4-[(2'-Cyano-biphen-yl-4-yl)meth-yl]morpholin-4-ium tetra-fluoridoborate.

In the crystal structure of the title compound, C(18)H(19)N(2)O(+)·BF(4) (-), bifurcated N-H⋯(F,F) hydrogen bonds link the protonated 4'-morpholine-methyl-biphenyl-2-carbonitrile cations and slightly distorted tetra-fluoro-borate anions. π-π inter-actions [centroid-centroid distance = 3.805 (3) Å] help to consolidate the packing. The dihedral angle between the benzene rings in the cation is 57.24 (11)°.

Related literature

For a related structure, see: SiMa (2010 ▶).

Experimental

Crystal data

C18H19N2O+·BF4 −

M = 366.16

Triclinic,

a = 9.059 (6) Å

b = 9.859 (8) Å

c = 10.597 (8) Å

α = 76.324 (14)°

β = 83.71 (2)°

γ = 86.50 (3)°

V = 913.5 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.978, T max = 0.978

9817 measured reflections

4098 independent reflections

3039 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.202

S = 1.06

4098 reflections

239 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101186X/jh2276sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101186X/jh2276Isup2.hkl

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

C18H19N2O+·BF4−	Z = 2
Mr = 366.16	F(000) = 380
Triclinic, P1	Dx = 1.331 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.059 (6) Å	Cell parameters from 2199 reflections
b = 9.859 (8) Å	θ = 2.6–27.4°
c = 10.597 (8) Å	µ = 0.11 mm−1
α = 76.324 (14)°	T = 298 K
β = 83.71 (2)°	Prism, colourless
γ = 86.50 (3)°	0.20 × 0.20 × 0.20 mm
V = 913.5 (12) Å3

Rigaku SCXmini diffractometer	4098 independent reflections
Radiation source: fine-focus sealed tube	3039 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 13.6612 pixels mm-1	θmax = 27.4°, θmin = 2.6°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
Tmin = 0.978, Tmax = 0.978	l = −13→13
9817 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.1049P)2 + 0.2107P] where P = (Fo2 + 2Fc2)/3
4098 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.49 e Å−3
1 restraint	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.9918 (2)	0.3886 (3)	0.3969 (2)	0.0559 (5)
C2	1.0478 (2)	0.2599 (2)	0.47565 (19)	0.0472 (5)
C3	1.1901 (2)	0.2084 (3)	0.4395 (2)	0.0613 (6)
H3A	1.2463	0.2570	0.3658	0.074*
C4	1.2460 (3)	0.0863 (3)	0.5129 (3)	0.0662 (7)
H4A	1.3404	0.0522	0.4890	0.079*
C5	1.1631 (3)	0.0144 (3)	0.6214 (2)	0.0644 (6)
H5A	1.2009	−0.0692	0.6700	0.077*
C6	1.0234 (2)	0.0653 (2)	0.6593 (2)	0.0533 (5)
H6A	0.9695	0.0162	0.7341	0.064*
C7	0.9623 (2)	0.1888 (2)	0.58744 (18)	0.0436 (4)
C8	0.8154 (2)	0.24449 (19)	0.63377 (18)	0.0424 (4)
C9	0.7937 (2)	0.2673 (2)	0.75930 (19)	0.0521 (5)
H9A	0.8707	0.2464	0.8128	0.062*
C10	0.6601 (2)	0.3203 (3)	0.8053 (2)	0.0564 (5)
H10A	0.6487	0.3376	0.8885	0.068*
C11	0.5416 (2)	0.3483 (2)	0.7281 (2)	0.0475 (5)
C12	0.5617 (2)	0.3237 (2)	0.6039 (2)	0.0513 (5)
H12A	0.4831	0.3409	0.5519	0.062*
C13	0.6973 (2)	0.2736 (2)	0.55624 (19)	0.0480 (5)
H13A	0.7098	0.2594	0.4720	0.058*
C14	0.3952 (2)	0.4050 (2)	0.7809 (2)	0.0570 (6)
H14A	0.4119	0.4897	0.8081	0.068*
H14B	0.3293	0.4291	0.7120	0.068*
C16	0.2802 (2)	0.1734 (2)	0.8569 (2)	0.0523 (5)
H16A	0.3689	0.1267	0.8251	0.063*
H16B	0.2158	0.1995	0.7870	0.063*
C17	0.2012 (3)	0.0752 (2)	0.9722 (3)	0.0633 (6)
H17A	0.1733	−0.0066	0.9457	0.076*
H17B	0.2678	0.0446	1.0400	0.076*
C18	0.1109 (3)	0.2580 (3)	1.0663 (2)	0.0645 (6)
H18A	0.1768	0.2267	1.1345	0.077*
H18B	0.0222	0.3002	1.1034	0.077*
C19	0.1868 (2)	0.3662 (2)	0.9572 (2)	0.0550 (5)
H19A	0.1184	0.4039	0.8922	0.066*
H19B	0.2162	0.4423	0.9914	0.066*
N1	0.9501 (3)	0.4903 (3)	0.3325 (2)	0.0805 (7)
N2	0.32178 (17)	0.30144 (17)	0.89484 (16)	0.0432 (4)
H2	0.384 (2)	0.273 (3)	0.958 (2)	0.064 (7)*
O1	0.07139 (17)	0.14212 (18)	1.02265 (16)	0.0638 (4)
B1	0.5558 (3)	0.2295 (3)	1.1710 (3)	0.0583 (6)
