



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901500763X/pk2549sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S205698901500763X/pk2549Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901500763X/pk2549Isup3.cml |
CCDC reference: 1060276
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean
(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
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 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.
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.
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.
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.
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.
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).
C24H32O2P+·Br−·CHCl3 | F(000) = 2400 |
Mr = 582.74 | Dx = 1.395 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 23.6380 (18) Å | Cell parameters from 9180 reflections |
b = 13.6273 (10) Å | θ = 2.3–25.3° |
c = 18.1817 (13) Å | µ = 1.85 mm−1 |
β = 108.702 (1)° | T = 173 K |
V = 5547.5 (7) Å3 | Plate, colourless |
Z = 8 | 0.34 × 0.15 × 0.09 mm |
Bruker SMART APEX CCD area-detector diffractometer | 5090 independent reflections |
Radiation source: sealed tube | 3862 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 8 pixels mm-1 | θmax = 25.4°, θmin = 1.8° |
ω and φ scans | h = −28→28 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −15→16 |
Tmin = 0.667, Tmax = 0.745 | l = −19→21 |
25767 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H-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 reflections | Δρmax = 1.30 e Å−3 |
373 parameters | Δρmin = −1.10 e Å−3 |
66 restraints |
C24H32O2P+·Br−·CHCl3 | V = 5547.5 (7) Å3 |
Mr = 582.74 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 23.6380 (18) Å | µ = 1.85 mm−1 |
b = 13.6273 (10) Å | T = 173 K |
c = 18.1817 (13) Å | 0.34 × 0.15 × 0.09 mm |
β = 108.702 (1)° |
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 = 0.745 | Rint = 0.040 |
25767 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 66 restraints |
wR(F2) = 0.206 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.1214P)2 + 22.4904P] where P = (Fo2 + 2Fc2)/3 |
5090 reflections | Δρmax = 1.30 e Å−3 |
373 parameters | Δρmin = −1.10 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
P1 | 0.69139 (4) | 0.39763 (7) | 0.58769 (6) | 0.0214 (3) | |
O1 | 0.80869 (13) | 0.3191 (2) | 0.60430 (17) | 0.0309 (7) | |
O2 | 0.58476 (13) | 0.3136 (2) | 0.46946 (18) | 0.0305 (7) | |
