Literature DB >> 22606169

4-[(2'-Cyano-biphenyl-4-yl)meth-yl]morpholin-4-ium perchlorate.

Abstract

In the title salt, C(18)H(19)n class="Chemical">N(2)O(+)·ClO(4) (-), the morpholinium ring adopts a chair conformation, while the two benzene rings make a dihedral angle of 62.65 (17)°. Inter-molecular N-H⋯N hydrogen bonds and weak C-H⋯O inter-actions occur in the crystal structure.

Entities: CellLine Chemical Disease Species

Year: 2012 PMID： 22606169 PMCID： PMC3344166 DOI： 10.1107/S1600536812012792

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

The title complound was investigated as part of a search for dielectric ferroelectric materials. For background to ferroelectric materials, see: Haertling (1999 ▶); Homes et al. (2001 ▶).

Experimental

Crystal data

C18H19N2O+·n class="Chemical">ClO4 − M = 378.80 Monoclinic, a = 22.997 (5) Å b = 10.679 (2) Å c = 14.899 (3) Å β = 92.96 (3)° V = 3654.2 (13) Å3 Z = 8 Mo Kα radiation μ = 0.24 mm−1 T = 293 K 0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer 18531 measured reflections 4191 independent reflections 2478 reflections with I > 2σ(I) R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.070 wR(F 2) = 0.202 S = 1.04 4191 reflections 235 parameters 1 restraint H-atom parameters constrained Δρmax = 0.59 e Å−3 Δρmin = −0.34 e Å−3 Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012792/xu5487sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012792/xu5487Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812012792/xu5487Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₈H₁₉N₂O⁺·ClO₄⁻	F(000) = 1584
M_r = 378.80	D_x = 1.377 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4191 reflections
a = 22.997 (5) Å	θ = 2.6–27.5°
b = 10.679 (2) Å	µ = 0.24 mm⁻¹
c = 14.899 (3) Å	T = 293 K
β = 92.96 (3)°	Prism, colorless
V = 3654.2 (13) Å³	0.20 × 0.20 × 0.20 mm
Z = 8

