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In the title salt solvate, C24H32O2P+·Br·CHCl3, the P atom has a distorted tetra­hedral geometry, and the planes of the phenyl rings form a dihedral angle of 71.86 (14)° with one another. The bromide anion is disordered and was modelled over three positions (occupancy ratio 0.50:0.35:0.15). The crystal also contains one disordered chloro­form solvent mol­ecule that was modeled over three positions (occupancy ratio 0.50:0.35:0.15). Weak inter­molecular inter­actions (C—H...Br and C—H...O) exist between the complex cation and the bromide anion fragments. The resulting supramolecular structure is an oval-shaped arrangement of phosphonium salt molecules that surround the disordered bromide anion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901500763X/pk2549sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901500763X/pk2549Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901500763X/pk2549Isup3.cml
Supplementary material

CCDC reference: 1060276

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in solvent or counterion
  • R factor = 0.064
  • wR factor = 0.206
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C High Ueq as Compared to Neighbors for ..... C11 Check PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... C5 Check PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.0070 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A .. BR1A .. 2.95 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B .. BR1B .. 2.95 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B .. BR1C .. 2.97 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B .. BR1A .. 2.97 Ang.
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 12 Note PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 8 Report PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings Differ Please Check PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large. 0.12 Report PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large. 22.49 Why ? PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 1 Report PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 7 Report PLAT173_ALERT_4_G The CIF-Embedded .res File Contains DANG Records 9 Report PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records 3 Report PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records 3 Report PLAT300_ALERT_4_G Atom Site Occupancy of *Cl1A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *Cl2A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *Cl3A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *C1A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of <Cl1B is Constrained at 0.350 Check PLAT300_ALERT_4_G Atom Site Occupancy of <Cl2B is Constrained at 0.350 Check PLAT300_ALERT_4_G Atom Site Occupancy of <Cl3B is Constrained at 0.350 Check PLAT300_ALERT_4_G Atom Site Occupancy of <C1B is Constrained at 0.350 Check PLAT300_ALERT_4_G Atom Site Occupancy of <Cl1C is Constrained at 0.150 Check PLAT300_ALERT_4_G Atom Site Occupancy of <Cl2C is Constrained at 0.150 Check PLAT300_ALERT_4_G Atom Site Occupancy of <Cl3C is Constrained at 0.150 Check PLAT300_ALERT_4_G Atom Site Occupancy of <C1C is Constrained at 0.150 Check PLAT300_ALERT_4_G Atom Site Occupancy of *Br1A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of <Br1B is Constrained at 0.350 Check PLAT300_ALERT_4_G Atom Site Occupancy of <Br1C is Constrained at 0.150 Check PLAT302_ALERT_4_G Anion/Solvent Disorder ............ Percentage = 100 Note PLAT304_ALERT_4_G Non-Integer Number of Atoms ( 2.50) in Resd. # 2 Check PLAT304_ALERT_4_G Non-Integer Number of Atoms ( 1.75) in Resd. # 3 Check PLAT304_ALERT_4_G Non-Integer Number of Atoms ( 0.75) in Resd. # 4 Check PLAT304_ALERT_4_G Non-Integer Number of Atoms ( 0.50) in Resd. # 5 Check PLAT304_ALERT_4_G Non-Integer Number of Atoms ( 0.35) in Resd. # 6 Check PLAT304_ALERT_4_G Non-Integer Number of Atoms ( 0.15) in Resd. # 7 Check PLAT432_ALERT_2_G Short Inter X...Y Contact Cl1B .. C7 .. 3.12 Ang. PLAT433_ALERT_4_G Short Inter X...Y Contact Cl2C .. C11 .. 3.15 Ang. PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 66 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 7 ALERT level C = Check. Ensure it is not caused by an omission or oversight 35 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 32 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Structural commentary top

The molecular structure of I is shown in Figure 1, along with the atom numbering scheme. Compound I crystallized in the monoclinic space group C2/c, and the asymmetric unit contains the entire molecule along with one disordered bromide anion and one disordered molecule of chloro­form. Atom P1 has a distorted tetra­hedral geometry with C—P—C bond angles ranging from 106.37 (18) to 113.10 (18)°.