C1 | 0.81047 (17) | 0.3556 (3) | 0.6659 (2) | 0.0243 (9) | |
C2 | 0.75533 (17) | 0.4046 (3) | 0.6746 (2) | 0.0254 (9) | |
H2A | 0.7644 | 0.4745 | 0.6883 | 0.030* | |
H2B | 0.7452 | 0.3731 | 0.7178 | 0.030* | |
C3 | 0.67433 (17) | 0.2690 (3) | 0.5678 (2) | 0.0233 (8) | |
H3A | 0.7025 | 0.2410 | 0.5432 | 0.028* | |
H3B | 0.6805 | 0.2342 | 0.6176 | 0.028* | |
C4 | 0.61055 (17) | 0.2511 (3) | 0.5150 (2) | 0.0237 (8) | |
C5 | 0.86786 (19) | 0.3561 (3) | 0.7359 (2) | 0.0306 (10) | |
C6 | 0.9052 (3) | 0.2661 (5) | 0.7318 (4) | 0.0618 (17) | |
H6A | 0.8827 | 0.2065 | 0.7342 | 0.093* | |
H6B | 0.9424 | 0.2670 | 0.7757 | 0.093* | |
H6C | 0.9145 | 0.2671 | 0.6830 | 0.093* | |
C7 | 0.9016 (3) | 0.4498 (5) | 0.7256 (4) | 0.0568 (15) | |
H7A | 0.8757 | 0.5071 | 0.7213 | 0.085* | |
H7B | 0.9129 | 0.4440 | 0.6784 | 0.085* | |
H7C | 0.9377 | 0.4577 | 0.7707 | 0.085* | |
C8 | 0.8561 (3) | 0.3630 (6) | 0.8130 (3) | 0.0650 (18) | |
H8A | 0.8354 | 0.4247 | 0.8152 | 0.098* | |
H8B | 0.8942 | 0.3613 | 0.8555 | 0.098* | |
H8C | 0.8313 | 0.3076 | 0.8181 | 0.098* | |
C9 | 0.63073 (18) | 0.4559 (3) | 0.6102 (2) | 0.0273 (9) | |
C10 | 0.6175 (2) | 0.4284 (5) | 0.6759 (3) | 0.0496 (14) | |
H10 | 0.6406 | 0.3793 | 0.7095 | 0.060* | |
C11 | 0.5699 (3) | 0.4733 (6) | 0.6925 (4) | 0.0682 (19) | |
H11 | 0.5607 | 0.4554 | 0.7379 | 0.082* | |
C12 | 0.5360 (2) | 0.5440 (4) | 0.6428 (4) | 0.0560 (16) | |
H12 | 0.5036 | 0.5745 | 0.6542 | 0.067* | |
C13 | 0.5489 (2) | 0.5695 (4) | 0.5781 (4) | 0.0557 (16) | |
H13 | 0.5254 | 0.6176 | 0.5440 | 0.067* | |
C14 | 0.5961 (2) | 0.5261 (4) | 0.5616 (3) | 0.0458 (13) | |
H14 | 0.6049 | 0.5447 | 0.5160 | 0.055* | |
C15 | 0.70589 (17) | 0.4604 (3) | 0.5093 (2) | 0.0240 (8) | |
C16 | 0.69455 (19) | 0.4162 (3) | 0.4366 (2) | 0.0291 (9) | |
H16 | 0.6794 | 0.3512 | 0.4281 | 0.035* | |
C17 | 0.7055 (2) | 0.4676 (4) | 0.3773 (3) | 0.0365 (11) | |
H17 | 0.6985 | 0.4374 | 0.3281 | 0.044* | |
C18 | 0.7268 (2) | 0.5631 (4) | 0.3890 (3) | 0.0402 (11) | |
H18 | 0.7330 | 0.5989 | 0.3474 | 0.048* | |
C19 | 0.7389 (2) | 0.6061 (4) | 0.4609 (3) | 0.0411 (12) | |
H19 | 0.7543 | 0.6710 | 0.4689 | 0.049* | |
C20 | 0.7288 (2) | 0.5556 (3) | 0.5220 (3) | 0.0353 (10) | |
H20 | 0.7374 | 0.5854 | 0.5716 | 0.042* | |
C21 | 0.58202 (18) | 0.1535 (3) | 0.5240 (3) | 0.0285 (9) | |
C22 | 0.6255 (2) | 0.0693 (4) | 0.5296 (3) | 0.0435 (12) | |
H22A | 0.6409 | 0.0723 | 0.4856 | 0.065* | |
H22B | 0.6049 | 0.0067 | 0.5285 | 0.065* | |
H22C | 0.6588 | 0.0747 | 0.5783 | 0.065* | |
C23 | 0.5652 (2) | 0.1610 (4) | 0.5987 (3) | 0.0456 (12) | |
H23A | 0.6016 | 0.1661 | 0.6435 | 0.068* | |
H23B | 0.5428 | 0.1024 | 0.6040 | 0.068* | |
H23C | 0.5404 | 0.2194 | 0.5962 | 0.068* | |
C24 | 0.5254 (2) | 0.1393 (4) | 0.4537 (3) | 0.0427 (12) | |
H24A | 0.4981 | 0.1943 | 0.4506 | 0.064* | |
H24B | 0.5058 | 0.0778 | 0.4596 | 0.064* | |
H24C | 0.5364 | 0.1367 | 0.4061 | 0.064* | |
Cl1A | 0.61055 (18) | 0.1585 (4) | 0.9366 (2) | 0.1062 (18) | 0.5 |
Cl2A | 0.53420 (17) | 0.1851 (3) | 0.77966 (18) | 0.0794 (11) | 0.5 |
Cl3A | 0.5717 (5) | 0.3487 (3) | 0.8797 (5) | 0.094 (3) | 0.5 |
C1A | 0.5960 (3) | 0.2348 (4) | 0.8538 (3) | 0.061 (3) | 0.5 |
H1A | 0.6319 | 0.2423 | 0.8365 | 0.074* | 0.5 |
Cl1B | 0.5809 (3) | 0.1342 (3) | 0.8669 (5) | 0.0963 (18) | 0.35 |
Cl2B | 0.6295 (4) | 0.2351 (6) | 1.0065 (4) | 0.061 (2) | 0.35 |
Cl3B | 0.5721 (5) | 0.3442 (4) | 0.8666 (6) | 0.096 (5) | 0.35 |
C1B | 0.6172 (5) | 0.2428 (4) | 0.9116 (10) | 0.078 (4) | 0.35 |
H1B | 0.6565 | 0.2479 | 0.9022 | 0.093* | 0.35 |
Cl1C | 0.6129 (8) | 0.2150 (13) | 0.9961 (6) | 0.060 (5) | 0.15 |
Cl2C | 0.5472 (5) | 0.3486 (8) | 0.8770 (10) | 0.045 (3) | 0.15 |
Cl3C | 0.6339 (3) | 0.2186 (5) | 0.8493 (5) | 0.0368 (17) | 0.15 |
C1C | 0.5777 (5) | 0.2284 (8) | 0.8944 (7) | 0.051 (5) | 0.15 |
H1C | 0.5460 | 0.1775 | 0.8740 | 0.061* | 0.15 |
Br1B | 0.7228 (3) | 0.1780 (6) | 0.7727 (5) | 0.0420 (5) | 0.35 |
Br1C | 0.7376 (2) | 0.1642 (3) | 0.7613 (3) | 0.0420 (5) | 0.15 |
Br1A | 0.7134 (2) | 0.1856 (4) | 0.7786 (3) | 0.0420 (5) | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0198 (5) | 0.0230 (5) | 0.0183 (5) | 0.0017 (4) | 0.0015 (4) | −0.0006 (4) |
O1 | 0.0306 (16) | 0.0357 (17) | 0.0222 (16) | 0.0038 (13) | 0.0026 (12) | −0.0079 (13) |
O2 | 0.0246 (15) | 0.0291 (16) | 0.0307 (17) | 0.0039 (12) | −0.0011 (13) | 0.0053 (13) |
C1 | 0.023 (2) | 0.023 (2) | 0.024 (2) | 0.0004 (16) | 0.0030 (16) | 0.0006 (17) |
C2 | 0.0222 (19) | 0.030 (2) | 0.0189 (19) | −0.0005 (16) | 0.0000 (15) | −0.0048 (16) |
C3 | 0.0196 (19) | 0.0214 (19) | 0.024 (2) | −0.0006 (15) | 0.0004 (16) | −0.0012 (16) |
C4 | 0.0218 (19) | 0.026 (2) | 0.022 (2) | 0.0043 (16) | 0.0049 (16) | −0.0032 (17) |
C5 | 0.026 (2) | 0.039 (2) | 0.021 (2) | 0.0037 (18) | −0.0012 (17) | −0.0057 (18) |
C6 | 0.042 (3) | 0.072 (4) | 0.054 (4) | 0.024 (3) | −0.009 (3) | −0.006 (3) |
C7 | 0.042 (3) | 0.064 (4) | 0.057 (4) | −0.012 (3) | 0.006 (3) | −0.011 (3) |
C8 | 0.036 (3) | 0.120 (6) | 0.029 (3) | 0.009 (3) | −0.004 (2) | −0.007 (3) |
C9 | 0.024 (2) | 0.025 (2) | 0.029 (2) | −0.0022 (16) | 0.0042 (17) | −0.0087 (17) |
C10 | 0.037 (3) | 0.078 (4) | 0.034 (3) | 0.015 (3) | 0.013 (2) | 0.008 (3) |
C11 | 0.049 (3) | 0.122 (6) | 0.042 (3) | 0.011 (4) | 0.025 (3) | −0.014 (4) |
C12 | 0.033 (3) | 0.059 (4) | 0.078 (4) | 0.004 (3) | 0.021 (3) | −0.032 (3) |
C13 | 0.038 (3) | 0.039 (3) | 0.092 (5) | 0.016 (2) | 0.025 (3) | 0.002 (3) |
C14 | 0.043 (3) | 0.042 (3) | 0.059 (3) | 0.014 (2) | 0.025 (3) | 0.011 (2) |
C15 | 0.0220 (19) | 0.027 (2) | 0.021 (2) | 0.0041 (16) | 0.0036 (16) | 0.0037 (16) |
C16 | 0.030 (2) | 0.029 (2) | 0.027 (2) | 0.0009 (17) | 0.0077 (18) | −0.0013 (18) |
C17 | 0.040 (3) | 0.048 (3) | 0.022 (2) | 0.006 (2) | 0.0098 (19) | 0.004 (2) |
C18 | 0.037 (3) | 0.045 (3) | 0.043 (3) | 0.005 (2) | 0.017 (2) | 0.016 (2) |
C19 | 0.041 (3) | 0.030 (2) | 0.055 (3) | −0.005 (2) | 0.018 (2) | 0.005 (2) |
C20 | 0.037 (2) | 0.033 (2) | 0.035 (3) | −0.0035 (19) | 0.010 (2) | −0.006 (2) |
C21 | 0.023 (2) | 0.029 (2) | 0.029 (2) | −0.0031 (17) | 0.0013 (17) | 0.0030 (18) |
C22 | 0.040 (3) | 0.030 (2) | 0.055 (3) | 0.000 (2) | 0.008 (2) | 0.004 (2) |
C23 | 0.041 (3) | 0.058 (3) | 0.039 (3) | −0.010 (2) | 0.014 (2) | 0.003 (2) |
C24 | 0.034 (3) | 0.040 (3) | 0.043 (3) | −0.012 (2) | −0.004 (2) | 0.002 (2) |
Cl1A | 0.066 (2) | 0.165 (5) | 0.081 (3) | 0.035 (3) | 0.014 (2) | 0.074 (3) |
Cl2A | 0.096 (3) | 0.090 (3) | 0.0519 (19) | 0.032 (2) | 0.0233 (18) | −0.0061 (17) |
Cl3A | 0.105 (8) | 0.092 (6) | 0.077 (4) | 0.007 (5) | 0.017 (5) | −0.015 (4) |
C1A | 0.057 (8) | 0.071 (9) | 0.061 (8) | 0.013 (7) | 0.026 (7) | 0.022 (7) |
Cl1B | 0.082 (4) | 0.084 (4) | 0.119 (5) | −0.001 (3) | 0.028 (4) | −0.001 (4) |
Cl2B | 0.062 (4) | 0.056 (5) | 0.069 (3) | 0.008 (3) | 0.029 (3) | 0.020 (3) |
Cl3B | 0.078 (8) | 0.092 (7) | 0.094 (7) | −0.011 (6) | −0.005 (5) | 0.041 (5) |
C1B | 0.076 (9) | 0.075 (8) | 0.082 (7) | −0.009 (7) | 0.025 (8) | 0.020 (8) |
Cl1C | 0.063 (10) | 0.029 (6) | 0.099 (10) | 0.001 (7) | 0.039 (7) | 0.023 (6) |
Cl2C | 0.052 (7) | 0.028 (4) | 0.047 (6) | 0.008 (4) | 0.006 (6) | 0.004 (4) |
Cl3C | 0.033 (4) | 0.034 (4) | 0.049 (4) | −0.002 (3) | 0.022 (3) | −0.017 (3) |
C1C | 0.048 (10) | 0.031 (9) | 0.081 (10) | 0.004 (9) | 0.033 (8) | −0.001 (10) |
Br1B | 0.0474 (16) | 0.0398 (10) | 0.0380 (10) | 0.0058 (9) | 0.0124 (8) | 0.0082 (7) |
