1-(2,3-Di­hydroxy­prop­yl)-4-{2-[4-(di­methyl­amino)­phen­yl]vin­yl}pyridinium chloride

Gainsford, G.J.; Bhuiyan, M.D.H.; Kay, A.J.

doi:10.1107/S1600536813033254

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 1| January 2014| Pages o83-o84

https://doi.org/10.1107/S1600536813033254

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1-(2,3-Dihydroxypropyl)-4-{2-[4-(dimethylamino)phenyl]vinyl}pyridinium chloride

Graeme J. Gainsford,^a ^* M. Delower H. Bhuiyan ^a and Andrew J. Kay ^a

^aCallaghan Innovation, PO Box 31-310, Lower Hutt, New Zealand
^*Correspondence e-mail: g.gainsford@irl.cri.nz

(Received 28 November 2013; accepted 8 December 2013; online 21 December 2013)

The title compound, C₁₈H₂₃N₂O₂⁺·Cl⁻, crystallizes with two independent cations and anions per cell. Each cation has twofold rotational disorder about the linking vinyl groups but with unequal occupancies [0.963 (5):0.037 (5) and 0.860 (8):0.140 (8)]. The two independent cations are close to being related by an inversion centre but the data does not support the expected centrosymmetric space-group assignment. The conclusion is that the differing rotational disorder has lead to an overall non-centrosymmetric lattice. In the crystal, the molecules pack in layers parallel to (133) and (-13-3), chain-linked with motif C¹₂(7) by the dihydroxypropyl O–H⋯Cl⋯H–O hydrogen bonds. Other lattice binding is provided by O—H⋯Cl, C—H⋯Cl and C—H⋯N interactions.

CCDC reference: 975724

Related literature

For applications of organic push–pull chromophores, see: Kay et al. (2004 ); Bass et al. (2001 ); Prasad et al. (1988 ). For a related example of rotational disorder, see: Moreno-Fuquen et al. (2009 ). For details of the synthesis, see: Kay et al. (2001 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₂₃N₂O₂⁺·Cl⁻
M_r = 334.83
Monoclinic, P 2₁
a = 8.4452 (3) Å
b = 13.2433 (5) Å
c = 15.3649 (6) Å
β = 100.077 (3)°
V = 1691.94 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 123 K
0.55 × 0.10 × 0.09 mm

Data collection

Bruker–Nonius APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.651, T_max = 0.746
38193 measured reflections
7581 independent reflections
5545 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.096
S = 1.02
7581 reflections
474 parameters
13 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack parameter determined using 2152 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter: 0.07 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯Cl1	0.83 (3)	2.20 (3)	3.024 (3)	174 (4)
O2—H2O⋯Cl1ⁱ	0.83 (3)	2.27 (3)	3.086 (3)	169 (4)
C2—H2⋯O2′ⁱ	0.95	2.40	3.222 (5)	145
C5A—H5A⋯Cl2ⁱⁱ	0.95	2.78	3.687 (5)	159
C8—H8A⋯N2ⁱⁱ	0.99	2.65	3.637 (5)	176
O1′—H1O′⋯Cl2	0.84 (3)	2.25 (3)	3.083 (3)	171 (4)
O2′—H2O′⋯Cl2ⁱⁱⁱ	0.83 (3)	2.29 (3)	3.104 (3)	169 (4)
C6′—H6′⋯O2ⁱⁱⁱ	0.95	2.40	3.236 (6)	147
Symmetry codes: (i) x+1, y, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ) and Mercury.

Supporting information

CCDC reference: 975724

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813033254/sj5376sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033254/sj5376Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813033254/sj5376Isup3.cml

checkCIF report

Comment top

Organic push–pull chromophores with large second-order nonlinear optical (NLO) properties are in demand due to their potential applications in photonic devices and optical information processing (Kay et al., 2004; Bass et al., 2001; Prasad et al., 1988). A significant number of organic compounds available in the literature with large molecular NLO responses contain N,N-disubstituted anilines as this nucleus is an excellent electron donor. Due to the lack of tethering functionality of these chromophores, the possibility of synthesizing polymer containing chromophores is restricted. In this work, we have synthesized a new NLO chromophore containing an N,N-dimethyl aniline donor and an acceptor based on the dihydroxypropyl pyridinium chloride. The dihydroxypropyl substituent on the acceptor pyridinium nucleus will allow for covalent attachment of the molecule to a polymer backbone.

The asymmetric unit of the title compound (I) contains two independent 1-(2,3-dihydroxy-propyl)-4-[2-(4-dimethylamino-phenyl)-vinyl]-pyridinium cations (with primed and unprimed labels) and chloride anions almost related by an inversion centre (Fig. 1) in space group P2₁. The screw axis and the c glide defining data number, average intensities and ratio of intensity/standard deviations were 61, 1/5, 0.4 and 906, 1.9, 3.1 respectively. The corresponding centosymmetric, and more usual, space group found for these compounds, P2₁/c was rejected through the small but significant presence of the required glide plane absences; this was confirmed in attempted least squares refinements. At the conclusion of both space group refinements, the difference Fourier maps show the presence of two partially occupied rotational conformers about the alkene atoms (C9═C10, C9'═ C10') apparently confined to the vinyl linking atoms, also related by the same inversion centre (Fig. 2). Inclusion of the carbon atoms located on the Fourier difference map (see experimental) improved the agreement factors by about ~0.7% and results in a featureless difference map. Such rotational disorder is not uncommon amongst compounds containing C═C and C═N linkages: for example see Moreno-Fuquen et al. (2009).

