N,N-Dimethylpyridin-4-aminium 1-phenyl­cyclo­pentane-1-carboxyl­ate monohydrate

He, G.; Aitipamula, S.; Chow, P.S.; Tan, R.B.H.

doi:10.1107/S1600536811015200

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1227

doi:10.1107/S1600536811015200

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N,N-Dimethylpyridin-4-aminium 1-phenylcyclopentane-1-carboxylate monohydrate

Guangwen He,^a ^* Srinivasulu Aitipamula,^a Pui Shan Chow ^a and Reginald B. H. Tan ^a,^b ^*

^aInstitute of Chemical and Engineering Sciences, A*STAR (Agency for Science, Technology and Research), 1 Pesek Road, Jurong Island, Singapore 627833, and ^bDepartment of Chemical & Biomolecular Engineering, National University of Singapore, 4 Engineering Drive 4, Singapore 117576
^*Correspondence e-mail: he_guangwen@ices.a-star.edu.sg, reginald_tan@ices.a-star.edu.sg

(Received 19 April 2011; accepted 22 April 2011; online 29 April 2011)

The cation of the title salt, C₇H₁₁N₂⁺·C₁₂H₁₃O₂⁻·H₂O, is planar (r.m.s. deviation = 0.0184 Å). In the crystal, the cation, anion and water molecule are linked by O—H⋯O and N—H⋯O hydrogen bonds, forming a chain running along the a axis.

Related literature

For the structure of 4-dimethylaminopyridine, see: Ohms & Guth (1984 ). For the structure of 1-phenylcyclopentane-1-carboxylic acid, see: Margulis (1975 ). For recent molecular co-crystals and salts of 4-dimethylaminopyridine, see: Dastidar et al. (1993 ). For recent molecular co-crystals of 1-phenylcyclopentane-1-carboxylic acid, see: He et al. (2010 , 2011 ). For comparative bond dimensions in pyridinium carboxylates, see: Kumar et al. (2009 ).

Experimental

Crystal data

C₇H₁₁N₂⁺·C₁₂H₁₃O₂⁻·H₂O
M_r = 330.42
Monoclinic, P 2₁ /n
a = 6.1666 (12) Å
b = 18.206 (4) Å
c = 15.702 (3) Å
β = 97.33 (3)°
V = 1748.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 110 K
0.44 × 0.33 × 0.22 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.964, T_max = 0.982
12519 measured reflections
4233 independent reflections
3945 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.139
S = 1.13
4233 reflections
231 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H7⋯O2	0.94 (2)	1.72 (2)	2.6458 (15)	168 (2)
O3—H3⋯O2	0.87 (2)	1.93 (2)	2.7935 (14)	167 (2)
O3—H6⋯O1ⁱ	0.87 (2)	1.90 (2)	2.7634 (15)	169 (2)
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015200/ng5153sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015200/ng5153Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811015200/ng5153Isup3.cml

checkCIF report

Comment top

Substituted pyridines such as 4-dimethylaminopyridine was found to form binary salt hydrate with l-tartaric acid (Dastidar et al., 1993). The authors have shown that this molecular complex possesses high nonlinear optical (NLO) effects, viz. second harmonic generation (SHG) in the crystalline state. In our previous work, we have demonstrated the formation of a salt and a cocrystal of a substituted pyridine, 2-aminopyridine, with 1-phenylcyclopropane-1-carboxylic acid and 1-phenylcyclopentane-1-carboxylic acid, respectively (He et al., 2010; He et al., 2011). Here we have selected 4-dimethylaminopyridine and 1-phenylcyclopentane-1-carboxylic acid as a model molecular pair.

The crystal structure of the title salt hydrate contains each one molecule of 4-dimethylaminopyridinium ion, 1-phenylcyclopentane-1-carboxylate ion, and water (Fig. 1). The title molecular complex is a salt rather than a cocrystal is evident by the proton transfer from the carboxylic acid to the pyridine nitrogen of the 4-dimethylaminopyridine, which was located in the difference Fourier map during the refinement cycles. Furthermore, the C—O/C=O bond distances (1.2412 (16) Å and 1.2700 (16) Å) and C—N—C angle of pyridine group (119.93 (12)°) are in well agreement with the corresponding distances/angles that are generally observed for a carboxylic acid-pyridine salts (Kumar et al., 2009). In the crystal structure, the translation related 1-phenylcyclopentane-1-carboxylate ions are connected via water molecules involving O—H···O hydrogen bonds (Table 1) and generate infinite hydrogen bonded chains along the crystallographic a-axis (Fig. 2). The 4-dimethylaminopyridinium ion hydrogen bonded to one of the O atoms of the carboxylate ion via N—H···O hydrogen bond (Fig. 2). The hydrogen bonded chians close pack to build up the overall crystal structure (Fig. 3). A TGA experiment indicates an initial weight loss (ca 6%) upon heating (Fig. 4). This number matches with the water content in the title salt hydrate, implying that the resulting molecular complex is indeed a hydrate.

Related literature top

For the structure of 4-dimethylaminopyridine, see: Ohms & Guth (1984). For the structure of 1-phenylcyclopentane-1-carboxylic acid, see: Margulis (1975). For recent molecular co-crystals and salts of 4-dimethylaminopyridine, see: Dastidar et al. (1993). For recent molecular co-crystals of 1-phenylcyclopentane-1-carboxylic acid, see: He et al. (2010, 2011). For comparison bond dimensions in pyridinium carboxylates, see: Kumar et al. (2009).

Experimental top

0.1224 g (1 mmol) of 4-dimethylaminopyridine (Alfa Aesar, 99%) and 0.1902 g (1 mmol) of 1-phenylcyclopentane-1-carboxylic acid (Alfa Aesar, 98%) and were dissolved into 7 ml of acetonitrile/water (90/10 v/v%) (acetonitrile, Fisher Scientific, HPLC; deionized water). Solution was then filtered through a 0.22 µm PTFE filter. Filtered solution was finally sealed with Parafilm and small holes were made to allow solvent to slowly evaporate. The colorless block-shaped crystal (0.44 × 0.33 × 0.22 mm) suitable for single-crystal X-ray diffraction (Rigaku Saturn 70 CCD area detector with Mo K_α radiation = 0.71073 Å at 50 kV and 40 mA) was collected after three day. TGA-DSC experiment of the resulting crystals was run using a TA Instrument SDT-TGA (SDT2960) at a ramping rate of 10 °C/min to 1000 °C.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structures of 4-dimethylaminopyridine, 1-phenylcyclopentane-1-carboxylic acid and water, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A supramolecular unit in the crystal structure of the title salt hydrate, featuring the O—H···O interaction between the carboxylate ion and the water molecule and the N—H···O interaction between the carboxylate ion and the pyridinium ions.
	Fig. 3. Part of the crystal structure of the title salt hydrate, showing the close packing of hydrogen bonded chains.
	Fig. 4. Profiles of heat flow and weight loss of the title salt hydrate determined by DSC and TGA, respectively.

N,N-Dimethylpyridin-4-aminium 1-phenylcyclopentane-1-carboxylate monohydrate top

Crystal data top

C₇H₁₁N₂⁺·C₁₂H₁₃O₂⁻·H₂O	F(000) = 712
M_r = 330.42	D_x = 1.255 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5283 reflections
a = 6.1666 (12) Å	θ = 2.2–31.0°
b = 18.206 (4) Å	µ = 0.09 mm⁻¹
c = 15.702 (3) Å	T = 110 K
β = 97.33 (3)°	Block, colorless
V = 1748.4 (6) Å³	0.44 × 0.33 × 0.22 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	4233 independent reflections
Radiation source: fine-focus sealed tube	3945 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω scans	θ_max = 28.3°, θ_min = 2.9°
Absorption correction: multi-scan (Blessing, 1995)	h = −8→8
T_min = 0.964, T_max = 0.982	k = −21→23
12519 measured reflections	l = −20→20

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ²(F_o²) + (0.0729P)² + 0.4696P] where P = (F_o² + 2F_c²)/3
4233 reflections	(Δ/σ)_max < 0.001
231 parameters	Δρ_max = 0.23 e Å⁻³
3 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₇H₁₁N₂⁺·C₁₂H₁₃O₂⁻·H₂O	V = 1748.4 (6) Å³
M_r = 330.42	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.1666 (12) Å	µ = 0.09 mm⁻¹
b = 18.206 (4) Å	T = 110 K
c = 15.702 (3) Å	0.44 × 0.33 × 0.22 mm
β = 97.33 (3)°

Data collection top

Bruker APEXII diffractometer	4233 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	3945 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.982	R_int = 0.017
12519 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	3 restraints
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.23 e Å⁻³
4233 reflections	Δρ_min = −0.21 e Å⁻³
231 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
O3	0.46197 (17)	0.37281 (6)	0.40367 (7)	0.0322 (2)
H3	0.337 (3)	0.3496 (12)	0.3979 (14)	0.062 (6)*
H6	0.561 (3)	0.3390 (10)	0.4004 (13)	0.053 (6)*
C1	−0.0970 (2)	0.21395 (7)	0.17867 (8)	0.0237 (3)
H1	−0.2349	0.1936	0.1864	0.028*
C2	0.3042 (2)	0.27379 (7)	0.15451 (8)	0.0270 (3)
H2	0.4419	0.2941	0.1463	0.032*
C3	−0.06856 (19)	0.25206 (7)	0.38099 (7)	0.0206 (2)
C4	−0.0648 (2)	0.24247 (7)	0.09887 (8)	0.0261 (3)
H4	−0.1802	0.2410	0.0526	0.031*
C5	0.2731 (2)	0.24498 (7)	0.23453 (8)	0.0232 (3)
H5	0.3897	0.2458	0.2803	0.028*
C6	0.03032 (19)	0.18630 (7)	0.33520 (7)	0.0206 (2)
C7	0.07135 (19)	0.21492 (7)	0.24761 (7)	0.0203 (2)
C8	0.2357 (2)	0.15696 (7)	0.39066 (8)	0.0256 (3)
H8A	0.3231	0.1256	0.3564	0.031*
H8B	0.3283	0.1978	0.4160	0.031*
C9	0.1353 (2)	0.27300 (7)	0.08674 (8)	0.0277 (3)
H9	0.1567	0.2932	0.0326	0.033*
C10	−0.1238 (2)	0.11900 (7)	0.33039 (8)	0.0269 (3)
H10A	−0.2786	0.1346	0.3193	0.032*
H10B	−0.0928	0.0852	0.2841	0.032*
C11	−0.0764 (3)	0.08142 (8)	0.41878 (9)	0.0361 (3)
H11A	−0.1933	0.0928	0.4545	0.043*
H11B	−0.0680	0.0275	0.4120	0.043*
C12	0.1442 (3)	0.11201 (9)	0.46066 (9)	0.0367 (3)
H12A	0.1235	0.1436	0.5104	0.044*
H12B	0.2450	0.0715	0.4807	0.044*
O1	−0.26922 (15)	0.25454 (6)	0.38244 (6)	0.0300 (2)
O2	0.06558 (15)	0.30076 (5)	0.41263 (6)	0.0302 (2)
C13	0.1993 (2)	0.49016 (7)	0.62159 (8)	0.0232 (3)
H13	0.3239	0.5208	0.6343	0.028*
C14	0.0210 (2)	0.49587 (7)	0.67079 (8)	0.0227 (3)
C15	−0.1584 (2)	0.40174 (7)	0.57900 (9)	0.0275 (3)
H15	−0.2822	0.3714	0.5629	0.033*
C16	−0.1610 (2)	0.44957 (7)	0.64561 (9)	0.0270 (3)
H16	−0.2856	0.4519	0.6754	0.032*
C17	0.1905 (2)	0.44045 (7)	0.55616 (8)	0.0247 (3)
H17	0.3111	0.4367	0.5243	0.030*
C18	0.2073 (2)	0.59162 (8)	0.76179 (9)	0.0325 (3)
H18A	0.2461	0.6166	0.7105	0.049*
H18B	0.3331	0.5634	0.7886	0.049*
H18C	0.1658	0.6282	0.8026	0.049*
C19	−0.1612 (3)	0.54665 (9)	0.78639 (10)	0.0383 (3)
H19A	−0.1988	0.4973	0.8047	0.057*
H19B	−0.2870	0.5680	0.7503	0.057*
H19C	−0.1224	0.5777	0.8370	0.057*
N1	0.01572 (18)	0.39651 (6)	0.53538 (7)	0.0254 (2)
N2	0.02411 (19)	0.54214 (6)	0.73743 (7)	0.0274 (2)
H7	0.012 (4)	0.3632 (12)	0.4892 (15)	0.056 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0281 (5)	0.0291 (5)	0.0406 (6)	−0.0046 (4)	0.0092 (4)	−0.0074 (4)
C1	0.0227 (5)	0.0241 (6)	0.0235 (6)	0.0010 (4)	0.0000 (4)	−0.0030 (5)
C2	0.0290 (6)	0.0267 (6)	0.0260 (6)	−0.0025 (5)	0.0063 (5)	−0.0011 (5)
C3	0.0219 (5)	0.0241 (6)	0.0159 (5)	−0.0011 (4)	0.0024 (4)	−0.0003 (4)
C4	0.0306 (6)	0.0261 (6)	0.0201 (6)	0.0041 (5)	−0.0024 (5)	−0.0032 (5)
C5	0.0229 (6)	0.0243 (6)	0.0217 (6)	−0.0005 (4)	0.0005 (4)	−0.0030 (4)
C6	0.0204 (5)	0.0221 (6)	0.0190 (5)	−0.0020 (4)	0.0017 (4)	−0.0025 (4)
C7	0.0219 (5)	0.0204 (6)	0.0183 (5)	0.0020 (4)	0.0016 (4)	−0.0030 (4)
C8	0.0268 (6)	0.0257 (6)	0.0235 (6)	0.0022 (5)	0.0003 (5)	0.0010 (5)
C9	0.0371 (7)	0.0256 (6)	0.0206 (6)	0.0020 (5)	0.0048 (5)	0.0000 (5)
C10	0.0309 (6)	0.0238 (6)	0.0260 (6)	−0.0077 (5)	0.0036 (5)	−0.0043 (5)
C11	0.0483 (8)	0.0301 (7)	0.0302 (7)	−0.0111 (6)	0.0066 (6)	0.0017 (6)
C12	0.0434 (8)	0.0365 (8)	0.0287 (7)	−0.0050 (6)	−0.0014 (6)	0.0089 (6)
O1	0.0213 (4)	0.0349 (5)	0.0343 (5)	−0.0002 (4)	0.0053 (4)	−0.0061 (4)
O2	0.0251 (5)	0.0301 (5)	0.0357 (5)	−0.0041 (4)	0.0049 (4)	−0.0140 (4)
C13	0.0235 (6)	0.0208 (6)	0.0249 (6)	−0.0005 (4)	0.0013 (4)	0.0003 (4)
C14	0.0267 (6)	0.0184 (6)	0.0226 (6)	0.0023 (4)	0.0014 (4)	0.0014 (4)
C15	0.0284 (6)	0.0225 (6)	0.0305 (6)	−0.0025 (5)	0.0000 (5)	0.0005 (5)
C16	0.0266 (6)	0.0251 (6)	0.0298 (6)	−0.0017 (5)	0.0052 (5)	0.0000 (5)
C17	0.0259 (6)	0.0241 (6)	0.0239 (6)	0.0043 (5)	0.0029 (4)	0.0015 (5)
C18	0.0406 (8)	0.0270 (7)	0.0299 (7)	−0.0053 (6)	0.0042 (5)	−0.0072 (5)
C19	0.0465 (9)	0.0346 (8)	0.0371 (8)	0.0005 (6)	0.0184 (6)	−0.0083 (6)
N1	0.0298 (5)	0.0209 (5)	0.0243 (5)	0.0017 (4)	−0.0005 (4)	−0.0022 (4)
N2	0.0318 (6)	0.0246 (6)	0.0266 (5)	0.0000 (4)	0.0061 (4)	−0.0044 (4)