Supra­molecular features top

Weak inter­molecular C—H···Br and C—H···O inter­actions can be found throughout the crystal lattice (Table 1). CH···O hydrogen bonds (2.43 Å) exist between the carbonyl oxygen O1 and an aromatic hydrogen H16 (Figure 2). The bromide ion is engaged in a variety of weak inter­actions with nearby hydrogen atoms, with inter­atomic H···Br distances ranging from 2.70 to 2.97 Å. In the fragment that has the highest occupancy ratio (50%), a weak CH···Br inter­action is also present between the chloro­form molecule and bromide ion. Based on the amount of disorder present in this structure, it is clear these inter­molecular inter­actions are quite weak in nature.

Synthesis and crystallization top

The title compound was prepared via an Arbuzov reaction between bromo­pinacolone and an excess of iso-propoxydi­phenyl phosphane following the procedure of Schuster et al. (2009). 1H NMR (CDCl3, 300 MHz), δ 7.95-7.27 (m, 10H), 5.47 (d, JHP =6 Hz, 4H), 3.6 (d, J=2 Hz, 2H), 1.1 (s, 18 H). Crystals of I suitable for analysis by X-Ray diffraction were grown from vapor diffusion of ethyl acetate into a solution of CHCl3 containing Tb(NO3)3.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The positions of all hydrogen atoms were calculated geometrically and refined to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C) for methine, methyl­ene and aryl groups, and Uiso(H) = 1.5Ueq(C) for methyl groups.

The disordered bromide ion was modelled over three positions with a 50:35:15 occupancy ratio. An EADP instruction was included in the refinement to constrain the thermal ellipoids of these fragments to the same size and shape. The disordered chloro­form molecule was also modelled in three parts with a 50:35:15 occupancy ratio. To restrain the CHCl3 geometry to accepted values, each C—Cl bond length was restrained with a DFIX instruction to 1.78 Å, and the Cl—Cl inter­atomic bond distances were restrained with a DANG instruction to 2.87 Å. Finally, each chlofororm fragment was treated with SIMU and DELU instructions to ensure uniform thermal ellipsoids.

Related literature top

The title compound was synthesized following using an Arbuzov reaction, as described by Schuster et al. (2009). The Cambridge Structural Database (CSD, Version 5.36, November 2014; Groom & Allen, 2014) contains four structures of acyclic tetravalent phosphonium salts where the P atom is bonded to two phenyl rings and two β-carbonyl groups. In each structure, the phosphonium salt is coordinated to a silver(I) (Vicente et al., 1989) or palladium(II) (Vicente et al., 1990) metal center via the carbon α to the P atom.

Structure description top

The molecular structure of I is shown in Figure 1, along with the atom numbering scheme. Compound I crystallized in the monoclinic space group C2/c, and the asymmetric unit contains the entire molecule along with one disordered bromide anion and one disordered molecule of chloro­form. Atom P1 has a distorted tetra­hedral geometry with C—P—C bond angles ranging from 106.37 (18) to 113.10 (18)°.

Weak inter­molecular C—H···Br and C—H···O inter­actions can be found throughout the crystal lattice (Table 1). CH···O hydrogen bonds (2.43 Å) exist between the carbonyl oxygen O1 and an aromatic hydrogen H16 (Figure 2). The bromide ion is engaged in a variety of weak inter­actions with nearby hydrogen atoms, with inter­atomic H···Br distances ranging from 2.70 to 2.97 Å. In the fragment that has the highest occupancy ratio (50%), a weak CH···Br inter­action is also present between the chloro­form molecule and bromide ion. Based on the amount of disorder present in this structure, it is clear these inter­molecular inter­actions are quite weak in nature.

The title compound was synthesized following using an Arbuzov reaction, as described by Schuster et al. (2009). The Cambridge Structural Database (CSD, Version 5.36, November 2014; Groom & Allen, 2014) contains four structures of acyclic tetravalent phosphonium salts where the P atom is bonded to two phenyl rings and two β-carbonyl groups. In each structure, the phosphonium salt is coordinated to a silver(I) (Vicente et al., 1989) or palladium(II) (Vicente et al., 1990) metal center via the carbon α to the P atom.