Br1C | 0.0474 (16) | 0.0398 (10) | 0.0380 (10) | 0.0058 (9) | 0.0124 (8) | 0.0082 (7) |
Br1A | 0.0474 (16) | 0.0398 (10) | 0.0380 (10) | 0.0058 (9) | 0.0124 (8) | 0.0082 (7) |
P1—C2 | 1.805 (4) | C15—C16 | 1.398 (6) |
P1—C3 | 1.809 (4) | C15—C20 | 1.397 (6) |
P1—C9 | 1.798 (4) | C16—H16 | 0.9500 |
P1—C15 | 1.786 (4) | C16—C17 | 1.379 (6) |
O1—C1 | 1.214 (5) | C17—H17 | 0.9500 |
O2—C4 | 1.208 (5) | C17—C18 | 1.387 (7) |
C1—C2 | 1.517 (6) | C18—H18 | 0.9500 |
C1—C5 | 1.534 (6) | C18—C19 | 1.376 (7) |
C2—H2A | 0.9900 | C19—H19 | 0.9500 |
C2—H2B | 0.9900 | C19—C20 | 1.391 (7) |
C3—H3A | 0.9900 | C20—H20 | 0.9500 |
C3—H3B | 0.9900 | C21—C22 | 1.522 (6) |
C3—C4 | 1.526 (5) | C21—C23 | 1.536 (7) |
C4—C21 | 1.523 (6) | C21—C24 | 1.537 (6) |
C5—C6 | 1.526 (7) | C22—H22A | 0.9800 |
C5—C7 | 1.549 (8) | C22—H22B | 0.9800 |
C5—C8 | 1.517 (7) | C22—H22C | 0.9800 |
C6—H6A | 0.9800 | C23—H23A | 0.9800 |
C6—H6B | 0.9800 | C23—H23B | 0.9800 |
C6—H6C | 0.9800 | C23—H23C | 0.9800 |
C7—H7A | 0.9800 | C24—H24A | 0.9800 |
C7—H7B | 0.9800 | C24—H24B | 0.9800 |
C7—H7C | 0.9800 | C24—H24C | 0.9800 |
C8—H8A | 0.9800 | Cl1A—C1A | 1.770 (5) |
C8—H8B | 0.9800 | Cl2A—Cl2Ai | 1.631 (7) |
C8—H8C | 0.9800 | Cl2A—C1A | 1.774 (5) |
C9—C10 | 1.379 (7) | Cl3A—C1A | 1.772 (5) |
C9—C14 | 1.380 (7) | C1A—H1A | 1.0000 |
C10—H10 | 0.9500 | Cl1B—C1B | 1.772 (5) |
C10—C11 | 1.397 (8) | Cl2B—C1B | 1.66 (2) |
C11—H11 | 0.9500 | Cl3B—C1B | 1.776 (5) |
C11—C12 | 1.386 (10) | C1B—H1B | 1.0000 |
C12—H12 | 0.9500 | Cl1C—C1C | 1.778 (5) |
C12—C13 | 1.351 (9) | Cl2C—C1C | 1.777 (5) |
C13—H13 | 0.9500 | Cl3C—C1C | 1.776 (5) |
C13—C14 | 1.378 (7) | C1C—H1C | 1.0000 |
C14—H14 | 0.9500 | ||
C2—P1—C3 | 107.24 (19) | C13—C14—C9 | 120.9 (5) |
C9—P1—C2 | 106.40 (19) | C13—C14—H14 | 119.6 |
C9—P1—C3 | 109.30 (19) | C16—C15—P1 | 121.4 (3) |
C15—P1—C2 | 110.60 (19) | C20—C15—P1 | 118.4 (3) |
C15—P1—C3 | 113.08 (19) | C20—C15—C16 | 120.2 (4) |
C15—P1—C9 | 110.0 (2) | C15—C16—H16 | 120.2 |
O1—C1—C2 | 120.0 (4) | C17—C16—C15 | 119.6 (4) |
O1—C1—C5 | 121.8 (4) | C17—C16—H16 | 120.2 |
C2—C1—C5 | 118.2 (3) | C16—C17—H17 | 119.8 |
P1—C2—H2A | 109.0 | C16—C17—C18 | 120.4 (4) |
P1—C2—H2B | 109.0 | C18—C17—H17 | 119.8 |
C1—C2—P1 | 113.1 (3) | C17—C18—H18 | 120.0 |
C1—C2—H2A | 109.0 | C19—C18—C17 | 120.0 (4) |
C1—C2—H2B | 109.0 | C19—C18—H18 | 120.0 |
H2A—C2—H2B | 107.8 | C18—C19—H19 | 119.6 |
P1—C3—H3A | 108.9 | C18—C19—C20 | 120.8 (4) |
P1—C3—H3B | 108.9 | C20—C19—H19 | 119.6 |
H3A—C3—H3B | 107.8 | C15—C20—H20 | 120.5 |
C4—C3—P1 | 113.1 (3) | C19—C20—C15 | 118.9 (4) |
C4—C3—H3A | 108.9 | C19—C20—H20 | 120.5 |
C4—C3—H3B | 108.9 | C4—C21—C23 | 106.6 (4) |
O2—C4—C3 | 119.9 (4) | C4—C21—C24 | 108.5 (4) |
O2—C4—C21 | 123.1 (4) | C22—C21—C4 | 110.6 (3) |
C21—C4—C3 | 117.0 (3) | C22—C21—C23 | 110.6 (4) |
C1—C5—C7 | 104.9 (4) | C22—C21—C24 | 110.5 (4) |
C6—C5—C1 | 109.2 (4) | C23—C21—C24 | 109.9 (4) |
C6—C5—C7 | 109.2 (5) | C21—C22—H22A | 109.5 |
C8—C5—C1 | 113.1 (4) | C21—C22—H22B | 109.5 |
C8—C5—C6 | 112.0 (5) | C21—C22—H22C | 109.5 |
C8—C5—C7 | 108.3 (5) | H22A—C22—H22B | 109.5 |
C5—C6—H6A | 109.5 | H22A—C22—H22C | 109.5 |
C5—C6—H6B | 109.5 | H22B—C22—H22C | 109.5 |
C5—C6—H6C | 109.5 | C21—C23—H23A | 109.5 |
H6A—C6—H6B | 109.5 | C21—C23—H23B | 109.5 |
H6A—C6—H6C | 109.5 | C21—C23—H23C | 109.5 |
H6B—C6—H6C | 109.5 | H23A—C23—H23B | 109.5 |
C5—C7—H7A | 109.5 | H23A—C23—H23C | 109.5 |
C5—C7—H7B | 109.5 | H23B—C23—H23C | 109.5 |
C5—C7—H7C | 109.5 | C21—C24—H24A | 109.5 |
H7A—C7—H7B | 109.5 | C21—C24—H24B | 109.5 |
H7A—C7—H7C | 109.5 | C21—C24—H24C | 109.5 |
H7B—C7—H7C | 109.5 | H24A—C24—H24B | 109.5 |
C5—C8—H8A | 109.5 | H24A—C24—H24C | 109.5 |
C5—C8—H8B | 109.5 | H24B—C24—H24C | 109.5 |
C5—C8—H8C | 109.5 | Cl2Ai—Cl2A—C1A | 154.5 (3) |
H8A—C8—H8B | 109.5 | Cl1A—C1A—Cl2A | 108.1 (4) |
H8A—C8—H8C | 109.5 | Cl1A—C1A—Cl3A | 106.2 (4) |
H8B—C8—H8C | 109.5 | Cl1A—C1A—H1A | 112.0 |
C10—C9—P1 | 119.7 (4) | Cl2A—C1A—H1A | 112.0 |
C10—C9—C14 | 119.4 (4) | Cl3A—C1A—Cl2A | 106.2 (4) |
C14—C9—P1 | 120.8 (4) | Cl3A—C1A—H1A | 112.0 |
C9—C10—H10 | 120.4 | Cl1B—C1B—Cl3B | 107.9 (4) |
C9—C10—C11 | 119.3 (5) | Cl1B—C1B—H1B | 108.7 |
C11—C10—H10 | 120.4 | Cl2B—C1B—Cl1B | 108.7 (10) |
C10—C11—H11 | 120.0 | Cl2B—C1B—Cl3B | 114.0 (10) |
C12—C11—C10 | 120.1 (6) | Cl2B—C1B—H1B | 108.7 |
C12—C11—H11 | 120.0 | Cl3B—C1B—H1B | 108.7 |
C11—C12—H12 | 120.0 | Cl1C—C1C—H1C | 111.1 |
C13—C12—C11 | 120.1 (5) | Cl2C—C1C—Cl1C | 107.9 (4) |
C13—C12—H12 | 120.0 | Cl2C—C1C—H1C | 111.1 |
C12—C13—H13 | 119.9 | Cl3C—C1C—Cl1C | 107.6 (4) |
C12—C13—C14 | 120.3 (5) | Cl3C—C1C—Cl2C | 107.9 (4) |
C14—C13—H13 | 119.9 | Cl3C—C1C—H1C | 111.1 |
C9—C14—H14 | 119.6 | ||
P1—C3—C4—O2 | 26.8 (5) | C3—C4—C21—C22 | −44.8 (5) |
P1—C3—C4—C21 | −152.1 (3) | C3—C4—C21—C23 | 75.5 (4) |
P1—C9—C10—C11 | −179.3 (5) | C3—C4—C21—C24 | −166.2 (4) |
P1—C9—C14—C13 | 178.9 (4) | C5—C1—C2—P1 | −179.7 (3) |
P1—C15—C16—C17 | 179.1 (3) | C9—P1—C2—C1 | 178.4 (3) |
P1—C15—C20—C19 | −178.4 (3) | C9—P1—C3—C4 | 44.9 (3) |