Geometric parameters (Å, º) top

O3—H3	0.874 (15)	C11—C12	1.538 (2)
O3—H6	0.872 (15)	C11—H11A	0.9900
C1—C4	1.3937 (18)	C11—H11B	0.9900
C1—C7	1.4010 (16)	C12—H12A	0.9900
C1—H1	0.9500	C12—H12B	0.9900
C2—C9	1.3908 (19)	C13—C17	1.3649 (18)
C2—C5	1.3970 (18)	C13—C14	1.4262 (17)
C2—H2	0.9500	C13—H13	0.9500
C3—O1	1.2414 (15)	C14—N2	1.3416 (16)
C3—O2	1.2696 (15)	C14—C16	1.4189 (17)
C3—C6	1.5603 (16)	C15—N1	1.3488 (18)
C4—C9	1.3885 (19)	C15—C16	1.3625 (19)
C4—H4	0.9500	C15—H15	0.9500
C5—C7	1.3981 (17)	C16—H16	0.9500
C5—H5	0.9500	C17—N1	1.3485 (17)
C6—C7	1.5218 (16)	C17—H17	0.9500
C6—C8	1.5382 (17)	C18—N2	1.4571 (18)
C6—C10	1.5465 (16)	C18—H18A	0.9800
C8—C12	1.5345 (19)	C18—H18B	0.9800
C8—H8A	0.9900	C18—H18C	0.9800
C8—H8B	0.9900	C19—N2	1.4587 (18)
C9—H9	0.9500	C19—H19A	0.9800
C10—C11	1.5414 (19)	C19—H19B	0.9800
C10—H10A	0.9900	C19—H19C	0.9800
C10—H10B	0.9900	N1—H7	0.94 (2)

