4-[(2′-Cyano­biphenyl-4-yl)meth­yl]morpholin-4-ium hexa­fluoridophosphate

Xue, H.Y.; Wang, S.J.

doi:10.1107/S160053681201358X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1382

doi:10.1107/S160053681201358X

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4-[(2′-Cyanobiphenyl-4-yl)methyl]morpholin-4-ium hexafluoridophosphate

Hua Yu Xue ^a and Shi Juan Wang ^a ^*

^aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Nanjing 210048, People's Republic of China
^*Correspondence e-mail: xuehuayu@njcc.edu.cn

(Received 20 March 2012; accepted 29 March 2012; online 13 April 2012)

In the cation of the title compound, C₁₈H₁₉N₂O⁺·PF₆⁻, the morpholine ring adopts the usual chair conformation and the dihedral angle between the benzene rings is 67.55 (11)°. The F atoms of the anion are disordered over two orientations with a refined occupancy ratio of 0.65 (2):0.35 (2). In the crystal, intermolecular N—H⋯N hydrogen bonds link the cations into chains parallel to the c axis. The crystal packing is further enforced by interionic C—H⋯F hydrogen bonds.

Related literature

For the screening of molecular salts with physicochemical properties, see: Tong & Whitesell (1998 ); Shanker (1994 ). For the structures of related salts, see: SiMa (2010 ); Li et al. (2011 ).

Experimental

Crystal data

C₁₈H₁₉N₂O⁺·PF₆⁻
M_r = 424.32
Monoclinic, C 2/c
a = 24.912 (11) Å
b = 10.757 (5) Å
c = 14.925 (7) Å
β = 91.07 (3)°
V = 3999 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.813, T_max = 1.000
21155 measured reflections
4512 independent reflections
3216 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.084
wR(F²) = 0.218
S = 1.19
4512 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1ⁱ	0.91	2.04	2.942 (4)	171
C10—H10A⋯F1ⁱⁱ	0.93	2.43	3.296 (9)	155
C14—H14A⋯F3	0.97	2.39	3.355 (12)	171
C15—H15A⋯F6	0.97	2.46	3.377 (8)	158
C15—H15B⋯F3ⁱⁱ	0.97	2.48	3.412 (10)	161
C15—H15B⋯F3′ⁱⁱ	0.97	2.54	3.51 (2)	172
C10—H10A⋯F1′ⁱⁱ	0.93	2.45	3.26 (2)	145
C14—H14B⋯F1′ⁱⁱ	0.97	2.38	3.097 (16)	130
C5—H5A⋯F2′ⁱⁱⁱ	0.93	2.48	3.41 (2)	178
C17—H17B⋯F6′^iv	0.97	2.47	3.29 (3)	143
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iv) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681201358X/rz2727sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201358X/rz2727Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201358X/rz2727Isup3.cml

checkCIF report

Comment top

The title compound was prepared as part of our ongoing studies of hydrogen-bonding interactions in the crystal structure of protonated amines. The importance of molecular salts in pharmaceutical formulations is well known. For a given active ingredient, the isolation and selection of a salt with the appropriate physicochemical properties involves significant screening activity, as discussed at some length in the literature (Tong & Whitesell, 1998; Shanker, 1994). Here we report the synthesis and crystal structure of the title compound, 4-[(2'-cyanobiphenyl-4-yl)methyl]morpholin-4-ium hexafluorophosphate.

In the title compound (Fig. 1), bond distances and angles agree very well with those reported for a closely related nitrate (SiMa, 2010) and tetrafluoridoborate (Li et al., 2011) derivatives. In the cation, the morpholine ring adopts the usual chair conformation, and the dihedral angle formed by the phenyl rings is 67.55 (11)°. The hexafluorophosphate anion displays a distorted octahedral geometry, the fluorine atoms being disordered over two orientations with site occupancies of 0.65 (2) and 0.35 (2) for the major and minor components of disorder, respectively. In the structure, the cations interact through intermolecular N–H···N hydrogen bonds (Table 1) to form chains parallel to the c axis (Fig. 2). Crystal packing is further consolidated by interionic C–H···O hydrogen bonds.

Related literature top

For the screening of molecular salts with physicochemical properties, see: Tong & Whitesell (1998); Shanker (1994). For the structures of related salts, see: SiMa (2010); Li et al. (2011).

Experimental top

To a stirred solution of 4'-(morpholinomethyl)biphenyl-2-carbonitrile (5.56 g, 0.02 mol) in methanol (30 mL), hexafluorophosphoric acid (4.17 g, 0.02 mol) was added at the room temperature. The precipitate was filtered and washed with a small amount of ethanol 95%. Single crystals suitable for X-ray diffraction analysis were obtained from slow evaporation of a solution of the title compound in water at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Partial crystal packing of the title compound showing a chain of cations interacting via intermolecular N—H···N hydrogen bonds (dashed lines).

4-[(2'-Cyanobiphenyl-4-yl)methyl]morpholin-4-ium hexafluoridophosphate top

Crystal data top

C₁₈H₁₉N₂O⁺·PF⁶⁻	F(000) = 1744
M_r = 424.32	D_x = 1.410 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4512 reflections
a = 24.912 (11) Å	θ = 2.6–27.4°
b = 10.757 (5) Å	µ = 0.20 mm⁻¹
c = 14.925 (7) Å	T = 293 K
β = 91.07 (3)°	Prism, colourless
V = 3999 (3) Å³	0.20 × 0.20 × 0.20 mm
Z = 8

Data collection top

Rigaku Mercury2 diffractometer	4512 independent reflections
Radiation source: fine-focus sealed tube	3216 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.4°, θ_min = 2.1°
CCD_Profile_fitting scans	h = −32→31
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
T_min = 0.813, T_max = 1.000	l = −19→19
21155 measured reflections

Refinement top

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.218	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0935P)² + 1.2795P] where P = (F_o² + 2F_c²)/3
4512 reflections	(Δ/σ)_max < 0.001
308 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₈H₁₉N₂O⁺·PF⁶⁻	V = 3999 (3) Å³
M_r = 424.32	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.912 (11) Å	µ = 0.20 mm⁻¹
b = 10.757 (5) Å	T = 293 K
c = 14.925 (7) Å	0.20 × 0.20 × 0.20 mm
β = 91.07 (3)°

