Dicyclo-hexyl-ammonium 2-methoxy-benzoate.

The asymmetric unit of the title compound, C(12)H(24)N(+)·C(8)H(7)O(3) (-), contains one dicyclo-hexyl-ammonium cation and one 2-methoxy-benzoate anion. Two cations and two anions are linked together to form a four-ion cluster through a set of N-H⋯O hydrogen bonds. Weak C-H⋯O hydrogen bonds connect the clusters into chains that are stacked along the crystallographic c axis.

Related literature

For the crystal structures of dicyclo­hexyl­ammonium salts of monocarboxylic acids, see: Ng et al. (1999 ▶); Ng, Naumov et al. 2001 ▶), Ng & Hook (1999 ▶); Subramanian et al. (2000 ▶). For the crystal structures of dicyclo­hexyl­ammonium salts of dicarboxylic acids, see: Ballabh et al. (2005 ▶); Trivedi et al. (2005 ▶); Ng, Chantrapromma et al. (2001 ▶). For related literature, see: Zain & Ng (2007 ▶); Trivedi et al. (2004 ▶); Ng et al. (1991 ▶); Allen et al. (1987 ▶).

Experimental

Crystal data

C12H24N+·C8H7O3 −

M = 333.46

Monoclinic,

a = 9.2798 (5) Å

b = 17.7978 (9) Å

c = 12.1513 (7) Å

β = 104.720 (5)°

V = 1941.04 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (1) K

0.62 × 0.41 × 0.35 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer

Absorption correction: none

19673 measured reflections

3789 independent reflections

2750 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.175

S = 1.03

3789 reflections

225 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2003 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2003 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶), Mercury (Macrae et al., 2006 ▶), RasTop (Valadon, 2000–2003 ▶) and POV-RAY (Persistence of Vision, 2004 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808007587/wn2244sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007587/wn2244Isup2.hkl

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

C12H24N+·C8H7O3–	Dx = 1.141 Mg m−3
Mr = 333.46	Melting point: 416 K
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 742 reflections
a = 9.2798 (5) Å	θ = 6.4–21.2º
b = 17.7978 (9) Å	µ = 0.08 mm−1
c = 12.1513 (7) Å	T = 293 (1) K
β = 104.720 (5)º	Cell measurement pressure: 101(1) kPa
V = 1941.04 (18) Å3	Prismatic, colourless
Z = 4	0.62 × 0.41 × 0.35 mm
F000 = 728

Oxford Diffraction Xcalibur CCD diffractometer	3789 independent reflections
Radiation source: fine-focus sealed tube	2750 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.042
T = 293(1) K	θmax = 26.0º
P = 101(1) kPa	θmin = 4.1º
ω scans	h = −11→11
Absorption correction: none	k = −21→21
19673 measured reflections	l = −14→14

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)] = 0.068	w = 1/[σ2(Fo2) + (0.0745P)2 + 0.785P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.175	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.37 e Å−3
3789 reflections	Δρmin = −0.16 e Å−3
225 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (4)
Secondary atom site location: difference Fourier map

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
O1	0.2706 (2)	0.08567 (10)	1.00183 (17)	0.0842 (6)
O2	0.04537 (19)	0.13445 (12)	0.96352 (17)	0.0852 (6)
O3	0.0699 (2)	0.14787 (12)	0.72365 (14)	0.0819 (6)
N1	0.2059 (2)	−0.06289 (11)	1.02163 (16)	0.0491 (5)
H1	0.114 (3)	−0.0780 (13)	1.0175 (19)	0.059*
H2	0.209 (2)	−0.0112 (15)	1.0178 (19)	0.059*
C1	0.1749 (2)	0.13270 (11)	0.95593 (17)	0.0471 (5)
C2	0.2251 (2)	0.19520 (11)	0.89133 (17)	0.0438 (5)
C3	0.3308 (3)	0.24641 (13)	0.9464 (2)	0.0634 (6)
H3	0.3731	0.2413	1.0241	0.076*
C4	0.3748 (4)	0.30529 (15)	0.8877 (3)	0.0898 (10)
H4	0.4465	0.3392	0.9258	0.108*
C5	0.3122 (4)	0.31337 (16)	0.7736 (3)	0.0894 (10)
H5	0.3400	0.3535	0.7345	0.107*
C6	0.2088 (3)	0.26265 (16)	0.7164 (2)	0.0750 (8)
H6	0.1671	0.2682	0.6388	0.090*
C7	0.1666 (2)	0.20300 (13)	0.77480 (19)	0.0537 (6)
C8	0.0317 (4)	0.1435 (2)	0.6036 (2)	0.0992 (11)
H8B	−0.0221	0.1878	0.5722	0.149*
H8C	−0.0295	0.1000	0.5795	0.149*
H8A	0.1208	0.1395	0.5776	0.149*
C9	0.2458 (2)	−0.09394 (12)	0.91808 (18)	0.0507 (5)
H9	0.3437	−0.0742	0.9162	0.061*
C10	0.1326 (3)	−0.06616 (16)	0.8135 (2)	0.0761 (7)
H10A	0.1324	−0.0117	0.8129	0.091*
H10B	0.0340	−0.0830	0.8159	0.091*
C11	0.1681 (4)	−0.09527 (19)	0.7053 (2)	0.0940 (10)
H11B	0.0913	−0.0787	0.6397	0.113*
H11A	0.2622	−0.0742	0.6992	0.113*
C12	0.1775 (4)	−0.17925 (19)	0.7044 (3)	0.0950 (10)
H12B	0.2082	−0.1956	0.6377	0.114*
H12A	0.0800	−0.2005	0.7005	0.114*
C13	0.2877 (5)	−0.2071 (2)	0.8103 (3)	0.1075 (11)
H13A	0.3869	−0.1911	0.8086	0.129*
H13B	0.2865	−0.2616	0.8106	0.129*
C14	0.2540 (3)	−0.17841 (14)	0.9200 (2)	0.0760 (8)
H14B	0.1600	−0.1991	0.9271	0.091*
H14A	0.3316	−0.1948	0.9852	0.091*
C15	0.3019 (2)	−0.08294 (11)	1.13645 (17)	0.0471 (5)
H15	0.2968	−0.1374	1.1467	0.057*
C16	0.2390 (2)	−0.04421 (14)	1.2256 (2)	0.0599 (6)
H16A	0.2334	0.0094	1.2110	0.072*
H16B	0.1386	−0.0623	1.2194	0.072*
C17	0.3332 (3)	−0.05828 (17)	1.3448 (2)	0.0743 (7)
H17B	0.3262	−0.1109	1.3637	0.089*
H17A	0.2947	−0.0287	1.3981	0.089*
C18	0.4956 (3)	−0.03803 (17)	1.3571 (2)	0.0755 (7)
H18A	0.5047	0.0159	1.3490	0.091*
H18B	0.5541	−0.0522	1.4323	0.091*
C19	0.5553 (3)	−0.07794 (15)	1.2679 (2)	0.0717 (7)
H19B	0.6573	−0.0623	1.2748	0.086*
H19A	0.5555	−0.1317	1.2812	0.086*
C20	0.4629 (2)	−0.06121 (14)	1.1488 (2)	0.0594 (6)
H20A	0.5021	−0.0890	1.0941	0.071*
H20B	0.4689	−0.0080	1.1329	0.071*

	U11	U22	U33	U12	U13	U23
O1	0.1052 (14)	0.0553 (11)	0.1037 (15)	0.0129 (10)	0.0479 (12)	0.0276 (10)
O2	0.0615 (10)	0.1125 (16)	0.0879 (14)	−0.0220 (10)	0.0307 (9)	0.0165 (11)
O3	0.0777 (11)	0.1234 (17)	0.0406 (9)	−0.0256 (11)	0.0079 (8)	−0.0009 (9)
N1	0.0455 (9)	0.0437 (10)	0.0621 (12)	0.0020 (8)	0.0210 (8)	0.0081 (8)
C1	0.0600 (12)	0.0460 (12)	0.0374 (11)	−0.0104 (10)	0.0166 (9)	−0.0060 (9)
C2	0.0455 (10)	0.0423 (11)	0.0465 (12)	0.0037 (8)	0.0168 (9)	0.0004 (8)
C3	0.0789 (16)	0.0585 (14)	0.0571 (14)	−0.0167 (12)	0.0252 (12)	−0.0057 (11)
C4	0.121 (2)	0.0557 (16)	0.108 (3)	−0.0344 (16)	0.056 (2)	−0.0122 (15)
C5	0.127 (3)	0.0545 (16)	0.108 (3)	0.0052 (17)	0.068 (2)	0.0244 (16)
C6	0.0877 (18)	0.0762 (18)	0.0692 (17)	0.0236 (15)	0.0344 (14)	0.0327 (14)
C7	0.0502 (11)	0.0625 (14)	0.0503 (13)	0.0092 (10)	0.0164 (10)	0.0082 (10)
C8	0.091 (2)	0.152 (3)	0.0475 (16)	0.004 (2)	0.0051 (14)	−0.0046 (18)
C9	0.0505 (11)	0.0522 (12)	0.0529 (13)	−0.0041 (9)	0.0196 (10)	0.0033 (9)
C10	0.0922 (19)	0.0692 (17)	0.0626 (17)	0.0069 (14)	0.0116 (14)	0.0055 (13)
C11	0.125 (3)	0.091 (2)	0.0612 (18)	−0.0079 (19)	0.0165 (17)	0.0017 (15)
C12	0.121 (3)	0.093 (2)	0.071 (2)	−0.0183 (19)	0.0259 (18)	−0.0164 (17)
C13	0.164 (3)	0.078 (2)	0.088 (2)	0.027 (2)	0.046 (2)	−0.0125 (17)
C14	0.107 (2)	0.0544 (15)	0.0715 (18)	0.0130 (14)	0.0313 (15)	0.0015 (12)
C15	0.0506 (11)	0.0382 (10)	0.0542 (13)	0.0017 (8)	0.0165 (10)	0.0060 (9)
C16	0.0547 (12)	0.0597 (14)	0.0712 (16)	−0.0047 (10)	0.0268 (11)	−0.0068 (11)
C17	0.0851 (18)	0.0795 (18)	0.0591 (16)	−0.0140 (14)	0.0200 (13)	−0.0135 (13)
C18	0.0735 (16)	0.0733 (17)	0.0737 (18)	−0.0050 (13)	0.0074 (13)	−0.0142 (14)
C19	0.0571 (13)	0.0656 (16)	0.0864 (19)	0.0069 (12)	0.0071 (13)	−0.0050 (14)
C20	0.0476 (11)	0.0629 (14)	0.0698 (16)	0.0050 (10)	0.0189 (11)	0.0007 (11)

O1—C1	1.244 (3)	C11—C12	1.498 (5)
O2—C1	1.229 (3)	C11—H11B	0.9700
O3—C7	1.368 (3)	C11—H11A	0.9700
O3—C8	1.413 (3)	C12—C13	1.510 (5)
N1—C15	1.495 (3)	C12—H12B	0.9700
N1—C9	1.504 (3)	C12—H12A	0.9700
N1—H1	0.88 (2)	C13—C14	1.532 (4)
N1—H2	0.92 (3)	C13—H13A	0.9700
C1—C2	1.502 (3)	C13—H13B	0.9700
C2—C3	1.381 (3)	C14—H14B	0.9700
C2—C7	1.389 (3)	C14—H14A	0.9700
C3—C4	1.386 (4)	C15—C20	1.513 (3)
C3—H3	0.9300	C15—C16	1.520 (3)
C4—C5	1.368 (4)	C15—H15	0.9800
C4—H4	0.9300	C16—C17	1.511 (3)
C5—C6	1.371 (4)	C16—H16A	0.9700
C5—H5	0.9300	C16—H16B	0.9700
C6—C7	1.387 (3)	C17—C18	1.520 (4)
C6—H6	0.9300	C17—H17B	0.9700
C8—H8B	0.9600	C17—H17A	0.9700
C8—H8C	0.9600	C18—C19	1.513 (4)
C8—H8A	0.9600	C18—H18A	0.9700
C9—C14	1.505 (3)	C18—H18B	0.9700
C9—C10	1.511 (3)	C19—C20	1.513 (3)
C9—H9	0.9800	C19—H19B	0.9700
C10—C11	1.526 (4)	C19—H19A	0.9700
C10—H10A	0.9700	C20—H20A	0.9700
C10—H10B	0.9700	C20—H20B	0.9700
C7—O3—C8	118.2 (2)	C11—C12—H12B	109.5
C15—N1—C9	118.55 (16)	C13—C12—H12B	109.5
C15—N1—H1	108.5 (15)	C11—C12—H12A	109.5
C9—N1—H1	106.2 (15)	C13—C12—H12A	109.5
C15—N1—H2	105.4 (14)	H12B—C12—H12A	108.1
C9—N1—H2	107.8 (14)	C12—C13—C14	112.8 (3)
H1—N1—H2	110 (2)	C12—C13—H13A	109.0
O2—C1—O1	125.7 (2)	C14—C13—H13A	109.0
O2—C1—C2	117.3 (2)	C12—C13—H13B	109.0
O1—C1—C2	116.86 (18)	C14—C13—H13B	109.0
C3—C2—C7	118.3 (2)	H13A—C13—H13B	107.8
C3—C2—C1	120.77 (19)	C9—C14—C13	109.9 (2)
C7—C2—C1	120.94 (18)	C9—C14—H14B	109.7
C2—C3—C4	121.0 (3)	C13—C14—H14B	109.7
C2—C3—H3	119.5	C9—C14—H14A	109.7
C4—C3—H3	119.5	C13—C14—H14A	109.7
C5—C4—C3	119.8 (3)	H14B—C14—H14A	108.2
C5—C4—H4	120.1	N1—C15—C20	111.74 (17)
C3—C4—H4	120.1	N1—C15—C16	108.11 (17)
C4—C5—C6	120.4 (2)	C20—C15—C16	111.23 (18)
C4—C5—H5	119.8	N1—C15—H15	108.6
C6—C5—H5	119.8	C20—C15—H15	108.6
C5—C6—C7	119.8 (3)	C16—C15—H15	108.6
C5—C6—H6	120.1	C17—C16—C15	112.00 (19)
C7—C6—H6	120.1	C17—C16—H16A	109.2
O3—C7—C6	123.7 (2)	C15—C16—H16A	109.2
O3—C7—C2	115.66 (19)	C17—C16—H16B	109.2
C6—C7—C2	120.6 (2)	C15—C16—H16B	109.2
O3—C8—H8B	109.5	H16A—C16—H16B	107.9
O3—C8—H8C	109.5	C16—C17—C18	111.9 (2)
H8B—C8—H8C	109.5	C16—C17—H17B	109.2
O3—C8—H8A	109.5	C18—C17—H17B	109.2
H8B—C8—H8A	109.5	C16—C17—H17A	109.2
H8C—C8—H8A	109.5	C18—C17—H17A	109.2
N1—C9—C14	112.10 (18)	H17B—C17—H17A	107.9
N1—C9—C10	108.46 (18)	C19—C18—C17	110.6 (2)
C14—C9—C10	111.2 (2)	C19—C18—H18A	109.5
N1—C9—H9	108.3	C17—C18—H18A	109.5
C14—C9—H9	108.3	C19—C18—H18B	109.5
C10—C9—H9	108.3	C17—C18—H18B	109.5
C9—C10—C11	110.9 (2)	H18A—C18—H18B	108.1
C9—C10—H10A	109.5	C20—C19—C18	111.8 (2)
C11—C10—H10A	109.5	C20—C19—H19B	109.3
C9—C10—H10B	109.5	C18—C19—H19B	109.3
C11—C10—H10B	109.5	C20—C19—H19A	109.3
H10A—C10—H10B	108.0	C18—C19—H19A	109.3
C12—C11—C10	111.7 (3)	H19B—C19—H19A	107.9
C12—C11—H11B	109.3	C19—C20—C15	110.46 (19)
C10—C11—H11B	109.3	C19—C20—H20A	109.6
C12—C11—H11A	109.3	C15—C20—H20A	109.6
C10—C11—H11A	109.3	C19—C20—H20B	109.6
H11B—C11—H11A	107.9	C15—C20—H20B	109.6
C11—C12—C13	110.5 (3)	H20A—C20—H20B	108.1

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2···O1	0.92 (3)	1.84 (3)	2.735 (3)	163 (2)
N1—H1···O2i	0.88 (2)	1.85 (3)	2.703 (2)	162 (2)
C20—H20A···O1ii	0.97	2.66	3.457 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2⋯O1	0.92 (3)	1.84 (3)	2.735 (3)	163 (2)
N1—H1⋯O2i	0.88 (2)	1.85 (3)	2.703 (2)	162 (2)
C20—H20A⋯O1ii	0.97	2.66	3.457 (3)	140

Symmetry codes: (i) ; (ii) .