Synthesis and crystallization top

The title compound was prepared via an Arbuzov reaction between bromo­pinacolone and an excess of iso-propoxydi­phenyl phosphane following the procedure of Schuster et al. (2009). 1H NMR (CDCl3, 300 MHz), δ 7.95-7.27 (m, 10H), 5.47 (d, JHP =6 Hz, 4H), 3.6 (d, J=2 Hz, 2H), 1.1 (s, 18 H). Crystals of I suitable for analysis by X-Ray diffraction were grown from vapor diffusion of ethyl acetate into a solution of CHCl3 containing Tb(NO3)3.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 1. The positions of all hydrogen atoms were calculated geometrically and refined to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C) for methine, methyl­ene and aryl groups, and Uiso(H) = 1.5Ueq(C) for methyl groups.

The disordered bromide ion was modelled over three positions with a 50:35:15 occupancy ratio. An EADP instruction was included in the refinement to constrain the thermal ellipoids of these fragments to the same size and shape. The disordered chloro­form molecule was also modelled in three parts with a 50:35:15 occupancy ratio. To restrain the CHCl3 geometry to accepted values, each C—Cl bond length was restrained with a DFIX instruction to 1.78 Å, and the Cl—Cl inter­atomic bond distances were restrained with a DANG instruction to 2.87 Å. Finally, each chlofororm fragment was treated with SIMU and DELU instructions to ensure uniform thermal ellipsoids.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: CrystalMaker (Palmer, 2007); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009; Bourhis et al., 2015).

Figures top
[Figure 1] Fig. 1. Structure of the asymmetric unit of I along with the atom numbering scheme. This drawing is done with 50% probability ellipsoids using standard CPK colors; only one position of the disordered bromide ion and chloroform molecule is shown, and all hydrogen atoms have been omitted for clarity.
[Figure 2] Fig. 2. Weak intermolecular interactions (denoted with dashed lines) found throughout the crystal lattice of the title compound (Table 1). Only the major position of the disordered fragments are shown. The aryl rings, tert-butyl groups, and all hydrogen atoms not involved in these interactions have been omitted for clarity. This drawing is done as a ball and stick with standard CPK colors. Symmetry codes: (i) 3/2 - x, -1/2 + y, 3/2 - z; (ii) 3/2 - x, 1/2 - y, 1 - z.
Bis(3,3-dimethyl-2-oxobutyl)diphenylphosphonium bromide chloroform monosolvate top
Crystal data top
C24H32O2P+·Br·CHCl3F(000) = 2400
Mr = 582.74Dx = 1.395 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 23.6380 (18) ÅCell parameters from 9180 reflections
b = 13.6273 (10) Åθ = 2.3–25.3°
c = 18.1817 (13) ŵ = 1.85 mm1
β = 108.702 (1)°T = 173 K
V = 5547.5 (7) Å3Plate, colourless
Z = 80.34 × 0.15 × 0.09 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5090 independent reflections
Radiation source: sealed tube3862 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 8 pixels mm-1θmax = 25.4°, θmin = 1.8°
ω and φ scansh = 2828
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
k = 1516
Tmin = 0.667, Tmax = 0.745l = 1921
25767 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.206 w = 1/[σ2(Fo2) + (0.1214P)2 + 22.4904P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
5090 reflectionsΔρmax = 1.30 e Å3
373 parametersΔρmin = 1.10 e Å3
66 restraints
Crystal data top
C24H32O2P+·Br·CHCl3V = 5547.5 (7) Å3
Mr = 582.74Z = 8
Monoclinic, C2/cMo Kα radiation
a = 23.6380 (18) ŵ = 1.85 mm1
b = 13.6273 (10) ÅT = 173 K
c = 18.1817 (13) Å0.34 × 0.15 × 0.09 mm
β = 108.702 (1)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5090 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
3862 reflections with I > 2σ(I)
Tmin = 0.667, Tmax = 0.745Rint = 0.040
25767 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06466 restraints
wR(F2) = 0.206H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.1214P)2 + 22.4904P]
where P = (Fo2 + 2Fc2)/3
5090 reflectionsΔρmax = 1.30 e Å3
373 parametersΔρmin = 1.10 e Å3
Special details top

Experimental. SADABS-2012/1 (Bruker, 2013) was used for absorption correction. wR2(int) was 0.0613 before and 0.0433 after correction. The Ratio of minimum to maximum transmission is 0.8956. The λ/2 correction factor is 0.0015.

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
xyzUiso*/UeqOcc. (<1)
P10.69139 (4)0.39763 (7)0.58769 (6)0.0214 (3)
O10.80869 (13)0.3191 (2)0.60430 (17)0.0309 (7)
O20.58476 (13)0.3136 (2)0.46946 (18)0.0305 (7)
C10.81047 (17)0.3556 (3)0.6659 (2)0.0243 (9)
C20.75533 (17)0.4046 (3)0.6746 (2)0.0254 (9)
H2A0.76440.47450.68830.030*
H2B0.74520.37310.71780.030*
C30.67433 (17)0.2690 (3)0.5678 (2)0.0233 (8)
H3A0.70250.24100.54320.028*
H3B0.68050.23420.61760.028*
C40.61055 (17)0.2511 (3)0.5150 (2)0.0237 (8)
C50.86786 (19)0.3561 (3)0.7359 (2)0.0306 (10)
C60.9052 (3)0.2661 (5)0.7318 (4)0.0618 (17)
H6A0.88270.20650.73420.093*
H6B0.94240.26700.77570.093*
H6C0.91450.26710.68300.093*
C70.9016 (3)0.4498 (5)0.7256 (4)0.0568 (15)
H7A0.87570.50710.72130.085*
H7B0.91290.44400.67840.085*
H7C0.93770.45770.77070.085*
C80.8561 (3)0.3630 (6)0.8130 (3)0.0650 (18)
H8A0.83540.42470.81520.098*
H8B0.89420.36130.85550.098*
H8C0.83130.30760.81810.098*
C90.63073 (18)0.4559 (3)0.6102 (2)0.0273 (9)
C100.6175 (2)0.4284 (5)0.6759 (3)0.0496 (14)
H100.64060.37930.70950.060*
C110.5699 (3)0.4733 (6)0.6925 (4)0.0682 (19)
H110.56070.45540.73790.082*
C120.5360 (2)0.5440 (4)0.6428 (4)0.0560 (16)
H120.50360.57450.65420.067*
C130.5489 (2)0.5695 (4)0.5781 (4)0.0557 (16)
H130.52540.61760.54400.067*
C140.5961 (2)0.5261 (4)0.5616 (3)0.0458 (13)
H140.60490.54470.51600.055*
C150.70589 (17)0.4604 (3)0.5093 (2)0.0240 (8)
C160.69455 (19)0.4162 (3)0.4366 (2)0.0291 (9)
H160.67940.35120.42810.035*
C170.7055 (2)0.4676 (4)0.3773 (3)0.0365 (11)
H170.69850.43740.32810.044*
C180.7268 (2)0.5631 (4)0.3890 (3)0.0402 (11)
H180.73300.59890.34740.048*
C190.7389 (2)0.6061 (4)0.4609 (3)0.0411 (12)
H190.75430.67100.46890.049*
C200.7288 (2)0.5556 (3)0.5220 (3)0.0353 (10)
H200.73740.58540.57160.042*
C210.58202 (18)0.1535 (3)0.5240 (3)0.0285 (9)
C220.6255 (2)0.0693 (4)0.5296 (3)0.0435 (12)
H22A0.64090.07230.48560.065*
H22B0.60490.00670.52850.065*
H22C0.65880.07470.57830.065*
C230.5652 (2)0.1610 (4)0.5987 (3)0.0456 (12)
H23A0.60160.16610.64350.068*
H23B0.54280.10240.60400.068*
H23C0.54040.21940.59620.068*
C240.5254 (2)0.1393 (4)0.4537 (3)0.0427 (12)
H24A0.49810.19430.45060.064*
H24B0.50580.07780.45960.064*
H24C0.53640.13670.40610.064*
Cl1A0.61055 (18)0.1585 (4)0.9366 (2)0.1062 (18)0.5
Cl2A0.53420 (17)0.1851 (3)0.77966 (18)0.0794 (11)0.5
Cl3A0.5717 (5)0.3487 (3)0.8797 (5)0.094 (3)0.5
C1A0.5960 (3)0.2348 (4)0.8538 (3)0.061 (3)0.5
H1A0.63190.24230.83650.074*0.5
Cl1B0.5809 (3)0.1342 (3)0.8669 (5)0.0963 (18)0.35
Cl2B0.6295 (4)0.2351 (6)1.0065 (4)0.061 (2)0.35
Cl3B0.5721 (5)0.3442 (4)0.8666 (6)0.096 (5)0.35
C1B0.6172 (5)0.2428 (4)0.9116 (10)0.078 (4)0.35
H1B0.65650.24790.90220.093*0.35
Cl1C0.6129 (8)0.2150 (13)0.9961 (6)0.060 (5)0.15
Cl2C0.5472 (5)0.3486 (8)0.8770 (10)0.045 (3)0.15
Cl3C0.6339 (3)0.2186 (5)0.8493 (5)0.0368 (17)0.15
C1C0.5777 (5)0.2284 (8)0.8944 (7)0.051 (5)0.15
H1C0.54600.17750.87400.061*0.15
Br1B0.7228 (3)0.1780 (6)0.7727 (5)0.0420 (5)0.35
Br1C0.7376 (2)0.1642 (3)0.7613 (3)0.0420 (5)0.15
Br1A0.7134 (2)0.1856 (4)0.7786 (3)0.0420 (5)0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0198 (5)0.0230 (5)0.0183 (5)0.0017 (4)0.0015 (4)0.0006 (4)
O10.0306 (16)0.0357 (17)0.0222 (16)0.0038 (13)0.0026 (12)0.0079 (13)
O20.0246 (15)0.0291 (16)0.0307 (17)0.0039 (12)0.0011 (13)0.0053 (13)
C10.023 (2)0.023 (2)0.024 (2)0.0004 (16)0.0030 (16)0.0006 (17)
C20.0222 (19)0.030 (2)0.0189 (19)0.0005 (16)0.0000 (15)0.0048 (16)
C30.0196 (19)0.0214 (19)0.024 (2)0.0006 (15)0.0004 (16)0.0012 (16)
C40.0218 (19)0.026 (2)0.022 (2)0.0043 (16)0.0049 (16)0.0032 (17)
C50.026 (2)0.039 (2)0.021 (2)0.0037 (18)0.0012 (17)0.0057 (18)
C60.042 (3)0.072 (4)0.054 (4)0.024 (3)0.009 (3)0.006 (3)
C70.042 (3)0.064 (4)0.057 (4)0.012 (3)0.006 (3)0.011 (3)
C80.036 (3)0.120 (6)0.029 (3)0.009 (3)0.004 (2)0.007 (3)
C90.024 (2)0.025 (2)0.029 (2)0.0022 (16)0.0042 (17)0.0087 (17)
C100.037 (3)0.078 (4)0.034 (3)0.015 (3)0.013 (2)0.008 (3)
C110.049 (3)0.122 (6)0.042 (3)0.011 (4)0.025 (3)0.014 (4)
C120.033 (3)0.059 (4)0.078 (4)0.004 (3)0.021 (3)0.032 (3)
C130.038 (3)0.039 (3)0.092 (5)0.016 (2)0.025 (3)0.002 (3)
C140.043 (3)0.042 (3)0.059 (3)0.014 (2)0.025 (3)0.011 (2)
C150.0220 (19)0.027 (2)0.021 (2)0.0041 (16)0.0036 (16)0.0037 (16)
C160.030 (2)0.029 (2)0.027 (2)0.0009 (17)0.0077 (18)0.0013 (18)
C170.040 (3)0.048 (3)0.022 (2)0.006 (2)0.0098 (19)0.004 (2)
C180.037 (3)0.045 (3)0.043 (3)0.005 (2)0.017 (2)0.016 (2)
C190.041 (3)0.030 (2)0.055 (3)0.005 (2)0.018 (2)0.005 (2)
C200.037 (2)0.033 (2)0.035 (3)0.0035 (19)0.010 (2)0.006 (2)
