C34—H34A119.9
C7—C12—C11118.7 (9)C34—C35—C30121.1 (8)
C7—C12—H12A120.7C34—C35—H35A119.4
C11—C12—H12A120.7C30—C35—H35A119.4
C18—C13—C14118.1 (7)C41—C36—C37120.7 (9)
C18—C13—H13A121.0C41—C36—H36A119.7
C14—C13—H13A121.0C37—C36—H36A119.7
C15—C14—C13121.2 (8)C36—C37—C38120.2 (8)
C15—C14—H14A119.4C36—C37—H37A119.9
C13—C14—H14A119.4C38—C37—H37A119.9
C16—C15—C14120.6 (7)C39—C38—C37119.1 (8)
C16—C15—H15A119.7C39—C38—P2121.0 (6)
C14—C15—H15A119.7C37—C38—P2119.8 (6)
C15—C16—C17119.1 (7)C38—C39—C40119.9 (8)
C15—C16—P1121.5 (6)C38—C39—H39A120.1
C17—C16—P1119.4 (6)C40—C39—H39A120.1
C18—C17—C16119.9 (7)C41—C40—C39119.9 (8)
C18—C17—H17A120.0C41—C40—H40A120.1
C16—C17—H17A120.0C39—C40—H40A120.1
C17—C18—C13121.0 (8)C36—C41—C40120.1 (9)
C17—C18—H18A119.5C36—C41—H41A120.0
C13—C18—H18A119.5C40—C41—H41A120.0
C20—C19—P1115.2 (5)C43—C42—P2115.9 (5)
C20—C19—H19A108.5C43—C42—H42A108.3
P1—C19—H19A108.5P2—C42—H42A108.3
C20—C19—H19B108.5C43—C42—H42B108.3
P1—C19—H19B108.5P2—C42—H42B108.3
H19A—C19—H19B107.5H42A—C42—H42B107.4
C21—C20—C19110.5 (7)C42—C43—C44113.3 (6)
C21—C20—H20A109.5C42—C43—H43A108.9
C19—C20—H20A109.5C44—C43—H43A108.9
C21—C20—H20B109.5C42—C43—H43B108.9
C19—C20—H20B109.5C44—C43—H43B108.9
H20A—C20—H20B108.1H43A—C43—H43B107.7
C20—C21—C22111.8 (7)C45—C44—C43110.2 (6)
C20—C21—H21A109.3C45—C44—H44A109.6
C22—C21—H21A109.3C43—C44—H44A109.6
C20—C21—H21B109.3C45—C44—H44B109.6
C22—C21—H21B109.3C43—C44—H44B109.6
H21A—C21—H21B107.9H44A—C44—H44B108.1
C23—C22—C21114.4 (7)C46—C45—C44118.5 (7)
C23—C22—H22A108.7C46—C45—H45A107.7
C21—C22—H22A108.7C44—C45—H45A107.7
C23—C22—H22B108.7C46—C45—H45B107.7
C21—C22—H22B108.7C44—C45—H45B107.7
H22A—C22—H22B107.6H45A—C45—H45B107.1
O1—C23—O2122.6 (8)O3—C46—O4120.7 (9)
O1—C23—C22124.9 (8)O3—C46—C45123.4 (9)
O2—C23—C22112.5 (8)O4—C46—C45115.8 (8)
C6—C1—C2—C31.5 (17)C29—C24—C25—C261.4 (12)
C1—C2—C3—C41.6 (15)C24—C25—C26—C271.0 (12)
C1—C2—C3—P1179.6 (8)C25—C26—C27—C282.2 (12)
C9—P1—C3—C297.1 (8)C25—C26—C27—P2177.5 (6)
C16—P1—C3—C221.8 (9)C38—P2—C27—C28169.5 (6)
C19—P1—C3—C2143.2 (7)C32—P2—C27—C2849.0 (7)
C9—P1—C3—C484.1 (8)C42—P2—C27—C2872.0 (7)
C16—P1—C3—C4156.9 (7)C38—P2—C27—C2610.8 (8)
C19—P1—C3—C435.6 (8)C32—P2—C27—C26131.3 (6)
C2—C3—C4—C52.9 (13)C42—P2—C27—C26107.8 (7)
P1—C3—C4—C5178.3 (7)C26—C27—C28—C291.1 (12)
C3—C4—C5—C64.4 (15)P2—C27—C28—C29178.6 (6)
C4—C5—C6—C14.2 (16)C25—C24—C29—C282.5 (13)
C2—C1—C6—C52.6 (16)C27—C28—C29—C241.2 (13)
C12—C7—C8—C95.4 (16)C35—C30—C31—C320.4 (15)
C7—C8—C9—C103.7 (13)C30—C31—C32—C330.0 (13)
C7—C8—C9—P1176.9 (7)C30—C31—C32—P2174.1 (7)
C3—P1—C9—C10171.5 (7)C38—P2—C32—C31100.5 (7)
C16—P1—C9—C1051.3 (8)C27—P2—C32—C3121.0 (8)
C19—P1—C9—C1070.2 (8)C42—P2—C32—C31141.8 (7)
C3—P1—C9—C87.9 (8)C38—P2—C32—C3373.6 (7)
C16—P1—C9—C8128.1 (7)C27—P2—C32—C33164.9 (6)
C19—P1—C9—C8110.4 (7)C42—P2—C32—C3344.1 (7)
C8—C9—C10—C111.3 (14)C31—C32—C33—C340.2 (13)
P1—C9—C10—C11179.2 (7)P2—C32—C33—C34174.1 (7)
C9—C10—C11—C120.3 (15)C32—C33—C34—C350.0 (14)
C8—C7—C12—C114.5 (16)C33—C34—C35—C300.4 (15)
C10—C11—C12—C71.9 (15)C31—C30—C35—C340.6 (15)
C18—C13—C14—C151.8 (13)C41—C36—C37—C380.1 (15)
C13—C14—C15—C161.0 (13)C36—C37—C38—C392.1 (13)
C14—C15—C16—C170.5 (12)C36—C37—C38—P2175.2 (7)
C14—C15—C16—P1178.4 (6)C27—P2—C38—C39103.7 (7)
C9—P1—C16—C1526.9 (8)C32—P2—C38—C3916.9 (7)
C3—P1—C16—C1593.5 (7)C42—P2—C38—C39136.3 (6)
C19—P1—C16—C15147.4 (7)C27—P2—C38—C3773.6 (7)
C9—P1—C16—C17155.1 (6)C32—P2—C38—C37165.8 (6)
C3—P1—C16—C1784.4 (7)C42—P2—C38—C3746.4 (7)
C19—P1—C16—C1734.6 (7)C37—C38—C39—C401.0 (12)
C15—C16—C17—C181.1 (12)P2—C38—C39—C40176.3 (6)
P1—C16—C17—C18179.1 (6)C38—C39—C40—C412.4 (12)
C16—C17—C18—C130.2 (13)C37—C36—C41—C403.6 (15)
C14—C13—C18—C171.2 (13)C39—C40—C41—C364.7 (14)
C9—P1—C19—C2068.5 (6)C38—P2—C42—C43168.8 (5)
C3—P1—C19—C20171.4 (5)C27—P2—C42—C4370.5 (7)
C16—P1—C19—C2050.9 (7)C32—P2—C42—C4350.0 (7)
P1—C19—C20—C21178.2 (6)P2—C42—C43—C44174.5 (5)
C19—C20—C21—C22168.7 (7)C42—C43—C44—C45169.7 (6)
C20—C21—C22—C2367.3 (10)C43—C44—C45—C46165.2 (7)
C21—C22—C23—O119.9 (13)C44—C45—C46—O3154.3 (10)
C21—C22—C23—O2161.1 (8)C44—C45—C46—O428.9 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2B···Br1i0.822.353.148 (7)165
O4—H4B···Br2ii0.822.413.199 (7)163
C14—H14A···O1iii0.932.583.357 (10)141
C17—H17A···Br2iv0.932.773.691 (7)169
C19—H19A···Br2iv0.972.883.790 (7)157
C19—H19B···O1i0.972.413.351 (10)163
C33—H33A···Br20.932.793.623 (9)150
C37—H37A···Br1v0.932.823.574 (8)139
Symmetry codes: (i) x+2, y+2, z+1; (ii) x, y+1, z+1; (iii) x+3, y+2, z+1; (iv) x+1, y+1, z; (v) x1, y, z.

