Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, [OPPh2(2-CH2C5H4NH)]BF4, the phospho­rus atom displays a tetra­hedral geometry, with the nitro­gen of the pyridyl group protonated and having tetra­fluoro­borate as counter-anion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047179/ym2033sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047179/ym2033Isup2.hkl
Contains datablock I

CCDC reference: 630539

Key indicators

  • Single-crystal X-ray study
  • T = 110 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.138
  • Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for B1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

2-(Diphenylphosphinoylmethyl)pyridinium tetrafluoroborate top
Crystal data top
C18H17NOP+·BF4F(000) = 1568
Mr = 381.11Dx = 1.391 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4891 reflections
a = 16.7528 (15) Åθ = 2.3–28.9°
b = 13.9287 (17) ŵ = 0.20 mm1
c = 15.661 (2) ÅT = 110 K
β = 95.314 (4)°Block, colorless
V = 3638.7 (7) Å30.29 × 0.25 × 0.21 mm
Z = 8
Data collection top
Bruker APEX CCD area-detector
diffractometer
4726 independent reflections
Radiation source: fine-focus sealed tube3915 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 29.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS, Bruker, 2000)
h = 2219
Tmin = 0.958, Tmax = 0.960k = 1818
14958 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0684P)2 + 4.7739P]
where P = (Fo2 + 2Fc2)/3
4726 reflections(Δ/σ)max = 0.001
239 parametersΔρmax = 0.65 e Å3
0 restraintsΔρmin = 0.57 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.12999 (2)0.13722 (3)0.21304 (3)0.01466 (12)
C10.14074 (10)0.14601 (12)0.33002 (11)0.0178 (3)
H1A0.19010.18220.34890.021*
H1B0.09450.18130.34960.021*
C30.21554 (10)0.00480 (13)0.40151 (11)0.0208 (4)
H30.26480.03880.40280.025*
C20.14494 (9)0.04814 (12)0.36900 (10)0.0165 (3)
C50.14205 (11)0.13773 (14)0.43108 (13)0.0249 (4)
H50.14050.20180.45180.030*
C40.21426 (10)0.08853 (14)0.43224 (12)0.0237 (4)
H40.26270.11880.45410.028*
C60.07283 (11)0.09199 (14)0.39939 (13)0.0259 (4)
H60.02280.12420.39870.031*
C70.10845 (9)0.25679 (12)0.17494 (10)0.0159 (3)
C120.05666 (9)0.26688 (13)0.09984 (11)0.0198 (3)
H120.03350.21170.07170.024*
C110.03931 (10)0.35780 (14)0.06669 (12)0.0257 (4)
H110.00460.36470.01560.031*
C80.14092 (10)0.33822 (13)0.21700 (11)0.0215 (4)
H80.17540.33190.26840.026*
C90.12241 (11)0.42880 (13)0.18318 (12)0.0238 (4)
H90.14410.48440.21180.029*
C100.07242 (10)0.43828 (14)0.10780 (13)0.0254 (4)
H100.06090.50020.08440.031*
C130.22466 (9)0.09971 (12)0.17851 (11)0.0174 (3)
C180.29336 (10)0.15760 (14)0.19020 (13)0.0246 (4)
H180.29140.21770.21860.030*
C150.29886 (13)0.01938 (16)0.10691 (13)0.0307 (4)
H150.30110.07950.07860.037*
C140.22759 (11)0.01126 (13)0.13754 (11)0.0224 (4)
H140.18120.02810.13050.027*
C160.36621 (13)0.03805 (17)0.11788 (15)0.0368 (5)
H160.41450.01720.09640.044*
C170.36453 (11)0.12621 (16)0.15988 (16)0.0348 (5)
H170.41150.16460.16780.042*
O10.06584 (7)0.06754 (9)0.18240 (8)0.0224 (3)
B10.12519 (12)0.75309 (16)0.08558 (16)0.0273 (5)
F10.10055 (8)0.82067 (11)0.02406 (9)0.0421 (3)
F20.19457 (8)0.78232 (10)0.13255 (10)0.0486 (4)
F30.13956 (10)0.66594 (12)0.04854 (14)0.0736 (6)
F40.06365 (10)0.74127 (16)0.13657 (14)0.0825 (7)
N10.07583 (8)0.00194 (11)0.36942 (10)0.0203 (3)
H1C0.0270 (16)0.0281 (18)0.3457 (16)0.040 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01029 (19)0.0162 (2)0.0176 (2)0.00135 (14)0.00191 (14)0.00048 (15)
C10.0171 (7)0.0179 (8)0.0186 (8)0.0000 (6)0.0030 (6)0.0005 (6)
C30.0132 (7)0.0259 (9)0.0229 (8)0.0012 (6)0.0002 (6)0.0020 (7)
C20.0134 (7)0.0205 (8)0.0161 (7)0.0014 (6)0.0036 (5)0.0007 (6)
C50.0254 (9)0.0215 (9)0.0281 (9)0.0003 (7)0.0042 (7)0.0053 (7)
C40.0180 (8)0.0270 (10)0.0259 (9)0.0044 (7)0.0002 (6)0.0053 (7)
C60.0183 (8)0.0265 (10)0.0333 (10)0.0060 (7)0.0045 (7)0.0060 (8)
C70.0116 (6)0.0184 (8)0.0181 (8)0.0015 (6)0.0028 (6)0.0003 (6)
C120.0133 (7)0.0243 (9)0.0214 (8)0.0018 (6)0.0003 (6)0.0002 (7)
C110.0162 (7)0.0323 (10)0.0274 (9)0.0006 (7)0.0043 (7)0.0082 (8)
C80.0214 (8)0.0206 (9)0.0219 (8)0.0000 (6)0.0005 (6)0.0010 (7)
C90.0239 (8)0.0191 (9)0.0286 (9)0.0009 (7)0.0035 (7)0.0011 (7)
C100.0181 (8)0.0239 (9)0.0345 (10)0.0044 (7)0.0035 (7)0.0086 (8)
C130.0149 (7)0.0187 (8)0.0189 (8)0.0020 (6)0.0041 (6)0.0031 (6)
C180.0155 (7)0.0216 (9)0.0377 (11)0.0002 (6)0.0072 (7)0.0051 (8)
C150.0374 (10)0.0328 (11)0.0229 (9)0.0187 (9)0.0078 (8)0.0025 (8)
C140.0251 (8)0.0225 (9)0.0196 (8)0.0046 (7)0.0016 (6)0.0012 (7)
C160.0310 (10)0.0428 (13)0.0398 (12)0.0201 (9)0.0206 (9)0.0176 (10)
C170.0177 (8)0.0353 (12)0.0531 (14)0.0046 (8)0.0125 (8)0.0187 (10)
O10.0160 (5)0.0233 (7)0.0278 (7)0.0066 (5)0.0008 (5)0.0022 (5)
B10.0180 (9)0.0256 (11)0.0374 (12)0.0032 (8)0.0020 (8)0.0010 (9)
F10.0354 (7)0.0499 (9)0.0388 (7)0.0047 (6)0.0088 (5)0.0104 (6)
F20.0426 (8)0.0362 (8)0.0610 (9)0.0027 (6)0.0284 (7)0.0029 (7)
F30.0527 (9)0.0435 (9)0.1182 (16)0.0188 (7)0.0264 (10)0.0404 (10)
F40.0478 (10)0.1108 (17)0.0947 (15)0.0331 (10)0.0375 (9)0.0542 (13)
N10.0109 (6)0.0234 (8)0.0266 (8)0.0011 (5)0.0025 (5)0.0056 (6)
Geometric parameters (Å, º) top
P1—O11.4939 (12)C11—H110.9500
P1—C71.7946 (17)C8—C91.392 (3)
P1—C131.8000 (17)C8—H80.9500
P1—C11.8283 (18)C9—C101.389 (3)
C1—C21.493 (2)C9—H90.9500
C1—H1A0.9900C10—H100.9500
C1—H1B0.9900C13—C141.392 (3)
C3—C21.382 (2)C13—C181.403 (2)
C3—C41.387 (3)C18—C171.394 (3)
C3—H30.9500C18—H180.9500
C2—N11.352 (2)C15—C161.381 (3)
C5—C61.375 (3)C15—C141.394 (3)
C5—C41.389 (3)C15—H150.9500
C5—H50.9500C14—H140.9500
C4—H40.9500C16—C171.394 (3)
C6—N11.342 (2)C16—H160.9500
C6—H60.9500C17—H170.9500
C7—C81.396 (2)B1—F41.371 (3)
C7—C121.402 (2)B1—F31.376 (3)
C12—C111.389 (3)B1—F21.378 (2)
C12—H120.9500B1—F11.382 (3)
C11—C101.383 (3)N1—H1C0.96 (3)
O1—P1—C7112.31 (7)C9—C8—C7119.57 (16)
O1—P1—C13110.04 (8)C9—C8—H8120.2
C7—P1—C13108.97 (8)C7—C8—H8120.2
O1—P1—C1111.51 (8)C10—C9—C8120.33 (17)
C7—P1—C1105.61 (8)C10—C9—H9119.8
C13—P1—C1108.22 (8)C8—C9—H9119.8
C2—C1—P1110.20 (12)C11—C10—C9120.19 (17)
C2—C1—H1A109.6C11—C10—H10119.9
P1—C1—H1A109.6C9—C10—H10119.9
C2—C1—H1B109.6C14—C13—C18120.35 (16)
P1—C1—H1B109.6C14—C13—P1117.71 (13)
H1A—C1—H1B108.1C18—C13—P1121.93 (14)
C2—C3—C4119.79 (16)C17—C18—C13119.49 (19)
C2—C3—H3120.1C17—C18—H18120.3
C4—C3—H3120.1C13—C18—H18120.3
N1—C2—C3118.47 (16)C16—C15—C14119.7 (2)
N1—C2—C1117.72 (14)C16—C15—H15120.1
C3—C2—C1123.76 (15)C14—C15—H15120.1
C6—C5—C4118.72 (17)C13—C14—C15119.83 (18)
C6—C5—H5120.6C13—C14—H14120.1
C4—C5—H5120.6C15—C14—H14120.1
C3—C4—C5119.95 (16)C15—C16—C17121.13 (18)
C3—C4—H4120.0C15—C16—H16119.4
C5—C4—H4120.0C17—C16—H16119.4
N1—C6—C5120.12 (16)C18—C17—C16119.48 (19)
N1—C6—H6119.9C18—C17—H17120.3
C5—C6—H6119.9C16—C17—H17120.3
C8—C7—C12119.86 (16)F4—B1—F3108.0 (2)
C8—C7—P1122.65 (12)F4—B1—F2111.5 (2)
C12—C7—P1117.49 (13)F3—B1—F2108.28 (17)
C11—C12—C7119.77 (16)F4—B1—F1107.19 (17)
C11—C12—H12120.1F3—B1—F1111.1 (2)
C7—C12—H12120.1F2—B1—F1110.70 (18)
C10—C11—C12120.26 (16)C6—N1—C2122.94 (15)
C10—C11—H11119.9C6—N1—H1C118.9 (16)
C12—C11—H11119.9C2—N1—H1C118.1 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···O1i0.96 (3)1.67 (3)2.6212 (18)169 (2)
C1—H1A···F2ii0.992.383.356 (2)169
C18—H18···F2ii0.952.493.265 (3)139
C3—H3···F3ii0.952.463.345 (2)155
C6—H6···F4iii0.952.403.271 (3)152
Symmetry codes: (i) x, y, z+1/2; (ii) x+1/2, y1/2, z+1/2; (iii) x, y1, z+1/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

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

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

Buy online

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

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

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

Terms and conditions of use
Contact us

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