C210.023 (2)0.029 (2)0.029 (2)0.0031 (17)0.0013 (17)0.0030 (18)
C220.040 (3)0.030 (2)0.055 (3)0.000 (2)0.008 (2)0.004 (2)
C230.041 (3)0.058 (3)0.039 (3)0.010 (2)0.014 (2)0.003 (2)
C240.034 (3)0.040 (3)0.043 (3)0.012 (2)0.004 (2)0.002 (2)
Cl1A0.066 (2)0.165 (5)0.081 (3)0.035 (3)0.014 (2)0.074 (3)
Cl2A0.096 (3)0.090 (3)0.0519 (19)0.032 (2)0.0233 (18)0.0061 (17)
Cl3A0.105 (8)0.092 (6)0.077 (4)0.007 (5)0.017 (5)0.015 (4)
C1A0.057 (8)0.071 (9)0.061 (8)0.013 (7)0.026 (7)0.022 (7)
Cl1B0.082 (4)0.084 (4)0.119 (5)0.001 (3)0.028 (4)0.001 (4)
Cl2B0.062 (4)0.056 (5)0.069 (3)0.008 (3)0.029 (3)0.020 (3)
Cl3B0.078 (8)0.092 (7)0.094 (7)0.011 (6)0.005 (5)0.041 (5)
C1B0.076 (9)0.075 (8)0.082 (7)0.009 (7)0.025 (8)0.020 (8)
Cl1C0.063 (10)0.029 (6)0.099 (10)0.001 (7)0.039 (7)0.023 (6)
Cl2C0.052 (7)0.028 (4)0.047 (6)0.008 (4)0.006 (6)0.004 (4)
Cl3C0.033 (4)0.034 (4)0.049 (4)0.002 (3)0.022 (3)0.017 (3)
C1C0.048 (10)0.031 (9)0.081 (10)0.004 (9)0.033 (8)0.001 (10)
Br1B0.0474 (16)0.0398 (10)0.0380 (10)0.0058 (9)0.0124 (8)0.0082 (7)
Br1C0.0474 (16)0.0398 (10)0.0380 (10)0.0058 (9)0.0124 (8)0.0082 (7)
Br1A0.0474 (16)0.0398 (10)0.0380 (10)0.0058 (9)0.0124 (8)0.0082 (7)
Geometric parameters (Å, º) top
P1—C21.805 (4)C15—C161.398 (6)
P1—C31.809 (4)C15—C201.397 (6)
P1—C91.798 (4)C16—H160.9500
P1—C151.786 (4)C16—C171.379 (6)
O1—C11.214 (5)C17—H170.9500
O2—C41.208 (5)C17—C181.387 (7)
C1—C21.517 (6)C18—H180.9500
C1—C51.534 (6)C18—C191.376 (7)
C2—H2A0.9900C19—H190.9500
C2—H2B0.9900C19—C201.391 (7)
C3—H3A0.9900C20—H200.9500
C3—H3B0.9900C21—C221.522 (6)
C3—C41.526 (5)C21—C231.536 (7)
C4—C211.523 (6)C21—C241.537 (6)
C5—C61.526 (7)C22—H22A0.9800
C5—C71.549 (8)C22—H22B0.9800
C5—C81.517 (7)C22—H22C0.9800
C6—H6A0.9800C23—H23A0.9800
C6—H6B0.9800C23—H23B0.9800
C6—H6C0.9800C23—H23C0.9800
C7—H7A0.9800C24—H24A0.9800
C7—H7B0.9800C24—H24B0.9800
C7—H7C0.9800C24—H24C0.9800
C8—H8A0.9800Cl1A—C1A1.770 (5)
C8—H8B0.9800Cl2A—Cl2Ai1.631 (7)
C8—H8C0.9800Cl2A—C1A1.774 (5)
C9—C101.379 (7)Cl3A—C1A1.772 (5)
C9—C141.380 (7)C1A—H1A1.0000
C10—H100.9500Cl1B—C1B1.772 (5)
C10—C111.397 (8)Cl2B—C1B1.66 (2)
C11—H110.9500Cl3B—C1B1.776 (5)
C11—C121.386 (10)C1B—H1B1.0000
C12—H120.9500Cl1C—C1C1.778 (5)
C12—C131.351 (9)Cl2C—C1C1.777 (5)
C13—H130.9500Cl3C—C1C1.776 (5)
C13—C141.378 (7)C1C—H1C1.0000
C14—H140.9500
C2—P1—C3107.24 (19)C13—C14—C9120.9 (5)
C9—P1—C2106.40 (19)C13—C14—H14119.6
C9—P1—C3109.30 (19)C16—C15—P1121.4 (3)
C15—P1—C2110.60 (19)C20—C15—P1118.4 (3)
C15—P1—C3113.08 (19)C20—C15—C16120.2 (4)
C15—P1—C9110.0 (2)C15—C16—H16120.2
O1—C1—C2120.0 (4)C17—C16—C15119.6 (4)
O1—C1—C5121.8 (4)C17—C16—H16120.2
C2—C1—C5118.2 (3)C16—C17—H17119.8
P1—C2—H2A109.0C16—C17—C18120.4 (4)
P1—C2—H2B109.0C18—C17—H17119.8
C1—C2—P1113.1 (3)C17—C18—H18120.0
C1—C2—H2A109.0C19—C18—C17120.0 (4)
C1—C2—H2B109.0C19—C18—H18120.0
H2A—C2—H2B107.8C18—C19—H19119.6
P1—C3—H3A108.9C18—C19—C20120.8 (4)
P1—C3—H3B108.9C20—C19—H19119.6
H3A—C3—H3B107.8C15—C20—H20120.5
C4—C3—P1113.1 (3)C19—C20—C15118.9 (4)
C4—C3—H3A108.9C19—C20—H20120.5
C4—C3—H3B108.9C4—C21—C23106.6 (4)
O2—C4—C3119.9 (4)C4—C21—C24108.5 (4)
O2—C4—C21123.1 (4)C22—C21—C4110.6 (3)
C21—C4—C3117.0 (3)C22—C21—C23110.6 (4)
C1—C5—C7104.9 (4)C22—C21—C24110.5 (4)
C6—C5—C1109.2 (4)C23—C21—C24109.9 (4)
C6—C5—C7109.2 (5)C21—C22—H22A109.5
C8—C5—C1113.1 (4)C21—C22—H22B109.5
C8—C5—C6112.0 (5)C21—C22—H22C109.5
C8—C5—C7108.3 (5)H22A—C22—H22B109.5
C5—C6—H6A109.5H22A—C22—H22C109.5
C5—C6—H6B109.5H22B—C22—H22C109.5
C5—C6—H6C109.5C21—C23—H23A109.5
H6A—C6—H6B109.5C21—C23—H23B109.5
H6A—C6—H6C109.5C21—C23—H23C109.5
H6B—C6—H6C109.5H23A—C23—H23B109.5
C5—C7—H7A109.5H23A—C23—H23C109.5
C5—C7—H7B109.5H23B—C23—H23C109.5
C5—C7—H7C109.5C21—C24—H24A109.5
H7A—C7—H7B109.5C21—C24—H24B109.5
H7A—C7—H7C109.5C21—C24—H24C109.5
H7B—C7—H7C109.5H24A—C24—H24B109.5
C5—C8—H8A109.5H24A—C24—H24C109.5
C5—C8—H8B109.5H24B—C24—H24C109.5
C5—C8—H8C109.5Cl2Ai—Cl2A—C1A154.5 (3)
H8A—C8—H8B109.5Cl1A—C1A—Cl2A108.1 (4)
H8A—C8—H8C109.5Cl1A—C1A—Cl3A106.2 (4)
H8B—C8—H8C109.5Cl1A—C1A—H1A112.0
C10—C9—P1119.7 (4)Cl2A—C1A—H1A112.0
C10—C9—C14119.4 (4)Cl3A—C1A—Cl2A106.2 (4)
C14—C9—P1120.8 (4)Cl3A—C1A—H1A112.0
C9—C10—H10120.4Cl1B—C1B—Cl3B107.9 (4)
C9—C10—C11119.3 (5)Cl1B—C1B—H1B108.7
C11—C10—H10120.4Cl2B—C1B—Cl1B108.7 (10)
C10—C11—H11120.0Cl2B—C1B—Cl3B114.0 (10)
C12—C11—C10120.1 (6)Cl2B—C1B—H1B108.7
C12—C11—H11120.0Cl3B—C1B—H1B108.7
C11—C12—H12120.0Cl1C—C1C—H1C111.1
C13—C12—C11120.1 (5)Cl2C—C1C—Cl1C107.9 (4)
C13—C12—H12120.0Cl2C—C1C—H1C111.1
C12—C13—H13119.9Cl3C—C1C—Cl1C107.6 (4)
C12—C13—C14120.3 (5)Cl3C—C1C—Cl2C107.9 (4)