The two cations (Fig 1) are very similar with RMS fits of 0.020 Å and 1.28° (PLATON, Spek, 2009); excluding the dihydroxy end groups, they are approximately planar (maximum deviations from the 18 atom planes are 0.055 (4) & 0.057 (5) Å for atoms C16 & C16') corresponding to the angle between the phenyl and pyridinium rings of 1.6 (2) & 2.8 (2)° for the unprimed and primed cations respectively.

The molecules pack in layers parallel to (133) and (133 planes), chain-linked by dihydroxypropyl O—H···Cl···H—O hydrogen bonds with motif C¹₂(7) (Bernstein et al., 1995). Other lattice binding is provided by O—H···Cl and C—H···Cl, C—H···N interactions (Table 1).

Related literature top

For applications of organic push–pull chromophores, see: Kay et al. (2004); Bass et al. (2001); Prasad et al. (1988). For a related example of rotational disorder, see: Moreno-Fuquen et al. (2009). For details of the synthesis, see: Kay et al. (2001). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

We synthesized the title compound by following the procedure in Kay et al. (2001). Single crystals were grown by slow ethyl acetate diffusion into a methanol solution of the compound.

Structure description top

For applications of organic push–pull chromophores, see: Kay et al. (2004); Bass et al. (2001); Prasad et al. (1988). For a related example of rotational disorder, see: Moreno-Fuquen et al. (2009). For details of the synthesis, see: Kay et al. (2001). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006).

Figures top

	Fig. 1. Labelling of the major(a) conformer cations and anions of the title compound, with 50% thermal ellipsoids (Farrugia, 2012).
	Fig. 2. The total contents of the asymmetric unit, as for Fig. 1, with the minor cation rotamer (labelled b atoms) shown with filled bonds and major rotamer atoms (labelled a) connected with dotted bonds. The centre of the rotation is shown by inclusion of the C9 & C10 (a & b)labels.
	Fig. 3. Packing diagram of (I) without H atoms for clarity. Hydrogen bonds shown as dashed blue lines (Mercury; Macrae et al., 2006). Symmetry codes: (i) 1 + x, y, z (ii) -1 + x, y, z (iii) 1 - x, 1/2 + y, 1 - z (iv) 2 - x, 1/2 + y, 1 - z.

1-(2,3-Dihydroxypropyl)-4-{2-[4-(dimethylamino)phenyl]vinyl}pyridinium chloride top

Crystal data top

C₁₈H₂₃N₂O₂⁺·Cl⁻	F(000) = 712
M_r = 334.83	D_x = 1.314 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 8.4452 (3) Å	Cell parameters from 4999 reflections
b = 13.2433 (5) Å	θ = 2.7–23.4°
c = 15.3649 (6) Å	µ = 0.24 mm⁻¹
β = 100.077 (3)°	T = 123 K
V = 1691.94 (11) Å³	Needle, red
Z = 4	0.55 × 0.10 × 0.09 mm

Data collection top

Bruker–Nonius APEXII CCD area-detector diffractometer	7581 independent reflections
Radiation source: fine-focus sealed tube	5545 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
Detector resolution: 8.333 pixels mm^-1	θ_max = 27.3°, θ_min = 2.6°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (Blessing, 1995)	k = −17→17
T_min = 0.651, T_max = 0.746	l = −19→19
38193 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.042	w = 1/[σ²(F_o²) + (0.0362P)² + 0.2405P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.096	(Δ/σ)_max = 0.001
S = 1.02	Δρ_max = 0.18 e Å⁻³
7581 reflections	Δρ_min = −0.20 e Å⁻³
474 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
13 restraints	Extinction coefficient: 0.0039 (10)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack parameter determined using 2152 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.07 (4)

Crystal data top

C₁₈H₂₃N₂O₂⁺·Cl⁻	V = 1691.94 (11) Å³
M_r = 334.83	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 8.4452 (3) Å	µ = 0.24 mm⁻¹
b = 13.2433 (5) Å	T = 123 K
c = 15.3649 (6) Å	0.55 × 0.10 × 0.09 mm
β = 100.077 (3)°

Data collection top

Bruker–Nonius APEXII CCD area-detector diffractometer	7581 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	5545 reflections with I > 2σ(I)
T_min = 0.651, T_max = 0.746	R_int = 0.063
38193 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	Δρ_max = 0.18 e Å⁻³
S = 1.02	Δρ_min = −0.20 e Å⁻³
7581 reflections	Absolute structure: Flack parameter determined using 2152 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
474 parameters	Absolute structure parameter: 0.07 (4)
13 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.46974 (12)	0.13741 (8)	0.18879 (7)	0.0391 (3)
O1	0.8050 (3)	0.2226 (2)	0.20024 (17)	0.0340 (6)
H1O	0.716 (4)	0.196 (3)	0.200 (3)	0.041*
O2	1.1625 (3)	0.2328 (2)	0.2362 (2)	0.0367 (8)
H2O	1.241 (4)	0.211 (4)	0.216 (3)	0.044*
N1	0.8014 (4)	0.2692 (2)	0.3860 (2)	0.0238 (8)
N2	−0.2944 (4)	0.4615 (3)	0.6126 (2)	0.0267 (8)
C1	0.9463 (5)	0.2493 (3)	0.3480 (3)	0.0283 (10)
H1A	1.0312	0.2210	0.3942	0.034*
H1B	0.9866	0.3135	0.3272	0.034*
C2	0.6990 (6)	0.3426 (3)	0.3522 (3)	0.0291 (10)
H2	0.7222	0.3826	0.3046	0.035*
C3A	0.5613 (6)	0.3606 (4)	0.3857 (3)	0.0273 (11)	0.963 (5)
H3A	0.4895	0.4122	0.3606	0.033*	0.963 (5)
C4A	0.5256 (6)	0.3031 (4)	0.4569 (3)	0.0224 (10)	0.963 (5)
C5A	0.6362 (6)	0.2279 (4)	0.4900 (3)	0.0272 (12)	0.963 (5)
H5A	0.6177	0.1873	0.5382	0.033*	0.963 (5)
C6	0.7688 (5)	0.2128 (3)	0.4541 (3)	0.0306 (10)
H6	0.8417	0.1608	0.4773	0.037*
C7	0.9110 (4)	0.1751 (3)	0.2706 (2)	0.0257 (9)
H7	0.8584	0.1133	0.2898	0.031*
C8	1.0658 (5)	0.1459 (3)	0.2410 (3)	0.0298 (10)
H8A	1.1251	0.0969	0.2833	0.036*
H8B	1.0416	0.1132	0.1822	0.036*
C9A	0.3844 (5)	0.3174 (3)	0.4975 (3)	0.0274 (11)	0.963 (5)
H9A	0.3703	0.2733	0.5444	0.033*	0.963 (5)
C10A	0.2722 (5)	0.3887 (3)	0.4733 (3)	0.0243 (11)	0.963 (5)
H10A	0.2872	0.4319	0.4261	0.029*	0.963 (5)
C11A	0.1307 (5)	0.4060 (4)	0.5123 (3)	0.0221 (10)	0.963 (5)
C12A	0.0194 (6)	0.4797 (4)	0.4758 (3)	0.0262 (11)	0.963 (5)
H12A	0.0398	0.5175	0.4264	0.031*	0.963 (5)
C13	−0.1171 (5)	0.4989 (3)	0.5090 (3)	0.0257 (10)
H13	−0.1878	0.5506	0.4829	0.031*
C14	−0.1560 (5)	0.4442 (3)	0.5807 (3)	0.0239 (9)
C15	−0.0453 (5)	0.3693 (3)	0.6177 (3)	0.0287 (10)
H15	−0.0666	0.3308	0.6665	0.034*
C16	0.0916 (5)	0.3513 (3)	0.5845 (3)	0.0288 (10)
H16	0.1632	0.3002	0.6109	0.035*
C17	−0.3366 (5)	0.4042 (3)	0.6852 (3)	0.0317 (10)
H17A	−0.3928	0.3423	0.6624	0.038*
H17B	−0.4070	0.4447	0.7157	0.038*
H17C	−0.2387	0.3865	0.7266	0.038*
C18	−0.3998 (5)	0.5442 (3)	0.5770 (3)	0.0305 (10)
H18A	−0.3436	0.6085	0.5903	0.037*
H18B	−0.4968	0.5432	0.6038	0.037*
H18C	−0.4300	0.5363	0.5128	0.037*
Cl2	0.52229 (11)	0.62109 (8)	0.32090 (6)	0.0353 (3)
O1'	0.1812 (3)	0.67503 (19)	0.22476 (18)	0.0358 (6)
H1O'	0.276 (3)	0.668 (3)	0.251 (2)	0.043*
O2'	−0.1666 (4)	0.5388 (2)	0.2646 (2)	0.0375 (8)
H2O'	−0.256 (4)	0.558 (3)	0.273 (3)	0.045*
N1'	0.1959 (4)	0.5059 (2)	0.1129 (2)	0.0265 (8)
N2'	1.2916 (4)	0.3085 (3)	−0.1111 (2)	0.0301 (9)
C1'	0.0508 (5)	0.5298 (4)	0.1502 (3)	0.0315 (10)
H1C	−0.0047	0.4663	0.1606	0.038*