Rigaku Mercury2 diffractometer	2478 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.066
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
Detector resolution: 13.6612 pixels mm^-1	h = −29→29
CCD_Profile_fitting scans	k = −13→13
18531 measured reflections	l = −19→19
4191 independent 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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.202	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0836P)² + 4.9367P] where P = (F_o² + 2F_c²)/3
4191 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.59 e Å⁻³
1 restraint	Δρ_min = −0.34 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	U_iso*/U_eq
Cl1	0.14467 (4)	0.33074 (8)	0.21821 (6)	0.0575 (3)
O2	0.15678 (19)	0.4547 (4)	0.2333 (4)	0.169 (2)
O3	0.08570 (14)	0.3054 (5)	0.2221 (3)	0.1361 (16)
O4	0.1785 (2)	0.2616 (5)	0.2795 (3)	0.165 (2)
O5	0.16055 (18)	0.3058 (5)	0.1321 (3)	0.1407 (16)
N1	0.18775 (11)	0.9619 (2)	0.12783 (16)	0.0469 (6)
H1	0.1571	0.9991	0.1172	0.070*
C11	0.09773 (15)	0.9566 (3)	0.2946 (2)	0.0544 (8)
H11A	0.0957	1.0410	0.2796	0.065*
C9	0.05497 (14)	0.7774 (3)	0.3637 (2)	0.0491 (8)
C12	0.01047 (14)	0.7227 (3)	0.4209 (2)	0.0484 (8)
C18	0.04350 (14)	0.8644 (3)	0.5429 (2)	0.0481 (8)
N2	0.07272 (13)	0.9427 (3)	0.57063 (19)	0.0621 (8)
C6	0.14489 (14)	0.8859 (3)	0.27003 (19)	0.0511 (8)
C17	0.00559 (13)	0.7666 (3)	0.5091 (2)	0.0456 (7)
O1	0.22810 (13)	0.9243 (3)	−0.04846 (17)	0.0813 (9)
C1	0.18162 (17)	0.8401 (3)	0.0800 (2)	0.0637 (10)
H1A	0.1465	0.7981	0.0974	0.076*
H1B	0.2146	0.7870	0.0966	0.076*
C16	−0.03494 (14)	0.7160 (3)	0.5651 (2)	0.0561 (8)
H16A	−0.0378	0.7466	0.6232	0.067*
C10	0.05393 (15)	0.9032 (3)	0.3408 (2)	0.0529 (8)
H10A	0.0229	0.9526	0.3571	0.063*
C7	0.14461 (17)	0.7581 (4)	0.2892 (2)	0.0691 (11)
H7A	0.1749	0.7079	0.2710	0.083*
C4	0.23714 (16)	1.0349 (4)	0.0925 (2)	0.0612 (9)
H4B	0.2737	0.9941	0.1100	0.073*
H4C	0.2378	1.1183	0.1183	0.073*
C8	0.10025 (18)	0.7053 (4)	0.3347 (3)	0.0687 (11)
H8A	0.1007	0.6197	0.3461	0.082*
C13	−0.02633 (18)	0.6260 (4)	0.3924 (3)	0.0658 (10)
H13A	−0.0239	0.5939	0.3347	0.079*
C5	0.19543 (15)	0.9467 (4)	0.2283 (2)	0.0598 (9)
H5B	0.2300	0.8969	0.2421	0.072*
H5C	0.2017	1.0286	0.2553	0.072*
C2	0.17854 (19)	0.8610 (4)	−0.0204 (3)	0.0775 (12)
H2B	0.1753	0.7808	−0.0508	0.093*
H2C	0.1440	0.9095	−0.0373	0.093*
C3	0.23077 (19)	1.0439 (4)	−0.0083 (3)	0.0776 (12)
H3B	0.1956	1.0901	−0.0254	0.093*
H3C	0.2636	1.0897	−0.0302	0.093*
C15	−0.07050 (16)	0.6209 (4)	0.5342 (3)	0.0669 (10)
H15A	−0.0974	0.5861	0.5714	0.080*
C14	−0.06639 (18)	0.5771 (4)	0.4484 (3)	0.0739 (11)
H14A	−0.0910	0.5132	0.4276	0.089*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0575 (5)	0.0613 (5)	0.0536 (5)	−0.0065 (4)	0.0016 (4)	0.0024 (4)
O2	0.138 (4)	0.073 (2)	0.288 (6)	0.009 (2)	−0.070 (4)	−0.045 (3)
O3	0.070 (2)	0.234 (5)	0.105 (3)	−0.045 (3)	0.0218 (18)	−0.030 (3)
O4	0.152 (4)	0.166 (4)	0.172 (4)	−0.017 (3)	−0.058 (3)	0.105 (4)
O5	0.131 (3)	0.204 (5)	0.093 (3)	−0.004 (3)	0.050 (2)	−0.013 (3)
N1	0.0430 (14)	0.0590 (16)	0.0390 (13)	0.0028 (12)	0.0041 (11)	0.0011 (12)
C11	0.065 (2)	0.057 (2)	0.0423 (17)	0.0102 (17)	0.0091 (15)	0.0034 (15)
C9	0.0586 (19)	0.0542 (19)	0.0345 (15)	0.0071 (16)	0.0033 (14)	0.0018 (14)
C12	0.0531 (18)	0.0508 (18)	0.0410 (17)	0.0039 (15)	0.0011 (14)	0.0037 (14)
C18	0.0490 (19)	0.058 (2)	0.0377 (16)	0.0062 (16)	0.0078 (14)	0.0009 (15)
N2	0.0631 (19)	0.070 (2)	0.0531 (17)	−0.0088 (16)	0.0029 (14)	−0.0086 (15)
C6	0.0535 (19)	0.070 (2)	0.0296 (15)	0.0066 (16)	0.0025 (13)	0.0023 (15)
C17	0.0445 (16)	0.0491 (18)	0.0435 (17)	0.0022 (14)	0.0039 (13)	0.0038 (14)
O1	0.088 (2)	0.102 (2)	0.0570 (16)	−0.0190 (17)	0.0321 (14)	−0.0119 (15)
C1	0.067 (2)	0.068 (2)	0.057 (2)	−0.0121 (19)	0.0167 (18)	−0.0106 (18)
C16	0.0545 (19)	0.061 (2)	0.054 (2)	0.0009 (17)	0.0109 (16)	0.0085 (17)
C10	0.059 (2)	0.059 (2)	0.0415 (17)	0.0151 (16)	0.0104 (15)	0.0036 (15)
C7	0.071 (2)	0.076 (3)	0.062 (2)	0.031 (2)	0.0225 (19)	0.018 (2)
C4	0.061 (2)	0.065 (2)	0.058 (2)	−0.0091 (18)	0.0111 (17)	−0.0017 (18)
C8	0.087 (3)	0.057 (2)	0.064 (2)	0.021 (2)	0.021 (2)	0.0148 (18)
C13	0.079 (3)	0.066 (2)	0.052 (2)	−0.010 (2)	−0.0044 (19)	−0.0075 (18)
C5	0.054 (2)	0.089 (3)	0.0355 (16)	−0.0001 (18)	−0.0010 (14)	0.0057 (17)
C2	0.082 (3)	0.101 (3)	0.051 (2)	−0.023 (2)	0.019 (2)	−0.020 (2)
C3	0.084 (3)	0.094 (3)	0.056 (2)	−0.013 (2)	0.019 (2)	0.012 (2)
C15	0.058 (2)	0.068 (2)	0.076 (3)	−0.0089 (19)	0.0103 (19)	0.015 (2)
C14	0.073 (3)	0.061 (2)	0.087 (3)	−0.018 (2)	−0.004 (2)	0.001 (2)

Cl1—O2	1.369 (4)	C1—C2	1.511 (5)
Cl1—O5	1.377 (4)	C1—H1A	0.9700
Cl1—O4	1.383 (4)	C1—H1B	0.9700
Cl1—O3	1.387 (3)	C16—C15	1.369 (5)
N1—C1	1.486 (4)	C16—H16A	0.9300
N1—C4	1.495 (4)	C10—H10A	0.9300
N1—C5	1.507 (4)	C7—C8	1.374 (5)
N1—H1	0.8180	C7—H7A	0.9300
C11—C10	1.373 (5)	C4—C3	1.505 (5)
C11—C6	1.385 (4)	C4—H4B	0.9700
C11—H11A	0.9300	C4—H4C	0.9700
C9—C8	1.382 (5)	C8—H8A	0.9300
C9—C10	1.386 (5)	C13—C14	1.378 (5)
C9—C12	1.485 (4)	C13—H13A	0.9300
C12—C13	1.388 (5)	C5—H5B	0.9700
C12—C17	1.404 (4)	C5—H5C	0.9700
C18—N2	1.136 (4)	C2—H2B	0.9700
C18—C17	1.435 (5)	C2—H2C	0.9700
C6—C7	1.395 (5)	C3—H3B	0.9700
C6—C5	1.494 (5)	C3—H3C	0.9700
C17—C16	1.393 (4)	C15—C14	1.369 (5)
O1—C2	1.407 (5)	C15—H15A	0.9300
O1—C3	1.411 (5)	C14—H14A	0.9300

O2—Cl1—O5	106.2 (3)	C9—C10—H10A	119.3
O2—Cl1—O4	107.8 (3)	C8—C7—C6	120.9 (3)
O5—Cl1—O4	110.1 (3)	C8—C7—H7A	119.5
O2—Cl1—O3	111.9 (3)	C6—C7—H7A	119.5
O5—Cl1—O3	107.9 (3)	N1—C4—C3	110.4 (3)
O4—Cl1—O3	112.8 (3)	N1—C4—H4B	109.6
C1—N1—C4	110.0 (3)	C3—C4—H4B	109.6
C1—N1—C5	112.7 (3)	N1—C4—H4C	109.6
C4—N1—C5	110.7 (3)	C3—C4—H4C	109.6
C1—N1—H1	105.8	H4B—C4—H4C	108.1
C4—N1—H1	109.9	C7—C8—C9	121.1 (3)
C5—N1—H1	107.5	C7—C8—H8A	119.5
C10—C11—C6	120.7 (3)	C9—C8—H8A	119.5
C10—C11—H11A	119.6	C14—C13—C12	120.8 (4)
C6—C11—H11A	119.6	C14—C13—H13A	119.6
C8—C9—C10	117.8 (3)	C12—C13—H13A	119.6
C8—C9—C12	120.9 (3)	C6—C5—N1	114.0 (3)
C10—C9—C12	121.3 (3)	C6—C5—H5B	108.8
C13—C12—C17	117.3 (3)	N1—C5—H5B	108.8
C13—C12—C9	122.9 (3)	C6—C5—H5C	108.8
C17—C12—C9	119.8 (3)	N1—C5—H5C	108.8
N2—C18—C17	178.8 (4)	H5B—C5—H5C	107.7
C11—C6—C7	117.8 (3)	O1—C2—C1	111.5 (3)
C11—C6—C5	120.6 (3)	O1—C2—H2B	109.3
C7—C6—C5	121.5 (3)	C1—C2—H2B	109.3
C16—C17—C12	121.3 (3)	O1—C2—H2C	109.3
C16—C17—C18	119.0 (3)	C1—C2—H2C	109.3
C12—C17—C18	119.7 (3)	H2B—C2—H2C	108.0
C2—O1—C3	109.1 (3)	O1—C3—C4	111.4 (3)
N1—C1—C2	110.2 (3)	O1—C3—H3B	109.3
N1—C1—H1A	109.6	C4—C3—H3B	109.3
C2—C1—H1A	109.6	O1—C3—H3C	109.3
N1—C1—H1B	109.6	C4—C3—H3C	109.3
C2—C1—H1B	109.6	H3B—C3—H3C	108.0
H1A—C1—H1B	108.1	C14—C15—C16	120.0 (4)
C15—C16—C17	119.5 (3)	C14—C15—H15A	120.0
C15—C16—H16A	120.3	C16—C15—H15A	120.0
C17—C16—H16A	120.3	C15—C14—C13	121.1 (4)
C11—C10—C9	121.5 (3)	C15—C14—H14A	119.4
C11—C10—H10A	119.3	C13—C14—H14A	119.4

