Tetra-n-propyl­ammonium chloride monohydrate

Yang, Y.-X.; Li, Q.; Ng, S.W.

doi:10.1107/S1600536809009532

organic compounds

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Volume 65| Part 4| April 2009| Page o815

doi:10.1107/S1600536809009532

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Tetra-n-propylammonium chloride monohydrate

Yun-Xia Yang,^a Qi Li ^a and Seik Weng Ng ^b ^*

^aCollege of Chemistry, Beijing Normal University, Beijing 100875, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 14 March 2009; accepted 16 March 2009; online 25 March 2009)

The crystal structure of the title salt hydrate, C₁₂H₂₈N⁺·Cl⁻·H₂O, consists of non-interacting cations and anions. The water molecule forms hydrogen bonds to two chloride ions, about a center of inversion, generating a planar eight-membered {⋯H—O—H⋯Cl}₂ ring.

Related literature

For the corresponding undecahydrated fluoride, see: Lipkowski et al. (1992 , 1997 ). For the anhydrous bromide, see: Zalkin (1957 ). For the anhydrous iodide, see: Yoshida et al. (1994 )

Experimental

Crystal data

C₁₂H₂₈N⁺·Cl⁻·H₂O
M_r = 239.82
Monoclinic, P 2₁ /n
a = 8.4228 (2) Å
b = 17.4383 (4) Å
c = 10.6885 (2) Å
β = 97.892 (1)°
V = 1555.05 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 295 K
0.60 × 0.40 × 0.35 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.769, T_max = 1.000 (expected range = 0.710–0.923)
9762 measured reflections
3562 independent reflections
2719 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.150
S = 1.02
3562 reflections
144 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H11⋯Cl1	0.86 (1)	2.37 (1)	3.227 (2)	175 (2)
O1—H12⋯Cl1ⁱ	0.86 (1)	2.51 (1)	3.352 (2)	168 (3)
Symmetry code: (i) -x+1, -y+1, -z+1.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009532/tk2397sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009532/tk2397Isup2.hkl

checkCIF report

Related literature top

For the corresponding undecahydated fluoride, see: Lipkowski et al. (1992, 1997). For the anhydrous bromide, see: Zalkin (1957). For the anhydrous iodide, see: Yoshida et al. (1994)

Experimental top

The salt was one of the possible products of the reaction of tetra-n-propylammonium hydroxide, guanidnium chloride and 1,3,5-tri(4-carboxyphenyl)benzene in a water/ethanol mixture. The other products were not identified.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the asymmetric unit of the title compound and its centrosymmetric mate; displacement ellipsoids are set at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Dashed lines denote hydrogen bonds.

Tetra-n-propylammonium chloride monohydrate top

Crystal data top

C₁₂H₂₈N⁺·Cl⁻·H₂O	F(000) = 536
M_r = 239.82	D_x = 1.024 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3424 reflections
a = 8.4228 (2) Å	θ = 2.3–27.8°
b = 17.4383 (4) Å	µ = 0.23 mm⁻¹
c = 10.6885 (2) Å	T = 295 K
β = 97.892 (1)°	Block, colorless
V = 1555.05 (6) Å³	0.60 × 0.40 × 0.35 mm
Z = 4

Data collection top

Bruker SMART APEXII diffractometer	3562 independent reflections
Radiation source: fine-focus sealed tube	2719 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.769, T_max = 1.000	k = −22→15
9762 measured reflections	l = −13→13

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.08P)² + 0.2641P] where P = (F_o² + 2F_c²)/3
3562 reflections	(Δ/σ)_max = 0.001
144 parameters	Δρ_max = 0.30 e Å⁻³
3 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₂H₂₈N⁺·Cl⁻·H₂O	V = 1555.05 (6) Å³
M_r = 239.82	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.4228 (2) Å	µ = 0.23 mm⁻¹
b = 17.4383 (4) Å	T = 295 K
c = 10.6885 (2) Å	0.60 × 0.40 × 0.35 mm
β = 97.892 (1)°

Data collection top

Bruker SMART APEXII diffractometer	3562 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2719 reflections with I > 2σ(I)
T_min = 0.769, T_max = 1.000	R_int = 0.021
9762 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	3 restraints
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.30 e Å⁻³
3562 reflections	Δρ_min = −0.26 e Å⁻³
144 parameters

Special details top

Experimental. A somewhat large crystal was used in the measurements, but this does not seem to have had an adverse efffect on the quality of the diffraction data.

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
Cl1	0.49841 (5)	0.65518 (2)	0.49054 (4)	0.06695 (19)
O1	0.7153 (2)	0.50593 (9)	0.57075 (19)	0.0885 (5)
H11	0.661 (3)	0.5471 (8)	0.553 (2)	0.116 (9)*
H12	0.655 (3)	0.4680 (9)	0.543 (3)	0.148 (13)*
N1	0.00272 (15)	0.67045 (7)	0.32316 (12)	0.0479 (3)
C1	0.11887 (19)	0.63243 (9)	0.24594 (14)	0.0509 (4)
H1A	0.2255	0.6522	0.2742	0.061*
H1B	0.1205	0.5779	0.2638	0.061*
C2	0.0833 (3)	0.64325 (11)	0.10428 (16)	0.0693 (5)
H2A	−0.0220	0.6227	0.0738	0.083*
H2B	0.0831	0.6975	0.0843	0.083*
C3	0.2080 (3)	0.60277 (16)	0.0399 (2)	0.0971 (8)
H3A	0.1855	0.6107	−0.0496	0.146*
H3B	0.2058	0.5489	0.0579	0.146*
H3C	0.3121	0.6230	0.0705	0.146*
C4	−0.1683 (2)	0.64589 (12)	0.27918 (17)	0.0646 (5)
H4A	−0.2367	0.6678	0.3358	0.077*
H4B	−0.2012	0.6673	0.1959	0.077*
C5	−0.1959 (3)	0.56022 (15)	0.2729 (2)	0.0900 (7)
H5A	−0.1734	0.5384	0.3569	0.108*
H5B	−0.1240	0.5368	0.2204	0.108*
C6	−0.3680 (3)	0.5438 (2)	0.2183 (3)	0.1355 (14)
H6A	−0.3851	0.4894	0.2146	0.203*
H6B	−0.3893	0.5649	0.1347	0.203*
H6C	−0.4386	0.5667	0.2708	0.203*
C7	0.0544 (2)	0.64638 (9)	0.45924 (14)	0.0516 (4)
H7A	0.0347	0.5918	0.4659	0.062*
H7B	0.1692	0.6542	0.4787	0.062*
C8	−0.0258 (2)	0.68710 (12)	0.55843 (16)	0.0659 (5)
H8A	−0.1408	0.6791	0.5424	0.079*
H8B	−0.0052	0.7418	0.5556	0.079*
C9	0.0402 (3)	0.65545 (14)	0.68748 (19)	0.0851 (7)
H9A	−0.0114	0.6804	0.7511	0.128*
H9B	0.1536	0.6647	0.7036	0.128*
H9C	0.0203	0.6013	0.6894	0.128*
C10	0.0095 (2)	0.75695 (9)	0.30981 (17)	0.0585 (4)
H10A	−0.0243	0.7701	0.2220	0.070*
H10B	−0.0671	0.7795	0.3590	0.070*
C11	0.1705 (3)	0.79260 (11)	0.3505 (2)	0.0802 (6)
H11A	0.2444	0.7768	0.2933	0.096*
H11B	0.2122	0.7746	0.4345	0.096*
C12	0.1596 (3)	0.87896 (12)	0.3513 (2)	0.0921 (7)
H12A	0.2638	0.9002	0.3782	0.138*
H12B	0.0873	0.8947	0.4085	0.138*
H12C	0.1207	0.8969	0.2678	0.138*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0595 (3)	0.0543 (3)	0.0819 (3)	0.00883 (18)	−0.0084 (2)	−0.0134 (2)
O1	0.0763 (10)	0.0649 (10)	0.1177 (13)	0.0160 (8)	−0.0101 (9)	0.0075 (9)
N1	0.0450 (7)	0.0476 (7)	0.0500 (7)	0.0069 (5)	0.0023 (5)	0.0061 (5)
C1	0.0534 (8)	0.0449 (8)	0.0543 (8)	0.0083 (7)	0.0067 (7)	0.0053 (6)
C2	0.0840 (13)	0.0695 (12)	0.0544 (9)	0.0188 (10)	0.0100 (9)	0.0099 (8)
C3	0.125 (2)	0.1048 (18)	0.0659 (12)	0.0372 (15)	0.0271 (13)	0.0045 (12)
C4	0.0482 (9)	0.0874 (13)	0.0561 (9)	−0.0014 (8)	−0.0001 (7)	−0.0002 (8)
C5	0.0818 (14)	0.0948 (17)	0.0936 (15)	−0.0340 (12)	0.0128 (12)	−0.0136 (12)
C6	0.099 (2)	0.207 (4)	0.103 (2)	−0.078 (2)	0.0222 (16)	−0.055 (2)
C7	0.0525 (8)	0.0511 (9)	0.0495 (8)	0.0052 (7)	0.0011 (6)	0.0064 (6)
C8	0.0613 (10)	0.0782 (12)	0.0572 (10)	0.0087 (9)	0.0040 (8)	−0.0026 (9)
C9	0.0846 (15)	0.1143 (19)	0.0561 (10)	0.0104 (12)	0.0080 (10)	0.0030 (11)
C10	0.0639 (10)	0.0469 (9)	0.0645 (9)	0.0174 (7)	0.0082 (8)	0.0082 (7)
C11	0.0746 (13)	0.0472 (10)	0.1188 (17)	0.0000 (9)	0.0133 (12)	0.0074 (10)
C12	0.133 (2)	0.0500 (11)	0.0923 (15)	0.0012 (12)	0.0120 (14)	−0.0009 (10)

Geometric parameters (Å, º) top

O1—H11	0.858 (10)	C6—H6A	0.9600
O1—H12	0.859 (10)	C6—H6B	0.9600
N1—C4	1.514 (2)	C6—H6C	0.9600
N1—C1	1.517 (2)	C7—C8	1.511 (2)
N1—C10	1.517 (2)	C7—H7A	0.9700
N1—C7	1.5189 (18)	C7—H7B	0.9700
C1—C2	1.514 (2)	C8—C9	1.519 (3)
C1—H1A	0.9700	C8—H8A	0.9700
C1—H1B	0.9700	C8—H8B	0.9700
C2—C3	1.508 (3)	C9—H9A	0.9600
C2—H2A	0.9700	C9—H9B	0.9600
C2—H2B	0.9700	C9—H9C	0.9600
C3—H3A	0.9600	C10—C11	1.501 (3)
C3—H3B	0.9600	C10—H10A	0.9700
C3—H3C	0.9600	C10—H10B	0.9700
C4—C5	1.512 (3)	C11—C12	1.509 (3)
C4—H4A	0.9700	C11—H11A	0.9700
C4—H4B	0.9700	C11—H11B	0.9700
C5—C6	1.514 (3)	C12—H12A	0.9600
C5—H5A	0.9700	C12—H12B	0.9600
C5—H5B	0.9700	C12—H12C	0.9600

