Di­cyclo­hexyl­ammonium bromo­acetate: a low mol­ecular mass organogelator with a one-dimensional secondary ammonium mono­carboxyl­ate (SAM) synthon

The asymmetric unit of the title salt, C₁₂H₂₄N⁺·C₂H₂BrO₂⁻, contains a di­cyclo­hexyl­ammonium cation connected to a bromo­acetate anion by means of an N—H...O hydrogen bond. In the crystal, the ion pairs assemble via N—H...O inter­actions, forming zigzag infinite chains parallel to the c axis with the (...H—N—H...O—C—O...)_n motif that is considered to be a prerequisite for ensuring gelation properties of secondary ammonium mono­carboxyl­ate salts. The title salt was characterized by FT–IR, X-ray powder diffraction (XRPD), TG–DTA and ¹H NMR spectroscopy in solution. Gelation experiments revealed that di­cyclo­hexyl­ammonium bromo­acetate forms mol­ecular gels with di­methyl­formamide and dimethyl sulfoxide. Scanning electron microscopy (SEM) was used to reveal morphological features of dried gels.

Computing details

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Dicyclohexylammonium bromoacetate

Crystal data

C12H24N^+·C2H2BrO2^−	F(000) = 672
Mr = 320.27	Dx = 1.446 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.847 (3) Å	Cell parameters from 7011 reflections
b = 17.679 (6) Å	θ = 3–29°
c = 9.564 (3) Å	µ = 2.79 mm^−1
β = 100.38 (2)°	T = 100 K
V = 1471.4 (8) Å^3	Block, colorless
Z = 4	0.50 × 0.50 × 0.25 mm

Data collection

Kuma KM-4 diffractometer with a CCD camera	2944 reflections with I > 2σ(I)
Radiation source: normal focus sealed tube	Rint = 0.028
ω scans	θmax = 28.6°, θmin = 3.1°
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2010), based on expressions derived by Clark & Reid (1995)]	h = −11→11
Tmin = 0.290, Tmax = 0.605	k = −23→22
9495 measured reflections	l = −12→11
3512 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.065P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3512 reflections	Δρmax = 0.49 e Å^−3
171 parameters	Δρmin = −0.56 e Å^−3

Special details

Experimental. Absorption correction: CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.23304 (3)	0.08121 (2)	0.10283 (2)	0.02045 (10)
O1	0.32380 (19)	0.13568 (8)	0.40957 (14)	0.0205 (3)
O2	0.34629 (18)	0.25941 (8)	0.36829 (15)	0.0197 (3)
C2	0.2452 (2)	0.18425 (11)	0.1729 (2)	0.0176 (4)
H2A	0.3092	0.2140	0.1181	0.021*
H2B	0.1406	0.2064	0.1546	0.021*
C1	0.3120 (2)	0.19262 (11)	0.3317 (2)	0.0144 (4)
N1	0.42308 (19)	0.12749 (9)	0.69680 (18)	0.0137 (3)
H1N	0.391 (3)	0.1687 (14)	0.749 (3)	0.027 (7)*
H2N	0.396 (3)	0.1376 (14)	0.597 (3)	0.032 (7)*
C11	0.3454 (2)	0.05616 (12)	0.7307 (2)	0.0137 (4)
H11	0.3745	0.0463	0.8350	0.016*
C21	0.1731 (2)	0.06916 (11)	0.6952 (2)	0.0165 (4)
H21A	0.1437	0.0831	0.5937	0.020*
H21B	0.1450	0.1117	0.7529	0.020*
C31	0.0847 (2)	−0.00185 (11)	0.7248 (2)	0.0184 (4)
H31A	0.1022	−0.0112	0.8285	0.022*
H31B	−0.0266	0.0067	0.6922	0.022*
C41	0.1346 (3)	−0.07146 (12)	0.6497 (2)	0.0205 (4)
H41A	0.0825	−0.1168	0.6789	0.025*
H41B	0.1027	−0.0654	0.5456	0.025*
C51	0.3075 (3)	−0.08272 (10)	0.6852 (2)	0.0181 (4)
H51A	0.3368	−0.1260	0.6300	0.022*
H51B	0.3379	−0.0948	0.7874	0.022*
C61	0.3931 (2)	−0.01174 (11)	0.6509 (2)	0.0161 (4)
H61A	0.5053	−0.0198	0.6784	0.019*
H61B	0.3696	−0.0019	0.5473	0.019*
C12	0.5950 (2)	0.13028 (11)	0.7294 (2)	0.0144 (4)
H12	0.6362	0.0876	0.6789	0.017*
C22	0.6552 (2)	0.12221 (11)	0.8895 (2)	0.0157 (4)
H22A	0.6086	0.1617	0.9416	0.019*
H22B	0.6252	0.0722	0.9224	0.019*
C32	0.8300 (2)	0.12990 (12)	0.9213 (2)	0.0175 (4)
H32A	0.8764	0.0866	0.8787	0.021*
H32B	0.8661	0.1281	1.0255	0.021*
C42	0.8837 (2)	0.20376 (12)	0.8628 (2)	0.0182 (4)
H42A	0.8478	0.2471	0.9136	0.022*
H42B	0.9974	0.2050	0.8796	0.022*
C52	0.8217 (2)	0.21107 (12)	0.7040 (2)	0.0183 (4)
H52A	0.8524	0.2606	0.6698	0.022*
H52B	0.8667	0.1709	0.6521	0.022*
C62	0.6473 (2)	0.20447 (11)	0.6732 (2)	0.0163 (4)
H62A	0.6020	0.2472	0.7183	0.020*
H62B	0.6101	0.2074	0.5693	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02770 (15)	0.01755 (14)	0.01514 (13)	−0.00290 (8)	0.00129 (9)	−0.00297 (7)
O1	0.0319 (8)	0.0148 (7)	0.0137 (7)	−0.0023 (6)	0.0009 (6)	0.0020 (5)
O2	0.0292 (8)	0.0158 (7)	0.0142 (7)	−0.0043 (6)	0.0045 (6)	−0.0013 (5)
C2	0.0243 (11)	0.0142 (10)	0.0134 (9)	−0.0002 (8)	0.0008 (8)	−0.0002 (7)
C1	0.0136 (9)	0.0172 (9)	0.0125 (9)	−0.0003 (7)	0.0029 (7)	0.0004 (7)
N1	0.0156 (8)	0.0133 (8)	0.0122 (8)	0.0010 (6)	0.0025 (6)	0.0005 (6)
C11	0.0145 (9)	0.0154 (9)	0.0113 (9)	−0.0016 (8)	0.0026 (7)	0.0008 (7)
C21	0.0164 (10)	0.0175 (10)	0.0157 (9)	0.0016 (8)	0.0035 (8)	0.0030 (8)
C31	0.0177 (10)	0.0212 (11)	0.0164 (9)	−0.0012 (8)	0.0033 (8)	−0.0001 (8)
C41	0.0224 (11)	0.0201 (11)	0.0187 (10)	−0.0065 (8)	0.0029 (9)	−0.0005 (8)
C51	0.0224 (11)	0.0139 (10)	0.0180 (10)	−0.0001 (8)	0.0037 (9)	−0.0002 (7)
C61	0.0171 (10)	0.0159 (10)	0.0153 (9)	0.0003 (8)	0.0033 (8)	−0.0014 (8)
C12	0.0146 (9)	0.0154 (9)	0.0125 (9)	−0.0014 (7)	0.0010 (7)	−0.0009 (7)
C22	0.0176 (10)	0.0165 (10)	0.0122 (9)	0.0004 (8)	0.0005 (8)	0.0027 (7)
C32	0.0177 (10)	0.0165 (10)	0.0173 (9)	−0.0003 (8)	0.0007 (8)	0.0009 (8)
C42	0.0195 (10)	0.0174 (10)	0.0170 (9)	−0.0044 (8)	0.0010 (8)	−0.0009 (8)
C52	0.0193 (10)	0.0205 (10)	0.0151 (9)	−0.0046 (8)	0.0033 (8)	−0.0016 (8)
C62	0.0204 (10)	0.0159 (10)	0.0121 (9)	−0.0011 (8)	0.0015 (8)	0.0022 (7)

Geometric parameters (Å, º)

Br1—C2	1.937 (2)	C51—C61	1.531 (3)
O1—C1	1.245 (2)	C51—H51A	0.9900
O2—C1	1.253 (2)	C51—H51B	0.9900
C2—C1	1.534 (3)	C61—H61A	0.9900
C2—H2A	0.9900	C61—H61B	0.9900
C2—H2B	0.9900	C12—C62	1.521 (3)
N1—C12	1.497 (3)	C12—C22	1.535 (3)
N1—C11	1.499 (2)	C12—H12	1.0000
N1—H1N	0.96 (2)	C22—C32	1.527 (3)
N1—H2N	0.96 (3)	C22—H22A	0.9900
C11—C21	1.518 (3)	C22—H22B	0.9900
C11—C61	1.523 (3)	C32—C42	1.530 (3)
C11—H11	1.0000	C32—H32A	0.9900
C21—C31	1.532 (3)	C32—H32B	0.9900
C21—H21A	0.9900	C42—C52	1.525 (3)
C21—H21B	0.9900	C42—H42A	0.9900
C31—C41	1.529 (3)	C42—H42B	0.9900
C31—H31A	0.9900	C52—C62	1.522 (3)
C31—H31B	0.9900	C52—H52A	0.9900
C41—C51	1.520 (3)	C52—H52B	0.9900
C41—H41A	0.9900	C62—H62A	0.9900
C41—H41B	0.9900	C62—H62B	0.9900
C1—C2—Br1	114.87 (14)	H51A—C51—H51B	108.0
C1—C2—H2A	108.6	C11—C61—C51	110.26 (16)
Br1—C2—H2A	108.6	C11—C61—H61A	109.6
C1—C2—H2B	108.6	C51—C61—H61A	109.6
Br1—C2—H2B	108.6	C11—C61—H61B	109.6
H2A—C2—H2B	107.5	C51—C61—H61B	109.6
O1—C1—O2	127.20 (18)	H61A—C61—H61B	108.1
O1—C1—C2	119.33 (17)	N1—C12—C62	108.51 (16)
O2—C1—C2	113.45 (16)	N1—C12—C22	111.18 (16)
C12—N1—C11	118.10 (15)	C62—C12—C22	111.07 (16)
C12—N1—H1N	104.7 (16)	N1—C12—H12	108.7
C11—N1—H1N	109.6 (15)	C62—C12—H12	108.7
C12—N1—H2N	105.5 (17)	C22—C12—H12	108.7
C11—N1—H2N	109.1 (16)	C32—C22—C12	110.33 (17)
H1N—N1—H2N	110 (2)	C32—C22—H22A	109.6
N1—C11—C21	107.79 (16)	C12—C22—H22A	109.6
N1—C11—C61	112.04 (16)	C32—C22—H22B	109.6
C21—C11—C61	111.43 (16)	C12—C22—H22B	109.6
N1—C11—H11	108.5	H22A—C22—H22B	108.1
C21—C11—H11	108.5	C22—C32—C42	111.92 (17)
C61—C11—H11	108.5	C22—C32—H32A	109.2
C11—C21—C31	111.08 (16)	C42—C32—H32A	109.2
C11—C21—H21A	109.4	C22—C32—H32B	109.2
C31—C21—H21A	109.4	C42—C32—H32B	109.2
C11—C21—H21B	109.4	H32A—C32—H32B	107.9
C31—C21—H21B	109.4	C52—C42—C32	110.91 (17)
H21A—C21—H21B	108.0	C52—C42—H42A	109.5
C41—C31—C21	111.92 (17)	C32—C42—H42A	109.5
C41—C31—H31A	109.2	C52—C42—H42B	109.5
C21—C31—H31A	109.2	C32—C42—H42B	109.5
C41—C31—H31B	109.2	H42A—C42—H42B	108.0
C21—C31—H31B	109.2	C62—C52—C42	110.90 (16)
H31A—C31—H31B	107.9	C62—C52—H52A	109.5
C51—C41—C31	111.37 (17)	C42—C52—H52A	109.5
C51—C41—H41A	109.4	C62—C52—H52B	109.5
C31—C41—H41A	109.4	C42—C52—H52B	109.5
C51—C41—H41B	109.4	H52A—C52—H52B	108.0
C31—C41—H41B	109.4	C12—C62—C52	111.12 (16)
H41A—C41—H41B	108.0	C12—C62—H62A	109.4
C41—C51—C61	111.21 (16)	C52—C62—H62A	109.4
C41—C51—H51A	109.4	C12—C62—H62B	109.4
C61—C51—H51A	109.4	C52—C62—H62B	109.4
C41—C51—H51B	109.4	H62A—C62—H62B	108.0
C61—C51—H51B	109.4
Br1—C2—C1—O1	−14.5 (2)	C41—C51—C61—C11	57.0 (2)
Br1—C2—C1—O2	166.90 (14)	C11—N1—C12—C62	174.60 (15)
C12—N1—C11—C21	177.12 (16)	C11—N1—C12—C22	−63.0 (2)
C12—N1—C11—C61	−59.9 (2)	N1—C12—C22—C32	−176.65 (15)
N1—C11—C21—C31	179.09 (15)	C62—C12—C22—C32	−55.7 (2)
C61—C11—C21—C31	55.8 (2)	C12—C22—C32—C42	55.0 (2)
C11—C21—C31—C41	−53.6 (2)	C22—C32—C42—C52	−55.2 (2)
C21—C31—C41—C51	53.5 (2)	C32—C42—C52—C62	55.6 (2)
C31—C41—C51—C61	−55.2 (2)	N1—C12—C62—C52	179.59 (15)
N1—C11—C61—C51	−178.30 (16)	C22—C12—C62—C52	57.1 (2)
C21—C11—C61—C51	−57.4 (2)	C42—C52—C62—C12	−56.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2^i	0.99	2.51	3.350 (3)	142
N1—H1N···O2^ii	0.96 (2)	1.80 (2)	2.748 (2)	172 (2)
N1—H2N···O1	0.96 (3)	1.79 (3)	2.733 (2)	167 (2)

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