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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2660–o2661.
Published online 2009 October 7. doi:  10.1107/S1600536809038835
PMCID: PMC2970997

A redetermination of (2-methoxy­phen­yl)diphenyl­phosphine

Abstract

The asymmetric unit of the title triphenyl­phosphine compound, C19H17OP, consists of two crystallographically independent mol­ecules with similar conformations. One of these two mol­ecules has a whole-mol­ecule disorder over two positions with refined occupancies of 0.753 (3) and 0.247 (3). The dihedral angles between the three benzene rings are 89.69 (7), 76.54 (7) and 86.02 (7)° in the non-disordered mol­ecule and the corresponding angles are 88.3 (4), 83.2 (4) and 84.2 (3)° for the major component and 80.2 (11), 89.5 (11) and 74.4 (9)° for the minor component of the disordered mol­ecule. This structure has been reported previously [Suomalainen et al. (2000 [triangle]). Eur. J. Inorg. Chem. pp. 2607–2613]; however, the disorder detailed here was not mentioned in that determination. In the crystal structure, the mol­ecules are stacked down the b axis and stabilized by C—H(...)π inter­actions.

Related literature

For a previous report of this mol­ecule, see: Suomalainen et al. (2000 [triangle]). For P–C bond lengths and C–P–C angles in related structures, see: Dunne & Orpen (1991 [triangle]); Shawkataly et al. (2009 [triangle]). For the stereochemistry of 2-methoxy­phenyl diphenyl­phosphine complexes, see: Dahlenburg et al. (1997 [triangle]); Moreno et al. (2005 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

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Object name is e-65-o2660-scheme1.jpg

Experimental

Crystal data

  • C19H17OP
  • M r = 292.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2660-efi1.jpg
  • a = 31.1813 (8) Å
  • b = 7.1474 (2) Å
  • c = 28.3025 (8) Å
  • β = 90.3795 (12)°
  • V = 6307.5 (3) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.17 mm−1
  • T = 100 K
  • 0.78 × 0.24 × 0.13 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.879, T max = 0.978
  • 49460 measured reflections
  • 11740 independent reflections
  • 8873 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.123
  • S = 1.10
  • 11740 reflections
  • 566 parameters
  • 157 restraints
  • H-atom parameters constrained
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809038835/sj2649sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038835/sj2649Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors would like to thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research grant No. 1001/PJJAUH/811115. HKF thanks USM for the Research University Golden Goose grant No. 1001/PFIZIK/811012. CSY thanks USM for the award of a USM Fellowship.

supplementary crystallographic information

Comment

Substituted triphenylphosphines as well as the parent compound have found widespread use as ligands in transition-metal chemistry, notably in homogeneous catalysis. The structure of the title compound was reported by Suomalainen et al., (2000) for the first time. However, the whole-molecule disorder in one of the the two molecules in the asymmetric unit present in 2-methoxyphenyl diphenylphosphine (I) has not been reported. This resulted in large residual peaks in the difference map in his solution. This prompts us to redetermine the structure. Our redetermination has taken care of these large residual peaks which are the consequence of the whole-molecule disorder as shown in molecules B and C (Fig. 1, 2 & 3).

Interestingly, the evidence of the disorder in this ligand has however been reported by Moreno et al., (2005) in a ruthenium complex.

This study was taken up as part of a project to study the stereochemistry of substituted triphenylphosphine ligands.

The asymmetric unit of (I), consists of two crystallographically independent molecules, A and B/C, with similar conformation (Fig. 1, 2 & 3). Molecule B/C are the major/minor components of the whole-molecule disorder over two positions with refined occupancies of 0.753 (3) and 0.247 (3) respectively. The P–C bond lengths and C–P–C angles for the asymmetric unit are comparable to the related structures (Dunne & Orpen, 1991; Suomalainen et al., 2000; Shawkataly et al., 2009). The dihedral angles between the three benzene rings [C1A–C6A/C7A–C12A, C1A–C6A/C13A–C18A and C7A–C13A/C13A–C18A] are 89.69 (7), 76.54 (7) and 86.02 (7)° in molecule A and the corresponding angles for major B and minor C components of the whole-molecule are 88.3 (4), 83.2 (4), 84.2 (3)° and 80.2 (11), 89.5 (11), 74.4 (9)°, respectively.

In the crystal structure, the molecules are stacked down the b axis (Fig. 4) and stabilized by the C—H···π interactions (Table 1).

Experimental

The title compound was supplied by Strem Chemicals. Single crystals of (I) were obtained by slow evaporation of ethanol solution.

Refinement

All hydrogen atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.96 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating-group model was applied for methyl groups. The same Uij parameters were used for atom pair C14B/C14C and all disordered atoms were subjected to rigid bond restraints (SAME and DELU). The C molecule is statistically disordered about the inversion center (3/4, 3/4, 0) with no actual close contacts (i.e. given a C molecule, the opposite molecule is a B molecule).

Figures

Fig. 1.
The molecular structure of the title compound with 30% probability ellipsoids for non-H atoms. Both disorder components are shown, with open bonds for the minor disorder component.
Fig. 2.
The molecular structure of the title compound with atoms label and 50% probability ellipsoids for non-H atoms. Only major disorder component is shown.
Fig. 3.
The molecular structure of the title compound with atoms label and 50% probability ellipsoids for non-H atoms. Only minor disorder component is shown.
Fig. 4.
The crystal packing of the title compound, viewed down the b axis, showing the molecules stacked down the b axis. Only the major disorder component is shown.

Crystal data

C19H17OPF(000) = 2464
Mr = 292.30Dx = 1.231 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9973 reflections
a = 31.1813 (8) Åθ = 2.9–31.4°
b = 7.1474 (2) ŵ = 0.17 mm1
c = 28.3025 (8) ÅT = 100 K
β = 90.3795 (12)°Needle, colourless
V = 6307.5 (3) Å30.78 × 0.24 × 0.13 mm
Z = 16

Data collection

Bruker SMART APEXII CCD area-detector diffractometer11740 independent reflections
Radiation source: fine-focus sealed tube8873 reflections with I > 2σ(I)
graphiteRint = 0.035
[var phi] and ω scansθmax = 33.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −47→47
Tmin = 0.879, Tmax = 0.978k = −10→10
49460 measured reflectionsl = −42→43

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0294P)2 + 8.0384P] where P = (Fo2 + 2Fc2)/3
11740 reflections(Δ/σ)max = 0.001
566 parametersΔρmax = 0.33 e Å3
157 restraintsΔρmin = −0.25 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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)

xyzUiso*/UeqOcc. (<1)
P1A0.922433 (11)0.68949 (6)0.081792 (13)0.02379 (8)
O1A0.98898 (3)0.42835 (19)0.06278 (4)0.0356 (3)
C1A0.89016 (4)0.5270 (2)0.04611 (5)0.0227 (3)
C2A0.87439 (4)0.5889 (2)0.00231 (5)0.0268 (3)
H2AA0.88050.7097−0.00780.032*
C3A0.84983 (5)0.4716 (3)−0.02601 (5)0.0311 (3)
H3AA0.83930.5148−0.05480.037*
C4A0.84080 (5)0.2902 (3)−0.01165 (5)0.0309 (3)
H4AA0.82450.2116−0.03090.037*
C5A0.85617 (5)0.2268 (2)0.03158 (5)0.0293 (3)
H5AA0.85010.10570.04150.035*
C6A0.88069 (4)0.3442 (2)0.06009 (5)0.0256 (3)
H6AA0.89100.30040.08900.031*
C7A0.88118 (4)0.8042 (2)0.11748 (5)0.0236 (3)
C8A0.83846 (5)0.7462 (2)0.11895 (5)0.0274 (3)
H8AA0.83000.64030.10230.033*
C9A0.80846 (5)0.8451 (2)0.14506 (6)0.0312 (3)
H9AA0.78000.80650.14520.037*
C10A0.82081 (5)1.0009 (2)0.17091 (6)0.0332 (3)
H10A0.80081.06570.18880.040*
C11A0.86316 (6)1.0596 (2)0.17001 (6)0.0339 (3)
H11A0.87161.16380.18740.041*
C12A0.89293 (5)0.9637 (2)0.14327 (5)0.0291 (3)
H12A0.92111.00570.14240.035*
C13A0.94579 (4)0.5263 (2)0.12501 (5)0.0235 (3)
C14A0.93348 (5)0.5143 (2)0.17235 (5)0.0264 (3)
H14A0.91180.59180.18350.032*
C15A0.95316 (5)0.3878 (2)0.20307 (5)0.0317 (3)
H15A0.94470.38110.23450.038*
C16A0.98528 (5)0.2724 (2)0.18670 (6)0.0334 (3)
H16A0.99840.18810.20720.040*
C17A0.99830 (5)0.2808 (2)0.13978 (6)0.0311 (3)
H17A1.01990.20240.12890.037*
C18A0.97864 (4)0.4080 (2)0.10933 (5)0.0277 (3)
C19A1.01988 (7)0.3008 (4)0.04412 (7)0.0544 (6)
H19A1.02360.32460.01100.082*
H19B1.01000.17480.04850.082*
H19C1.04680.31750.06030.082*
P1B0.63959 (15)0.6772 (5)0.13064 (12)0.0268 (4)0.753 (3)
O1B0.58298 (5)0.4273 (3)0.08223 (7)0.0445 (5)0.753 (3)
C1B0.6620 (3)0.7991 (12)0.1822 (3)0.0232 (12)0.753 (3)
C2B0.6393 (3)0.9541 (11)0.1994 (3)0.0254 (9)0.753 (3)
H2BA0.61420.99220.18440.031*0.753 (3)
C3B0.6543 (3)1.0510 (12)0.2388 (3)0.0308 (11)0.753 (3)
H3BA0.63861.15060.25080.037*0.753 (3)
C4B0.6923 (2)0.9991 (11)0.2598 (3)0.0334 (15)0.753 (3)
H4BA0.70291.06740.28530.040*0.753 (3)
C5B0.7149 (3)0.8462 (12)0.2434 (3)0.0325 (15)0.753 (3)
H5BA0.74040.81150.25830.039*0.753 (3)
C6B0.7000 (3)0.7437 (12)0.2049 (3)0.0233 (9)0.753 (3)
H6BA0.71510.63960.19430.028*0.753 (3)
C7B0.68283 (18)0.5167 (9)0.1152 (3)0.0244 (11)0.753 (3)
C8B0.68720 (17)0.3390 (7)0.1351 (2)0.0257 (7)0.753 (3)
H8BA0.66670.29530.15620.031*0.753 (3)
C9B0.7221 (2)0.2265 (10)0.1235 (3)0.0352 (14)0.753 (3)
H9BA0.72470.10770.13660.042*0.753 (3)
C10B0.7534 (2)0.2906 (9)0.0922 (3)0.0375 (14)0.753 (3)
H10B0.77650.21520.08440.045*0.753 (3)
C11B0.7493 (2)0.4669 (8)0.0733 (3)0.0383 (12)0.753 (3)
H11B0.77030.51170.05300.046*0.753 (3)
C12B0.71416 (17)0.5798 (9)0.0841 (3)0.0337 (13)0.753 (3)
H12B0.71160.69770.07050.040*0.753 (3)
C13B0.60176 (18)0.5166 (9)0.16012 (18)0.0257 (9)0.753 (3)
C14B0.5956 (2)0.4999 (9)0.20859 (17)0.0304 (10)0.753 (3)
H14B0.61300.56850.22910.037*0.753 (3)
C15B0.56431 (18)0.3837 (8)0.22724 (15)0.0410 (10)0.753 (3)
H15B0.55980.37950.25970.049*0.753 (3)
C16B0.54009 (16)0.2750 (8)0.19734 (18)0.0511 (12)0.753 (3)
H16B0.51970.19450.20990.061*0.753 (3)
C17B0.54545 (16)0.2829 (8)0.14911 (18)0.0481 (12)0.753 (3)
H17B0.52900.20730.12930.058*0.753 (3)
C18B0.5757 (2)0.4047 (11)0.13005 (18)0.0381 (11)0.753 (3)
C19B0.55769 (8)0.3189 (5)0.04961 (13)0.0667 (11)0.753 (3)
H19D0.56540.35080.01780.100*0.753 (3)
H19E0.52780.34530.05430.100*0.753 (3)
H19F0.56290.18820.05490.100*0.753 (3)
P1C0.6453 (5)0.6726 (14)0.1308 (4)0.0283 (15)0.247 (3)
O1C0.72148 (13)0.7423 (6)0.07269 (15)0.0252 (10)0.247 (3)
C1C0.6668 (8)0.781 (3)0.1856 (8)0.018 (2)0.247 (3)
C2C0.6454 (9)0.937 (4)0.2032 (10)0.030 (3)0.247 (3)
H2CA0.61990.97400.18880.037*0.247 (3)
C3C0.6608 (8)1.040 (4)0.2415 (10)0.031 (4)0.247 (3)
H3CA0.64631.14720.25090.037*0.247 (3)
C4C0.6969 (6)0.985 (3)0.2652 (7)0.022 (2)0.247 (3)
H4CA0.70531.04340.29310.027*0.247 (3)
C5C0.7207 (7)0.839 (3)0.2466 (8)0.017 (2)0.247 (3)
H5CA0.74690.80690.26020.021*0.247 (3)
C6C0.7054 (9)0.741 (4)0.2080 (11)0.029 (3)0.247 (3)
H6CA0.72200.64320.19630.035*0.247 (3)
C7C0.6038 (7)0.515 (3)0.1504 (5)0.027 (3)0.247 (3)
C8C0.5923 (5)0.512 (2)0.1981 (4)0.0179 (18)0.247 (3)
H8CA0.60500.59370.21950.022*0.247 (3)
C9C0.5611 (6)0.381 (3)0.2131 (3)0.027 (2)0.247 (3)
H9CA0.55520.36870.24510.032*0.247 (3)
C10C0.5388 (5)0.270 (2)0.1800 (3)0.027 (2)0.247 (3)
H10C0.51740.18750.18950.033*0.247 (3)
C11C0.5496 (5)0.286 (3)0.1329 (3)0.029 (2)0.247 (3)
H11C0.53480.21580.11050.035*0.247 (3)
C12C0.5818 (6)0.404 (3)0.1183 (4)0.026 (3)0.247 (3)
H12C0.58880.41010.08640.031*0.247 (3)
C13C0.6904 (5)0.507 (3)0.1199 (8)0.020 (2)0.247 (3)
C14C0.6915 (6)0.321 (3)0.1361 (9)0.0304 (10)0.247 (3)
H14C0.66960.28160.15600.037*0.247 (3)
C15C0.7225 (6)0.196 (3)0.1247 (8)0.019 (2)0.247 (3)
H15C0.72260.07530.13720.023*0.247 (3)
C16C0.7535 (7)0.254 (3)0.0939 (9)0.024 (2)0.247 (3)
H16C0.77550.17150.08630.029*0.247 (3)
C17C0.7538 (6)0.428 (2)0.0736 (6)0.024 (2)0.247 (3)
H17C0.77400.45850.05090.028*0.247 (3)
C18C0.7232 (5)0.559 (2)0.0877 (6)0.020 (2)0.247 (3)
C19C0.74898 (19)0.7931 (10)0.0343 (2)0.0293 (14)0.247 (3)
H19I0.74240.91820.02430.044*0.247 (3)
H19G0.74450.70820.00850.044*0.247 (3)
H19H0.77840.78680.04460.044*0.247 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
P1A0.01805 (15)0.02824 (19)0.02511 (16)−0.00272 (14)0.00114 (12)0.00586 (15)
O1A0.0244 (5)0.0477 (7)0.0347 (6)0.0082 (5)0.0081 (4)0.0068 (5)
C1A0.0180 (5)0.0287 (7)0.0215 (6)0.0011 (5)0.0010 (4)0.0040 (5)
C2A0.0230 (6)0.0322 (8)0.0252 (6)0.0035 (6)0.0004 (5)0.0077 (6)
C3A0.0278 (7)0.0425 (9)0.0229 (6)0.0034 (7)−0.0034 (5)0.0055 (6)
C4A0.0262 (7)0.0401 (9)0.0262 (7)−0.0003 (6)−0.0044 (5)−0.0028 (6)
C5A0.0270 (7)0.0302 (8)0.0306 (7)−0.0014 (6)−0.0019 (6)0.0034 (6)
C6A0.0235 (6)0.0307 (8)0.0226 (6)−0.0021 (6)−0.0015 (5)0.0066 (6)
C7A0.0225 (6)0.0234 (7)0.0249 (6)−0.0013 (5)−0.0005 (5)0.0064 (5)
C8A0.0232 (6)0.0263 (7)0.0328 (7)−0.0021 (6)0.0020 (5)0.0013 (6)
C9A0.0234 (6)0.0319 (8)0.0383 (8)0.0021 (6)0.0034 (6)0.0018 (7)
C10A0.0380 (8)0.0301 (8)0.0316 (7)0.0074 (7)0.0036 (6)0.0020 (7)
C11A0.0442 (9)0.0266 (8)0.0309 (7)−0.0016 (7)−0.0037 (6)−0.0006 (6)
C12A0.0295 (7)0.0279 (8)0.0298 (7)−0.0060 (6)−0.0024 (6)0.0047 (6)
C13A0.0164 (5)0.0286 (7)0.0255 (6)−0.0030 (5)−0.0027 (5)0.0019 (6)
C14A0.0254 (6)0.0279 (7)0.0258 (6)−0.0020 (6)−0.0027 (5)0.0003 (6)
C15A0.0383 (8)0.0308 (8)0.0260 (7)−0.0020 (7)−0.0085 (6)0.0020 (6)
C16A0.0359 (8)0.0296 (8)0.0345 (8)−0.0017 (7)−0.0158 (6)0.0035 (7)
C17A0.0220 (6)0.0319 (8)0.0395 (8)0.0017 (6)−0.0063 (6)0.0006 (7)
C18A0.0172 (6)0.0338 (8)0.0320 (7)−0.0028 (6)−0.0019 (5)0.0024 (6)
C19A0.0431 (10)0.0717 (16)0.0486 (11)0.0230 (11)0.0186 (8)0.0086 (11)
P1B0.0223 (7)0.0251 (6)0.0331 (7)−0.0009 (4)−0.0026 (4)0.0016 (5)
O1B0.0230 (7)0.0508 (11)0.0596 (12)−0.0003 (7)−0.0055 (7)−0.0228 (9)
C1B0.0171 (14)0.019 (2)0.033 (2)0.0003 (12)0.0018 (11)0.0087 (14)
C2B0.022 (3)0.0197 (15)0.0346 (18)0.0056 (14)0.0058 (14)0.0072 (15)
C3B0.032 (3)0.0228 (18)0.0381 (19)0.0035 (15)0.0141 (16)0.0051 (14)
C4B0.042 (3)0.0262 (19)0.032 (2)−0.0050 (17)0.0038 (16)−0.0053 (18)
C5B0.024 (3)0.037 (2)0.036 (2)−0.0034 (16)−0.0011 (16)0.0020 (16)
C6B0.020 (2)0.0192 (17)0.0303 (19)−0.0017 (14)0.0025 (14)−0.0032 (15)
C7B0.0172 (18)0.0297 (15)0.026 (2)−0.0052 (12)−0.0023 (17)−0.0002 (12)
C8B0.0198 (15)0.0315 (17)0.0257 (11)0.0019 (10)0.0014 (11)−0.0023 (12)
C9B0.033 (2)0.032 (3)0.040 (3)0.0024 (16)−0.0053 (16)−0.0005 (18)
C10B0.0193 (15)0.048 (4)0.045 (3)0.000 (2)0.0028 (14)−0.012 (2)
C11B0.0277 (19)0.040 (3)0.047 (2)−0.0135 (18)0.0116 (15)−0.0087 (19)
C12B0.029 (2)0.0335 (19)0.038 (2)−0.0073 (14)0.0024 (18)−0.0023 (15)
C13B0.0163 (11)0.0194 (13)0.042 (3)−0.0016 (9)0.0003 (16)0.0011 (18)
C14B0.0233 (15)0.0258 (14)0.042 (2)0.0020 (11)−0.0002 (15)0.0160 (17)
C15B0.0272 (16)0.0299 (16)0.066 (3)0.0030 (12)0.017 (2)0.016 (2)
C16B0.0222 (15)0.0285 (16)0.103 (4)−0.0010 (12)0.017 (2)0.009 (3)
C17B0.0208 (12)0.0288 (17)0.095 (4)−0.0038 (10)0.003 (3)−0.009 (4)
C18B0.0203 (16)0.0334 (18)0.061 (3)0.0038 (12)0.000 (2)−0.010 (2)
C19B0.0240 (11)0.079 (2)0.097 (2)0.0046 (13)−0.0092 (13)−0.057 (2)
P1C0.031 (4)0.0269 (19)0.0274 (18)−0.0050 (17)−0.0063 (16)0.0141 (16)
O1C0.025 (2)0.024 (2)0.027 (2)−0.0006 (16)0.0063 (15)0.0068 (17)
C1C0.026 (7)0.008 (4)0.019 (4)0.000 (4)0.005 (4)0.001 (4)
C2C0.014 (5)0.033 (7)0.043 (5)0.011 (3)−0.001 (3)0.017 (4)
C3C0.027 (6)0.021 (6)0.044 (7)0.004 (4)0.009 (4)−0.012 (5)
C4C0.013 (3)0.030 (5)0.024 (4)−0.003 (3)0.005 (3)0.008 (3)
C5C0.012 (4)0.012 (4)0.028 (5)0.000 (3)−0.001 (3)−0.009 (3)
C6C0.012 (4)0.037 (7)0.039 (6)0.004 (4)−0.007 (3)0.006 (4)
C7C0.032 (5)0.038 (5)0.013 (4)0.004 (3)0.004 (3)0.004 (3)
C8C0.012 (3)0.019 (4)0.023 (4)0.001 (2)−0.004 (3)0.013 (3)
C9C0.028 (4)0.033 (4)0.019 (3)0.002 (3)0.001 (3)0.007 (4)
C10C0.022 (4)0.027 (4)0.034 (4)−0.009 (3)−0.002 (4)0.003 (5)
C11C0.034 (6)0.031 (4)0.022 (3)−0.004 (4)−0.002 (3)0.000 (4)
C12C0.026 (6)0.023 (4)0.029 (5)−0.009 (4)0.005 (3)−0.003 (4)
C13C0.017 (5)0.023 (4)0.019 (4)−0.001 (3)−0.009 (4)−0.004 (3)
C14C0.0233 (15)0.0258 (14)0.042 (2)0.0020 (11)−0.0002 (15)0.0160 (17)
C15C0.012 (4)0.023 (5)0.023 (5)0.001 (3)0.009 (3)0.008 (4)
C16C0.030 (5)0.017 (4)0.025 (5)−0.006 (3)−0.001 (3)0.005 (4)
C17C0.030 (5)0.025 (5)0.016 (3)−0.001 (3)0.006 (3)0.000 (3)
C18C0.024 (5)0.020 (4)0.017 (3)−0.011 (3)−0.002 (4)0.006 (3)
C19C0.026 (3)0.035 (3)0.026 (3)0.001 (2)0.005 (2)0.010 (2)

Geometric parameters (Å, °)

P1A—C7A1.8343 (15)C9B—C10B1.396 (7)
P1A—C1A1.8351 (15)C9B—H9BA0.9300
P1A—C13A1.8370 (15)C10B—C11B1.375 (6)
O1A—C18A1.3661 (18)C10B—H10B0.9300
O1A—C19A1.430 (2)C11B—C12B1.397 (6)
C1A—C6A1.397 (2)C11B—H11B0.9300
C1A—C2A1.4021 (19)C12B—H12B0.9300
C2A—C3A1.387 (2)C13B—C14B1.392 (6)
C2A—H2AA0.9300C13B—C18B1.418 (6)
C3A—C4A1.389 (2)C14B—C15B1.389 (6)
C3A—H3AA0.9300C14B—H14B0.9300
C4A—C5A1.387 (2)C15B—C16B1.372 (6)
C4A—H4AA0.9300C15B—H15B0.9300
C5A—C6A1.390 (2)C16B—C17B1.378 (6)
C5A—H5AA0.9300C16B—H16B0.9300
C6A—H6AA0.9300C17B—C18B1.396 (6)
C7A—C8A1.3957 (19)C17B—H17B0.9300
C7A—C12A1.401 (2)C19B—H19D0.9600
C8A—C9A1.389 (2)C19B—H19E0.9600
C8A—H8AA0.9300C19B—H19F0.9600
C9A—C10A1.386 (2)P1C—C7C1.807 (15)
C9A—H9AA0.9300P1C—C1C1.855 (12)
C10A—C11A1.386 (2)P1C—C13C1.864 (15)
C10A—H10A0.9300O1C—C18C1.381 (13)
C11A—C12A1.383 (2)O1C—C19C1.434 (7)
C11A—H11A0.9300C1C—C6C1.386 (14)
C12A—H12A0.9300C1C—C2C1.394 (13)
C13A—C14A1.399 (2)C2C—C3C1.390 (14)
C13A—C18A1.403 (2)C2C—H2CA0.9300
C14A—C15A1.394 (2)C3C—C4C1.367 (14)
C14A—H14A0.9300C3C—H3CA0.9300
C15A—C16A1.380 (2)C4C—C5C1.385 (13)
C15A—H15A0.9300C4C—H4CA0.9300
C16A—C17A1.392 (2)C5C—C6C1.381 (14)
C16A—H16A0.9300C5C—H5CA0.9300
C17A—C18A1.392 (2)C6C—H6CA0.9300
C17A—H17A0.9300C7C—C12C1.382 (16)
C19A—H19A0.9600C7C—C8C1.399 (14)
C19A—H19B0.9600C8C—C9C1.416 (16)
C19A—H19C0.9600C8C—H8CA0.9300
P1B—C7B1.825 (6)C9C—C10C1.410 (13)
P1B—C1B1.834 (5)C9C—H9CA0.9300
P1B—C13B1.849 (5)C10C—C11C1.382 (10)
O1B—C18B1.383 (5)C10C—H10C0.9300
O1B—C19B1.437 (3)C11C—C12C1.376 (14)
C1B—C6B1.402 (5)C11C—H11C0.9300
C1B—C2B1.403 (5)C12C—H12C0.9300
C2B—C3B1.389 (5)C13C—C14C1.407 (17)
C2B—H2BA0.9300C13C—C18C1.424 (16)
C3B—C4B1.375 (6)C14C—C15C1.359 (17)
C3B—H3BA0.9300C14C—H14C0.9300
C4B—C5B1.383 (6)C15C—C16C1.373 (16)
C4B—H4BA0.9300C15C—H15C0.9300
C5B—C6B1.392 (5)C16C—C17C1.368 (15)
C5B—H5BA0.9300C16C—H16C0.9300
C6B—H6BA0.9300C17C—C18C1.393 (14)
C7B—C12B1.395 (7)C17C—H17C0.9300
C7B—C8B1.396 (6)C19C—H19I0.9600
C8B—C9B1.395 (6)C19C—H19G0.9600
C8B—H8BA0.9300C19C—H19H0.9600
C7A—P1A—C1A101.65 (6)C8B—C9B—H9BA119.7
C7A—P1A—C13A101.15 (6)C10B—C9B—H9BA119.7
C1A—P1A—C13A100.27 (7)C11B—C10B—C9B119.0 (6)
C18A—O1A—C19A116.89 (14)C11B—C10B—H10B120.5
C6A—C1A—C2A118.15 (13)C9B—C10B—H10B120.5
C6A—C1A—P1A123.50 (10)C10B—C11B—C12B121.0 (5)
C2A—C1A—P1A118.35 (12)C10B—C11B—H11B119.5
C3A—C2A—C1A120.62 (15)C12B—C11B—H11B119.5
C3A—C2A—H2AA119.7C7B—C12B—C11B120.3 (5)
C1A—C2A—H2AA119.7C7B—C12B—H12B119.8
C2A—C3A—C4A120.51 (14)C11B—C12B—H12B119.8
C2A—C3A—H3AA119.7C14B—C13B—C18B117.5 (4)
C4A—C3A—H3AA119.7C14B—C13B—P1B126.2 (4)
C5A—C4A—C3A119.58 (15)C18B—C13B—P1B116.3 (4)
C5A—C4A—H4AA120.2C15B—C14B—C13B121.8 (5)
C3A—C4A—H4AA120.2C15B—C14B—H14B119.1
C4A—C5A—C6A120.03 (15)C13B—C14B—H14B119.1
C4A—C5A—H5AA120.0C16B—C15B—C14B119.3 (4)
C6A—C5A—H5AA120.0C16B—C15B—H15B120.3
C5A—C6A—C1A121.11 (13)C14B—C15B—H15B120.3
C5A—C6A—H6AA119.4C15B—C16B—C17B121.2 (4)
C1A—C6A—H6AA119.4C15B—C16B—H16B119.4
C8A—C7A—C12A118.18 (14)C17B—C16B—H16B119.4
C8A—C7A—P1A123.82 (12)C16B—C17B—C18B119.7 (4)
C12A—C7A—P1A117.94 (11)C16B—C17B—H17B120.2
C9A—C8A—C7A120.74 (15)C18B—C17B—H17B120.2
C9A—C8A—H8AA119.6O1B—C18B—C17B124.5 (4)
C7A—C8A—H8AA119.6O1B—C18B—C13B115.2 (4)
C10A—C9A—C8A120.25 (15)C17B—C18B—C13B120.4 (4)
C10A—C9A—H9AA119.9C7C—P1C—C1C105.1 (12)
C8A—C9A—H9AA119.9C7C—P1C—C13C101.4 (10)
C9A—C10A—C11A119.68 (15)C1C—P1C—C13C97.7 (10)
C9A—C10A—H10A120.2C18C—O1C—C19C116.7 (7)
C11A—C10A—H10A120.2C6C—C1C—C2C114.7 (12)
C12A—C11A—C10A120.18 (15)C6C—C1C—P1C127.2 (13)
C12A—C11A—H11A119.9C2C—C1C—P1C117.5 (13)
C10A—C11A—H11A119.9C3C—C2C—C1C122.6 (14)
C11A—C12A—C7A120.94 (14)C3C—C2C—H2CA118.7
C11A—C12A—H12A119.5C1C—C2C—H2CA118.7
C7A—C12A—H12A119.5C4C—C3C—C2C120.6 (15)
C14A—C13A—C18A118.12 (13)C4C—C3C—H3CA119.7
C14A—C13A—P1A124.53 (11)C2C—C3C—H3CA119.7
C18A—C13A—P1A117.34 (11)C3C—C4C—C5C118.1 (15)
C15A—C14A—C13A121.01 (15)C3C—C4C—H4CA120.9
C15A—C14A—H14A119.5C5C—C4C—H4CA120.9
C13A—C14A—H14A119.5C6C—C5C—C4C120.1 (16)
C16A—C15A—C14A119.70 (15)C6C—C5C—H5CA120.0
C16A—C15A—H15A120.2C4C—C5C—H5CA120.0
C14A—C15A—H15A120.2C5C—C6C—C1C123.4 (16)
C15A—C16A—C17A120.77 (14)C5C—C6C—H6CA118.3
C15A—C16A—H16A119.6C1C—C6C—H6CA118.3
C17A—C16A—H16A119.6C12C—C7C—C8C119.7 (12)
C18A—C17A—C16A119.24 (15)C12C—C7C—P1C120.6 (10)
C18A—C17A—H17A120.4C8C—C7C—P1C119.6 (11)
C16A—C17A—H17A120.4C7C—C8C—C9C118.7 (12)
O1A—C18A—C17A124.11 (14)C7C—C8C—H8CA120.6
O1A—C18A—C13A114.73 (13)C9C—C8C—H8CA120.6
C17A—C18A—C13A121.16 (14)C10C—C9C—C8C120.7 (10)
O1A—C19A—H19A109.5C10C—C9C—H9CA119.7
O1A—C19A—H19B109.5C8C—C9C—H9CA119.7
H19A—C19A—H19B109.5C11C—C10C—C9C118.0 (11)
O1A—C19A—H19C109.5C11C—C10C—H10C121.0
H19A—C19A—H19C109.5C9C—C10C—H10C121.0
H19B—C19A—H19C109.5C12C—C11C—C10C121.8 (12)
C7B—P1B—C1B102.2 (4)C12C—C11C—H11C119.1
C7B—P1B—C13B101.1 (3)C10C—C11C—H11C119.1
C1B—P1B—C13B100.2 (4)C11C—C12C—C7C120.8 (11)
C18B—O1B—C19B118.3 (3)C11C—C12C—H12C119.6
C6B—C1B—C2B119.4 (4)C7C—C12C—H12C119.6
C6B—C1B—P1B123.1 (4)C14C—C13C—C18C115.9 (13)
C2B—C1B—P1B117.5 (4)C14C—C13C—P1C124.2 (12)
C3B—C2B—C1B120.3 (5)C18C—C13C—P1C119.3 (12)
C3B—C2B—H2BA119.8C15C—C14C—C13C124.2 (16)
C1B—C2B—H2BA119.8C15C—C14C—H14C117.9
C4B—C3B—C2B119.8 (5)C13C—C14C—H14C117.9
C4B—C3B—H3BA120.1C14C—C15C—C16C117.1 (16)
C2B—C3B—H3BA120.1C14C—C15C—H15C121.4
C3B—C4B—C5B120.6 (5)C16C—C15C—H15C121.4
C3B—C4B—H4BA119.7C17C—C16C—C15C123.2 (17)
C5B—C4B—H4BA119.7C17C—C16C—H16C118.4
C4B—C5B—C6B120.7 (5)C15C—C16C—H16C118.4
C4B—C5B—H5BA119.7C16C—C17C—C18C119.0 (14)
C6B—C5B—H5BA119.7C16C—C17C—H17C120.5
C5B—C6B—C1B119.2 (5)C18C—C17C—H17C120.5
C5B—C6B—H6BA120.4O1C—C18C—C17C125.1 (12)
C1B—C6B—H6BA120.4O1C—C18C—C13C114.5 (11)
C12B—C7B—C8B118.8 (5)C17C—C18C—C13C120.4 (12)
C12B—C7B—P1B118.0 (4)O1C—C19C—H19I109.5
C8B—C7B—P1B123.1 (4)O1C—C19C—H19G109.5
C9B—C8B—C7B120.2 (5)H19I—C19C—H19G109.5
C9B—C8B—H8BA119.9O1C—C19C—H19H109.5
C7B—C8B—H8BA119.9H19I—C19C—H19H109.5
C8B—C9B—C10B120.6 (6)H19G—C19C—H19H109.5
C7A—P1A—C1A—C6A−90.02 (13)C8B—C7B—C12B—C11B−0.3 (12)
C13A—P1A—C1A—C6A13.75 (13)P1B—C7B—C12B—C11B176.2 (6)
C7A—P1A—C1A—C2A90.47 (12)C10B—C11B—C12B—C7B1.4 (12)
C13A—P1A—C1A—C2A−165.76 (11)C7B—P1B—C13B—C14B102.8 (7)
C6A—C1A—C2A—C3A0.5 (2)C1B—P1B—C13B—C14B−1.9 (7)
P1A—C1A—C2A—C3A−179.99 (11)C7B—P1B—C13B—C18B−79.4 (7)
C1A—C2A—C3A—C4A−0.6 (2)C1B—P1B—C13B—C18B175.9 (6)
C2A—C3A—C4A—C5A0.6 (2)C18B—C13B—C14B—C15B−2.2 (10)
C3A—C4A—C5A—C6A−0.4 (2)P1B—C13B—C14B—C15B175.6 (6)
C4A—C5A—C6A—C1A0.3 (2)C13B—C14B—C15B—C16B3.3 (10)
C2A—C1A—C6A—C5A−0.3 (2)C14B—C15B—C16B—C17B−1.8 (9)
P1A—C1A—C6A—C5A−179.81 (11)C15B—C16B—C17B—C18B−0.7 (9)
C1A—P1A—C7A—C8A8.97 (14)C19B—O1B—C18B—C17B0.2 (9)
C13A—P1A—C7A—C8A−94.10 (13)C19B—O1B—C18B—C13B−179.8 (5)
C1A—P1A—C7A—C12A−168.38 (11)C16B—C17B—C18B—O1B−178.3 (6)
C13A—P1A—C7A—C12A88.55 (12)C16B—C17B—C18B—C13B1.7 (11)
C12A—C7A—C8A—C9A0.4 (2)C14B—C13B—C18B—O1B179.7 (6)
P1A—C7A—C8A—C9A−176.94 (12)P1B—C13B—C18B—O1B1.6 (9)
C7A—C8A—C9A—C10A−1.4 (2)C14B—C13B—C18B—C17B−0.3 (11)
C8A—C9A—C10A—C11A1.0 (2)P1B—C13B—C18B—C17B−178.3 (6)
C9A—C10A—C11A—C12A0.3 (2)C7C—P1C—C1C—C6C105 (3)
C10A—C11A—C12A—C7A−1.3 (2)C13C—P1C—C1C—C6C1(4)
C8A—C7A—C12A—C11A0.9 (2)C7C—P1C—C1C—C2C−85 (3)
P1A—C7A—C12A—C11A178.43 (12)C13C—P1C—C1C—C2C171 (3)
C7A—P1A—C13A—C14A−2.63 (14)C6C—C1C—C2C—C3C−3(6)
C1A—P1A—C13A—C14A−106.80 (13)P1C—C1C—C2C—C3C−174 (3)
C7A—P1A—C13A—C18A178.33 (11)C1C—C2C—C3C—C4C−4(6)
C1A—P1A—C13A—C18A74.16 (12)C2C—C3C—C4C—C5C8(5)
C18A—C13A—C14A—C15A−0.3 (2)C3C—C4C—C5C—C6C−7(4)
P1A—C13A—C14A—C15A−179.29 (12)C4C—C5C—C6C—C1C0(6)
C13A—C14A—C15A—C16A0.0 (2)C2C—C1C—C6C—C5C4(6)
C14A—C15A—C16A—C17A0.0 (2)P1C—C1C—C6C—C5C175 (3)
C15A—C16A—C17A—C18A0.3 (2)C1C—P1C—C7C—C12C−178 (2)
C19A—O1A—C18A—C17A4.5 (2)C13C—P1C—C7C—C12C−76 (2)
C19A—O1A—C18A—C13A−175.18 (16)C1C—P1C—C7C—C8C6(2)
C16A—C17A—C18A—O1A179.78 (15)C13C—P1C—C7C—C8C107 (2)
C16A—C17A—C18A—C13A−0.5 (2)C12C—C7C—C8C—C9C6(3)
C14A—C13A—C18A—O1A−179.75 (13)P1C—C7C—C8C—C9C−177.2 (17)
P1A—C13A—C18A—O1A−0.65 (17)C7C—C8C—C9C—C10C−6(3)
C14A—C13A—C18A—C17A0.5 (2)C8C—C9C—C10C—C11C3(3)
P1A—C13A—C18A—C17A179.62 (12)C9C—C10C—C11C—C12C1(3)
C7B—P1B—C1B—C6B−9.5 (11)C10C—C11C—C12C—C7C−2(4)
C13B—P1B—C1B—C6B94.3 (10)C8C—C7C—C12C—C11C−2(4)
C7B—P1B—C1B—C2B170.9 (9)P1C—C7C—C12C—C11C−178.9 (19)
C13B—P1B—C1B—C2B−85.3 (10)C7C—P1C—C13C—C14C−15 (2)
C6B—C1B—C2B—C3B−0.5 (18)C1C—P1C—C13C—C14C93 (2)
P1B—C1B—C2B—C3B179.1 (9)C7C—P1C—C13C—C18C156.0 (17)
C1B—C2B—C3B—C4B2.5 (17)C1C—P1C—C13C—C18C−97 (2)
C2B—C3B—C4B—C5B−2.8 (15)C18C—C13C—C14C—C15C3(4)
C3B—C4B—C5B—C6B1.0 (16)P1C—C13C—C14C—C15C174 (2)
C4B—C5B—C6B—C1B1.1 (17)C13C—C14C—C15C—C16C−3(4)
C2B—C1B—C6B—C5B−1.3 (17)C14C—C15C—C16C—C17C−2(4)
P1B—C1B—C6B—C5B179.1 (9)C15C—C16C—C17C—C18C6(4)
C1B—P1B—C7B—C12B−89.0 (7)C19C—O1C—C18C—C17C10 (2)
C13B—P1B—C7B—C12B167.9 (6)C19C—O1C—C18C—C13C−169.5 (14)
C1B—P1B—C7B—C8B87.3 (8)C16C—C17C—C18C—O1C175 (2)
C13B—P1B—C7B—C8B−15.8 (7)C16C—C17C—C18C—C13C−5(3)
C12B—C7B—C8B—C9B−0.7 (12)C14C—C13C—C18C—O1C−179.5 (19)
P1B—C7B—C8B—C9B−177.0 (7)P1C—C13C—C18C—O1C9(2)
C7B—C8B—C9B—C10B0.7 (14)C14C—C13C—C18C—C17C1(3)
C8B—C9B—C10B—C11B0.4 (15)P1C—C13C—C18C—C17C−170.6 (17)
C9B—C10B—C11B—C12B−1.4 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4A—H4AA···Cg1i0.932.653.520 (9)156
C4A—H4AA···Cg2i0.932.583.471 (3)159
C17A—H17A···Cg3ii0.932.913.645 (8)137
C10C—H10C···Cg4ii0.932.783.561 (15)142

Symmetry codes: (i) −x+3/2, −y+1/2, −z; (ii) −x−1, −y−1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2649).

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