H11—O1—H12	107.3 (15)	C5—C6—H6C	109.5
C4—N1—C1	111.37 (13)	H6A—C6—H6C	109.5
C4—N1—C10	107.36 (12)	H6B—C6—H6C	109.5
C1—N1—C10	110.37 (12)	C8—C7—N1	116.43 (13)
C4—N1—C7	110.76 (12)	C8—C7—H7A	108.2
C1—N1—C7	106.19 (11)	N1—C7—H7A	108.2
C10—N1—C7	110.82 (12)	C8—C7—H7B	108.2
C2—C1—N1	115.83 (13)	N1—C7—H7B	108.2
C2—C1—H1A	108.3	H7A—C7—H7B	107.3
N1—C1—H1A	108.3	C7—C8—C9	108.86 (16)
C2—C1—H1B	108.3	C7—C8—H8A	109.9
N1—C1—H1B	108.3	C9—C8—H8A	109.9
H1A—C1—H1B	107.4	C7—C8—H8B	109.9
C3—C2—C1	110.06 (15)	C9—C8—H8B	109.9
C3—C2—H2A	109.6	H8A—C8—H8B	108.3
C1—C2—H2A	109.6	C8—C9—H9A	109.5
C3—C2—H2B	109.6	C8—C9—H9B	109.5
C1—C2—H2B	109.6	H9A—C9—H9B	109.5
H2A—C2—H2B	108.2	C8—C9—H9C	109.5
C2—C3—H3A	109.5	H9A—C9—H9C	109.5
C2—C3—H3B	109.5	H9B—C9—H9C	109.5
H3A—C3—H3B	109.5	C11—C10—N1	115.39 (13)
C2—C3—H3C	109.5	C11—C10—H10A	108.4
H3A—C3—H3C	109.5	N1—C10—H10A	108.4
H3B—C3—H3C	109.5	C11—C10—H10B	108.4
C5—C4—N1	115.29 (16)	N1—C10—H10B	108.4
C5—C4—H4A	108.5	H10A—C10—H10B	107.5
N1—C4—H4A	108.5	C10—C11—C12	111.21 (18)
C5—C4—H4B	108.5	C10—C11—H11A	109.4
N1—C4—H4B	108.5	C12—C11—H11A	109.4
H4A—C4—H4B	107.5	C10—C11—H11B	109.4
C4—C5—C6	109.7 (2)	C12—C11—H11B	109.4
C4—C5—H5A	109.7	H11A—C11—H11B	108.0
C6—C5—H5A	109.7	C11—C12—H12A	109.5
C4—C5—H5B	109.7	C11—C12—H12B	109.5
C6—C5—H5B	109.7	H12A—C12—H12B	109.5
H5A—C5—H5B	108.2	C11—C12—H12C	109.5
C5—C6—H6A	109.5	H12A—C12—H12C	109.5
C5—C6—H6B	109.5	H12B—C12—H12C	109.5
H6A—C6—H6B	109.5

C4—N1—C1—C2	54.78 (19)	C4—N1—C7—C8	−68.64 (19)
C10—N1—C1—C2	−64.37 (18)	C1—N1—C7—C8	170.30 (15)
C7—N1—C1—C2	175.45 (15)	C10—N1—C7—C8	50.42 (19)
N1—C1—C2—C3	179.85 (18)	N1—C7—C8—C9	179.81 (16)
C1—N1—C4—C5	53.15 (19)	C4—N1—C10—C11	179.35 (16)
C10—N1—C4—C5	174.08 (16)	C1—N1—C10—C11	−59.08 (19)
C7—N1—C4—C5	−64.80 (19)	C7—N1—C10—C11	58.3 (2)
N1—C4—C5—C6	−175.66 (17)	N1—C10—C11—C12	−171.82 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11···Cl1	0.86 (1)	2.37 (1)	3.227 (2)	175 (2)
O1—H12···Cl1ⁱ	0.86 (1)	2.51 (1)	3.352 (2)	168 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₂₈N⁺·Cl⁻·H₂O
M_r	239.82
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	8.4228 (2), 17.4383 (4), 10.6885 (2)
β (°)	97.892 (1)
V (Å³)	1555.05 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.60 × 0.40 × 0.35

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.769, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9762, 3562, 2719
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.150, 1.02
No. of reflections	3562
No. of parameters	144
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.26

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11···Cl1	0.86 (1)	2.37 (1)	3.227 (2)	175 (2)
O1—H12···Cl1ⁱ	0.86 (1)	2.51 (1)	3.352 (2)	168 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We thank Beijing Normal University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lipkowski, J., Luboradzki, R. & Udachin, K. A. (1997). Supramol. Chem. 8, 281–286. Web of Science CSD CrossRef CAS Google Scholar
Lipkowski, J., Luboradzki, R., Udachin, K. & Dyadin, Y. (1992). J. Inclusion Phenom. 13, 295. CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar
Yoshida, T., Nagata, K., Yasuniwa, M., Yoshimatsu, M. & Wunderlich, B. (1994). Acta Cryst. C50, 1758–1760. CSD CrossRef CAS IUCr Journals Google Scholar
Zalkin, A. (1957). Acta Cryst. 10, 557–560. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar