4-[(2'-Cyano-biphenyl-4-yl)methyl]-morpholin-4-ium nitrate.

The title ion pair, C(18)H(19)N(2)O(+)·NO(3) (-), features an N-H⋯O hydrogen bond linking the cation to the anion. The morpholine portion adopts a chair conformation; the aromatic rings of the biphenyl-ene portion are twisted [torsion angles for the four atoms involving the ar-yl-aryl bond = 35.1 (2)-40.4 (2)°].

Related literature

For the synthesis, see: Li et al. (2008 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C18H19N2O+·NO3 −

M = 341.36

Monoclinic,

a = 12.670 (6) Å

b = 13.120 (5) Å

c = 10.865 (5) Å

β = 110.927 (8)°

V = 1687.0 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.981, T max = 0.981

18242 measured reflections

3852 independent reflections

2848 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.178

S = 1.17

3852 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.24 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810027443/ng2795sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027443/ng2795Isup2.hkl

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

C18H19N2O+·NO3−	F(000) = 720
Mr = 341.36	Dx = 1.344 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3727 reflections
a = 12.670 (6) Å	θ = 2.3–27.5°
b = 13.120 (5) Å	µ = 0.10 mm−1
c = 10.865 (5) Å	T = 293 K
β = 110.927 (8)°	Prism, colourless
V = 1687.0 (12) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	3852 independent reflections
Radiation source: fine-focus sealed tube	2848 reflections with I > 2σ(I)
graphite	Rint = 0.052
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 1.7°
ω scans	h = −16→16
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −17→17
Tmin = 0.981, Tmax = 0.981	l = −14→14
18242 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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0839P)2 + 0.0408P] where P = (Fo2 + 2Fc2)/3
3852 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.24 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
N2	0.45201 (13)	0.21560 (12)	0.92144 (15)	0.0332 (4)
H2A	0.4862	0.2716	0.9032	0.040*
O1	0.63116 (14)	0.06839 (12)	0.98832 (15)	0.0521 (5)
C5	0.12498 (16)	0.35987 (15)	0.5246 (2)	0.0358 (5)
C6	0.12785 (18)	0.25575 (16)	0.5517 (2)	0.0417 (5)
H6A	0.0840	0.2110	0.4873	0.050*
C7	0.45639 (18)	0.13253 (16)	0.8303 (2)	0.0392 (5)
H7A	0.4217	0.1556	0.7399	0.047*
H7B	0.4140	0.0742	0.8423	0.047*
C9	0.26229 (17)	0.28322 (17)	0.7722 (2)	0.0393 (5)
C10	0.51627 (19)	0.18427 (17)	1.06051 (19)	0.0430 (5)
H10A	0.4767	0.1291	1.0849	0.052*
H10B	0.5206	0.2412	1.1190	0.052*
C11	0.19283 (18)	0.42418 (16)	0.6230 (2)	0.0419 (5)
H11A	0.1930	0.4937	0.6065	0.050*
C12	0.26004 (18)	0.38675 (17)	0.7450 (2)	0.0441 (5)
H12A	0.3041	0.4314	0.8093	0.053*
C13	0.05740 (17)	0.40207 (15)	0.3931 (2)	0.0371 (5)
C15	0.5770 (2)	0.10142 (19)	0.8560 (2)	0.0485 (6)
H15A	0.5782	0.0467	0.7964	0.058*
H15B	0.6181	0.1588	0.8389	0.058*
C16	−0.05099 (18)	0.36520 (16)	0.3153 (2)	0.0416 (5)
C17	0.19541 (18)	0.21840 (17)	0.6737 (2)	0.0447 (5)
H17A	0.1961	0.1488	0.6901	0.054*
C18	0.33288 (18)	0.24421 (19)	0.9069 (2)	0.0459 (6)
H18A	0.2960	0.1849	0.9265	0.055*
H18B	0.3359	0.2962	0.9716	0.055*
C19	0.1012 (2)	0.47979 (17)	0.3390 (2)	0.0482 (6)
H19A	0.1713	0.5072	0.3883	0.058*
C20	−0.1077 (2)	0.40316 (19)	0.1893 (2)	0.0533 (6)
H20A	−0.1783	0.3774	0.1390	0.064*
C21	0.63421 (19)	0.14995 (18)	1.0763 (2)	0.0494 (6)
H21A	0.6758	0.2068	1.0588	0.059*
H21B	0.6734	0.1278	1.1663	0.059*
C22	0.0438 (2)	0.5178 (2)	0.2140 (3)	0.0586 (7)
H22A	0.0755	0.5701	0.1807	0.070*
C23	−0.11159 (19)	0.29425 (19)	0.3668 (2)	0.0513 (6)
N1	−0.1659 (2)	0.2409 (2)	0.4032 (3)	0.0747 (7)
C25	−0.0596 (2)	0.4786 (2)	0.1392 (3)	0.0606 (7)
H25A	−0.0972	0.5031	0.0545	0.073*
O2	0.54586 (15)	0.38211 (13)	0.83891 (15)	0.0550 (5)
N3	0.60177 (17)	0.43391 (14)	0.93873 (18)	0.0465 (5)
O4	0.60072 (17)	0.40818 (14)	1.04806 (16)	0.0646 (5)
O3	0.65691 (17)	0.50803 (15)	0.92616 (18)	0.0771 (6)

	U11	U22	U33	U12	U13	U23
N2	0.0332 (9)	0.0350 (9)	0.0292 (9)	−0.0012 (7)	0.0086 (7)	0.0015 (7)
O1	0.0519 (10)	0.0499 (10)	0.0448 (9)	0.0160 (7)	0.0054 (8)	0.0012 (7)
C5	0.0265 (9)	0.0401 (11)	0.0396 (11)	0.0025 (8)	0.0102 (8)	−0.0027 (9)
C6	0.0344 (11)	0.0383 (12)	0.0457 (12)	−0.0037 (9)	0.0063 (9)	−0.0019 (9)
C7	0.0430 (12)	0.0375 (11)	0.0322 (11)	−0.0007 (9)	0.0075 (9)	−0.0028 (8)
C9	0.0290 (10)	0.0500 (12)	0.0385 (12)	0.0021 (9)	0.0115 (9)	0.0009 (9)
C10	0.0486 (13)	0.0479 (13)	0.0275 (10)	0.0041 (10)	0.0073 (9)	0.0029 (9)
C11	0.0402 (11)	0.0350 (11)	0.0454 (12)	0.0045 (9)	0.0089 (10)	−0.0062 (9)
C12	0.0394 (11)	0.0441 (12)	0.0418 (12)	0.0035 (9)	0.0059 (10)	−0.0089 (9)
C13	0.0327 (10)	0.0347 (11)	0.0406 (11)	0.0066 (8)	0.0092 (9)	−0.0026 (9)
C15	0.0489 (13)	0.0535 (14)	0.0397 (12)	0.0093 (11)	0.0116 (11)	−0.0016 (10)
C16	0.0348 (11)	0.0423 (12)	0.0436 (12)	0.0057 (9)	0.0089 (10)	−0.0037 (9)
C17	0.0367 (11)	0.0400 (12)	0.0508 (13)	−0.0032 (9)	0.0077 (10)	0.0064 (10)
C18	0.0361 (11)	0.0621 (15)	0.0405 (12)	0.0040 (10)	0.0149 (10)	0.0049 (10)
C19	0.0422 (12)	0.0469 (13)	0.0503 (14)	0.0010 (10)	0.0102 (11)	0.0017 (10)
C20	0.0441 (13)	0.0616 (16)	0.0428 (13)	0.0069 (11)	0.0015 (11)	−0.0046 (11)
C21	0.0446 (13)	0.0540 (14)	0.0388 (12)	0.0050 (10)	0.0018 (10)	−0.0002 (10)
C22	0.0632 (16)	0.0534 (15)	0.0562 (15)	0.0029 (12)	0.0178 (13)	0.0099 (12)
C23	0.0306 (11)	0.0584 (15)	0.0557 (15)	0.0016 (10)	0.0043 (11)	−0.0023 (12)
N1	0.0444 (13)	0.0834 (18)	0.0884 (18)	−0.0072 (12)	0.0139 (13)	0.0157 (14)
C25	0.0644 (17)	0.0659 (17)	0.0423 (13)	0.0150 (13)	0.0075 (12)	0.0088 (12)
O2	0.0617 (11)	0.0570 (10)	0.0381 (9)	−0.0137 (8)	0.0075 (8)	−0.0069 (7)
N3	0.0480 (11)	0.0412 (11)	0.0392 (11)	−0.0038 (8)	0.0022 (9)	0.0047 (8)
O4	0.0876 (14)	0.0602 (11)	0.0383 (9)	−0.0121 (9)	0.0129 (9)	0.0019 (8)
O3	0.0796 (14)	0.0641 (12)	0.0676 (13)	−0.0319 (10)	0.0018 (11)	0.0168 (10)

N2—C7	1.487 (3)	C13—C19	1.388 (3)
N2—C10	1.495 (3)	C13—C16	1.416 (3)
N2—C18	1.508 (3)	C15—H15A	0.9700
N2—H2A	0.9100	C15—H15B	0.9700
O1—C15	1.422 (3)	C16—C20	1.391 (3)
O1—C21	1.426 (3)	C16—C23	1.441 (3)
C5—C11	1.392 (3)	C17—H17A	0.9300
C5—C6	1.395 (3)	C18—H18A	0.9700
C5—C13	1.485 (3)	C18—H18B	0.9700
C6—C17	1.386 (3)	C19—C22	1.384 (3)
C6—H6A	0.9300	C19—H19A	0.9300
C7—C15	1.508 (3)	C20—C25	1.372 (4)
C7—H7A	0.9700	C20—H20A	0.9300
C7—H7B	0.9700	C21—H21A	0.9700
C9—C12	1.388 (3)	C21—H21B	0.9700
C9—C17	1.392 (3)	C22—C25	1.372 (4)
C9—C18	1.506 (3)	C22—H22A	0.9300
C10—C21	1.511 (3)	C23—N1	1.146 (3)
C10—H10A	0.9700	C25—H25A	0.9300
C10—H10B	0.9700	O2—N3	1.261 (2)
C11—C12	1.384 (3)	N3—O3	1.233 (2)
C11—H11A	0.9300	N3—O4	1.240 (2)
C12—H12A	0.9300
C7—N2—C10	109.59 (16)	C7—C15—H15A	109.4
C7—N2—C18	112.76 (16)	O1—C15—H15B	109.4
C10—N2—C18	109.72 (16)	C7—C15—H15B	109.4
C7—N2—H2A	108.2	H15A—C15—H15B	108.0
C10—N2—H2A	108.2	C20—C16—C13	121.0 (2)
C18—N2—H2A	108.2	C20—C16—C23	117.0 (2)
C15—O1—C21	109.68 (17)	C13—C16—C23	121.7 (2)
C11—C5—C6	117.98 (19)	C6—C17—C9	121.2 (2)
C11—C5—C13	119.90 (19)	C6—C17—H17A	119.4
C6—C5—C13	122.03 (19)	C9—C17—H17A	119.4
C17—C6—C5	120.6 (2)	C9—C18—N2	114.26 (17)
C17—C6—H6A	119.7	C9—C18—H18A	108.7
C5—C6—H6A	119.7	N2—C18—H18A	108.7
N2—C7—C15	110.57 (17)	C9—C18—H18B	108.7
N2—C7—H7A	109.5	N2—C18—H18B	108.7
C15—C7—H7A	109.5	H18A—C18—H18B	107.6
N2—C7—H7B	109.5	C22—C19—C13	122.1 (2)
C15—C7—H7B	109.5	C22—C19—H19A	119.0
H7A—C7—H7B	108.1	C13—C19—H19A	119.0
C12—C9—C17	118.2 (2)	C25—C20—C16	120.1 (2)
C12—C9—C18	120.0 (2)	C25—C20—H20A	119.9
C17—C9—C18	121.8 (2)	C16—C20—H20A	119.9
N2—C10—C21	110.85 (18)	O1—C21—C10	111.03 (18)
N2—C10—H10A	109.5	O1—C21—H21A	109.4
C21—C10—H10A	109.5	C10—C21—H21A	109.4
N2—C10—H10B	109.5	O1—C21—H21B	109.4
C21—C10—H10B	109.5	C10—C21—H21B	109.4
H10A—C10—H10B	108.1	H21A—C21—H21B	108.0
C12—C11—C5	121.4 (2)	C25—C22—C19	120.1 (3)
C12—C11—H11A	119.3	C25—C22—H22A	120.0
C5—C11—H11A	119.3	C19—C22—H22A	120.0
C11—C12—C9	120.7 (2)	N1—C23—C16	175.7 (3)
C11—C12—H12A	119.7	C20—C25—C22	120.1 (2)
C9—C12—H12A	119.7	C20—C25—H25A	120.0
C19—C13—C16	116.55 (19)	C22—C25—H25A	120.0
C19—C13—C5	120.05 (19)	O3—N3—O4	121.4 (2)
C16—C13—C5	123.37 (19)	O3—N3—O2	119.7 (2)
O1—C15—C7	111.16 (18)	O4—N3—O2	118.84 (19)
O1—C15—H15A	109.4
C11—C5—C6—C17	0.8 (3)	C5—C13—C16—C23	9.9 (3)
C13—C5—C6—C17	177.3 (2)	C5—C6—C17—C9	−0.2 (3)
C10—N2—C7—C15	−53.1 (2)	C12—C9—C17—C6	−0.3 (3)
C18—N2—C7—C15	−175.65 (17)	C18—C9—C17—C6	177.73 (19)
C7—N2—C10—C21	52.7 (2)	C12—C9—C18—N2	−90.3 (3)
C18—N2—C10—C21	177.06 (18)	C17—C9—C18—N2	91.7 (3)
C6—C5—C11—C12	−0.9 (3)	C7—N2—C18—C9	−61.1 (2)
C13—C5—C11—C12	−177.56 (19)	C10—N2—C18—C9	176.48 (18)
C5—C11—C12—C9	0.5 (3)	C16—C13—C19—C22	−1.7 (3)
C17—C9—C12—C11	0.1 (3)	C5—C13—C19—C22	176.6 (2)
C18—C9—C12—C11	−177.9 (2)	C13—C16—C20—C25	−1.0 (3)
C11—C5—C13—C19	36.9 (3)	C23—C16—C20—C25	173.4 (2)
C6—C5—C13—C19	−139.6 (2)	C15—O1—C21—C10	60.9 (2)
C11—C5—C13—C16	−144.9 (2)	N2—C10—C21—O1	−57.1 (2)
C6—C5—C13—C16	38.6 (3)	C13—C19—C22—C25	−0.1 (4)
C21—O1—C15—C7	−61.6 (2)	C20—C16—C23—N1	−30 (4)
N2—C7—C15—O1	58.4 (2)	C13—C16—C23—N1	144 (4)
C19—C13—C16—C20	2.3 (3)	C16—C20—C25—C22	−1.0 (4)
C5—C13—C16—C20	−176.0 (2)	C19—C22—C25—C20	1.5 (4)
C19—C13—C16—C23	−171.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.91	1.88	2.784 (2)	172
N2—H2A···O4	0.91	2.48	3.158 (3)	131
N2—H2A···N3	0.91	2.53	3.404 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2	0.91	1.88	2.784 (2)	172