Experimental details

Crystal data
Chemical formulaC23H24O2P+·Br
Mr443.29
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)9.2690 (19), 13.674 (3), 17.075 (3)
α, β, γ (°)88.91 (3), 87.15 (3), 81.07 (3)
V3)2135.1 (8)
Z4
Radiation typeMo Kα
µ (mm1)2.02
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.583, 0.824
No. of measured, independent and
observed [I > 2σ(I)] reflections
8913, 8367, 3700
Rint0.055
(sin θ/λ)max1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.084, 0.196, 0.99
No. of reflections8367
No. of parameters475
No. of restraints121
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.72, 0.60

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), X-CAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2B···Br1i0.822.353.148 (7)165.0
O4—H4B···Br2ii0.822.413.199 (7)163.0
C14—H14A···O1iii0.932.583.357 (10)141.0
C17—H17A···Br2iv0.932.773.691 (7)169.0
C19—H19A···Br2iv0.972.883.790 (7)157.0
C19—H19B···O1i0.972.413.351 (10)163.0
C33—H33A···Br20.932.793.623 (9)150.0
C37—H37A···Br1v0.932.823.574 (8)139.0
Symmetry codes: (i) x+2, y+2, z+1; (ii) x, y+1, z+1; (iii) x+3, y+2, z+1; (iv) x+1, y+1, z; (v) x1, y, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds