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The reaction of benzo­phenone imine with an excess of tetra­fluoro­boric acid in di­chloro­methane yielded the title compound, C13H12N+·BF4. The cation is non-planar and the crystal structure is stabilized by N—H...F and C—H...F short contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680200452X/ci6109sup1.cif
Contains datablocks I, ms153

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680200452X/ci6109Isup2.hkl
Contains datablock I

CCDC reference: 183802

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.060
  • wR factor = 0.196
  • Data-to-parameter ratio = 10.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Benzophenone iminium tetrafluoroborate top
Crystal data top
C13H12N+·BF4F(000) = 552
Mr = 269.05Dx = 1.385 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ynCell parameters from 2348 reflections
a = 5.9727 (4) Åθ = 2–70°
b = 15.082 (1) ŵ = 1.05 mm1
c = 14.3364 (10) ÅT = 200 K
β = 91.895 (4)°Block, white
V = 1290.72 (15) Å30.25 × 0.10 × 0.08 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
1624 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.065
Horizontally mounted graphite crystal monochromatorθmax = 68.4°, θmin = 4.3°
Detector resolution: 9 pixels mm-1h = 07
CCD scansk = 018
11038 measured reflectionsl = 1717
2306 independent reflections
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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196All H-atom parameters refined
S = 1.10 w = 1/[σ2(Fo2) + (0.1069P)2 + 0.3137P]
where P = (Fo2 + 2Fc2)/3
2306 reflections(Δ/σ)max = 0.001
220 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

Experimental. Anal. and spectroscopic data: Calcd for C13H12BF4N (269.05): C, 58.03; H, 4.50; N, 5.21. Found: C, 58.10; H, 4.55; N, 5.17. 1H NMR (CD2Cl2): δ 9.90 (s, br, 2 H, NH2), 7.88–7.60 (m, 10 H, Ph2) p.p.m.. 13C NMR (CD2Cl2): 184.4 (1 C, CNH2), 136.59 (2 C, CH, Ph), 132.1 (4 C, CH, Ph), 130.3 (2 C, C, Ph), 129.7 (4 C, CH, Ph) p.p.m..

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
C10.8688 (4)0.27992 (16)0.51965 (18)0.0542 (7)
C20.7895 (4)0.20242 (17)0.46724 (18)0.0548 (7)
C30.9348 (5)0.13219 (18)0.45107 (19)0.0582 (7)
C40.8674 (5)0.0612 (2)0.3971 (2)0.0674 (8)
C50.6519 (6)0.0590 (2)0.3577 (2)0.0771 (9)
C60.5077 (6)0.1283 (3)0.3740 (3)0.0813 (10)
C70.5723 (5)0.1994 (2)0.4273 (2)0.0702 (8)
C81.0505 (4)0.27364 (16)0.59144 (17)0.0537 (7)
C91.0644 (6)0.20021 (19)0.6498 (2)0.0607 (7)
C101.2404 (6)0.1930 (2)0.7146 (2)0.0695 (8)
C111.4004 (6)0.2580 (2)0.7217 (2)0.0734 (9)
C121.3841 (5)0.3326 (2)0.6659 (2)0.0692 (8)
C131.2108 (5)0.34047 (19)0.6007 (2)0.0605 (7)
B10.2697 (5)0.4366 (2)0.3484 (2)0.0577 (8)
F10.4824 (3)0.45061 (15)0.38620 (18)0.1093 (8)
F20.2663 (3)0.45451 (15)0.25612 (13)0.0970 (7)
F30.1200 (3)0.48922 (14)0.39319 (16)0.1001 (7)
F40.2126 (3)0.35000 (12)0.36554 (14)0.0902 (7)
N10.7842 (5)0.35776 (17)0.5018 (2)0.0664 (7)
H10.668 (7)0.366 (3)0.458 (3)0.110 (14)*
H20.827 (7)0.410 (3)0.538 (3)0.116 (14)*
H31.079 (5)0.1321 (17)0.480 (2)0.060 (8)*
H40.966 (5)0.0156 (19)0.3835 (19)0.060 (8)*
H50.606 (5)0.009 (2)0.319 (2)0.072 (8)*
H60.362 (7)0.130 (3)0.346 (3)0.103 (12)*
H70.475 (5)0.247 (2)0.440 (2)0.076 (9)*
H90.959 (5)0.1592 (19)0.6452 (18)0.053 (7)*
H101.245 (5)0.143 (2)0.753 (2)0.065 (8)*
H111.535 (7)0.250 (3)0.766 (3)0.113 (13)*
H121.496 (6)0.378 (3)0.674 (2)0.094 (11)*
H131.199 (5)0.390 (2)0.563 (2)0.076 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0527 (14)0.0534 (14)0.0573 (15)0.0065 (12)0.0103 (11)0.0051 (11)
C20.0508 (15)0.0606 (15)0.0532 (15)0.0041 (11)0.0042 (11)0.0023 (11)
C30.0546 (16)0.0596 (16)0.0602 (16)0.0054 (12)0.0011 (13)0.0022 (12)
C40.0710 (19)0.0606 (17)0.0706 (18)0.0061 (15)0.0010 (15)0.0093 (14)
C50.073 (2)0.082 (2)0.075 (2)0.0102 (17)0.0034 (16)0.0134 (17)
C60.0579 (19)0.106 (3)0.080 (2)0.0065 (18)0.0018 (16)0.0106 (19)
C70.0545 (17)0.086 (2)0.0696 (19)0.0094 (15)0.0016 (14)0.0063 (16)
C80.0575 (15)0.0508 (14)0.0533 (14)0.0074 (11)0.0072 (12)0.0013 (11)
C90.0731 (19)0.0532 (15)0.0559 (16)0.0011 (14)0.0034 (14)0.0007 (12)
C100.092 (2)0.0623 (17)0.0539 (16)0.0110 (16)0.0038 (15)0.0045 (13)
C110.078 (2)0.080 (2)0.0617 (18)0.0083 (17)0.0065 (15)0.0093 (15)
C120.0672 (19)0.076 (2)0.0644 (18)0.0044 (16)0.0013 (15)0.0081 (15)
C130.0677 (18)0.0544 (16)0.0599 (16)0.0017 (13)0.0111 (13)0.0017 (13)
B10.0534 (17)0.0536 (17)0.0656 (19)0.0085 (13)0.0033 (14)0.0024 (14)
F10.0732 (13)0.1164 (17)0.1357 (19)0.0103 (11)0.0365 (12)0.0279 (14)
F20.1037 (15)0.1168 (17)0.0706 (12)0.0269 (12)0.0039 (10)0.0219 (11)
F30.1015 (14)0.0831 (13)0.1166 (16)0.0259 (11)0.0147 (12)0.0212 (11)
F40.1120 (16)0.0637 (11)0.0945 (14)0.0016 (9)0.0034 (12)0.0002 (9)
N10.0642 (15)0.0639 (16)0.0714 (16)0.0152 (12)0.0067 (13)0.0058 (12)
Geometric parameters (Å, º) top
C1—N11.300 (3)C9—C101.384 (4)
C1—C21.460 (4)C9—H90.88 (3)
C1—C81.474 (4)C10—C111.371 (5)
C2—C31.393 (4)C10—H100.93 (3)
C2—C71.402 (4)C11—C121.382 (5)
C3—C41.373 (4)C11—H111.02 (4)
C3—H30.94 (3)C12—C131.377 (4)
C4—C51.389 (4)C12—H120.96 (4)
C4—H40.93 (3)C13—H130.93 (3)
C5—C61.379 (5)B1—F21.350 (4)
C5—H50.97 (3)B1—F31.370 (4)
C6—C71.366 (5)B1—F41.375 (4)
C6—H60.95 (4)B1—F11.380 (4)
C7—H70.95 (3)N1—H10.93 (5)
C8—C91.388 (4)N1—H20.97 (4)
C8—C131.394 (4)
N1—C1—C2120.3 (3)C10—C9—C8119.8 (3)
N1—C1—C8117.9 (3)C10—C9—H9121.1 (18)
C2—C1—C8121.8 (2)C8—C9—H9119.1 (18)
C3—C2—C7118.7 (3)C11—C10—C9120.4 (3)
C3—C2—C1120.1 (2)C11—C10—H10121.9 (18)
C7—C2—C1121.1 (2)C9—C10—H10117.8 (18)
C4—C3—C2120.9 (3)C10—C11—C12120.3 (3)
C4—C3—H3119.4 (16)C10—C11—H11120 (2)
C2—C3—H3119.6 (16)C12—C11—H11120 (2)
C3—C4—C5119.9 (3)C13—C12—C11120.0 (3)
C3—C4—H4121.1 (17)C13—C12—H12122 (2)
C5—C4—H4118.9 (17)C11—C12—H12118 (2)
C6—C5—C4119.2 (3)C12—C13—C8120.1 (3)
C6—C5—H5121.3 (18)C12—C13—H13120.6 (19)
C4—C5—H5119.4 (18)C8—C13—H13119.3 (19)
C7—C6—C5121.6 (3)F2—B1—F3110.8 (2)
C7—C6—H6117 (2)F2—B1—F4111.6 (3)
C5—C6—H6122 (2)F3—B1—F4107.3 (3)
C6—C7—C2119.7 (3)F2—B1—F1109.8 (3)
C6—C7—H7122.7 (19)F3—B1—F1109.5 (3)
C2—C7—H7117.7 (19)F4—B1—F1107.8 (2)
C9—C8—C13119.5 (3)C1—N1—H1122 (2)
C9—C8—C1120.0 (2)C1—N1—H2122 (3)
C13—C8—C1120.5 (2)H1—N1—H2115 (4)
N1—C1—C2—C3149.0 (3)N1—C1—C8—C9144.1 (3)
C8—C1—C2—C328.8 (4)C2—C1—C8—C938.0 (4)
N1—C1—C2—C726.8 (4)N1—C1—C8—C1336.7 (4)
C8—C1—C2—C7155.4 (3)C2—C1—C8—C13141.2 (3)
C7—C2—C3—C40.0 (4)C13—C8—C9—C101.7 (4)
C1—C2—C3—C4175.9 (3)C1—C8—C9—C10177.4 (3)
C2—C3—C4—C50.1 (5)C8—C9—C10—C110.2 (5)
C3—C4—C5—C60.4 (5)C9—C10—C11—C121.8 (5)
C4—C5—C6—C70.6 (5)C10—C11—C12—C132.2 (5)
C5—C6—C7—C20.5 (5)C11—C12—C13—C80.6 (4)
C3—C2—C7—C60.2 (4)C9—C8—C13—C121.3 (4)
C1—C2—C7—C6176.1 (3)C1—C8—C13—C12177.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···F10.93 (4)1.96 (4)2.786 (4)147 (4)
N1—H2···F3i0.97 (5)1.83 (4)2.804 (3)175 (4)
C7—H7···F40.95 (3)2.43 (3)3.230 (4)142 (2)
C11—H11···F4ii1.02 (4)2.31 (4)3.183 (4)143 (3)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+3/2, y+1/2, z+1/2.
 

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