H3—O3—H6	105.5 (18)	C12—C11—H11B	110.5
C4—C1—C7	120.90 (12)	C10—C11—H11B	110.5
C4—C1—H1	119.5	H11A—C11—H11B	108.7
C7—C1—H1	119.5	C8—C12—C11	105.83 (11)
C9—C2—C5	120.61 (12)	C8—C12—H12A	110.6
C9—C2—H2	119.7	C11—C12—H12A	110.6
C5—C2—H2	119.7	C8—C12—H12B	110.6
O1—C3—O2	124.66 (11)	C11—C12—H12B	110.6
O1—C3—C6	119.03 (10)	H12A—C12—H12B	108.7
O2—C3—C6	116.28 (10)	C17—C13—C14	119.77 (12)
C9—C4—C1	120.23 (12)	C17—C13—H13	120.1
C9—C4—H4	119.9	C14—C13—H13	120.1
C1—C4—H4	119.9	N2—C14—C16	121.50 (12)
C2—C5—C7	120.38 (12)	N2—C14—C13	122.20 (12)
C2—C5—H5	119.8	C16—C14—C13	116.30 (11)
C7—C5—H5	119.8	N1—C15—C16	121.53 (12)
C7—C6—C8	114.25 (10)	N1—C15—H15	119.2
C7—C6—C10	113.53 (10)	C16—C15—H15	119.2
C8—C6—C10	102.06 (10)	C15—C16—C14	120.47 (12)
C7—C6—C3	105.88 (9)	C15—C16—H16	119.8
C8—C6—C3	110.33 (10)	C14—C16—H16	119.8
C10—C6—C3	110.89 (10)	N1—C17—C13	121.96 (12)
C5—C7—C1	118.48 (11)	N1—C17—H17	119.0
C5—C7—C6	121.36 (10)	C13—C17—H17	119.0
C1—C7—C6	120.11 (10)	N2—C18—H18A	109.5
C12—C8—C6	103.84 (10)	N2—C18—H18B	109.5
C12—C8—H8A	111.0	H18A—C18—H18B	109.5
C6—C8—H8A	111.0	N2—C18—H18C	109.5
C12—C8—H8B	111.0	H18A—C18—H18C	109.5
C6—C8—H8B	111.0	H18B—C18—H18C	109.5
H8A—C8—H8B	109.0	N2—C19—H19A	109.5
C4—C9—C2	119.40 (12)	N2—C19—H19B	109.5
C4—C9—H9	120.3	H19A—C19—H19B	109.5
C2—C9—H9	120.3	N2—C19—H19C	109.5
C11—C10—C6	105.25 (10)	H19A—C19—H19C	109.5
C11—C10—H10A	110.7	H19B—C19—H19C	109.5
C6—C10—H10A	110.7	C17—N1—C15	119.93 (11)
C11—C10—H10B	110.7	C17—N1—H7	120.4 (13)
C6—C10—H10B	110.7	C15—N1—H7	119.7 (13)
H10A—C10—H10B	108.8	C14—N2—C18	121.77 (11)
C12—C11—C10	106.26 (11)	C14—N2—C19	120.81 (12)
C12—C11—H11A	110.5	C18—N2—C19	117.38 (11)
C10—C11—H11A	110.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H7···O2	0.94 (2)	1.72 (2)	2.6458 (15)	168 (2)
O3—H3···O2	0.87 (2)	1.93 (2)	2.7935 (14)	167 (2)
O3—H6···O1ⁱ	0.87 (2)	1.90 (2)	2.7634 (15)	169 (2)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₇H₁₁N₂⁺·C₁₂H₁₃O₂⁻·H₂O
M_r	330.42
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	110
a, b, c (Å)	6.1666 (12), 18.206 (4), 15.702 (3)
β (°)	97.33 (3)
V (Å³)	1748.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.44 × 0.33 × 0.22

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.964, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	12519, 4233, 3945
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.139, 1.13
No. of reflections	4233
No. of parameters	231
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)	0.23, −0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H7···O2	0.94 (2)	1.72 (2)	2.6458 (15)	168 (2)
O3—H3···O2	0.874 (15)	1.934 (16)	2.7935 (14)	167 (2)
O3—H6···O1ⁱ	0.872 (15)	1.902 (16)	2.7634 (15)	169 (2)

Symmetry code: (i) x+1, y, z.

Acknowledgements

This work was supported by the Science and Engineering Research Council of A*STAR (Agency for Science, Technology and Research), Singapore.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dastidar, P., Row, T. N. G., Prasad, B. R., Subramanian, C. K. & Bhattacharya, S. (1993). J. Chem. Soc. Perkin Trans. 2, pp. 2419–2422. CrossRef Google Scholar
He, G., Aitipamula, S., Chow, P. S. & Tan, R. B. H. (2010). Acta Cryst. E66, o3339–o3340. Web of Science CSD CrossRef IUCr Journals Google Scholar
He, G., Aitipamula, S., Chow, P. S. & Tan, R. B. H. (2011). Acta Cryst. E67, o552–o553. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kumar, T. L., Vishweshwar, P., Babu, J. M. & Vyas, K. (2009). Cryst. Growth Des. 9, 4822–4829. CAS Google Scholar
Margulis, T. N. (1975). Acta Cryst. B31, 1049–1052. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
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Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 5| May 2011| Page o1227

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

N,N-Di­methylpyridin-4-aminium 1-phenyl­cyclo­pentane-1-carboxyl­ate monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N,N-Dimethylpyridin-4-aminium 1-phenylcyclopentane-1-carboxylate monohydrate