C14—C13—H13119.9Cl3C—C1C—H1C111.1
C9—C14—H14119.6
P1—C3—C4—O226.8 (5)C3—C4—C21—C2244.8 (5)
P1—C3—C4—C21152.1 (3)C3—C4—C21—C2375.5 (4)
P1—C9—C10—C11179.3 (5)C3—C4—C21—C24166.2 (4)
P1—C9—C14—C13178.9 (4)C5—C1—C2—P1179.7 (3)
P1—C15—C16—C17179.1 (3)C9—P1—C2—C1178.4 (3)
P1—C15—C20—C19178.4 (3)C9—P1—C3—C444.9 (3)
O1—C1—C2—P11.7 (5)C9—P1—C15—C16112.2 (3)
O1—C1—C5—C629.7 (6)C9—P1—C15—C2067.6 (4)
O1—C1—C5—C787.1 (5)C9—C10—C11—C120.7 (10)
O1—C1—C5—C8155.1 (5)C10—C9—C14—C130.6 (8)
O2—C4—C21—C22136.3 (4)C10—C11—C12—C130.0 (10)
O2—C4—C21—C23103.4 (5)C11—C12—C13—C140.5 (9)
O2—C4—C21—C2414.9 (6)C12—C13—C14—C90.2 (9)
C2—P1—C3—C4159.8 (3)C14—C9—C10—C111.1 (8)
C2—P1—C9—C1051.0 (4)C15—P1—C2—C162.2 (3)
C2—P1—C9—C14130.8 (4)C15—P1—C3—C478.0 (3)
C2—P1—C15—C16130.6 (3)C15—P1—C9—C10170.8 (4)
C2—P1—C15—C2049.7 (4)C15—P1—C9—C1411.0 (4)
C2—C1—C5—C6151.7 (4)C15—C16—C17—C181.1 (7)
C2—C1—C5—C791.5 (5)C16—C15—C20—C191.3 (7)
C2—C1—C5—C826.3 (6)C16—C17—C18—C192.1 (7)
C3—P1—C2—C161.5 (3)C17—C18—C19—C201.4 (7)
C3—P1—C9—C1064.5 (4)C18—C19—C20—C150.3 (7)
C3—P1—C9—C14113.7 (4)C20—C15—C16—C170.7 (6)
C3—P1—C15—C1610.3 (4)Cl2Ai—Cl2A—C1A—Cl1A113.6 (8)
C3—P1—C15—C20169.9 (3)Cl2Ai—Cl2A—C1A—Cl3A0.0 (11)
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···Br1Bii0.992.853.840 (9)174
C2—H2A···Br1Cii0.992.753.712 (6)164
C2—H2A···Br1Aii0.992.953.941 (7)177
C2—H2B···Br1B0.992.953.767 (9)141
C2—H2B···Br1C0.992.973.717 (6)133
C2—H2B···Br1A0.992.973.831 (7)145
C3—H3B···Br1B0.992.783.740 (9)163
C3—H3B···Br1C0.992.703.644 (6)159
C3—H3B···Br1A0.992.863.816 (7)164
C16—H16···O1iii0.952.433.287 (5)150
C1A—H1A···Br1A1.002.593.527 (9)156
Symmetry codes: (ii) x+3/2, y+1/2, z+3/2; (iii) x+3/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···Br1Bi0.992.853.840 (9)173.7
C2—H2A···Br1Ci0.992.753.712 (6)164.3
C2—H2A···Br1Ai0.992.953.941 (7)176.9
C2—H2B···Br1B0.992.953.767 (9)140.9
C2—H2B···Br1C0.992.973.717 (6)132.6
C2—H2B···Br1A0.992.973.831 (7)145.3
C3—H3B···Br1B0.992.783.740 (9)163.4
C3—H3B···Br1C0.992.703.644 (6)159.1
C3—H3B···Br1A0.992.863.816 (7)163.7
C16—H16···O1ii0.952.433.287 (5)149.5
C1A—H1A···Br1A1.002.593.527 (9)156.0
Symmetry codes: (i) x+3/2, y+1/2, z+3/2; (ii) x+3/2, y+1/2, z+1.
 

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