H1D	−0.0237	0.5705	0.1070	0.038*
C2'	0.2335 (5)	0.5609 (3)	0.0466 (3)	0.0299 (10)
H2'	0.1642	0.6153	0.0250	0.036*
C3'A	0.3618 (6)	0.5448 (5)	0.0084 (4)	0.0272 (14)	0.860 (8)
H3'A	0.3782	0.5843	−0.0409	0.033*	0.860 (8)
C4'A	0.4716 (6)	0.4694 (5)	0.0416 (4)	0.0255 (13)	0.860 (8)
C5'A	0.4347 (7)	0.4125 (5)	0.1115 (4)	0.0289 (13)	0.860 (8)
H5'A	0.5061	0.3603	0.1359	0.035*	0.860 (8)
C6'	0.2939 (5)	0.4303 (3)	0.1473 (3)	0.0344 (11)
H6'	0.2691	0.3900	0.1943	0.041*
C7'	0.0910 (5)	0.5876 (3)	0.2360 (3)	0.0240 (9)
H7'	0.1530	0.5435	0.2828	0.029*
C8'	−0.0630 (5)	0.6221 (3)	0.2639 (2)	0.0292 (9)
H8C	−0.0390	0.6525	0.3236	0.035*
H8D	−0.1158	0.6740	0.2223	0.035*
C9'A	0.6120 (6)	0.4533 (4)	0.0014 (3)	0.0262 (13)	0.860 (8)
H9'A	0.6234	0.4949	−0.0475	0.031*	0.860 (8)
C0'A	0.7267 (6)	0.3854 (4)	0.0271 (3)	0.0277 (14)	0.860 (8)
H0'A	0.7135	0.3442	0.0759	0.033*	0.860 (8)
C1A'	0.8693 (7)	0.3668 (5)	−0.0108 (4)	0.0274 (16)	0.860 (8)
C12'	0.9755 (5)	0.2958 (4)	0.0236 (3)	0.0329 (11)
H12'	0.9535	0.2580	0.0727	0.040*
C13'	1.1137 (5)	0.2746 (3)	−0.0080 (3)	0.0300 (10)
H13'	1.1835	0.2230	0.0192	0.036*
C14'	1.1537 (5)	0.3282 (3)	−0.0805 (3)	0.0237 (9)
C15'	1.0459 (5)	0.4038 (3)	−0.1190 (3)	0.0294 (10)
H15'	1.0693	0.4419	−0.1675	0.035*
C16'	0.9064 (5)	0.4225 (4)	−0.0862 (3)	0.0333 (11)
H16'	0.8336	0.4726	−0.1134	0.040*
C17'	1.3372 (5)	0.3656 (4)	−0.1837 (3)	0.0383 (12)
H17D	1.2600	0.3524	−0.2380	0.046*
H17E	1.4450	0.3451	−0.1921	0.046*
H17F	1.3372	0.4379	−0.1700	0.046*
C18'	1.3947 (5)	0.2250 (4)	−0.0766 (3)	0.0368 (11)
H18D	1.4419	0.2383	−0.0148	0.044*
H18E	1.4807	0.2174	−0.1115	0.044*
H18F	1.3311	0.1627	−0.0803	0.044*
C3'B	0.410 (4)	0.524 (2)	0.0343 (17)	0.006 (3)*	0.140 (8)
H3'B	0.4688	0.5617	−0.0024	0.008*	0.140 (8)
C4'B	0.479 (3)	0.439 (3)	0.077 (2)	0.006 (3)*	0.140 (8)
C5'B	0.413 (3)	0.3892 (19)	0.1394 (17)	0.006 (3)*	0.140 (8)
H5'B	0.4545	0.3292	0.1725	0.008*	0.140 (8)
C9'B	0.628 (2)	0.3994 (16)	0.0562 (14)	0.006 (3)*	0.140 (8)
H9'B	0.6753	0.3443	0.0912	0.008*	0.140 (8)
C0'B	0.709 (3)	0.4332 (18)	−0.0095 (16)	0.006 (3)*	0.140 (8)
H0'B	0.6634	0.4898	−0.0426	0.008*	0.140 (8)
C1B'	0.863 (4)	0.391 (2)	−0.035 (2)	0.006 (3)*	0.140 (8)
C3B	0.597 (12)	0.347 (7)	0.348 (6)	0.006 (3)*	0.037 (5)
H3B	0.5409	0.3627	0.2911	0.008*	0.037 (5)
C4B	0.505 (9)	0.332 (8)	0.418 (8)	0.006 (3)*	0.037 (5)
C5B	0.600 (15)	0.265 (9)	0.478 (7)	0.006 (3)*	0.037 (5)
H5B	0.5642	0.2460	0.5297	0.008*	0.037 (5)
C9B	0.351 (8)	0.361 (6)	0.440 (4)	0.006 (3)*	0.037 (5)
H9B	0.2787	0.3887	0.3921	0.008*	0.037 (5)
C10B	0.290 (9)	0.355 (6)	0.515 (5)	0.006 (3)*	0.037 (5)
H10B	0.3700	0.3428	0.5658	0.008*	0.037 (5)
C11B	0.130 (8)	0.364 (7)	0.537 (7)	0.006 (3)*	0.037 (5)
C12B	0.072 (12)	0.456 (7)	0.501 (6)	0.006 (3)*	0.037 (5)
H12B	0.1379	0.4973	0.4707	0.008*	0.037 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0256 (6)	0.0416 (7)	0.0534 (7)	−0.0007 (5)	0.0158 (5)	−0.0082 (6)
O1	0.0258 (14)	0.0429 (15)	0.0330 (15)	−0.0025 (12)	0.0042 (11)	0.0092 (12)
O2	0.0278 (17)	0.0325 (17)	0.055 (2)	−0.0010 (15)	0.0217 (15)	−0.0060 (16)
