n-Tridecyl­amine chloride monohydrate

Zhang, L.; Di, Y.; Dan, W.

doi:10.1107/S1600536811006246

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o717

doi:10.1107/S1600536811006246

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n-Tridecylamine chloride monohydrate

Lijun Zhang,^a Youying Di ^a ^* and Wenyan Dan ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: diyouying@126.com

(Received 11 January 2011; accepted 18 February 2011; online 26 February 2011)

In the title compound, C₁₃H₃₀N⁺·Cl⁻·H₂O, the C₁₃H₂₇ alkyl chain is in an all-trans conformation. In the crystal, intermolecular N—H⋯Cl, N—H⋯O and O—H⋯Cl hydrogen bonds connect the components into layers parallel to (010), with the alkyl chains oriented approximately perpendicular to these layers.

Related literature

For applications of long-chain n-alkylammonium halides, see: Aratono et al. (1998 ); Tornblom et al. (2000 ); Ringsdorf et al. (1988 ). For details of phase transitions in n-alkylammonium chlorides, see: Terreros et al. (2000 ). For related structures, see: Rademeyer et al. (2009 ); Lundén (1974 ); Clark & Hudgens (1950 ).

Experimental

Crystal data

C₁₃H₃₀N⁺·Cl⁻·H₂O
M_r = 253.85
Monoclinic, P 2₁ /c
a = 4.7420 (5) Å
b = 45.250 (3) Å
c = 7.8191 (9) Å
β = 106.332 (2)°
V = 1610.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 298 K
0.34 × 0.33 × 0.03 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.928, T_max = 0.993
8230 measured reflections
2845 independent reflections
1379 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.124
S = 1.03
2845 reflections
147 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1	0.89	2.44	3.303 (3)	162
N1—H1B⋯Cl1ⁱ	0.89	2.36	3.236 (2)	170
N1—H1C⋯O1ⁱⁱ	0.89	2.05	2.901 (4)	159
O1—H1H⋯Cl1	0.85	2.45	3.290 (3)	170
O1—H1I⋯Cl1ⁱⁱⁱ	0.85	2.39	3.228 (2)	170
Symmetry codes: (i) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y, z-1; (iii) x-1, y, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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/S1600536811006246/lh5197sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006246/lh5197Isup2.hkl

checkCIF report

Comment top

Long-chain n-alkylammonium halides are widely used as surfactants (Aratono et al., 1998; Tornblom et al., 2000) and as models for biological membranes (Ringsdorf et al., 1988). It has been shown that phase transitions occur in n-alkylammonium chlorides (Terreros et al., 2000). As a part of our studies on novel potential phase transition materials with thermochemical properties, we report herein the crystal structure of the title compound (Fig. 1).

Atoms C2–C13 are essentially co-planar with a maximum deviation of 0.048 (3)Å for atom C2. The alkyl chain in related compounds is typically in the extended conformation e.g. in the isostructural n-tridecylamine bromide monohydrate compound (Rademeyer et al., 2009), n–dodecylammonium bromide (Lundén, 1974) and n–tridecylamine chloride (Clark & Hudgens, 1950). Although the methylene chain has the extended all–trans conformation, it is slightly bent in the vicinity of the ammonium group possibly to accommodate the hydrogen–bonding interactions. Only the C1–C2–C3–C4 torsion angle deviates significantly from 180 °, with a value of 169.84 (3)°. The crystal packing (Fig. 2) is stabilized by intermolecular N—H···Cl, N—H···O and O—H···Cl hydrogen bonds (Table 1 and Fig.2).

Related literature top

For applications of long-chain n-alkylammonium halides, see: Aratono et al. (1998); Tornblom et al. (2000); Ringsdorf et al. (1988). For details of phase transitions in n-alkylammonium chlorides, see: Terreros et al. (2000). For related structures, see: Rademeyer et al. (2009); Lundén (1974); Clark & Hudgens (1950).

Experimental top

n–Tridecylamine chloride monohydrate was prepared by the addition of hydrochloric acid to an ethanolic solution of n–tridecylamine. The mixture was heated and stirred under reflux for 6 h. Single crystals suitable for X–ray diffraction were prepared by evaporation of the resulting solution at room temperature. Analysis, calculated for C₁₃H₃₂ClNO (Mr =253.85): C 61.51, H 12.71, N 5.52, Cl 13.96%; found: C 61.50, H 12.72, N 5.51, Cl 13.95%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines.