O1—C1—C2—P1 | 1.7 (5) | C9—P1—C15—C16 | −112.2 (3) |
O1—C1—C5—C6 | −29.7 (6) | C9—P1—C15—C20 | 67.6 (4) |
O1—C1—C5—C7 | 87.1 (5) | C9—C10—C11—C12 | 0.7 (10) |
O1—C1—C5—C8 | −155.1 (5) | C10—C9—C14—C13 | 0.6 (8) |
O2—C4—C21—C22 | 136.3 (4) | C10—C11—C12—C13 | 0.0 (10) |
O2—C4—C21—C23 | −103.4 (5) | C11—C12—C13—C14 | −0.5 (9) |
O2—C4—C21—C24 | 14.9 (6) | C12—C13—C14—C9 | 0.2 (9) |
C2—P1—C3—C4 | 159.8 (3) | C14—C9—C10—C11 | −1.1 (8) |
C2—P1—C9—C10 | −51.0 (4) | C15—P1—C2—C1 | −62.2 (3) |
C2—P1—C9—C14 | 130.8 (4) | C15—P1—C3—C4 | −78.0 (3) |
C2—P1—C15—C16 | 130.6 (3) | C15—P1—C9—C10 | −170.8 (4) |
C2—P1—C15—C20 | −49.7 (4) | C15—P1—C9—C14 | 11.0 (4) |
C2—C1—C5—C6 | 151.7 (4) | C15—C16—C17—C18 | −1.1 (7) |
C2—C1—C5—C7 | −91.5 (5) | C16—C15—C20—C19 | 1.3 (7) |
C2—C1—C5—C8 | 26.3 (6) | C16—C17—C18—C19 | 2.1 (7) |
C3—P1—C2—C1 | 61.5 (3) | C17—C18—C19—C20 | −1.4 (7) |
C3—P1—C9—C10 | 64.5 (4) | C18—C19—C20—C15 | −0.3 (7) |
C3—P1—C9—C14 | −113.7 (4) | C20—C15—C16—C17 | −0.7 (6) |
C3—P1—C15—C16 | 10.3 (4) | Cl2Ai—Cl2A—C1A—Cl1A | 113.6 (8) |
C3—P1—C15—C20 | −169.9 (3) | Cl2Ai—Cl2A—C1A—Cl3A | 0.0 (11) |
Symmetry code: (i) −x+1, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···Br1Bii | 0.99 | 2.85 | 3.840 (9) | 174 |
C2—H2A···Br1Cii | 0.99 | 2.75 | 3.712 (6) | 164 |
C2—H2A···Br1Aii | 0.99 | 2.95 | 3.941 (7) | 177 |
C2—H2B···Br1B | 0.99 | 2.95 | 3.767 (9) | 141 |
C2—H2B···Br1C | 0.99 | 2.97 | 3.717 (6) | 133 |
C2—H2B···Br1A | 0.99 | 2.97 | 3.831 (7) | 145 |
C3—H3B···Br1B | 0.99 | 2.78 | 3.740 (9) | 163 |
C3—H3B···Br1C | 0.99 | 2.70 | 3.644 (6) | 159 |
C3—H3B···Br1A | 0.99 | 2.86 | 3.816 (7) | 164 |
C16—H16···O1iii | 0.95 | 2.43 | 3.287 (5) | 150 |
C1A—H1A···Br1A | 1.00 | 2.59 | 3.527 (9) | 156 |
Symmetry codes: (ii) −x+3/2, y+1/2, −z+3/2; (iii) −x+3/2, −y+1/2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···Br1Bi | 0.99 | 2.85 | 3.840 (9) | 173.7 |
C2—H2A···Br1Ci | 0.99 | 2.75 | 3.712 (6) | 164.3 |
C2—H2A···Br1Ai | 0.99 | 2.95 | 3.941 (7) | 176.9 |
C2—H2B···Br1B | 0.99 | 2.95 | 3.767 (9) | 140.9 |
C2—H2B···Br1C | 0.99 | 2.97 | 3.717 (6) | 132.6 |
C2—H2B···Br1A | 0.99 | 2.97 | 3.831 (7) | 145.3 |
C3—H3B···Br1B | 0.99 | 2.78 | 3.740 (9) | 163.4 |
C3—H3B···Br1C | 0.99 | 2.70 | 3.644 (6) | 159.1 |
C3—H3B···Br1A | 0.99 | 2.86 | 3.816 (7) | 163.7 |
C16—H16···O1ii | 0.95 | 2.43 | 3.287 (5) | 149.5 |
C1A—H1A···Br1A | 1.00 | 2.59 | 3.527 (9) | 156.0 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+3/2, −y+1/2, −z+1. |