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In both title pyridine derivatives, (I) and (II), the cation adopts an E configuration with respect to the C=C. In compound (I), the PF6 anion is disordered with occupancy factors of 0.614 (7):0.386 (7). In both the compounds, the crystal packing is stabilized by C—H...F inter­molecular inter­actions results into two-dimensional mol­ecular sheets, which are formed by R_{3}^{4}(14) ring motifs in compound (I), R_{6}^{6}(40) ring motifs in compound (II). In addition to that, the crystal packing is further stabilized by P—F...π inter­actions in compound (I) and π–π in compound (II).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019001403/lh5891sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019001403/lh5891Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019001403/lh5891IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019001403/lh5891Isup4.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019001403/lh5891IIsup5.cml
Supplementary material

CCDC references: 1893497; 971522

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.032
  • wR factor = 0.084
  • Data-to-parameter ratio = 10.5
Structure: II
  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.064
  • wR factor = 0.203
  • Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........ 6.11 Note PLAT260_ALERT_2_C Large Average Ueq of Residue Including P1 0.109 Check PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 ..F3 . 2.60 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 Note C15 H16 N O PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage 81 % PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 13 Note PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 12 Report PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check PLAT244_ALERT_4_G Low 'Solvent' Ueq as Compared to Neighbors of P1 Check PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 2 ) 86% Note PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 140 Note PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2018 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 10 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Datablock: II
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.500 From the CIF: _refine_ls_abs_structure_Flack_su 0.200 PLAT260_ALERT_2_C Large Average Ueq of Residue Including P1 0.134 Check PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00953 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 ..F6 . 2.59 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H16 ..F4 . 2.59 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H21B ..F2 . 2.64 Ang. PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 7 Note PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do ! PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large 0.11 Report PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check PLAT128_ALERT_4_G Alternate Setting for Input Space Group Cc Ic Note PLAT244_ALERT_4_G Low 'Solvent' Ueq as Compared to Neighbors of P1 Check PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety ..... C21 Check PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note F6 P PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 65 Note PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2018 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 11 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 9 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

For both structures, data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

4-[(E)-2-(4-Methoxyphenyl)ethenyl]-1-methylpyridin-1-ium hexafluoro-λ6-phosphane (I) top
Crystal data top
C15H16NO+·PF6F(000) = 380
Mr = 371.26Dx = 1.537 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2867 reflections
a = 6.4320 (2) Åθ = 2.7–26.0°
b = 9.3645 (3) ŵ = 0.24 mm1
c = 13.6070 (5) ÅT = 296 K
β = 101.868 (2)°Block, green
V = 802.06 (5) Å30.35 × 0.30 × 0.30 mm
Z = 2
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2867 independent reflections
Radiation source: fine-focus sealed tube2606 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω & φ scansθmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 77
Tmin = 0.921, Tmax = 0.932k = 911
8106 measured reflectionsl = 1616
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.032 w = 1/[σ2(Fo2) + (0.0459P)2 + 0.106P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.084(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.15 e Å3
2867 reflectionsΔρmin = 0.14 e Å3
273 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
140 restraintsExtinction coefficient: 0.016 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1198 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.08 (11)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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*/UeqOcc. (<1)
C10.6868 (5)0.3750 (4)0.1233 (2)0.0795 (9)
H1A0.79840.41990.17100.119*
H1B0.74300.33960.06790.119*
H1C0.62900.29710.15500.119*
C20.3506 (4)0.4329 (3)0.02002 (19)0.0562 (6)
C30.1982 (4)0.5355 (3)0.0083 (2)0.0638 (7)
H30.22040.62700.01820.077*
C40.0127 (4)0.5051 (3)0.07556 (19)0.0605 (6)
H40.08850.57640.09370.073*
C50.0260 (4)0.3690 (3)0.11688 (16)0.0494 (6)
C60.1323 (4)0.2680 (3)0.08913 (18)0.0559 (6)
H60.11220.17690.11670.067*
C70.3206 (4)0.2978 (3)0.0214 (2)0.0579 (7)
H70.42460.22810.00420.069*
C80.2243 (4)0.3294 (4)0.18350 (15)0.0536 (5)
H80.23770.23490.20490.064*
C90.3863 (4)0.4140 (3)0.21639 (19)0.0573 (6)
H90.36900.50980.19860.069*
C100.5907 (4)0.3729 (3)0.27799 (17)0.0500 (6)
C110.7440 (4)0.4771 (3)0.3090 (2)0.0601 (6)
H110.71390.57200.29150.072*
C120.9364 (5)0.4417 (3)0.3646 (2)0.0613 (7)
H121.03670.51310.38440.074*
C130.8419 (5)0.2036 (3)0.3640 (2)0.0593 (7)
H130.87590.10990.38360.071*
C140.6466 (5)0.2330 (3)0.3077 (2)0.0588 (7)
H140.54940.15940.28880.071*
C151.1961 (4)0.2735 (4)0.4540 (2)0.0741 (8)
H15A1.20610.17280.46750.111*
H15B1.21420.32500.51620.111*
H15C1.30480.30120.41890.111*
N10.9864 (3)0.3063 (2)0.39178 (14)0.0543 (6)
O10.5245 (3)0.4760 (2)0.08788 (15)0.0736 (6)
P10.74137 (10)0.83995 (8)0.65677 (4)0.05309 (18)
F10.7553 (11)0.7695 (5)0.7626 (3)0.1143 (17)0.614 (7)
F20.5074 (6)0.8863 (7)0.6568 (4)0.1075 (19)0.614 (7)
F30.6535 (12)0.6952 (7)0.6034 (6)0.0961 (19)0.614 (7)
F40.7210 (13)0.9108 (6)0.5533 (3)0.128 (2)0.614 (7)
F50.9725 (6)0.7933 (8)0.6592 (6)0.125 (2)0.614 (7)
F60.800 (3)0.9748 (11)0.7254 (10)0.109 (4)0.614 (7)
F1'0.8909 (17)0.7393 (7)0.7289 (7)0.112 (3)0.386 (7)
F2'0.5512 (16)0.7924 (12)0.6982 (8)0.140 (4)0.386 (7)
F3'0.705 (2)0.7182 (14)0.5738 (8)0.101 (3)0.386 (7)
F4'0.5990 (17)0.9410 (8)0.5792 (9)0.127 (4)0.386 (7)
F5'0.9347 (16)0.8884 (11)0.6106 (7)0.120 (3)0.386 (7)
F6'0.830 (4)0.9820 (15)0.7120 (14)0.084 (4)0.386 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0625 (16)0.083 (3)0.0841 (18)0.0033 (15)0.0058 (14)0.0087 (17)
C20.0537 (15)0.0581 (17)0.0568 (14)0.0038 (12)0.0116 (11)0.0032 (12)
C30.0628 (16)0.0509 (17)0.0749 (16)0.0001 (12)0.0080 (13)0.0089 (13)
C40.0593 (15)0.0527 (16)0.0669 (14)0.0059 (12)0.0070 (12)0.0023 (13)
C50.0503 (12)0.0519 (17)0.0473 (10)0.0017 (10)0.0130 (9)0.0013 (10)
C60.0586 (15)0.0464 (14)0.0637 (14)0.0030 (12)0.0145 (12)0.0061 (12)
C70.0516 (14)0.0518 (18)0.0697 (15)0.0023 (10)0.0114 (11)0.0056 (12)
C80.0580 (12)0.0529 (15)0.0515 (11)0.0006 (13)0.0147 (10)0.0023 (13)
C90.0562 (14)0.0503 (15)0.0651 (13)0.0013 (11)0.0116 (11)0.0012 (12)
C100.0523 (13)0.0486 (19)0.0512 (11)0.0008 (10)0.0157 (9)0.0026 (10)
C110.0652 (17)0.0521 (16)0.0623 (14)0.0028 (13)0.0113 (12)0.0033 (13)
C120.0594 (16)0.0594 (19)0.0648 (15)0.0099 (13)0.0123 (13)0.0080 (13)
C130.0645 (16)0.0513 (17)0.0620 (14)0.0023 (13)0.0129 (13)0.0010 (13)
C140.0569 (16)0.0503 (17)0.0700 (16)0.0082 (12)0.0144 (13)0.0036 (13)
C150.0552 (15)0.097 (2)0.0656 (15)0.0093 (15)0.0013 (12)0.0037 (16)
N10.0497 (11)0.0629 (19)0.0507 (10)0.0013 (9)0.0112 (8)0.0030 (9)
O10.0622 (11)0.0680 (14)0.0816 (12)0.0055 (10)0.0061 (9)0.0044 (11)
P10.0518 (3)0.0467 (3)0.0587 (3)0.0013 (3)0.0066 (2)0.0026 (3)
F10.172 (5)0.089 (3)0.079 (2)0.006 (3)0.017 (3)0.028 (2)
F20.0611 (19)0.140 (4)0.113 (3)0.024 (2)0.0018 (19)0.038 (3)
F30.095 (4)0.068 (3)0.116 (4)0.008 (2)0.001 (3)0.025 (3)
F40.213 (6)0.109 (4)0.073 (2)0.015 (4)0.057 (3)0.015 (2)
F50.063 (2)0.139 (5)0.173 (5)0.018 (2)0.019 (3)0.057 (4)
F60.111 (5)0.091 (6)0.121 (6)0.004 (4)0.018 (4)0.057 (5)
F1'0.136 (6)0.074 (4)0.099 (5)0.026 (4)0.037 (4)0.005 (4)
F2'0.115 (6)0.149 (7)0.182 (7)0.035 (5)0.092 (5)0.004 (6)
F3'0.116 (7)0.093 (6)0.092 (5)0.020 (4)0.018 (4)0.039 (4)
F4'0.127 (6)0.080 (4)0.136 (7)0.007 (4)0.064 (5)0.017 (4)
F5'0.115 (5)0.120 (6)0.146 (6)0.027 (4)0.079 (5)0.019 (5)
F6'0.102 (7)0.056 (5)0.091 (5)0.021 (5)0.010 (5)0.009 (4)
Geometric parameters (Å, º) top
C1—O11.418 (4)C11—H110.9300
C1—H1A0.9600C12—N11.341 (4)
C1—H1B0.9600C12—H120.9300
C1—H1C0.9600C13—N11.338 (3)
C2—O11.357 (3)C13—C141.358 (4)
C2—C31.370 (4)C13—H130.9300
C2—C71.382 (4)C14—H140.9300
C3—C41.376 (4)C15—N11.470 (3)
C3—H30.9300C15—H15A0.9600
C4—C51.395 (4)C15—H15B0.9600
C4—H40.9300C15—H15C0.9600
C5—C61.385 (4)P1—F2'1.515 (6)
C5—C81.452 (3)P1—F41.537 (4)
C6—C71.391 (4)P1—F51.543 (4)
C6—H60.9300P1—F1'1.545 (6)
C7—H70.9300P1—F4'1.566 (6)
C8—C91.312 (4)P1—F21.566 (4)
C8—H80.9300P1—F11.570 (4)
C9—C101.458 (4)P1—F61.570 (8)
C9—H90.9300P1—F5'1.571 (6)
C10—C111.390 (4)P1—F6'1.575 (12)
C10—C141.396 (4)P1—F31.586 (6)
C11—C121.352 (4)P1—F3'1.588 (10)
O1—C1—H1A109.5F2'—P1—F1'91.7 (6)
O1—C1—H1B109.5F4—P1—F1'140.3 (5)
H1A—C1—H1B109.5F5—P1—F1'48.9 (4)
O1—C1—H1C109.5F2'—P1—F4'91.4 (6)
H1A—C1—H1C109.5F5—P1—F4'127.8 (6)
H1B—C1—H1C109.5F1'—P1—F4'176.6 (7)
O1—C2—C3115.2 (3)F4—P1—F288.8 (3)
O1—C2—C7125.2 (3)F5—P1—F2178.8 (4)
C3—C2—C7119.7 (2)F1'—P1—F2129.9 (5)
C2—C3—C4121.0 (3)F4'—P1—F253.4 (5)
C2—C3—H3119.5F2'—P1—F155.5 (5)
C4—C3—H3119.5F4—P1—F1178.2 (4)
C3—C4—C5121.0 (3)F5—P1—F189.4 (4)
C3—C4—H4119.5F4'—P1—F1142.0 (6)
C5—C4—H4119.5F2—P1—F189.4 (3)
C6—C5—C4117.0 (2)F2'—P1—F697.4 (7)
C6—C5—C8119.9 (2)F4—P1—F699.3 (6)
C4—C5—C8123.1 (2)F5—P1—F695.9 (7)
C5—C6—C7122.3 (3)F1'—P1—F694.1 (6)
C5—C6—H6118.8F4'—P1—F687.2 (7)
C7—C6—H6118.8F2—P1—F683.7 (6)
C2—C7—C6118.9 (2)F1—P1—F680.3 (6)
C2—C7—H7120.5F2'—P1—F5'178.3 (5)
C6—C7—H7120.5F4—P1—F5'55.6 (4)
C9—C8—C5126.3 (3)F1'—P1—F5'89.4 (5)
C9—C8—H8116.8F4'—P1—F5'87.5 (6)
C5—C8—H8116.8F2—P1—F5'139.4 (5)
C8—C9—C10126.5 (3)F1—P1—F5'126.0 (5)
C8—C9—H9116.7F6—P1—F5'83.8 (6)
C10—C9—H9116.7F2'—P1—F6'108.1 (9)
C11—C10—C14116.5 (2)F4—P1—F6'91.5 (7)
C11—C10—C9119.2 (2)F5—P1—F6'88.7 (10)
C14—C10—C9124.2 (2)F1'—P1—F6'95.5 (8)
C12—C11—C10120.5 (3)F4'—P1—F6'85.1 (8)
C12—C11—H11119.7F2—P1—F6'91.0 (9)
C10—C11—H11119.7F1—P1—F6'88.3 (7)
N1—C12—C11121.7 (3)F5'—P1—F6'73.1 (9)
N1—C12—H12119.1F2'—P1—F371.4 (4)
C11—C12—H12119.1F4—P1—F389.7 (3)
N1—C13—C14121.5 (3)F5—P1—F391.1 (3)
N1—C13—H13119.3F1'—P1—F383.5 (4)
C14—C13—H13119.3F4'—P1—F396.0 (4)
C13—C14—C10120.4 (3)F2—P1—F389.1 (3)
C13—C14—H14119.8F1—P1—F390.5 (3)
C10—C14—H14119.8F6—P1—F3168.4 (6)
N1—C15—H15A109.5F5'—P1—F3107.5 (4)
N1—C15—H15B109.5F6'—P1—F3178.8 (8)
H15A—C15—H15B109.5F2'—P1—F3'92.4 (5)
N1—C15—H15C109.5F4—P1—F3'71.7 (5)
H15A—C15—H15C109.5F5—P1—F3'79.2 (5)
H15B—C15—H15C109.5F1'—P1—F3'89.7 (6)
C13—N1—C12119.3 (2)F4'—P1—F3'88.5 (7)
C13—N1—C15121.0 (3)F2—P1—F3'101.4 (5)
C12—N1—C15119.8 (2)F1—P1—F3'108.9 (5)
C2—O1—C1118.6 (3)F6—P1—F3'169.4 (7)
F2'—P1—F4123.0 (5)F5'—P1—F3'86.3 (5)
F2'—P1—F5139.2 (6)F6'—P1—F3'158.7 (9)
F4—P1—F592.4 (4)
O1—C2—C3—C4179.0 (2)C8—C9—C10—C142.9 (4)
C7—C2—C3—C41.8 (4)C14—C10—C11—C120.4 (4)
C2—C3—C4—C50.0 (4)C9—C10—C11—C12178.7 (2)
C3—C4—C5—C61.6 (4)C10—C11—C12—N10.1 (4)
C3—C4—C5—C8176.3 (2)N1—C13—C14—C100.6 (4)
C4—C5—C6—C71.5 (4)C11—C10—C14—C130.0 (4)
C8—C5—C6—C7176.5 (2)C9—C10—C14—C13179.0 (2)
O1—C2—C7—C6179.0 (2)C14—C13—N1—C120.9 (4)
C3—C2—C7—C61.9 (4)C14—C13—N1—C15179.1 (3)
C5—C6—C7—C20.2 (4)C11—C12—N1—C130.5 (4)
C6—C5—C8—C9179.4 (2)C11—C12—N1—C15178.7 (2)
C4—C5—C8—C92.8 (4)C3—C2—O1—C1178.2 (3)
C5—C8—C9—C10175.8 (2)C7—C2—O1—C12.7 (4)
C8—C9—C10—C11178.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1C···F2i0.962.513.220 (8)131
C12—H12···F3ii0.932.603.509 (8)165
C12—H12···F3ii0.932.533.454 (16)176
C13—H13···F5iii0.932.403.270 (9)156
C15—H15A···F4iii0.962.533.443 (7)160
C15—H15B···F2iv0.962.463.235 (5)138
C15—H15B···F5v0.962.493.162 (7)127
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x2, y, z1; (iii) x2, y1, z1; (iv) x1, y1/2, z; (v) x, y1/2, z.
4-{(E)-2-[4-(Dimethylamino)phenyl]ethenyl}-1-phenyl-1λ5-pyridin-\ 1-ylium hexafluoro-λ6-phosphane (II) top
Crystal data top
C21H21N2+·PF6F(000) = 920
Mr = 446.37Dx = 1.463 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 3926 reflections
a = 19.4596 (14) Åθ = 2.3–26.0°
b = 10.7416 (8) ŵ = 0.20 mm1
c = 11.9654 (9) ÅT = 296 K
β = 125.864 (2)°Block, yellow
V = 2026.9 (3) Å30.35 × 0.30 × 0.30 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3926 independent reflections
Radiation source: fine-focus sealed tube2895 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ & ω scansθmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 2323
Tmin = 0.933, Tmax = 0.943k = 1313
13796 measured reflectionsl = 1414
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.203 w = 1/[σ2(Fo2) + (0.1113P)2 + 2.2166P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
3926 reflectionsΔρmax = 0.49 e Å3
255 parametersΔρmin = 0.41 e Å3
65 restraintsAbsolute structure: Flack (1983), 1927 Fridel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.5 (2)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C10.0124 (4)0.0746 (5)0.2218 (7)0.0672 (15)
H10.00600.01940.14950.081*
C20.0338 (4)0.0925 (6)0.2738 (7)0.0755 (18)
H20.08560.05200.23320.091*
C30.0043 (4)0.1701 (6)0.3865 (8)0.0776 (17)
H30.03450.17850.42420.093*
C40.0694 (4)0.2339 (5)0.4407 (7)0.0746 (16)
H40.08840.28680.51490.090*
C50.1166 (3)0.2228 (5)0.3898 (6)0.0621 (13)
H50.16630.26810.42740.075*
C60.0876 (3)0.1414 (5)0.2800 (5)0.0537 (12)
C70.1625 (3)0.0050 (5)0.2239 (5)0.0556 (12)
H70.14600.06160.25300.067*
C80.2108 (3)0.0160 (5)0.1788 (5)0.0548 (12)
H80.22720.09710.17780.066*
C90.2369 (3)0.0807 (5)0.1335 (5)0.0535 (12)
C100.2116 (3)0.2004 (5)0.1416 (5)0.0600 (13)
H100.22800.26820.11400.072*
C110.1632 (3)0.2204 (5)0.1894 (5)0.0586 (13)
H110.14820.30100.19570.070*
C120.2873 (3)0.0638 (5)0.0829 (5)0.0569 (12)
H120.30220.13430.05660.068*
C130.3147 (3)0.0474 (5)0.0709 (5)0.0560 (12)
H130.29950.11650.09900.067*
C140.3642 (3)0.0719 (5)0.0201 (5)0.0541 (12)
C150.3748 (4)0.1927 (5)0.0088 (6)0.0614 (13)
H150.35050.25770.00800.074*
C160.4201 (4)0.2204 (5)0.0616 (6)0.0656 (14)
H160.42370.30240.08260.079*
C170.4603 (3)0.1265 (5)0.0834 (6)0.0600 (13)
C180.4494 (3)0.0039 (5)0.0559 (6)0.0626 (13)
H180.47440.06100.07150.075*
C190.4029 (3)0.0225 (5)0.0064 (5)0.0591 (13)
H190.39670.10500.01000.071*
C200.5037 (5)0.2756 (7)0.1855 (8)0.091 (2)
H20A0.53580.33110.10830.137*
H20B0.52840.27340.23530.137*
H20C0.44620.30450.24530.137*
C210.5524 (4)0.0558 (7)0.1456 (7)0.0751 (16)
H21A0.51510.01070.20240.113*
H21B0.57920.08950.18550.113*
H21C0.59500.02440.05500.113*
N10.5049 (3)0.1511 (5)0.1362 (5)0.0724 (13)
N20.1375 (2)0.1224 (4)0.2273 (4)0.0515 (10)
P10.26522 (10)0.40739 (11)0.33958 (15)0.0597 (4)
F50.1834 (3)0.4680 (5)0.2131 (5)0.1541 (16)
F40.3249 (3)0.5071 (4)0.3457 (7)0.1356 (14)
F30.3451 (3)0.3462 (6)0.4685 (5)0.1541 (16)
F20.2065 (3)0.3017 (4)0.3315 (7)0.1356 (14)
F60.2762 (3)0.3260 (6)0.2444 (6)0.1486 (17)
F10.2515 (3)0.4916 (5)0.4289 (6)0.1486 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.054 (3)0.051 (3)0.085 (4)0.003 (2)0.034 (3)0.011 (3)
C20.063 (4)0.061 (4)0.097 (5)0.006 (3)0.044 (4)0.024 (3)
C30.076 (4)0.067 (4)0.104 (5)0.022 (3)0.060 (4)0.023 (4)
C40.069 (4)0.058 (3)0.090 (4)0.019 (3)0.043 (3)0.002 (3)
C50.054 (3)0.049 (3)0.068 (3)0.010 (2)0.028 (3)0.003 (2)
C60.050 (3)0.042 (2)0.060 (3)0.004 (2)0.027 (2)0.009 (2)
C70.065 (3)0.043 (3)0.051 (3)0.007 (2)0.029 (2)0.004 (2)
C80.063 (3)0.043 (3)0.058 (3)0.007 (2)0.035 (2)0.002 (2)
C90.052 (3)0.051 (3)0.042 (2)0.002 (2)0.019 (2)0.0032 (19)
C100.059 (3)0.049 (3)0.061 (3)0.008 (2)0.029 (3)0.012 (2)
C110.058 (3)0.043 (3)0.061 (3)0.002 (2)0.027 (3)0.007 (2)
C120.057 (3)0.059 (3)0.048 (2)0.011 (2)0.027 (2)0.006 (2)
C130.053 (3)0.053 (3)0.050 (3)0.006 (2)0.024 (2)0.005 (2)
C140.046 (3)0.050 (3)0.049 (2)0.006 (2)0.018 (2)0.003 (2)
C150.058 (3)0.044 (3)0.065 (3)0.006 (2)0.027 (3)0.001 (2)
C160.063 (3)0.039 (3)0.074 (3)0.003 (2)0.029 (3)0.001 (2)
C170.054 (3)0.048 (3)0.056 (3)0.002 (2)0.020 (2)0.005 (2)
C180.062 (3)0.047 (3)0.076 (3)0.014 (2)0.039 (3)0.009 (2)
C190.069 (3)0.042 (3)0.070 (3)0.008 (2)0.042 (3)0.009 (2)
C200.085 (4)0.081 (4)0.096 (5)0.009 (4)0.046 (4)0.030 (4)
C210.063 (3)0.086 (4)0.082 (4)0.003 (3)0.045 (3)0.007 (3)
N10.067 (3)0.058 (3)0.091 (3)0.003 (2)0.046 (3)0.019 (2)
N20.050 (2)0.040 (2)0.052 (2)0.0041 (16)0.0224 (19)0.0060 (16)
P10.0620 (7)0.0432 (6)0.0712 (8)0.0011 (6)0.0376 (6)0.0017 (6)
F50.116 (3)0.133 (3)0.129 (3)0.033 (2)0.025 (2)0.040 (2)
F40.150 (3)0.080 (2)0.227 (4)0.0386 (19)0.139 (3)0.023 (2)
F30.116 (3)0.133 (3)0.129 (3)0.033 (2)0.025 (2)0.040 (2)
F20.150 (3)0.080 (2)0.227 (4)0.0386 (19)0.139 (3)0.023 (2)
F60.159 (3)0.155 (3)0.194 (4)0.054 (3)0.138 (3)0.096 (3)
F10.159 (3)0.155 (3)0.194 (4)0.054 (3)0.138 (3)0.096 (3)
Geometric parameters (Å, º) top
C1—C21.375 (9)C13—H130.9300
C1—C61.395 (8)C14—C151.389 (7)
C1—H10.9300C14—C191.406 (7)
C2—C31.391 (10)C15—C161.384 (8)
C2—H20.9300C15—H150.9300
C3—C41.363 (9)C16—C171.392 (8)
C3—H30.9300C16—H160.9300
C4—C51.372 (9)C17—N11.366 (7)
C4—H40.9300C17—C181.403 (7)
C5—C61.393 (7)C18—C191.371 (7)
C5—H50.9300C18—H180.9300
C6—N21.449 (7)C19—H190.9300
C7—C81.350 (7)C20—N11.456 (8)
C7—N21.360 (6)C20—H20A0.9600
C7—H70.9300C20—H20B0.9600
C8—C91.397 (7)C20—H20C0.9600
C8—H80.9300C21—N11.428 (8)
C9—C101.401 (7)C21—H21A0.9600
C9—C121.435 (8)C21—H21B0.9600
C10—C111.375 (8)C21—H21C0.9600
C10—H100.9300P1—F11.539 (4)
C11—N21.353 (6)P1—F61.547 (4)
C11—H110.9300P1—F41.550 (4)
C12—C131.348 (8)P1—F31.555 (4)
C12—H120.9300P1—F51.557 (4)
C13—C141.433 (7)P1—F21.574 (4)
C2—C1—C6118.4 (6)C15—C16—C17120.5 (5)
C2—C1—H1120.8C15—C16—H16119.8
C6—C1—H1120.8C17—C16—H16119.8
C1—C2—C3121.0 (6)N1—C17—C16121.7 (5)
C1—C2—H2119.5N1—C17—C18121.0 (5)
C3—C2—H2119.5C16—C17—C18117.2 (5)
C4—C3—C2118.9 (6)C19—C18—C17121.6 (5)
C4—C3—H3120.5C19—C18—H18119.2
C2—C3—H3120.5C17—C18—H18119.2
C3—C4—C5122.5 (6)C18—C19—C14121.6 (5)
C3—C4—H4118.8C18—C19—H19119.2
C5—C4—H4118.8C14—C19—H19119.2
C4—C5—C6117.8 (6)N1—C20—H20A109.5
C4—C5—H5121.1N1—C20—H20B109.5
C6—C5—H5121.1H20A—C20—H20B109.5
C5—C6—C1121.4 (5)N1—C20—H20C109.5
C5—C6—N2119.6 (4)H20A—C20—H20C109.5
C1—C6—N2119.0 (5)H20B—C20—H20C109.5
C8—C7—N2120.8 (5)N1—C21—H21A109.5
C8—C7—H7119.6N1—C21—H21B109.5
N2—C7—H7119.6H21A—C21—H21B109.5
C7—C8—C9121.9 (5)N1—C21—H21C109.5
C7—C8—H8119.1H21A—C21—H21C109.5
C9—C8—H8119.1H21B—C21—H21C109.5
C8—C9—C10115.6 (5)C17—N1—C21120.9 (5)
C8—C9—C12124.3 (5)C17—N1—C20120.1 (6)
C10—C9—C12120.1 (5)C21—N1—C20119.0 (5)
C11—C10—C9121.8 (5)C11—N2—C7120.2 (5)
C11—C10—H10119.1C11—N2—C6120.6 (4)
C9—C10—H10119.1C7—N2—C6119.1 (4)
N2—C11—C10119.7 (5)F1—P1—F6177.6 (4)
N2—C11—H11120.2F1—P1—F489.5 (3)
C10—C11—H11120.2F6—P1—F490.1 (3)
C13—C12—C9124.5 (5)F1—P1—F392.2 (3)
C13—C12—H12117.7F6—P1—F390.1 (3)
C9—C12—H12117.7F4—P1—F387.7 (3)
C12—C13—C14127.8 (5)F1—P1—F586.3 (3)
C12—C13—H13116.1F6—P1—F591.4 (3)
C14—C13—H13116.1F4—P1—F593.9 (3)
C15—C14—C19116.1 (5)F3—P1—F5177.8 (4)
C15—C14—C13120.8 (5)F1—P1—F292.9 (3)
C19—C14—C13123.1 (5)F6—P1—F287.5 (3)
C16—C15—C14122.9 (5)F4—P1—F2177.5 (3)
C16—C15—H15118.6F3—P1—F291.4 (3)
C14—C15—H15118.6F5—P1—F287.1 (3)
C6—C1—C2—C33.3 (8)C14—C15—C16—C172.4 (8)
C1—C2—C3—C43.4 (9)C15—C16—C17—N1179.6 (5)
C2—C3—C4—C51.1 (9)C15—C16—C17—C182.9 (8)
C3—C4—C5—C61.0 (8)N1—C17—C18—C19178.2 (5)
C4—C5—C6—C11.0 (7)C16—C17—C18—C191.5 (8)
C4—C5—C6—N2177.1 (5)C17—C18—C19—C140.5 (8)
C2—C1—C6—C51.1 (8)C15—C14—C19—C181.0 (7)
C2—C1—C6—N2179.2 (5)C13—C14—C19—C18179.6 (5)
N2—C7—C8—C90.2 (7)C16—C17—N1—C21173.9 (5)
C7—C8—C9—C101.7 (7)C18—C17—N1—C219.5 (8)
C7—C8—C9—C12179.2 (5)C16—C17—N1—C206.8 (9)
C8—C9—C10—C110.9 (7)C18—C17—N1—C20169.8 (6)
C12—C9—C10—C11179.9 (5)C10—C11—N2—C72.9 (7)
C9—C10—C11—N21.4 (8)C10—C11—N2—C6179.0 (4)
C8—C9—C12—C131.0 (8)C8—C7—N2—C112.1 (7)
C10—C9—C12—C13179.9 (5)C8—C7—N2—C6178.3 (4)
C9—C12—C13—C14179.2 (5)C5—C6—N2—C1153.1 (6)
C12—C13—C14—C15168.5 (5)C1—C6—N2—C11128.8 (5)
C12—C13—C14—C1910.0 (8)C5—C6—N2—C7123.1 (5)
C19—C14—C15—C160.4 (8)C1—C6—N2—C755.0 (6)
C13—C14—C15—C16178.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···F60.932.593.486 (8)162
C11—H11···F5i0.932.553.363 (8)146
C16—H16···F4ii0.932.593.289 (7)132
C21—H21B···F2iii0.962.643.516 (8)152
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z1/2; (iii) x+1/2, y1/2, z1/2.
 

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