n-Tridecylamine chloride monohydrate top

Crystal data top

C₁₃H₃₀N⁺·Cl⁻·H₂O	F(000) = 568
M_r = 253.85	D_x = 1.047 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 817 reflections
a = 4.7420 (5) Å	θ = 2.7–20.8°
b = 45.250 (3) Å	µ = 0.22 mm⁻¹
c = 7.8191 (9) Å	T = 298 K
β = 106.332 (2)°	Acicular, colourless
V = 1610.1 (3) Å³	0.34 × 0.33 × 0.03 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	2845 independent reflections
Radiation source: fine-focus sealed tube	1379 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
Detector resolution: 10 pixels mm^-1	θ_max = 25.0°, θ_min = 2.7°
ϕ and ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −53→46
T_min = 0.928, T_max = 0.993	l = −7→9
8230 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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0256P)²] where P = (F_o² + 2F_c²)/3
2845 reflections	(Δ/σ)_max = 0.001
147 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₃H₃₀N⁺·Cl⁻·H₂O	V = 1610.1 (3) Å³
M_r = 253.85	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.7420 (5) Å	µ = 0.22 mm⁻¹
b = 45.250 (3) Å	T = 298 K
c = 7.8191 (9) Å	0.34 × 0.33 × 0.03 mm
β = 106.332 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2845 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1379 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.993	R_int = 0.077
8230 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.03	Δρ_max = 0.25 e Å⁻³
2845 reflections	Δρ_min = −0.18 e Å⁻³
147 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
Cl1	0.77004 (19)	0.727389 (19)	0.54882 (12)	0.0578 (3)
N1	0.2908 (5)	0.72396 (5)	0.1504 (4)	0.0486 (8)
H1A	0.4378	0.7281	0.2466	0.073*
H1B	0.1648	0.7390	0.1270	0.073*
H1C	0.3618	0.7210	0.0578	0.073*
O1	0.3848 (5)	0.70538 (5)	0.8156 (3)	0.0690 (8)
H1H	0.5034	0.7102	0.7566	0.083*
H1I	0.2125	0.7103	0.7554	0.083*
C1	0.1369 (7)	0.69683 (6)	0.1834 (4)	0.0462 (9)
H1D	−0.0396	0.6941	0.0856	0.055*
H1E	0.0779	0.6994	0.2915	0.055*
C2	0.3263 (7)	0.66944 (6)	0.2017 (4)	0.0445 (9)
H2A	0.5028	0.6722	0.2995	0.053*
H2B	0.3852	0.6668	0.0935	0.053*
C3	0.1677 (7)	0.64186 (6)	0.2355 (4)	0.0467 (9)
H3A	−0.0251	0.6412	0.1498	0.056*
H3B	0.1397	0.6431	0.3534	0.056*
C4	0.3305 (7)	0.61334 (6)	0.2221 (4)	0.0444 (9)
H4A	0.5222	0.6140	0.3090	0.053*
H4B	0.3616	0.6123	0.1049	0.053*
C5	0.1730 (7)	0.58533 (6)	0.2526 (4)	0.0471 (9)
H5A	0.1495	0.5860	0.3718	0.056*
H5B	−0.0219	0.5851	0.1691	0.056*
C6	0.3292 (7)	0.55675 (6)	0.2317 (4)	0.0440 (9)
H6A	0.3543	0.5562	0.1128	0.053*
H6B	0.5234	0.5569	0.3159	0.053*
C7	0.1722 (7)	0.52882 (6)	0.2603 (4)	0.0450 (9)
H7A	−0.0231	0.5288	0.1773	0.054*
H7B	0.1496	0.5292	0.3798	0.054*
C8	0.3260 (6)	0.50019 (6)	0.2369 (4)	0.0440 (9)
H8A	0.3473	0.4997	0.1171	0.053*
H8B	0.5218	0.5003	0.3193	0.053*
C9	0.1705 (7)	0.47222 (6)	0.2666 (4)	0.0448 (9)
H9A	−0.0251	0.4721	0.1839	0.054*
H9B	0.1485	0.4727	0.3862	0.054*
C10	0.3245 (7)	0.44364 (6)	0.2439 (4)	0.0438 (9)
H10A	0.3458	0.4431	0.1242	0.053*
H10B	0.5204	0.4438	0.3263	0.053*
C11	0.1702 (7)	0.41561 (6)	0.2745 (4)	0.0448 (9)
H11A	0.1479	0.4162	0.3940	0.054*
H11B	−0.0253	0.4154	0.1917	0.054*
C12	0.3236 (7)	0.38729 (6)	0.2530 (5)	0.0522 (10)
H12A	0.5194	0.3876	0.3355	0.063*
H12B	0.3452	0.3867	0.1333	0.063*
C13	0.1688 (8)	0.35920 (7)	0.2844 (5)	0.0703 (12)
H13A	0.1532	0.3591	0.4042	0.105*
H13B	0.2798	0.3423	0.2668	0.105*
H13C	−0.0242	0.3584	0.2021	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0520 (5)	0.0590 (6)	0.0612 (6)	−0.0052 (5)	0.0137 (4)	−0.0036 (5)
N1	0.0485 (16)	0.0358 (17)	0.061 (2)	0.0041 (15)	0.0145 (14)	0.0002 (14)
O1	0.0659 (17)	0.0752 (17)	0.0683 (19)	0.0036 (15)	0.0230 (13)	0.0100 (14)
C1	0.044 (2)	0.034 (2)	0.062 (3)	0.0005 (18)	0.0178 (17)	0.0039 (16)
C2	0.046 (2)	0.035 (2)	0.053 (2)	−0.0022 (18)	0.0152 (17)	−0.0021 (16)
C3	0.052 (2)	0.039 (2)	0.053 (2)	−0.0043 (19)	0.0209 (18)	0.0011 (17)
C4	0.050 (2)	0.036 (2)	0.050 (2)	−0.0033 (18)	0.0191 (18)	0.0020 (16)
C5	0.053 (2)	0.041 (2)	0.049 (2)	−0.005 (2)	0.0189 (18)	0.0004 (17)
C6	0.048 (2)	0.039 (2)	0.048 (2)	−0.0014 (19)	0.0177 (17)	0.0012 (16)
C7	0.048 (2)	0.039 (2)	0.050 (2)	−0.0024 (19)	0.0178 (17)	0.0029 (17)
C8	0.047 (2)	0.040 (2)	0.047 (2)	−0.003 (2)	0.0170 (17)	0.0042 (16)
C9	0.051 (2)	0.037 (2)	0.049 (2)	−0.0035 (19)	0.0190 (18)	−0.0009 (16)
C10	0.048 (2)	0.040 (2)	0.047 (2)	−0.0014 (19)	0.0194 (17)	−0.0011 (16)
C11	0.050 (2)	0.039 (2)	0.048 (2)	−0.0033 (19)	0.0167 (17)	0.0026 (16)
C12	0.062 (2)	0.041 (2)	0.054 (3)	0.004 (2)	0.0163 (19)	0.0000 (17)
C13	0.094 (3)	0.043 (2)	0.076 (3)	−0.005 (2)	0.026 (2)	0.001 (2)

Geometric parameters (Å, º) top

N1—C1	1.487 (3)	C6—H6B	0.9700
N1—H1A	0.8900	C7—C8	1.523 (4)
N1—H1B	0.8900	C7—H7A	0.9700
N1—H1C	0.8900	C7—H7B	0.9700
O1—H1H	0.8499	C8—C9	1.515 (4)
O1—H1I	0.8499	C8—H8A	0.9700
C1—C2	1.513 (4)	C8—H8B	0.9700
C1—H1D	0.9700	C9—C10	1.520 (4)
C1—H1E	0.9700	C9—H9A	0.9700
C2—C3	1.518 (4)	C9—H9B	0.9700
C2—H2A	0.9700	C10—C11	1.517 (4)
C2—H2B	0.9700	C10—H10A	0.9700
C3—C4	1.523 (4)	C10—H10B	0.9700
C3—H3A	0.9700	C11—C12	1.506 (4)
C3—H3B	0.9700	C11—H11A	0.9700
C4—C5	1.524 (4)	C11—H11B	0.9700
C4—H4A	0.9700	C12—C13	1.522 (4)
C4—H4B	0.9700	C12—H12A	0.9700
C5—C6	1.522 (4)	C12—H12B	0.9700
C5—H5A	0.9700	C13—H13A	0.9600
C5—H5B	0.9700	C13—H13B	0.9600
C6—C7	1.515 (4)	C13—H13C	0.9600
C6—H6A	0.9700