F1	0.4631 (2)	0.33813 (19)	1.1168 (2)	0.1044 (7)
F2	0.70030 (18)	0.2643 (2)	1.13544 (18)	0.0962 (6)
F3	0.5250 (3)	0.1264 (2)	1.1129 (3)	0.1298 (9)
F4	0.5317 (2)	0.2022 (4)	1.29990 (17)	0.1466 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0508 (12)	0.0678 (14)	0.0446 (11)	−0.0121 (10)	−0.0021 (9)	−0.0030 (10)
C2	0.0432 (10)	0.0557 (11)	0.0435 (10)	−0.0053 (8)	−0.0042 (8)	−0.0122 (8)
C3	0.0464 (12)	0.0853 (16)	0.0557 (12)	−0.0068 (11)	0.0029 (9)	−0.0257 (12)
C4	0.0478 (12)	0.0833 (17)	0.0756 (16)	0.0131 (11)	−0.0107 (11)	−0.0360 (14)
C5	0.0664 (14)	0.0620 (13)	0.0698 (15)	0.0143 (11)	−0.0248 (12)	−0.0215 (12)
C6	0.0572 (12)	0.0519 (11)	0.0503 (11)	0.0005 (9)	−0.0105 (9)	−0.0090 (9)
C7	0.0411 (10)	0.0486 (10)	0.0421 (10)	−0.0043 (8)	−0.0064 (7)	−0.0107 (8)
C8	0.0398 (9)	0.0442 (10)	0.0409 (9)	−0.0062 (7)	−0.0018 (7)	−0.0049 (8)
C9	0.0424 (10)	0.0708 (13)	0.0423 (10)	−0.0109 (9)	−0.0033 (8)	−0.0099 (9)
C10	0.0463 (11)	0.0756 (15)	0.0490 (11)	−0.0132 (10)	0.0053 (8)	−0.0196 (10)
C11	0.0411 (10)	0.0427 (10)	0.0556 (11)	−0.0074 (8)	0.0039 (8)	−0.0077 (8)
C12	0.0441 (10)	0.0528 (11)	0.0541 (11)	−0.0020 (8)	−0.0094 (8)	−0.0047 (9)
C13	0.0476 (11)	0.0542 (11)	0.0423 (10)	−0.0019 (8)	−0.0062 (8)	−0.0106 (8)
C14	0.0495 (11)	0.0417 (10)	0.0723 (14)	−0.0059 (8)	0.0111 (10)	−0.0054 (10)
C16	0.0475 (11)	0.0501 (11)	0.0614 (12)	−0.0106 (8)	0.0070 (9)	−0.0208 (10)
C17	0.0554 (13)	0.0523 (12)	0.0777 (15)	−0.0121 (10)	0.0077 (11)	−0.0101 (11)
C18	0.0563 (13)	0.0836 (16)	0.0521 (12)	−0.0033 (11)	0.0075 (10)	−0.0183 (12)
C19	0.0485 (11)	0.0586 (12)	0.0594 (12)	0.0031 (9)	0.0049 (9)	−0.0224 (10)
N1	0.0768 (15)	0.0817 (15)	0.0685 (13)	−0.0147 (12)	−0.0147 (11)	0.0177 (12)
N2	0.0370 (8)	0.0448 (8)	0.0486 (9)	−0.0033 (6)	−0.0026 (7)	−0.0125 (7)
O1	0.0457 (8)	0.0748 (11)	0.0671 (10)	−0.0151 (7)	0.0091 (7)	−0.0123 (8)
B1	0.0525 (14)	0.0645 (15)	0.0594 (15)	0.0077 (11)	−0.0145 (11)	−0.0158 (12)
F1	0.1023 (14)	0.0844 (12)	0.1375 (16)	0.0327 (10)	−0.0665 (12)	−0.0316 (11)
F2	0.0606 (10)	0.1263 (15)	0.0970 (12)	−0.0091 (9)	−0.0087 (8)	−0.0145 (11)
F3	0.1141 (16)	0.0880 (13)	0.211 (3)	−0.0028 (11)	−0.0255 (16)	−0.0766 (16)
F4	0.0801 (13)	0.281 (3)	0.0580 (10)	0.0229 (16)	−0.0057 (8)	−0.0060 (14)

C1—N1	1.140 (3)	C13—H13A	0.9300
C1—C2	1.441 (3)	C14—N2	1.506 (3)
C2—C7	1.403 (3)	C14—H14A	0.9700
C2—C3	1.403 (3)	C14—H14B	0.9700
C3—C4	1.372 (4)	C16—N2	1.493 (3)
C3—H3A	0.9300	C16—C17	1.509 (3)
C4—C5	1.371 (4)	C16—H16A	0.9700
C4—H4A	0.9300	C16—H16B	0.9700
C5—C6	1.386 (3)	C17—O1	1.428 (3)
C5—H5A	0.9300	C17—H17A	0.9700
C6—C7	1.393 (3)	C17—H17B	0.9700
C6—H6A	0.9300	C18—O1	1.408 (3)
C7—C8	1.486 (3)	C18—C19	1.510 (3)
C8—C9	1.392 (3)	C18—H18A	0.9700
C8—C13	1.395 (3)	C18—H18B	0.9700
C9—C10	1.374 (3)	C19—N2	1.505 (3)
C9—H9A	0.9300	C19—H19A	0.9700
C10—C11	1.396 (3)	C19—H19B	0.9700
C10—H10A	0.9300	N2—H2	0.904 (16)
C11—C12	1.386 (3)	B1—F4	1.324 (3)
C11—C14	1.509 (3)	B1—F3	1.363 (3)
C12—C13	1.384 (3)	B1—F2	1.363 (3)
C12—H12A	0.9300	B1—F1	1.374 (3)
N1—C1—C2	178.5 (3)	N2—C14—H14B	109.2
C7—C2—C3	120.7 (2)	C11—C14—H14B	109.2
C7—C2—C1	120.47 (18)	H14A—C14—H14B	107.9
C3—C2—C1	118.78 (19)	N2—C16—C17	110.42 (18)
C4—C3—C2	120.0 (2)	N2—C16—H16A	109.6
C4—C3—H3A	120.0	C17—C16—H16A	109.6
C2—C3—H3A	120.0	N2—C16—H16B	109.6
C5—C4—C3	120.1 (2)	C17—C16—H16B	109.6
C5—C4—H4A	120.0	H16A—C16—H16B	108.1
C3—C4—H4A	120.0	O1—C17—C16	110.81 (19)
C4—C5—C6	120.5 (2)	O1—C17—H17A	109.5
C4—C5—H5A	119.8	C16—C17—H17A	109.5
C6—C5—H5A	119.8	O1—C17—H17B	109.5
C5—C6—C7	121.3 (2)	C16—C17—H17B	109.5
C5—C6—H6A	119.4	H17A—C17—H17B	108.1
C7—C6—H6A	119.4	O1—C18—C19	111.95 (18)
C6—C7—C2	117.45 (19)	O1—C18—H18A	109.2
C6—C7—C8	120.07 (17)	C19—C18—H18A	109.2
C2—C7—C8	122.40 (18)	O1—C18—H18B	109.2
C9—C8—C13	118.51 (18)	C19—C18—H18B	109.2
C9—C8—C7	119.17 (17)	H18A—C18—H18B	107.9
C13—C8—C7	122.31 (18)	N2—C19—C18	110.08 (18)
C10—C9—C8	121.01 (19)	N2—C19—H19A	109.6
C10—C9—H9A	119.5	C18—C19—H19A	109.6
C8—C9—H9A	119.5	N2—C19—H19B	109.6
C9—C10—C11	120.4 (2)	C18—C19—H19B	109.6
C9—C10—H10A	119.8	H19A—C19—H19B	108.2
C11—C10—H10A	119.8	C16—N2—C19	109.84 (16)
C12—C11—C10	118.88 (19)	C16—N2—C14	112.09 (17)
C12—C11—C14	121.43 (19)	C19—N2—C14	111.26 (16)
C10—C11—C14	119.7 (2)	C16—N2—H2	107.1 (16)
C13—C12—C11	120.69 (19)	C19—N2—H2	105.8 (16)
C13—C12—H12A	119.7	C14—N2—H2	110.5 (16)
C11—C12—H12A	119.7	C18—O1—C17	110.10 (17)
C12—C13—C8	120.45 (19)	F4—B1—F3	116.5 (3)
C12—C13—H13A	119.8	F4—B1—F2	108.7 (2)
C8—C13—H13A	119.8	F3—B1—F2	109.0 (2)
N2—C14—C11	112.09 (17)	F4—B1—F1	109.9 (2)
N2—C14—H14A	109.2	F3—B1—F1	102.7 (2)
C11—C14—H14A	109.2	F2—B1—F1	109.9 (2)
C7—C2—C3—C4	0.8 (3)	C9—C10—C11—C14	179.33 (19)
C1—C2—C3—C4	179.9 (2)	C10—C11—C12—C13	−0.8 (3)
C2—C3—C4—C5	0.1 (3)	C14—C11—C12—C13	179.01 (18)
C3—C4—C5—C6	−1.1 (4)	C11—C12—C13—C8	1.3 (3)
C4—C5—C6—C7	1.2 (3)	C9—C8—C13—C12	−0.2 (3)
C5—C6—C7—C2	−0.3 (3)	C7—C8—C13—C12	179.14 (18)
C5—C6—C7—C8	−177.10 (19)	C12—C11—C14—N2	114.6 (2)
C3—C2—C7—C6	−0.7 (3)	C10—C11—C14—N2	−65.7 (3)
C1—C2—C7—C6	−179.81 (19)	N2—C16—C17—O1	58.1 (3)
C3—C2—C7—C8	176.01 (18)	O1—C18—C19—N2	−56.8 (3)
C1—C2—C7—C8	−3.1 (3)	C17—C16—N2—C19	−53.4 (2)
C6—C7—C8—C9	54.6 (3)	C17—C16—N2—C14	−177.59 (18)
C2—C7—C8—C9	−122.0 (2)	C18—C19—N2—C16	52.3 (2)
C6—C7—C8—C13	−124.7 (2)	C18—C19—N2—C14	176.95 (18)
C2—C7—C8—C13	58.6 (3)	C11—C14—N2—C16	−64.1 (2)
C13—C8—C9—C10	−1.5 (3)	C11—C14—N2—C19	172.46 (17)
C7—C8—C9—C10	179.17 (19)	C19—C18—O1—C17	61.2 (2)
C8—C9—C10—C11	2.0 (3)	C16—C17—O1—C18	−61.4 (3)
C9—C10—C11—C12	−0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···F1	0.90 (2)	2.14 (2)	2.902 (3)	141 (2)
N2—H2···F3	0.90 (2)	2.35 (2)	3.219 (3)	161 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯F1	0.90 (2)	2.14 (2)	2.902 (3)	141 (2)
N2—H2⋯F3	0.90 (2)	2.35 (2)	3.219 (3)	161 (2)