Data collection top

Rigaku Mercury2 diffractometer	4512 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3216 reflections with I > 2σ(I)
T_min = 0.813, T_max = 1.000	R_int = 0.052
21155 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.084	0 restraints
wR(F²) = 0.218	H-atom parameters constrained
S = 1.19	Δρ_max = 0.16 e Å⁻³
4512 reflections	Δρ_min = −0.17 e Å⁻³
308 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N2	0.32167 (9)	0.0538 (2)	0.37953 (14)	0.0586 (6)
H2A	0.3533	0.0143	0.3918	0.070*
C11	0.36122 (12)	0.1175 (3)	0.23215 (17)	0.0587 (7)
C2	0.49042 (11)	0.2243 (3)	−0.01594 (18)	0.0597 (7)
C8	0.44407 (11)	0.2199 (3)	0.13211 (17)	0.0568 (7)
N1	0.42775 (12)	0.0475 (3)	−0.07023 (19)	0.0804 (8)
C1	0.48586 (12)	0.2708 (3)	0.07186 (18)	0.0598 (7)
C3	0.52800 (13)	0.2724 (3)	−0.0749 (2)	0.0750 (9)
H3A	0.5302	0.2411	−0.1328	0.090*
C15	0.27767 (13)	−0.0213 (3)	0.4206 (2)	0.0729 (9)
H15A	0.2431	0.0145	0.4041	0.088*
H15B	0.2787	−0.1056	0.3977	0.088*
C7	0.45498 (12)	0.1267 (3)	−0.04641 (19)	0.0624 (7)
C10	0.40494 (13)	0.0482 (3)	0.21080 (19)	0.0679 (8)
H10A	0.4072	−0.0341	0.2296	0.082*
C9	0.44606 (13)	0.0986 (3)	0.16145 (19)	0.0685 (8)
H9A	0.4756	0.0497	0.1478	0.082*
C14	0.31444 (13)	0.0585 (3)	0.27939 (19)	0.0697 (8)
H14A	0.2821	0.1050	0.2649	0.084*
H14B	0.3095	−0.0255	0.2570	0.084*
C12	0.35927 (15)	0.2401 (3)	0.2056 (3)	0.0877 (11)
H12A	0.3301	0.2892	0.2210	0.105*
O1	0.28375 (13)	0.0972 (4)	0.55657 (19)	0.1302 (13)
C13	0.40029 (15)	0.2908 (3)	0.1561 (3)	0.0877 (11)
H13A	0.3984	0.3738	0.1388	0.105*
C6	0.52083 (15)	0.3653 (3)	0.0969 (2)	0.0810 (10)
H6A	0.5191	0.3980	0.1545	0.097*
C4	0.56173 (15)	0.3664 (3)	−0.0467 (3)	0.0850 (10)
H4A	0.5869	0.3986	−0.0856	0.102*
C18	0.32429 (16)	0.1780 (4)	0.4223 (3)	0.0940 (12)
H18A	0.2924	0.2252	0.4062	0.113*
H18B	0.3553	0.2229	0.4009	0.113*
C16	0.28390 (18)	−0.0235 (5)	0.5209 (2)	0.1058 (14)
H16A	0.2547	−0.0710	0.5462	0.127*
H16B	0.3174	−0.0644	0.5373	0.127*
C5	0.55830 (15)	0.4125 (4)	0.0386 (3)	0.0916 (11)
H5A	0.5813	0.4759	0.0574	0.110*
C17	0.3284 (2)	0.1644 (5)	0.5233 (3)	0.140 (2)
H17A	0.3613	0.1211	0.5394	0.168*
H17B	0.3296	0.2461	0.5507	0.168*
P1	0.15365 (4)	0.14226 (9)	0.20740 (6)	0.0750 (3)
F1	0.1241 (5)	0.2534 (10)	0.2540 (7)	0.141 (3)	0.65 (2)
F2	0.1364 (4)	0.1889 (13)	0.1147 (8)	0.152 (4)	0.65 (2)
F3	0.2064 (5)	0.2159 (11)	0.2041 (10)	0.136 (4)	0.65 (2)
F4	0.0987 (4)	0.0652 (11)	0.2203 (5)	0.113 (2)	0.65 (2)
F5	0.1803 (6)	0.0238 (11)	0.1705 (8)	0.135 (4)	0.65 (2)
F6	0.1702 (3)	0.0918 (8)	0.3061 (6)	0.108 (2)	0.65 (2)
F1'	0.1419 (7)	0.2894 (14)	0.208 (3)	0.161 (9)	0.35 (2)
F2'	0.1432 (9)	0.147 (2)	0.1016 (11)	0.144 (8)	0.35 (2)
F3'	0.2163 (6)	0.186 (2)	0.1825 (12)	0.106 (5)	0.35 (2)
F4'	0.0981 (6)	0.116 (3)	0.2162 (15)	0.168 (10)	0.35 (2)
F5'	0.1754 (15)	0.0133 (19)	0.192 (2)	0.183 (12)	0.35 (2)
F6'	0.1687 (9)	0.147 (4)	0.3025 (11)	0.185 (10)	0.35 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0516 (13)	0.0768 (16)	0.0475 (12)	0.0046 (12)	0.0073 (9)	0.0004 (11)
C11	0.0619 (17)	0.0708 (18)	0.0434 (14)	0.0016 (14)	0.0008 (12)	0.0058 (12)
C2	0.0577 (16)	0.0639 (17)	0.0575 (16)	0.0037 (13)	0.0061 (13)	0.0023 (13)
C8	0.0634 (17)	0.0610 (17)	0.0461 (14)	0.0001 (13)	0.0020 (12)	0.0002 (12)
N1	0.0799 (19)	0.094 (2)	0.0675 (17)	−0.0107 (16)	−0.0001 (14)	−0.0165 (15)
C1	0.0620 (17)	0.0611 (17)	0.0566 (16)	−0.0026 (14)	0.0022 (13)	0.0024 (13)
C3	0.072 (2)	0.084 (2)	0.070 (2)	−0.0006 (17)	0.0195 (16)	0.0039 (16)
C15	0.071 (2)	0.085 (2)	0.0637 (18)	−0.0106 (17)	0.0155 (15)	0.0033 (15)
C7	0.0638 (18)	0.076 (2)	0.0481 (15)	0.0040 (16)	0.0055 (13)	−0.0039 (14)
C10	0.087 (2)	0.0641 (17)	0.0537 (16)	0.0120 (16)	0.0176 (15)	0.0115 (13)
C9	0.077 (2)	0.0720 (19)	0.0575 (17)	0.0198 (16)	0.0156 (15)	0.0090 (14)
C14	0.0677 (19)	0.091 (2)	0.0504 (16)	−0.0039 (17)	−0.0038 (13)	0.0087 (15)
C12	0.078 (2)	0.085 (2)	0.101 (3)	0.0250 (19)	0.032 (2)	0.026 (2)
O1	0.123 (2)	0.188 (3)	0.0812 (18)	−0.057 (2)	0.0535 (16)	−0.049 (2)
C13	0.097 (3)	0.0618 (19)	0.106 (3)	0.0170 (18)	0.034 (2)	0.0198 (18)
C6	0.091 (2)	0.083 (2)	0.069 (2)	−0.0196 (19)	−0.0070 (18)	−0.0045 (17)
C4	0.077 (2)	0.085 (2)	0.094 (3)	−0.0058 (19)	0.0180 (19)	0.017 (2)
C18	0.095 (3)	0.093 (3)	0.096 (3)	−0.028 (2)	0.040 (2)	−0.034 (2)
C16	0.103 (3)	0.153 (4)	0.062 (2)	−0.017 (3)	0.027 (2)	0.012 (2)
C5	0.080 (2)	0.088 (3)	0.107 (3)	−0.029 (2)	−0.001 (2)	0.011 (2)
C17	0.140 (4)	0.196 (5)	0.085 (3)	−0.075 (4)	0.052 (3)	−0.065 (3)
P1	0.0695 (6)	0.0775 (6)	0.0778 (6)	0.0104 (4)	−0.0032 (4)	−0.0038 (4)
F1	0.158 (7)	0.082 (4)	0.184 (7)	0.038 (4)	0.042 (4)	−0.015 (4)
F2	0.140 (5)	0.199 (9)	0.116 (7)	0.038 (6)	−0.024 (4)	0.072 (6)
F3	0.095 (5)	0.089 (4)	0.223 (10)	−0.024 (4)	−0.005 (5)	0.038 (5)
F4	0.097 (4)	0.146 (6)	0.096 (4)	−0.045 (4)	−0.004 (3)	−0.003 (3)
F5	0.157 (6)	0.112 (7)	0.138 (5)	0.028 (6)	0.075 (5)	−0.029 (5)
F6	0.095 (4)	0.136 (5)	0.093 (4)	0.011 (3)	−0.012 (2)	0.032 (4)
F1'	0.129 (10)	0.071 (7)	0.28 (3)	0.023 (6)	0.021 (10)	−0.022 (10)
F2'	0.167 (14)	0.198 (15)	0.068 (6)	−0.089 (13)	0.002 (7)	−0.033 (9)
F3'	0.061 (5)	0.143 (13)	0.113 (7)	0.024 (6)	−0.004 (5)	0.031 (7)
F4'	0.059 (6)	0.22 (3)	0.224 (16)	−0.005 (9)	0.043 (7)	−0.003 (13)
F5'	0.22 (2)	0.063 (8)	0.27 (3)	0.026 (9)	0.080 (17)	0.050 (12)
F6'	0.195 (14)	0.30 (3)	0.059 (8)	0.041 (16)	−0.016 (7)	−0.055 (11)