N1	0.0173 (18)	0.0271 (19)	0.029 (2)	−0.0026 (15)	0.0086 (14)	−0.0003 (16)
N2	0.0214 (19)	0.0282 (19)	0.031 (2)	0.0049 (16)	0.0057 (15)	0.0031 (17)
C1	0.021 (2)	0.036 (2)	0.030 (2)	−0.0027 (18)	0.0100 (18)	−0.0025 (19)
C2	0.031 (3)	0.022 (2)	0.034 (3)	0.0003 (19)	0.008 (2)	0.0018 (19)
C3A	0.024 (3)	0.027 (3)	0.031 (3)	0.003 (2)	0.005 (2)	−0.003 (2)
C4A	0.017 (2)	0.024 (3)	0.026 (3)	−0.001 (2)	0.0025 (19)	−0.003 (2)
C5A	0.026 (3)	0.024 (3)	0.033 (3)	0.000 (2)	0.008 (2)	0.002 (2)
C6	0.028 (2)	0.029 (2)	0.036 (3)	−0.0018 (19)	0.0085 (19)	0.001 (2)
C7	0.022 (2)	0.027 (2)	0.027 (2)	−0.0044 (18)	0.0031 (16)	0.0017 (18)
C8	0.029 (2)	0.029 (2)	0.033 (2)	0.0012 (19)	0.0091 (17)	0.002 (2)
C9A	0.028 (3)	0.026 (3)	0.029 (3)	−0.006 (2)	0.009 (2)	−0.004 (2)
C10A	0.027 (3)	0.023 (2)	0.022 (2)	−0.0025 (19)	0.0033 (19)	−0.001 (2)
C11A	0.018 (2)	0.021 (3)	0.028 (3)	−0.0019 (19)	0.0045 (19)	−0.003 (2)
C12A	0.023 (2)	0.029 (3)	0.024 (3)	0.0009 (19)	−0.0015 (19)	0.004 (2)
C13	0.023 (2)	0.027 (2)	0.025 (2)	0.0041 (18)	−0.0002 (18)	0.0015 (19)
C14	0.022 (2)	0.022 (2)	0.027 (2)	−0.0022 (17)	0.0044 (18)	−0.0050 (18)
C15	0.030 (2)	0.028 (2)	0.028 (2)	−0.0022 (19)	0.0061 (19)	0.002 (2)
C16	0.028 (2)	0.031 (2)	0.028 (2)	0.0039 (19)	0.006 (2)	−0.003 (2)
C17	0.029 (2)	0.032 (2)	0.037 (3)	0.004 (2)	0.011 (2)	0.005 (2)
C18	0.026 (2)	0.032 (2)	0.034 (3)	0.006 (2)	0.0063 (19)	−0.001 (2)
Cl2	0.0285 (5)	0.0390 (6)	0.0390 (6)	0.0064 (5)	0.0072 (4)	−0.0030 (5)
O1'	0.0276 (14)	0.0284 (14)	0.0486 (17)	−0.0042 (11)	−0.0008 (12)	0.0010 (12)
O2'	0.0325 (18)	0.0292 (17)	0.057 (2)	0.0004 (15)	0.0247 (16)	0.0018 (16)
N1'	0.0205 (18)	0.0269 (19)	0.033 (2)	−0.0015 (15)	0.0066 (15)	−0.0085 (17)
N2'	0.028 (2)	0.029 (2)	0.037 (2)	0.0055 (17)	0.0158 (17)	0.0049 (17)
C1'	0.018 (2)	0.042 (3)	0.036 (3)	−0.0042 (19)	0.0101 (18)	−0.009 (2)
C2'	0.032 (2)	0.027 (2)	0.031 (2)	−0.0012 (19)	0.0052 (19)	0.000 (2)
C3'A	0.019 (3)	0.031 (3)	0.030 (3)	−0.001 (2)	0.001 (2)	0.000 (2)
C4'A	0.022 (3)	0.025 (3)	0.030 (3)	−0.010 (2)	0.004 (2)	−0.006 (2)
C5'A	0.034 (3)	0.024 (3)	0.030 (4)	0.003 (2)	0.010 (3)	0.003 (2)
C6'	0.040 (3)	0.027 (2)	0.035 (3)	−0.001 (2)	0.002 (2)	−0.002 (2)
C7'	0.028 (2)	0.020 (2)	0.025 (2)	0.0014 (17)	0.0051 (17)	0.0024 (16)
C8'	0.033 (2)	0.025 (2)	0.030 (2)	0.001 (2)	0.0088 (17)	−0.002 (2)
C9'A	0.022 (3)	0.030 (3)	0.026 (3)	−0.002 (2)	0.002 (2)	−0.001 (2)
C0'A	0.026 (3)	0.032 (3)	0.025 (3)	−0.004 (2)	0.002 (2)	−0.003 (3)
C1A'	0.028 (3)	0.036 (4)	0.018 (3)	−0.007 (3)	0.004 (3)	−0.005 (3)
C12'	0.031 (3)	0.043 (3)	0.027 (2)	−0.012 (2)	0.012 (2)	−0.010 (2)
C13'	0.032 (3)	0.029 (2)	0.029 (2)	−0.007 (2)	0.005 (2)	−0.002 (2)
C14'	0.020 (2)	0.026 (2)	0.026 (2)	−0.0038 (17)	0.0037 (18)	−0.0053 (18)
C15'	0.027 (2)	0.033 (2)	0.029 (2)	0.0047 (19)	0.0053 (19)	0.000 (2)
C16'	0.022 (2)	0.034 (3)	0.041 (3)	0.0056 (19)	−0.004 (2)	−0.006 (2)
C17'	0.034 (3)	0.048 (3)	0.037 (3)	0.000 (2)	0.017 (2)	0.000 (2)
C18'	0.028 (2)	0.034 (3)	0.049 (3)	0.008 (2)	0.007 (2)	0.001 (2)

