e,e-trans-Cyclo­hexane-1,4-carb­oxy­lic acid–hexa­methyl­ene­tetra­mine (1/2)

Lemmerer, A.

doi:10.1107/S1600536810053626

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o248

doi:10.1107/S1600536810053626

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e,e-trans-Cyclohexane-1,4-carboxylic acid–hexamethylenetetramine (1/2)

Andreas Lemmerer ^a ^*

^aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag 3, PO WITS, 2050, Johannesburg, South Africa
^*Correspondence e-mail: andreas.lemmerer@wits.ac.za

(Received 21 December 2010; accepted 21 December 2010; online 8 January 2011)

The asymmetric unit of the title compound, 2C₆H₁₂N₄·C₈H₁₂O₄, contains one half-molecule of e,e-trans-cyclohexane-1,4-dicarboxylic acid (the complete molecule being generated by inversion symmetry) and one molecule of hexamethylenetetramine (HMTA), which are connected by O—H⋯N hydrogen bonds. This forms isolated trimers that pack in a herringbone fashion.

Related literature

For related co-crystals featuring one hydrogen bond to HMTA, see: Feng et al. (2006 ); Li et al. (2001 ); Mak et al. (1986 ). For related co-crystals featuring two hydrogen bonds to HMTA, see: Coupar et al. (1997a ); Gardon et al. (2003 ); Ghosh et al. (2005 ). For related co-crystals featuring three hydrogen bonds to HMTA, see: Coupar et al. (1997b ); De Bruyn et al. (1996 ); Jordan & Mak (1970 ). For related co-crystals featuring four hydrogen bonds to HMTA, see: Daka & Wheeler (2006 ); MacLean et al. (1999 ); Zakaria et al. (2003 ).

Experimental

Crystal data

2C₆H₁₂N₄·C₈H₁₂O₄
M_r = 452.57
Monoclinic, P 2₁ /n
a = 5.9182 (1) Å
b = 31.5242 (6) Å
c = 6.1193 (1) Å
β = 109.144 (1)°
V = 1078.52 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.1 mm⁻¹
T = 173 K
0.4 × 0.35 × 0.04 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: integration (XPREP; Bruker, 2004 ) T_min = 0.960, T_max = 0.996
13851 measured reflections
2594 independent reflections
2218 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.113
S = 0.89
2594 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84	1.84	2.6710 (12)	170

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker 2004); 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 ) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810053626/bt5446sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810053626/bt5446Isup2.hkl

checkCIF report

Comment top

The molecule hexamethylenetetramine (HMTA) acts as a good hydrogen bond acceptor for carboxylic acid or phenol hydrogen bond donors to make binary co-crystals. HMTA can accept any number from one to four hydrogen bonds due to its tetravalent hydrogen bond acceptors, the lone pairs on each of the four N atoms. Most common are two hydrogen bonds per HMTA molecule (Coupar et al., 1997a; Gardon et al., 2003; Ghosh et al., 2005.), with a smaller frequency of one, three or four hydrogen bonds (Coupar et al., 1997b; Daka & Wheeler, 2006; De Bruyn et al., 1996; Feng et al., 2006; Jordan & Mak, 1970; Li et al., 2001; MacLean et al., 1999; Mak et al., 1986; Zakaria et al., 2003.). The title compound is an example of HMTA only accepting one hydrogen bond. As the cis-cyclohexane-1,4-dicarboxylic acid (CHDA) molecule has two carboxylic acid groups, the observed hydrogen bonded assembly is dumb-bell shaped, where one central CHDA molecule (the bar) hydrogen bonds to two pendant HMTA molecules (the bells) (Fig. 2). The dumb-bell trimers are situated on a centre of inversion, located at the centre of the CHDA molecule. The dumbells pack in a herring-bone fashion (Fig. 3).

Related literature top

For related co-crystals featuring one hydrogen bond to HMTA, see: Feng et al. (2006); Li et al. (2001); Mak et al. (1986). For related co-crystals featuring two hydrogen bonds to HMTA, see: Coupar et al. (1997a); Gardon et al. (2003); Ghosh et al. (2005). For related co-crystals featuring three hydrogen bonds to HMTA, see: Coupar et al. (1997b); De Bruyn et al. (1996); Jordan & Mak (1970). For related co-crystals featuring four hydrogen bonds to HMTA, see: Daka & Wheeler (2006); MacLean et al. (1999); Zakaria et al. (2003).