C8—C9—C12—C13	−62.6 (5)	C5—C6—C7—C8	174.2 (3)
C10—C9—C12—C13	120.2 (4)	C1—N1—C4—C3	51.9 (4)
C8—C9—C12—C17	115.6 (4)	C5—N1—C4—C3	177.1 (3)
C10—C9—C12—C17	−61.7 (4)	C6—C7—C8—C9	−0.8 (6)
C10—C11—C6—C7	3.6 (5)	C10—C9—C8—C7	3.8 (6)
C10—C11—C6—C5	−173.6 (3)	C12—C9—C8—C7	−173.6 (3)
C13—C12—C17—C16	−0.6 (5)	C17—C12—C13—C14	0.9 (5)
C9—C12—C17—C16	−178.9 (3)	C9—C12—C13—C14	179.0 (4)
C13—C12—C17—C18	178.5 (3)	C11—C6—C5—N1	−85.9 (4)
C9—C12—C17—C18	0.3 (4)	C7—C6—C5—N1	97.0 (4)
N2—C18—C17—C16	−35 (18)	C1—N1—C5—C6	−62.2 (4)
N2—C18—C17—C12	146 (18)	C4—N1—C5—C6	174.2 (3)
C4—N1—C1—C2	−51.8 (4)	C3—O1—C2—C1	−62.5 (5)
C5—N1—C1—C2	−175.8 (3)	N1—C1—C2—O1	58.0 (5)
C12—C17—C16—C15	0.5 (5)	C2—O1—C3—C4	62.4 (4)
C18—C17—C16—C15	−178.7 (3)	N1—C4—C3—O1	−57.6 (4)
C6—C11—C10—C9	−0.6 (5)	C17—C16—C15—C14	−0.6 (6)
C8—C9—C10—C11	−3.1 (5)	C16—C15—C14—C13	0.8 (6)
C12—C9—C10—C11	174.2 (3)	C12—C13—C14—C15	−1.0 (6)
C11—C6—C7—C8	−2.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.82	2.12	2.921 (4)	166
C2—H2B···O4ⁱⁱ	0.97	2.57	3.255 (5)	128
C5—H5B···O4ⁱⁱⁱ	0.97	2.59	3.515 (6)	161
C5—H5C···O4^iv	0.97	2.57	3.474 (7)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2ⁱ	0.82	2.12	2.921 (4)	166
C2—H2B⋯O4ⁱⁱ	0.97	2.57	3.255 (5)	128
C5—H5B⋯O4ⁱⁱⁱ	0.97	2.59	3.515 (6)	161
C5—H5C⋯O4^iv	0.97	2.57	3.474 (7)	154

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

2 in total

1. Optical response of high-dielectric-constant perovskite-related oxide.

Authors: C C Homes; T Vogt; S M Shapiro; S Wakimoto; A P Ramirez
Journal: Science Date: 2001-07-27 Impact factor: 47.728

2. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2 in total