Geometric parameters (Å, º) top

O1—C7	1.424 (4)	C1'—C7'	1.511 (5)
O1—H1O	0.83 (3)	C1'—H1C	0.9900
O2—C8	1.420 (5)	C1'—H1D	0.9900
O2—H2O	0.83 (3)	C2'—C3'A	1.336 (6)
N1—C2	1.344 (5)	C2'—H2'	0.9500
N1—C6	1.352 (5)	C3'A—C4'A	1.397 (8)
N1—C1	1.469 (5)	C3'A—H3'A	0.9500
N2—C14	1.365 (5)	C4'A—C5'A	1.392 (7)
N2—C17	1.444 (5)	C4'A—C9'A	1.444 (7)
N2—C18	1.456 (5)	C5'A—C6'	1.414 (7)
C1—C7	1.531 (6)	C5'A—H5'A	0.9500
C1—H1A	0.9900	C6'—H6'	0.9500
C1—H1B	0.9900	C7'—C8'	1.510 (5)
C2—C3A	1.372 (6)	C7'—H7'	1.0000
C2—H2	0.9500	C8'—H8C	0.9900
C3A—C4A	1.409 (6)	C8'—H8D	0.9900
C3A—H3A	0.9500	C9'A—C0'A	1.331 (7)
C4A—C5A	1.398 (6)	C9'A—H9'A	0.9500
C4A—C9A	1.452 (6)	C0'A—C1A'	1.447 (8)
C5A—C6	1.348 (6)	C0'A—H0'A	0.9500
C5A—H5A	0.9500	C1A'—C12'	1.343 (8)
C6—H6	0.9500	C1A'—C16'	1.454 (7)
C7—C8	1.507 (5)	C12'—C13'	1.369 (6)
C7—H7	1.0000	C12'—H12'	0.9500
C8—H8A	0.9900	C13'—C14'	1.410 (6)
C8—H8B	0.9900	C13'—H13'	0.9500
C9A—C10A	1.344 (6)	C14'—C15'	1.411 (6)
C9A—H9A	0.9500	C15'—C16'	1.382 (6)
C10A—C11A	1.445 (6)	C15'—H15'	0.9500
C10A—H10A	0.9500	C16'—H16'	0.9500
C11A—C12A	1.402 (6)	C17'—H17D	0.9800
C11A—C16	1.412 (6)	C17'—H17E	0.9800
C12A—C13	1.363 (6)	C17'—H17F	0.9800
C12A—H12A	0.9500	C18'—H18D	0.9800
C13—C14	1.405 (5)	C18'—H18E	0.9800
C13—H13	0.9500	C18'—H18F	0.9800
C14—C15	1.412 (5)	C3'B—C4'B	1.38 (4)
C15—C16	1.364 (6)	C3'B—H3'B	0.95 (3)
C15—H15	0.9500	C4'B—C5'B	1.36 (4)
C16—H16	0.9500	C4'B—C9'B	1.45 (2)
C17—H17A	0.9800	C5'B—H5'B	0.98 (2)
C17—H17B	0.9800	C9'B—C0'B	1.39 (3)
C17—H17C	0.9800	C9'B—H9'B	0.9500
C18—H18A	0.9800	C0'B—C1B'	1.53 (4)
C18—H18B	0.9800	C0'B—H0'B	0.9500
C18—H18C	0.9800	C3B—C4B	1.44 (12)
O1'—C7'	1.413 (5)	C3B—H3B	0.94 (9)
O1'—H1O'	0.84 (3)	C4B—C5B	1.42 (14)
O2'—C8'	1.409 (5)	C4B—C9B	1.45 (3)
O2'—H2O'	0.83 (3)	C5B—H5B	0.93 (10)
N1'—C2'	1.336 (5)	C9B—C10B	1.35 (3)
N1'—C6'	1.347 (5)	C9B—H9B	0.9500
N1'—C1'	1.475 (5)	C10B—C11B	1.45 (3)
N2'—C14'	1.356 (5)	C10B—H10B	0.9500
N2'—C18'	1.449 (5)	C11B—C12B	1.39 (3)
N2'—C17'	1.455 (5)	C12B—H12B	0.95 (9)