C1—N1—H1A	109.5	C6—C7—C8	114.8 (3)
C1—N1—H1B	109.5	C6—C7—H7A	108.6
H1A—N1—H1B	109.5	C8—C7—H7A	108.6
C1—N1—H1C	109.5	C6—C7—H7B	108.6
H1A—N1—H1C	109.5	C8—C7—H7B	108.6
H1B—N1—H1C	109.5	H7A—C7—H7B	107.5
H1H—O1—H1I	108.1	C9—C8—C7	114.9 (2)
N1—C1—C2	112.7 (3)	C9—C8—H8A	108.5
N1—C1—H1D	109.1	C7—C8—H8A	108.5
C2—C1—H1D	109.1	C9—C8—H8B	108.5
N1—C1—H1E	109.1	C7—C8—H8B	108.5
C2—C1—H1E	109.1	H8A—C8—H8B	107.5
H1D—C1—H1E	107.8	C8—C9—C10	115.0 (3)
C1—C2—C3	112.3 (3)	C8—C9—H9A	108.5
C1—C2—H2A	109.1	C10—C9—H9A	108.5
C3—C2—H2A	109.1	C8—C9—H9B	108.5
C1—C2—H2B	109.1	C10—C9—H9B	108.5
C3—C2—H2B	109.1	H9A—C9—H9B	107.5
H2A—C2—H2B	107.9	C11—C10—C9	115.1 (3)
C2—C3—C4	113.5 (3)	C11—C10—H10A	108.5
C2—C3—H3A	108.9	C9—C10—H10A	108.5
C4—C3—H3A	108.9	C11—C10—H10B	108.5
C2—C3—H3B	108.9	C9—C10—H10B	108.5
C4—C3—H3B	108.9	H10A—C10—H10B	107.5
H3A—C3—H3B	107.7	C12—C11—C10	115.1 (3)
C3—C4—C5	114.5 (3)	C12—C11—H11A	108.5
C3—C4—H4A	108.6	C10—C11—H11A	108.5
C5—C4—H4A	108.6	C12—C11—H11B	108.5
C3—C4—H4B	108.6	C10—C11—H11B	108.5
C5—C4—H4B	108.6	H11A—C11—H11B	107.5
H4A—C4—H4B	107.6	C11—C12—C13	115.0 (3)
C6—C5—C4	114.5 (3)	C11—C12—H12A	108.5
C6—C5—H5A	108.6	C13—C12—H12A	108.5
C4—C5—H5A	108.6	C11—C12—H12B	108.5
C6—C5—H5B	108.6	C13—C12—H12B	108.5
C4—C5—H5B	108.6	H12A—C12—H12B	107.5
H5A—C5—H5B	107.6	C12—C13—H13A	109.5
C7—C6—C5	114.8 (3)	C12—C13—H13B	109.5
C7—C6—H6A	108.6	H13A—C13—H13B	109.5
C5—C6—H6A	108.6	C12—C13—H13C	109.5
C7—C6—H6B	108.6	H13A—C13—H13C	109.5
C5—C6—H6B	108.6	H13B—C13—H13C	109.5
H6A—C6—H6B	107.6

N1—C1—C2—C3	180.0 (3)	C6—C7—C8—C9	179.6 (3)
C1—C2—C3—C4	169.9 (3)	C7—C8—C9—C10	−179.8 (3)
C2—C3—C4—C5	−179.1 (3)	C8—C9—C10—C11	179.7 (3)
C3—C4—C5—C6	177.6 (3)	C9—C10—C11—C12	−179.7 (3)
C4—C5—C6—C7	−179.5 (3)	C10—C11—C12—C13	179.8 (3)
C5—C6—C7—C8	179.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1	0.89	2.44	3.303 (3)	162
N1—H1B···Cl1ⁱ	0.89	2.36	3.236 (2)	170
N1—H1C···O1ⁱⁱ	0.89	2.05	2.901 (4)	159
O1—H1H···Cl1	0.85	2.45	3.290 (3)	170
O1—H1I···Cl1ⁱⁱⁱ	0.85	2.39	3.228 (2)	170

Symmetry codes: (i) x−1, −y+3/2, z−1/2; (ii) x, y, z−1; (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₃₀N⁺·Cl⁻·H₂O
M_r	253.85
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	4.7420 (5), 45.250 (3), 7.8191 (9)
β (°)	106.332 (2)
V (Å³)	1610.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.34 × 0.33 × 0.03

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.928, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	8230, 2845, 1379
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.124, 1.03
No. of reflections	2845
No. of parameters	147
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.18

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), 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
N1—H1A···Cl1	0.89	2.44	3.303 (3)	162
N1—H1B···Cl1ⁱ	0.89	2.36	3.236 (2)	170
N1—H1C···O1ⁱⁱ	0.89	2.05	2.901 (4)	159
O1—H1H···Cl1	0.85	2.45	3.290 (3)	170
O1—H1I···Cl1ⁱⁱⁱ	0.85	2.39	3.228 (2)	170

Symmetry codes: (i) x−1, −y+3/2, z−1/2; (ii) x, y, z−1; (iii) x−1, y, z.

Acknowledgements

We acknowledge the National Natural Science Foundation of China (20973089) for financial support.

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