N,N-Dimethylpyridin-4-aminium 1-phenyl-cyclo-pentane-1-carboxyl-ate monohydrate.

The cation of the title salt, C(7)H(11)N(2) (+)·C(12)H(13)O(2) (-)·H(2)O, is planar (r.m.s. deviation = 0.0184 Å). In the crystal, the cation, anion and water mol-ecule 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 = 330.42

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.139

S = 1.13

4233 reflections

231 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

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 ▶).

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

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

Supplementary material file. DOI: 10.1107/S1600536811015200/ng5153Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H11N2+·C12H13O2−·H2O	F(000) = 712
Mr = 330.42	Dx = 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

Bruker APEXII diffractometer	4233 independent reflections
Radiation source: fine-focus sealed tube	3945 reflections with I > 2σ(I)
graphite	Rint = 0.017
ω scans	θmax = 28.3°, θmin = 2.9°
Absorption correction: multi-scan (Blessing, 1995)	h = −8→8
Tmin = 0.964, Tmax = 0.982	k = −21→23
12519 measured reflections	l = −20→20

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(Fo2) + (0.0729P)2 + 0.4696P] where P = (Fo2 + 2Fc2)/3
4233 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.23 e Å−3
3 restraints	Δρmin = −0.21 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	Uiso*/Ueq
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)*

	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)

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

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)

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) .