Geometric parameters (Å, º) top

N2—C18	1.482 (4)	O1—C16	1.403 (5)
N2—C15	1.502 (4)	O1—C17	1.423 (5)
N2—C14	1.503 (3)	C13—H13A	0.9300
N2—H2A	0.9100	C6—C5	1.385 (5)
C11—C10	1.362 (4)	C6—H6A	0.9300
C11—C12	1.378 (4)	C4—C5	1.370 (5)
C11—C14	1.513 (4)	C4—H4A	0.9300
C2—C3	1.396 (4)	C18—C17	1.516 (5)
C2—C1	1.409 (4)	C18—H18A	0.9700
C2—C7	1.440 (4)	C18—H18B	0.9700
C8—C9	1.377 (4)	C16—H16A	0.9700
C8—C13	1.384 (4)	C16—H16B	0.9700
C8—C1	1.492 (4)	C5—H5A	0.9300
N1—C7	1.142 (4)	C17—H17A	0.9700
C1—C6	1.386 (4)	C17—H17B	0.9700
C3—C4	1.375 (5)	P1—F4'	1.421 (17)
C3—H3A	0.9300	P1—F6'	1.463 (16)
C15—C16	1.502 (5)	P1—F5'	1.51 (2)
C15—H15A	0.9700	P1—F2	1.527 (8)
C15—H15B	0.9700	P1—F3	1.536 (9)
C10—C9	1.384 (4)	P1—F5	1.543 (9)
C10—H10A	0.9300	P1—F1	1.574 (7)
C9—H9A	0.9300	P1—F2'	1.597 (15)
C14—H14A	0.9700	P1—F1'	1.610 (14)
C14—H14B	0.9700	P1—F4	1.615 (9)
C12—C13	1.384 (5)	P1—F6	1.616 (7)
C12—H12A	0.9300	P1—F3'	1.678 (17)

C18—N2—C15	109.6 (2)	C6—C5—H5A	119.8
C18—N2—C14	113.7 (3)	O1—C17—C18	111.0 (3)
C15—N2—C14	110.5 (2)	O1—C17—H17A	109.4
C18—N2—H2A	107.6	C18—C17—H17A	109.4
C15—N2—H2A	107.6	O1—C17—H17B	109.4
C14—N2—H2A	107.6	C18—C17—H17B	109.4
C10—C11—C12	118.7 (3)	H17A—C17—H17B	108.0
C10—C11—C14	120.4 (3)	F4'—P1—F6'	98.6 (13)
C12—C11—C14	120.8 (3)	F4'—P1—F5'	100.7 (18)
C3—C2—C1	121.4 (3)	F6'—P1—F5'	95.1 (17)
C3—C2—C7	119.0 (3)	F4'—P1—F2	83.7 (11)
C1—C2—C7	119.5 (3)	F6'—P1—F2	158.7 (14)
C9—C8—C13	117.6 (3)	F5'—P1—F2	105.3 (13)
C9—C8—C1	121.2 (3)	F4'—P1—F3	160.1 (12)
C13—C8—C1	121.1 (3)	F6'—P1—F3	79.0 (11)
C6—C1—C2	116.7 (3)	F5'—P1—F3	99.2 (14)
C6—C1—C8	123.3 (3)	F2—P1—F3	91.6 (6)
C2—C1—C8	120.0 (3)	F4'—P1—F5	107.3 (14)
C4—C3—C2	119.5 (3)	F6'—P1—F5	105.6 (15)
C4—C3—H3A	120.2	F2—P1—F5	93.7 (7)
C2—C3—H3A	120.2	F3—P1—F5	92.3 (8)
C16—C15—N2	110.7 (3)	F4'—P1—F1	69.1 (11)
C16—C15—H15A	109.5	F6'—P1—F1	70.1 (14)
N2—C15—H15A	109.5	F5'—P1—F1	159.6 (10)
C16—C15—H15B	109.5	F2—P1—F1	91.4 (6)
N2—C15—H15B	109.5	F3—P1—F1	91.8 (5)
H15A—C15—H15B	108.1	F5—P1—F1	173.4 (5)
N1—C7—C2	178.5 (3)	F4'—P1—F2'	87.5 (11)
C11—C10—C9	120.9 (3)	F6'—P1—F2'	173.3 (14)
C11—C10—H10A	119.6	F5'—P1—F2'	86.4 (14)
C9—C10—H10A	119.6	F3—P1—F2'	94.3 (8)
C8—C9—C10	121.2 (3)	F5—P1—F2'	74.8 (10)
C8—C9—H9A	119.4	F1—P1—F2'	110.0 (9)
C10—C9—H9A	119.4	F4'—P1—F1'	90.9 (12)
N2—C14—C11	113.5 (2)	F6'—P1—F1'	90.5 (12)
N2—C14—H14A	108.9	F5'—P1—F1'	166.2 (12)
C11—C14—H14A	108.9	F2—P1—F1'	68.3 (10)
N2—C14—H14B	108.9	F3—P1—F1'	69.4 (7)
C11—C14—H14B	108.9	F5—P1—F1'	153.1 (13)
H14A—C14—H14B	107.7	F2'—P1—F1'	86.7 (11)
C11—C12—C13	120.6 (3)	F6'—P1—F4	96.0 (13)
C11—C12—H12A	119.7	F5'—P1—F4	81.5 (13)
C13—C12—H12A	119.7	F2—P1—F4	93.0 (6)
C16—O1—C17	109.3 (3)	F3—P1—F4	175.0 (6)
C8—C13—C12	120.9 (3)	F5—P1—F4	89.4 (7)
C8—C13—H13A	119.5	F1—P1—F4	86.1 (6)
C12—C13—H13A	119.5	F2'—P1—F4	90.7 (7)
C5—C6—C1	121.8 (3)	F1'—P1—F4	110.5 (8)
C5—C6—H6A	119.1	F4'—P1—F6	94.7 (11)
C1—C6—H6A	119.1	F5'—P1—F6	74.9 (13)
C5—C4—C3	120.1 (3)	F2—P1—F6	178.3 (5)
C5—C4—H4A	119.9	F3—P1—F6	90.0 (5)
C3—C4—H4A	119.9	F5—P1—F6	86.8 (6)
N2—C18—C17	110.0 (3)	F1—P1—F6	88.0 (4)
N2—C18—H18A	109.7	F2'—P1—F6	161.3 (9)
C17—C18—H18A	109.7	F1'—P1—F6	111.8 (12)
N2—C18—H18B	109.7	F4—P1—F6	85.4 (4)
C17—C18—H18B	109.7	F4'—P1—F3'	170.8 (13)
H18A—C18—H18B	108.2	F6'—P1—F3'	89.0 (11)
O1—C16—C15	111.3 (3)	F5'—P1—F3'	83.6 (14)
O1—C16—H16A	109.4	F2—P1—F3'	87.4 (7)
C15—C16—H16A	109.4	F5—P1—F3'	75.2 (9)
O1—C16—H16B	109.4	F1—P1—F3'	109.2 (8)
C15—C16—H16B	109.4	F2'—P1—F3'	84.6 (9)
H16A—C16—H16B	108.0	F1'—P1—F3'	83.9 (9)
C4—C5—C6	120.4 (3)	F4—P1—F3'	164.7 (8)
C4—C5—H5A	119.8	F6—P1—F3'	94.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1ⁱ	0.91	2.04	2.942 (4)	171
C10—H10A···F1ⁱⁱ	0.93	2.43	3.296 (9)	155
C14—H14A···F3	0.97	2.39	3.355 (12)	171
C15—H15A···F6	0.97	2.46	3.377 (8)	158
C15—H15B···F3ⁱⁱ	0.97	2.48	3.412 (10)	161
C15—H15B···F3′ⁱⁱ	0.97	2.54	3.51 (2)	172
C10—H10A···F1′ⁱⁱ	0.93	2.45	3.26 (2)	145
C14—H14B···F1′ⁱⁱ	0.97	2.38	3.097 (16)	130
C5—H5A···F2′ⁱⁱⁱ	0.93	2.48	3.41 (2)	178
C17—H17B···F6′^iv	0.97	2.47	3.29 (3)	143

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉N₂O⁺·PF⁶⁻
M_r	424.32
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	24.912 (11), 10.757 (5), 14.925 (7)
β (°)	91.07 (3)
V (Å³)	3999 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.813, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	21155, 4512, 3216
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.084, 0.218, 1.19
No. of reflections	4512
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.17

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1ⁱ	0.91	2.04	2.942 (4)	170.5
C10—H10A···F1ⁱⁱ	0.93	2.43	3.296 (9)	155.3
C14—H14A···F3	0.97	2.39	3.355 (12)	170.6
C15—H15A···F6	0.97	2.46	3.377 (8)	158.2
C15—H15B···F3ⁱⁱ	0.97	2.48	3.412 (10)	161.0
C15—H15B···F3'ⁱⁱ	0.97	2.54	3.51 (2)	172
C10—H10A···F1'ⁱⁱ	0.93	2.45	3.26 (2)	145
C14—H14B···F1'ⁱⁱ	0.97	2.38	3.097 (16)	130
C5—H5A···F2'ⁱⁱⁱ	0.93	2.48	3.41 (2)	178
C17—H17B···F6'^iv	0.97	2.47	3.29 (3)	143

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

References

Li, X., Huang, X. & Li, K. (2011). Acta Cryst. E67, o1061. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Shanker, R. (1994). Pharm. Res. A11, S–236. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
SiMa, W. (2010). Acta Cryst. E66, o2042. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tong, W. & Whitesell, G. (1998). Pharm. Dev. Technol. A3, 215–223. CrossRef Google Scholar

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Volume 68| Part 5| May 2012| Page o1382

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