C7—O1—H1O	105 (3)	C7'—C1'—H1D	109.2
C8—O2—H2O	104 (3)	H1C—C1'—H1D	107.9
C2—N1—C6	119.6 (4)	N1'—C2'—C3'A	124.6 (5)
C2—N1—C1	120.0 (3)	N1'—C2'—H2'	117.7
C6—N1—C1	120.3 (4)	C3'A—C2'—H2'	117.7
C14—N2—C17	122.1 (3)	C2'—C3'A—C4'A	119.5 (5)
C14—N2—C18	119.8 (3)	C2'—C3'A—H3'A	120.3
C17—N2—C18	118.0 (3)	C4'A—C3'A—H3'A	120.3
N1—C1—C7	111.2 (3)	C5'A—C4'A—C3'A	116.4 (5)
N1—C1—H1A	109.4	C5'A—C4'A—C9'A	124.2 (6)
C7—C1—H1A	109.4	C3'A—C4'A—C9'A	119.4 (5)
N1—C1—H1B	109.4	C4'A—C5'A—C6'	121.8 (5)
C7—C1—H1B	109.4	C4'A—C5'A—H5'A	119.1
H1A—C1—H1B	108.0	C6'—C5'A—H5'A	119.1
N1—C2—C3A	120.7 (4)	N1'—C6'—C5'A	118.2 (5)
N1—C2—H2	119.6	N1'—C6'—H6'	120.9
C3A—C2—H2	119.6	C5'A—C6'—H6'	120.9
C2—C3A—C4A	120.6 (4)	O1'—C7'—C8'	107.3 (3)
C2—C3A—H3A	119.7	O1'—C7'—C1'	110.6 (3)
C4A—C3A—H3A	119.7	C8'—C7'—C1'	109.1 (3)
C5A—C4A—C3A	116.6 (4)	O1'—C7'—H7'	109.9
C5A—C4A—C9A	118.9 (5)	C8'—C7'—H7'	109.9
C3A—C4A—C9A	124.5 (5)	C1'—C7'—H7'	109.9
C6—C5A—C4A	120.4 (4)	O2'—C8'—C7'	109.4 (3)
C6—C5A—H5A	119.8	O2'—C8'—H8C	109.8
C4A—C5A—H5A	119.8	C7'—C8'—H8C	109.8
C5A—C6—N1	122.1 (4)	O2'—C8'—H8D	109.8
C5A—C6—H6	119.0	C7'—C8'—H8D	109.8
N1—C6—H6	119.0	H8C—C8'—H8D	108.2
O1—C7—C8	110.3 (3)	C0'A—C9'A—C4'A	125.6 (5)
O1—C7—C1	108.5 (3)	C0'A—C9'A—H9'A	117.2
C8—C7—C1	109.7 (3)	C4'A—C9'A—H9'A	117.2
O1—C7—H7	109.4	C9'A—C0'A—C1A'	127.6 (6)
C8—C7—H7	109.4	C9'A—C0'A—H0'A	116.2
C1—C7—H7	109.4	C1A'—C0'A—H0'A	116.2
O2—C8—C7	110.2 (3)	C12'—C1A'—C0'A	120.5 (5)
O2—C8—H8A	109.6	C12'—C1A'—C16'	116.5 (5)
C7—C8—H8A	109.6	C0'A—C1A'—C16'	123.0 (6)
O2—C8—H8B	109.6	C1A'—C12'—C13'	123.8 (5)
C7—C8—H8B	109.6	C1A'—C12'—H12'	118.1
H8A—C8—H8B	108.1	C13'—C12'—H12'	118.1
C10A—C9A—C4A	124.4 (5)	C12'—C13'—C14'	120.9 (4)
C10A—C9A—H9A	117.8	C12'—C13'—H13'	119.6
C4A—C9A—H9A	117.8	C14'—C13'—H13'	119.6
C9A—C10A—C11A	126.2 (5)	N2'—C14'—C15'	121.4 (4)
C9A—C10A—H10A	116.9	N2'—C14'—C13'	121.1 (4)
C11A—C10A—H10A	116.9	C15'—C14'—C13'	117.5 (4)
C12A—C11A—C16	116.0 (4)	C16'—C15'—C14'	120.2 (4)
C12A—C11A—C10A	119.3 (5)	C16'—C15'—H15'	119.9
C16—C11A—C10A	124.6 (5)	C14'—C15'—H15'	119.9
C13—C12A—C11A	122.1 (4)	C15'—C16'—C1A'	121.0 (4)
C13—C12A—H12A	118.9	C15'—C16'—H16'	119.5
C11A—C12A—H12A	118.9	C1A'—C16'—H16'	119.5
C12A—C13—C14	121.7 (4)	N2'—C17'—H17D	109.5
C12A—C13—H13	119.1	N2'—C17'—H17E	109.5
C14—C13—H13	119.1	H17D—C17'—H17E	109.5
N2—C14—C13	121.9 (4)	N2'—C17'—H17F	109.5
N2—C14—C15	121.4 (4)	H17D—C17'—H17F	109.5
C13—C14—C15	116.7 (4)	H17E—C17'—H17F	109.5
C16—C15—C14	121.1 (4)	N2'—C18'—H18D	109.5
C16—C15—H15	119.5	N2'—C18'—H18E	109.5
C14—C15—H15	119.5	H18D—C18'—H18E	109.5
C15—C16—C11A	122.3 (4)	N2'—C18'—H18F	109.5
C15—C16—H16	118.8	H18D—C18'—H18F	109.5
C11A—C16—H16	118.8	H18E—C18'—H18F	109.5
N2—C17—H17A	109.5	C4'B—C3'B—H3'B	119 (3)
N2—C17—H17B	109.5	C5'B—C4'B—C3'B	123 (2)
H17A—C17—H17B	109.5	C5'B—C4'B—C9'B	117 (3)
N2—C17—H17C	109.5	C3'B—C4'B—C9'B	120 (3)
H17A—C17—H17C	109.5	C4'B—C5'B—H5'B	127 (3)
H17B—C17—H17C	109.5	C0'B—C9'B—C4'B	127 (2)
N2—C18—H18A	109.5	C0'B—C9'B—H9'B	116.5
N2—C18—H18B	109.5	C4'B—C9'B—H9'B	116.5
H18A—C18—H18B	109.5	C9'B—C0'B—C1B'	128 (2)
N2—C18—H18C	109.5	C9'B—C0'B—H0'B	115.8
H18A—C18—H18C	109.5	C1B'—C0'B—H0'B	115.8
H18B—C18—H18C	109.5	C4B—C3B—H3B	118 (10)
C7'—O1'—H1O'	110 (3)	C5B—C4B—C3B	105 (7)
C8'—O2'—H2O'	111 (3)	C5B—C4B—C9B	116 (10)
C2'—N1'—C6'	119.5 (4)	C3B—C4B—C9B	139 (10)
C2'—N1'—C1'	120.3 (4)	C4B—C5B—H5B	119 (10)
C6'—N1'—C1'	120.2 (4)	C10B—C9B—C4B	133 (8)
C14'—N2'—C18'	121.2 (4)	C10B—C9B—H9B	113.4
C14'—N2'—C17'	121.6 (4)	C4B—C9B—H9B	113.4
C18'—N2'—C17'	117.1 (3)	C9B—C10B—C11B	135 (8)
N1'—C1'—C7'	111.9 (3)	C9B—C10B—H10B	112.6
N1'—C1'—H1C	109.2	C11B—C10B—H10B	112.6
C7'—C1'—H1C	109.2	C12B—C11B—C10B	105 (8)
N1'—C1'—H1D	109.2	C11B—C12B—H12B	120 (10)

C2—N1—C1—C7	−87.1 (4)	N1'—C2'—C3'A—C4'A	−3.7 (8)
C6—N1—C1—C7	91.8 (4)	C2'—C3'A—C4'A—C5'A	2.5 (7)
C6—N1—C2—C3A	−0.4 (6)	C2'—C3'A—C4'A—C9'A	−178.7 (4)
C1—N1—C2—C3A	178.4 (4)	C3'A—C4'A—C5'A—C6'	−0.2 (7)
N1—C2—C3A—C4A	0.8 (7)	C9'A—C4'A—C5'A—C6'	−178.8 (5)
C2—C3A—C4A—C5A	−0.4 (6)	C2'—N1'—C6'—C5'A	0.4 (6)
C2—C3A—C4A—C9A	179.1 (4)	C1'—N1'—C6'—C5'A	−177.7 (4)
C3A—C4A—C5A—C6	−0.3 (7)	C4'A—C5'A—C6'—N1'	−1.3 (7)
C9A—C4A—C5A—C6	−179.8 (4)	N1'—C1'—C7'—O1'	54.5 (5)
C4A—C5A—C6—N1	0.6 (7)	N1'—C1'—C7'—C8'	172.2 (3)
C2—N1—C6—C5A	−0.3 (6)	O1'—C7'—C8'—O2'	172.2 (3)
C1—N1—C6—C5A	−179.2 (4)	C1'—C7'—C8'—O2'	52.4 (4)
N1—C1—C7—O1	66.8 (4)	C5'A—C4'A—C9'A—C0'A	−2.3 (8)
N1—C1—C7—C8	−172.6 (3)	C3'A—C4'A—C9'A—C0'A	179.0 (5)
O1—C7—C8—O2	75.1 (4)	C4'A—C9'A—C0'A—C1A'	−179.8 (5)
C1—C7—C8—O2	−44.4 (5)	C9'A—C0'A—C1A'—C12'	179.2 (5)
C5A—C4A—C9A—C10A	178.0 (4)	C9'A—C0'A—C1A'—C16'	−0.6 (9)
C3A—C4A—C9A—C10A	−1.5 (7)	C0'A—C1A'—C12'—C13'	−179.4 (5)
C4A—C9A—C10A—C11A	−179.5 (4)	C16'—C1A'—C12'—C13'	0.4 (8)
C9A—C10A—C11A—C12A	−176.0 (4)	C1A'—C12'—C13'—C14'	0.3 (7)
C9A—C10A—C11A—C16	2.0 (7)	C18'—N2'—C14'—C15'	−174.4 (4)
C16—C11A—C12A—C13	1.2 (7)	C17'—N2'—C14'—C15'	1.3 (6)
C10A—C11A—C12A—C13	179.3 (4)	C18'—N2'—C14'—C13'	6.4 (6)
C11A—C12A—C13—C14	−1.4 (7)	C17'—N2'—C14'—C13'	−177.8 (4)
C17—N2—C14—C13	178.7 (4)	C12'—C13'—C14'—N2'	178.9 (4)
C18—N2—C14—C13	−5.1 (6)	C12'—C13'—C14'—C15'	−0.2 (6)
C17—N2—C14—C15	−0.6 (6)	N2'—C14'—C15'—C16'	−179.7 (4)
C18—N2—C14—C15	175.6 (3)	C13'—C14'—C15'—C16'	−0.6 (6)
C12A—C13—C14—N2	−178.4 (4)	C14'—C15'—C16'—C1A'	1.3 (7)
C12A—C13—C14—C15	0.9 (6)	C12'—C1A'—C16'—C15'	−1.2 (7)
N2—C14—C15—C16	178.9 (4)	C0'A—C1A'—C16'—C15'	178.5 (5)
C13—C14—C15—C16	−0.4 (6)	C5'B—C4'B—C9'B—C0'B	175 (2)
C14—C15—C16—C11A	0.2 (6)	C3'B—C4'B—C9'B—C0'B	−5 (4)
C12A—C11A—C16—C15	−0.6 (6)	C4'B—C9'B—C0'B—C1B'	−178 (3)
C10A—C11A—C16—C15	−178.6 (4)	C5B—C4B—C9B—C10B	17 (15)
C2'—N1'—C1'—C7'	−101.2 (5)	C3B—C4B—C9B—C10B	−167 (10)
C6'—N1'—C1'—C7'	76.9 (5)	C4B—C9B—C10B—C11B	−166 (10)
C6'—N1'—C2'—C3'A	2.2 (7)	C9B—C10B—C11B—C12B	−53 (13)
C1'—N1'—C2'—C3'A	−179.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Cl1	0.83 (3)	2.20 (3)	3.024 (3)	174 (4)
O2—H2O···Cl1ⁱ	0.83 (3)	2.27 (3)	3.086 (3)	169 (4)
C2—H2···O2′ⁱ	0.95	2.40	3.222 (5)	145
C5A—H5A···Cl2ⁱⁱ	0.95	2.78	3.687 (5)	159
C8—H8A···N2ⁱⁱ	0.99	2.65	3.637 (5)	176
O1′—H1O′···Cl2	0.84 (3)	2.25 (3)	3.083 (3)	171 (4)
O2′—H2O′···Cl2ⁱⁱⁱ	0.83 (3)	2.29 (3)	3.104 (3)	169 (4)
C6′—H6′···O2ⁱⁱⁱ	0.95	2.40	3.236 (6)	147

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Cl1	0.83 (3)	2.20 (3)	3.024 (3)	174 (4)
O2—H2O···Cl1ⁱ	0.83 (3)	2.27 (3)	3.086 (3)	169 (4)
C2—H2···O2'ⁱ	0.95	2.40	3.222 (5)	145.2
C5A—H5A···Cl2ⁱⁱ	0.95	2.78	3.687 (5)	159.1
C8—H8A···N2ⁱⁱ	0.99	2.65	3.637 (5)	176.0
O1'—H1O'···Cl2	0.84 (3)	2.25 (3)	3.083 (3)	171 (4)
O2'—H2O'···Cl2ⁱⁱⁱ	0.83 (3)	2.29 (3)	3.104 (3)	169 (4)
C6'—H6'···O2ⁱⁱⁱ	0.95	2.40	3.236 (6)	146.5

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

Acknowledgements

This work was supported by the New Zealand Foundation for Science and Innovation grant (contract C08X0704). We thank Dr C. Fitchett of the University of Canterbury, New Zealand, for the data collection.

References

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Volume 70| Part 1| January 2014| Pages o83-o84

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-(2,3-Di­hy­droxy­prop­yl)-4-{2-[4-(di­methyl­amino)­phen­yl]vin­yl}pyridinium chloride

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organic compounds

1-(2,3-Dihydroxypropyl)-4-{2-[4-(dimethylamino)phenyl]vinyl}pyridinium chloride