Experimental top

Crystals where grown by slow evaporation at ambient conditions of a methanol solution containing a 2:1 stoichiometric quantity of hexamethylenetetramine and cis-1,4-cyclohexanecarboxylic acid.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker 2004); 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) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of (I) (50% probability displacement ellipsoids). Symmetry code: (i):2 - x, 1 - y, 2 - z.
	Fig. 2. Hydrogen bonded centrosymmetric trimers formed by simple hydrogen bonds (red dashed lines) between one CHDA and two HMTA molecules.
	Fig. 3. Packing diagram of the trimers viewed down the c axis.

e,etrans-Cyclohexane-1,4-carboxylic acid–hexamethylenetetramine (1/2) top

Crystal data top

2C₆H₁₂N₄·C₈H₁₂O₄	F(000) = 488
M_r = 452.57	D_x = 1.394 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5661 reflections
a = 5.9182 (1) Å	θ = 3.7–28.3°
b = 31.5242 (6) Å	µ = 0.1 mm⁻¹
c = 6.1193 (1) Å	T = 173 K
β = 109.144 (1)°	Plate, colourless
V = 1078.52 (3) Å³	0.4 × 0.35 × 0.04 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	2218 reflections with I > 2σ(I)
ω scans	R_int = 0.045
Absorption correction: integration (XPREP; Bruker, 2004)	θ_max = 28.0°, θ_min = 1.3°
T_min = 0.960, T_max = 0.996	h = −7→7
13851 measured reflections	k = −41→41
2594 independent reflections	l = −8→8

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.0739P)² + 0.3667P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.113	(Δ/σ)_max = 0.001
S = 0.89	Δρ_max = 0.39 e Å⁻³
2594 reflections	Δρ_min = −0.19 e Å⁻³
146 parameters

Crystal data top

2C₆H₁₂N₄·C₈H₁₂O₄	V = 1078.52 (3) Å³
M_r = 452.57	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.9182 (1) Å	µ = 0.1 mm⁻¹
b = 31.5242 (6) Å	T = 173 K
c = 6.1193 (1) Å	0.4 × 0.35 × 0.04 mm
β = 109.144 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2594 independent reflections
Absorption correction: integration (XPREP; Bruker, 2004)	2218 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.996	R_int = 0.045
13851 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 0.89	Δρ_max = 0.39 e Å⁻³
2594 reflections	Δρ_min = −0.19 e Å⁻³
146 parameters

Special details top

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004)

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
C1	−0.0247 (2)	0.63264 (4)	0.4650 (2)	0.0246 (3)
H1A	−0.1214	0.6094	0.3707	0.029*
H1B	−0.0231	0.6289	0.6261	0.029*
C2	−0.1335 (2)	0.67841 (4)	0.1382 (2)	0.0282 (3)
H2A	−0.2086	0.7058	0.0755	0.034*
H2B	−0.2303	0.6555	0.041	0.034*
C3	0.2502 (2)	0.71082 (4)	0.2722 (2)	0.0290 (3)
H3A	0.1799	0.7386	0.2111	0.035*
H3B	0.4155	0.7101	0.2667	0.035*
C4	0.2168 (2)	0.63619 (4)	0.2177 (2)	0.0282 (3)
H4A	0.3818	0.6348	0.2117	0.034*
H4B	0.1235	0.613	0.1201	0.034*
C5	0.3614 (2)	0.66535 (4)	0.6002 (2)	0.0256 (3)
H5A	0.3658	0.662	0.7623	0.031*
H5B	0.5281	0.6642	0.5986	0.031*
C6	0.0111 (2)	0.70746 (4)	0.5164 (2)	0.0267 (3)
H6A	0.0126	0.7045	0.678	0.032*
H6B	−0.0621	0.7352	0.4574	0.032*
N1	0.22317 (16)	0.62980 (3)	0.45945 (16)	0.0202 (2)
N2	−0.13588 (17)	0.67350 (3)	0.37597 (19)	0.0250 (2)
N3	0.1098 (2)	0.67701 (3)	0.12396 (18)	0.0273 (2)
N4	0.25799 (18)	0.70679 (3)	0.51366 (18)	0.0257 (2)
C7	0.76647 (19)	0.52006 (3)	0.88313 (19)	0.0188 (2)
H7	0.6734	0.4942	0.8128	0.023*
C8	0.9750 (2)	0.52451 (4)	0.78814 (19)	0.0219 (2)
H8A	0.9119	0.5271	0.6175	0.026*
H8B	1.0667	0.5506	0.851	0.026*
C9	1.1394 (2)	0.48596 (4)	0.85539 (19)	0.0213 (2)
H9A	1.0504	0.4603	0.7819	0.026*
H9B	1.2758	0.4897	0.7973	0.026*
C10	0.6008 (2)	0.55801 (3)	0.8143 (2)	0.0212 (2)
O1	0.47562 (17)	0.55861 (3)	0.59260 (15)	0.0319 (2)
H1	0.3883	0.5803	0.5629	0.048*
O2	0.58343 (19)	0.58498 (3)	0.94835 (17)	0.0397 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0217 (5)	0.0197 (6)	0.0322 (6)	0.0004 (4)	0.0087 (5)	0.0055 (4)
C2	0.0237 (6)	0.0261 (6)	0.0265 (6)	0.0051 (5)	−0.0031 (5)	0.0042 (5)
C3	0.0264 (6)	0.0249 (6)	0.0384 (7)	0.0007 (5)	0.0145 (5)	0.0100 (5)
C4	0.0356 (7)	0.0266 (6)	0.0238 (6)	0.0119 (5)	0.0115 (5)	0.0007 (5)
C5	0.0203 (5)	0.0246 (6)	0.0253 (6)	0.0009 (4)	−0.0015 (4)	0.0010 (4)
C6	0.0330 (6)	0.0203 (6)	0.0297 (6)	0.0059 (5)	0.0143 (5)	−0.0018 (4)
N1	0.0193 (5)	0.0187 (5)	0.0205 (5)	0.0044 (3)	0.0038 (4)	0.0017 (3)
N2	0.0178 (5)	0.0221 (5)	0.0353 (6)	0.0038 (4)	0.0091 (4)	0.0049 (4)
N3	0.0350 (6)	0.0273 (6)	0.0206 (5)	0.0083 (4)	0.0104 (4)	0.0052 (4)
N4	0.0247 (5)	0.0190 (5)	0.0296 (5)	−0.0022 (4)	0.0037 (4)	−0.0008 (4)
C7	0.0179 (5)	0.0154 (5)	0.0212 (5)	0.0034 (4)	0.0039 (4)	0.0004 (4)
C8	0.0242 (6)	0.0216 (5)	0.0206 (5)	0.0059 (4)	0.0084 (4)	0.0050 (4)
C9	0.0216 (5)	0.0220 (6)	0.0218 (5)	0.0056 (4)	0.0090 (4)	0.0026 (4)
C10	0.0183 (5)	0.0181 (5)	0.0246 (6)	0.0025 (4)	0.0037 (4)	0.0006 (4)
O1	0.0369 (5)	0.0259 (5)	0.0249 (5)	0.0161 (4)	−0.0007 (4)	−0.0002 (3)
O2	0.0487 (6)	0.0305 (5)	0.0306 (5)	0.0201 (4)	0.0002 (4)	−0.0064 (4)

Geometric parameters (Å, º) top

C1—N2	1.4676 (14)	C5—H5B	0.99
C1—N1	1.4808 (15)	C6—N2	1.4663 (16)
C1—H1A	0.99	C6—N4	1.4671 (16)
C1—H1B	0.99	C6—H6A	0.99
C2—N2	1.4678 (17)	C6—H6B	0.99
C2—N3	1.4713 (17)	C7—C10	1.5160 (15)
C2—H2A	0.99	C7—C9ⁱ	1.5238 (15)
C2—H2B	0.99	C7—C8	1.5331 (15)
C3—N3	1.4679 (17)	C7—H7	1
C3—N4	1.4686 (16)	C8—C9	1.5268 (15)
C3—H3A	0.99	C8—H8A	0.99
C3—H3B	0.99	C8—H8B	0.99
C4—N3	1.4657 (15)	C9—C7ⁱ	1.5238 (15)
C4—N1	1.4812 (15)	C9—H9A	0.99
C4—H4A	0.99	C9—H9B	0.99
C4—H4B	0.99	C10—O2	1.2091 (15)
C5—N4	1.4662 (15)	C10—O1	1.3154 (14)
C5—N1	1.4848 (15)	O1—H1	0.84
C5—H5A	0.99

N2—C1—N1	111.82 (9)	H6A—C6—H6B	107.8
N2—C1—H1A	109.3	C1—N1—C4	108.27 (9)
N1—C1—H1A	109.3	C1—N1—C5	107.61 (9)
N2—C1—H1B	109.3	C4—N1—C5	107.78 (9)
N1—C1—H1B	109.3	C6—N2—C1	108.39 (9)
H1A—C1—H1B	107.9	C6—N2—C2	107.89 (9)
N2—C2—N3	112.54 (9)	C1—N2—C2	108.14 (9)
N2—C2—H2A	109.1	C4—N3—C3	108.13 (10)
N3—C2—H2A	109.1	C4—N3—C2	107.97 (10)
N2—C2—H2B	109.1	C3—N3—C2	107.96 (9)
N3—C2—H2B	109.1	C5—N4—C6	107.94 (9)
H2A—C2—H2B	107.8	C5—N4—C3	108.17 (10)
N3—C3—N4	112.56 (9)	C6—N4—C3	107.91 (9)
N3—C3—H3A	109.1	C10—C7—C9ⁱ	111.75 (9)
N4—C3—H3A	109.1	C10—C7—C8	110.48 (9)
N3—C3—H3B	109.1	C9ⁱ—C7—C8	110.30 (9)
N4—C3—H3B	109.1	C10—C7—H7	108.1
H3A—C3—H3B	107.8	C9ⁱ—C7—H7	108.1
N3—C4—N1	112.12 (9)	C8—C7—H7	108.1
N3—C4—H4A	109.2	C9—C8—C7	110.25 (9)
N1—C4—H4A	109.2	C9—C8—H8A	109.6
N3—C4—H4B	109.2	C7—C8—H8A	109.6
N1—C4—H4B	109.2	C9—C8—H8B	109.6
H4A—C4—H4B	107.9	C7—C8—H8B	109.6
N4—C5—N1	112.20 (9)	H8A—C8—H8B	108.1
N4—C5—H5A	109.2	C7ⁱ—C9—C8	111.31 (9)
N1—C5—H5A	109.2	C7ⁱ—C9—H9A	109.4
N4—C5—H5B	109.2	C8—C9—H9A	109.4
N1—C5—H5B	109.2	C7ⁱ—C9—H9B	109.4
H5A—C5—H5B	107.9	C8—C9—H9B	109.4
N2—C6—N4	112.61 (9)	H9A—C9—H9B	108
N2—C6—H6A	109.1	O2—C10—O1	123.03 (11)
N4—C6—H6A	109.1	O2—C10—C7	123.88 (10)
N2—C6—H6B	109.1	O1—C10—C7	113.09 (10)
N4—C6—H6B	109.1	C10—O1—H1	109.5

N2—C1—N1—C4	−57.93 (12)	N2—C2—N3—C4	58.78 (12)
N2—C1—N1—C5	58.31 (12)	N2—C2—N3—C3	−57.91 (12)
N3—C4—N1—C1	57.99 (13)	N1—C5—N4—C6	58.47 (13)
N3—C4—N1—C5	−58.15 (13)	N1—C5—N4—C3	−58.05 (13)
N4—C5—N1—C1	−58.63 (12)	N2—C6—N4—C5	−58.39 (12)
N4—C5—N1—C4	57.94 (12)	N2—C6—N4—C3	58.29 (12)
N4—C6—N2—C1	58.57 (13)	N3—C3—N4—C5	58.48 (12)
N4—C6—N2—C2	−58.32 (12)	N3—C3—N4—C6	−58.06 (12)
N1—C1—N2—C6	−58.43 (13)	C10—C7—C8—C9	−179.28 (9)
N1—C1—N2—C2	58.29 (12)	C9ⁱ—C7—C8—C9	56.67 (13)
N3—C2—N2—C6	58.06 (12)	C7—C8—C9—C7ⁱ	−57.25 (13)
N3—C2—N2—C1	−58.99 (12)	C9ⁱ—C7—C10—O2	13.98 (17)
N1—C4—N3—C3	58.54 (13)	C8—C7—C10—O2	−109.24 (14)
N1—C4—N3—C2	−58.04 (13)	C9ⁱ—C7—C10—O1	−165.62 (10)
N4—C3—N3—C4	−58.70 (13)	C8—C7—C10—O1	71.17 (12)
N4—C3—N3—C2	57.88 (12)

Symmetry code: (i) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.84	2.6710 (12)	170

Experimental details

Crystal data
Chemical formula	2C₆H₁₂N₄·C₈H₁₂O₄
M_r	452.57
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	5.9182 (1), 31.5242 (6), 6.1193 (1)
β (°)	109.144 (1)
V (Å³)	1078.52 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.1
Crystal size (mm)	0.4 × 0.35 × 0.04

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Integration (XPREP; Bruker, 2004)
T_min, T_max	0.960, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	13851, 2594, 2218
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.113, 0.89
No. of reflections	2594
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.19

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.84	2.6710 (12)	170

Acknowledgements

The University of the Witwatersrand and the Molecular Sciences Institute are thanked for providing the infrastructure and financial support to do this work.

References

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