Di­methyl­ammonium 2-amino-5-nitro­terephthalate hemihydrate

Krueger, M.; Albat, M.; Pieper, F.; Stock, N.

doi:10.1107/S2414314616000481

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 1| January 2016| x160048

doi:10.1107/S2414314616000481

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Dimethylammonium 2-amino-5-nitroterephthalate hemihydrate

Martin Krueger,^a Martin Albat,^a Florian Pieper ^a and Norbert Stock ^a ^*

^aMax-Eyth-Strasse 2, 24118 Kiel, Germany
^*Correspondence e-mail: stock@ac.uni-kiel.de

Edited by J. Simpson, University of Otago, New Zealand (Received 18 December 2015; accepted 8 January 2016; online 16 January 2016)

The asymmetric unit of the title compound, C₂H₈N⁺·C₈H₅N₂O₆⁻·0.5H₂O, comprises a monodeprotonated 2-amino-5-nitroterephthalate anion and a dimethylammonium counter-ion on general positions and a water molecule that lies on a twofold rotation axis. Extensive hydrogen bonding is observed between the carboxylate group and the dimethylammonium ion, the water molecule and the carboxylic acid group, as well as between the amino group, the water molecule and the carboxylic acid group (N—H⋯O and O—H⋯O hydrogen bonds are involved).

Keywords: crystal structure; dimethylammonium 2-amino-5-nitroterephtalate; functionalized terephthalic acid; H-bonding.

CCDC reference: 1446285

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Chemical scheme

Structure description

The title compound comprises a mono-deprotonated benzene 1,4-dicarboxylic acid with an NH₂ and an NO₂ group at the 2- and 5-positions, respectively (Fig. 1). Charge balance is accomplished with a dimethylammonium counter-cation. Extensive N—H⋯O and O—H⋯O hydrogen bonding between the cation, the anion and the water molecule leads to a three-dimensional structure (Table 1, Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H3B⋯O1	0.89	1.87	2.761 (4)	175
N1—H3A⋯O1ⁱ	0.89	2.01	2.880 (4)	164
N3—H6B⋯O4	0.86	2.11	2.736 (4)	130
N3—H6B⋯O4ⁱⁱ	0.86	2.32	3.035 (4)	141
N3—H6A⋯O7ⁱⁱⁱ	0.86	2.10	2.959 (3)	173
O3—H9⋯O2^iv	0.82	1.80	2.614 (3)	169
O7—H7⋯O2^v	0.89 (4)	1.85 (4)	2.743 (3)	176 (4)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y, -z+1; (iii) x, y-1, z; (iv) $[x, -y+1, z-{\script{1\over 2}}]$ ; (v) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Figure 1
The components of the title compound (the atom O7 lies on a twofold axis) showing the atom labelling with displacement ellipsoids drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.

Figure 2
Crystal packing of the title compound viewed along the crystallographic b axis. Hydrogen bonds are shown as dashed lines.

Functionalized terephthalate ions are of special interest for the synthesis of porous coordination polymers in order to tune host–guest interactions within functionalized pore surfaces (Biswas et al., 2011 ). A compound with the same cation but the non-functionalized terephthalate ion, which does not contain an additional water molecule, has been reported (Zhao et al., 2007 ). Extensive hydrogen bonding is also observed in this structure. Thus, the terephthalate ions are linked to each other by O—H⋯O hydrogen bonds, forming a one-dimensional polymeric chain. In addition, the terephthalate anions and dimethylammonium cations are connected into a three-dimensional structure by N—H⋯O hydrogen-bonds (Zhao et al., 2007).

Synthesis and crystallization

Dimethylammonium 2-amino-5-nitroterephtalate hemi hydrate was obtained from 10 mg 2-amino-5-nitro-terephthalic acid (0.18 mmol), 0.256 ml DMF and 0.244 ml H₂O. A 2 ml teflon-lined steel autoclave was used for the synthesis. The reactor was heated to 150°C for 24 h then cooled down to room temperature over 12 h, to give crystals suitable for X-ray data collection.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	2C₂H₈N⁺·2C₈H₅N₂O₆⁻·H₂O
M_r	560.48
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	21.494 (4), 6.4300 (13), 19.193 (4)
β (°)	99.98 (3)
V (Å³)	2612.5 (9)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.12
Crystal size (mm)	0.21 × 0.12 × 0.05

Data collection
Diffractometer	Stoe IPDS1 diffractometer
Absorption correction	Numerical (X-SHAPE and X-RED; Stoe, 2008 )
T_min, T_max	0.96, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	8870, 2305, 1218
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.139, 1.00
No. of reflections	2305
No. of parameters	191
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23
Computer programs: X-AREA (Stoe, 2008), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg, 1999 ), publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1446285

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2414314616000481/sj4003sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616000481/sj4003Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616000481/sj4003Isup3.cml

checkCIF report

Synthesis and crystallization top

Dimethylammonium 2-amino-5-nitroterephtalate hemi hydrate was obtained from 10 mg 2-amino-5-nitro-terephthalic acid (0.18 mmol), 0.256 ml DMF and 244 ml H₂O. A 2 ml teflon lined steel autoclave was used for the synthesis. The reactor was heated to 150 °C for 24 h then cooled down to room temperature over 12 h, to give crystals suitable for X-ray data collection.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1

Experimental top

Dimethylammonium 2-amino-5-nitroterephtalate hemi hydrate was obtained from 10 mg 2-amino-5-nitro-terephthalic acid (0.18 mmol), 0.256 ml DMF and 244 ml H₂O. A 2 ml teflon-lined steel autoclave was used for the synthesis. The reactor was heated to 150°C for 24 h then cooled down to room temperature over 12 h, to give crystals suitable for X-ray data collection.

Structure description top

The title compound consists of a mono-deprotonated benzene 1,4-dicarboxylic acid with an NH₂ and an NO₂ group at the 2- and 5-positions, respectively, Fig. 1. Charge balance is accomplished with a dimethylammonium counter-cation. Extensive N—H···O and O—H···O hydrogen bonding, Table 1, between the cation, the anion and the water molecule leads to a three-dimensional structure, Fig. 2.

Functionalized terephthalate ions are of special interest for the synthesis of porous coordination polymers in order to tune host–guest interactions within functionalized pore surfaces (Biswas et al., 2011). A compound with the same cation but the non-functionalized terephthalate ion, which does not contain an additional water molecule, has been reported (Zhao et al., 2007). Extensive hydrogen bonding is also observed in this structure. Thus, the terephthalate ions are linked to each other by O—H···O hydrogen bonds, forming a one-dimensional polymeric chain. In addition, the terephthalate anions and dimethylammonium cations are connected into a three-dimensional structure by N—H···O hydrogen-bonds (Zhao et al., 2007).

Computing details top

Data collection: X-AREA (Stoe, 2008); cell refinement: X-AREA (Stoe, 2008); data reduction: X-AREA (Stoe, 2008); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. : The asymmetric unit of the title compound showing the atom labelling with displacement ellipsoids drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. : Crystal packing of the title compound viewed along the crystallographic b axis. Hydrogen bonds are shown as dashed lines.

Dimethylammonium 2-amino-5-nitroterephthalate hemihydrate top

Crystal data top

2C₂H₈N⁺·2C₈H₅N₂O₆⁻·H₂O	F(000) = 1176
M_r = 560.48	D_x = 1.425 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.494 (4) Å	Cell parameters from 9323 reflections
b = 6.4300 (13) Å	θ = 2.1–25°
c = 19.193 (4) Å	µ = 0.12 mm⁻¹
β = 99.98 (3)°	T = 293 K
V = 2612.5 (9) Å³	Needle, brown
Z = 4	0.21 × 0.12 × 0.05 mm

Data collection top

Stoe IPDS-1 diffractometer	1218 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.087
Phi scan	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: numerical (X-SHAPE and X-RED; Stoe, 2008)	h = −25→25
T_min = 0.96, T_max = 0.98	k = −7→7
8870 measured reflections	l = −22→22
2305 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.139	w = 1/[σ²(F_o²) + (0.060P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2305 reflections	Δρ_max = 0.17 e Å⁻³
191 parameters	Δρ_min = −0.23 e Å⁻³

Crystal data top

2C₂H₈N⁺·2C₈H₅N₂O₆⁻·H₂O	V = 2612.5 (9) Å³
M_r = 560.48	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 21.494 (4) Å	µ = 0.12 mm⁻¹
b = 6.4300 (13) Å	T = 293 K
c = 19.193 (4) Å	0.21 × 0.12 × 0.05 mm
β = 99.98 (3)°

Data collection top

Stoe IPDS-1 diffractometer	2305 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED; Stoe, 2008)	1218 reflections with I > 2σ(I)
T_min = 0.96, T_max = 0.98	R_int = 0.087
8870 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.17 e Å⁻³
2305 reflections	Δρ_min = −0.23 e Å⁻³
191 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1647 (2)	0.5874 (7)	0.6545 (3)	0.0857 (13)
H1A	0.1554	0.6218	0.7003	0.103*
H1B	0.1810	0.7079	0.6343	0.103*
H1C	0.1268	0.5418	0.6243	0.103*
C2	0.2293 (2)	0.3567 (7)	0.5941 (2)	0.0754 (12)
H2A	0.2602	0.2476	0.6026	0.091*
H2B	0.1926	0.3071	0.5628	0.091*
H2C	0.2468	0.4732	0.5728	0.091*
N1	0.21164 (14)	0.4215 (5)	0.66167 (15)	0.0564 (7)
H3A	0.1965	0.3117	0.6815	0.091 (14)*
H3B	0.2462	0.4640	0.6906	0.085 (14)*
C3	0.38888 (14)	0.5454 (5)	0.67852 (15)	0.0394 (7)
C4	0.37102 (14)	0.6636 (5)	0.61645 (15)	0.0432 (7)
C5	0.38628 (15)	0.5967 (5)	0.55256 (15)	0.0482 (8)
H5	0.3741	0.6770	0.5122	0.064 (10)*
C6	0.41882 (14)	0.4154 (5)	0.54760 (15)	0.0432 (7)
C7	0.43852 (14)	0.2946 (5)	0.61005 (15)	0.0438 (8)
C8	0.42165 (15)	0.3674 (5)	0.67438 (15)	0.0452 (8)
H8	0.4337	0.2893	0.7153	0.057 (10)*
C9	0.36954 (16)	0.5969 (5)	0.74900 (15)	0.0439 (7)
C10	0.43132 (15)	0.3464 (6)	0.47806 (16)	0.0498 (8)
N2	0.33726 (14)	0.8558 (5)	0.61761 (15)	0.0572 (8)
N3	0.47084 (14)	0.1170 (5)	0.61051 (16)	0.0613 (8)
H6A	0.4812	0.0484	0.6493	0.077 (13)*
H6B	0.4813	0.0712	0.5721	0.076 (13)*
O1	0.31397 (11)	0.5663 (4)	0.75635 (12)	0.0555 (6)
O2	0.41281 (11)	0.6591 (4)	0.79741 (11)	0.0609 (7)
O3	0.40789 (14)	0.4728 (4)	0.42515 (13)	0.0717 (8)
H9	0.4136	0.4220	0.3876	0.17 (3)*
O4	0.45861 (13)	0.1878 (5)	0.46819 (12)	0.0748 (8)
O5	0.33347 (14)	0.9371 (4)	0.67470 (13)	0.0740 (8)
O6	0.31376 (18)	0.9364 (5)	0.56135 (15)	0.1048 (13)
O7	0.5000	0.9096 (6)	0.7500	0.0556 (9)
H7	0.529 (2)	0.826 (7)	0.737 (2)	0.100 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.089 (3)	0.071 (3)	0.095 (3)	0.013 (2)	0.009 (2)	−0.005 (2)
C2	0.076 (3)	0.085 (3)	0.066 (3)	−0.001 (2)	0.014 (2)	−0.010 (2)
N1	0.0667 (19)	0.0524 (19)	0.0493 (16)	−0.0100 (15)	0.0074 (15)	0.0073 (14)
C3	0.0457 (17)	0.0415 (18)	0.0313 (15)	−0.0016 (15)	0.0076 (13)	−0.0029 (12)
C4	0.0538 (18)	0.0402 (19)	0.0362 (16)	0.0059 (15)	0.0092 (13)	0.0002 (13)
C5	0.063 (2)	0.048 (2)	0.0341 (17)	0.0029 (16)	0.0104 (14)	0.0042 (14)
C6	0.0530 (18)	0.044 (2)	0.0338 (16)	0.0026 (15)	0.0096 (13)	−0.0021 (13)
C7	0.0474 (18)	0.044 (2)	0.0402 (18)	0.0049 (15)	0.0076 (14)	−0.0007 (13)
C8	0.0552 (19)	0.048 (2)	0.0331 (16)	0.0017 (16)	0.0096 (13)	0.0048 (14)
C9	0.057 (2)	0.043 (2)	0.0333 (16)	−0.0007 (15)	0.0129 (14)	0.0009 (13)
C10	0.058 (2)	0.054 (2)	0.0387 (17)	0.0031 (17)	0.0117 (15)	−0.0022 (16)
N2	0.075 (2)	0.0490 (19)	0.0479 (17)	0.0158 (15)	0.0123 (14)	0.0025 (14)
N3	0.082 (2)	0.058 (2)	0.0458 (17)	0.0266 (16)	0.0178 (14)	0.0051 (14)
O1	0.0532 (14)	0.0672 (17)	0.0488 (13)	−0.0041 (11)	0.0169 (10)	−0.0068 (11)
O2	0.0691 (16)	0.0805 (19)	0.0338 (11)	−0.0170 (13)	0.0105 (11)	−0.0075 (11)
O3	0.106 (2)	0.0723 (19)	0.0376 (13)	0.0244 (15)	0.0160 (14)	0.0045 (12)
O4	0.101 (2)	0.075 (2)	0.0511 (15)	0.0311 (17)	0.0185 (13)	−0.0058 (13)
O5	0.118 (2)	0.0561 (17)	0.0507 (16)	0.0237 (15)	0.0234 (14)	−0.0048 (12)
O6	0.165 (3)	0.096 (2)	0.0505 (16)	0.075 (2)	0.0096 (18)	0.0136 (16)
O7	0.059 (2)	0.056 (2)	0.052 (2)	0.000	0.0088 (16)	0.000

Geometric parameters (Å, º) top

C1—N1	1.458 (5)	C5—H5	0.9300
C1—H1A	0.9600	C6—C7	1.430 (4)
C1—H1B	0.9600	C6—C10	1.475 (4)
C1—H1C	0.9600	C7—N3	1.336 (4)
C2—N1	1.474 (4)	C7—C8	1.425 (4)
C2—H2A	0.9600	C8—H8	0.9300
C2—H2B	0.9600	C9—O1	1.243 (4)
C2—H2C	0.9600	C9—O2	1.261 (4)
N1—H3A	0.8900	C10—O4	1.208 (4)
N1—H3B	0.8900	C10—O3	1.330 (4)
C3—C8	1.354 (4)	N2—O6	1.225 (4)
C3—C4	1.409 (4)	N2—O5	1.229 (3)
C3—C9	1.519 (4)	N3—H6A	0.8600
C4—C5	1.391 (4)	N3—H6B	0.8600
C4—N2	1.435 (4)	O3—H9	0.8200
C5—C6	1.371 (4)	O7—H7	0.89 (4)

N1—C1—H1A	109.5	C6—C5—H5	119.2
N1—C1—H1B	109.5	C4—C5—H5	119.2
H1A—C1—H1B	109.5	C5—C6—C7	119.0 (3)
N1—C1—H1C	109.5	C5—C6—C10	119.6 (3)
H1A—C1—H1C	109.5	C7—C6—C10	121.4 (3)
H1B—C1—H1C	109.5	N3—C7—C8	119.0 (3)
N1—C2—H2A	109.5	N3—C7—C6	123.3 (3)
N1—C2—H2B	109.5	C8—C7—C6	117.7 (3)
H2A—C2—H2B	109.5	C3—C8—C7	122.8 (3)
N1—C2—H2C	109.5	C3—C8—H8	118.6
H2A—C2—H2C	109.5	C7—C8—H8	118.6
H2B—C2—H2C	109.5	O1—C9—O2	124.6 (3)
C1—N1—C2	113.8 (3)	O1—C9—C3	118.9 (3)
C1—N1—H3A	108.8	O2—C9—C3	116.4 (3)
C2—N1—H3A	108.8	O4—C10—O3	121.8 (3)
C1—N1—H3B	108.8	O4—C10—C6	124.5 (3)
C2—N1—H3B	108.8	O3—C10—C6	113.7 (3)
H3A—N1—H3B	107.7	O6—N2—O5	121.7 (3)
C8—C3—C4	118.3 (3)	O6—N2—C4	118.9 (3)
C8—C3—C9	117.5 (3)	O5—N2—C4	119.5 (3)
C4—C3—C9	124.0 (3)	C7—N3—H6A	120.0
C5—C4—C3	120.5 (3)	C7—N3—H6B	120.0
C5—C4—N2	118.5 (3)	H6A—N3—H6B	120.0
C3—C4—N2	121.0 (3)	C10—O3—H9	109.5
C6—C5—C4	121.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3B···O1	0.89	1.87	2.761 (4)	175
N1—H3A···O1ⁱ	0.89	2.01	2.880 (4)	164
N3—H6B···O4	0.86	2.11	2.736 (4)	130
N3—H6B···O4ⁱⁱ	0.86	2.32	3.035 (4)	141
N3—H6A···O7ⁱⁱⁱ	0.86	2.10	2.959 (3)	173
O3—H9···O2^iv	0.82	1.80	2.614 (3)	169
O7—H7···O2^v	0.89 (4)	1.85 (4)	2.743 (3)	176 (4)

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1, −y, −z+1; (iii) x, y−1, z; (iv) x, −y+1, z−1/2; (v) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H3B···O1	0.89	1.87	2.761 (4)	174.8
N1—H3A···O1ⁱ	0.89	2.01	2.880 (4)	164.1
N3—H6B···O4	0.86	2.11	2.736 (4)	129.7
N3—H6B···O4ⁱⁱ	0.86	2.32	3.035 (4)	140.8
N3—H6A···O7ⁱⁱⁱ	0.86	2.10	2.959 (3)	172.7
O3—H9···O2^iv	0.82	1.80	2.614 (3)	168.7
O7—H7···O2^v	0.89 (4)	1.85 (4)	2.743 (3)	176 (4)

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1, −y, −z+1; (iii) x, y−1, z; (iv) x, −y+1, z−1/2; (v) −x+1, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	2C₂H₈N⁺·2C₈H₅N₂O₆⁻·H₂O
M_r	560.48
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	21.494 (4), 6.4300 (13), 19.193 (4)
β (°)	99.98 (3)
V (Å³)	2612.5 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.21 × 0.12 × 0.05

Data collection
Diffractometer	Stoe IPDS1
Absorption correction	Numerical (X-SHAPE and X-RED; Stoe, 2008)
T_min, T_max	0.96, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	8870, 2305, 1218
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.139, 1.00
No. of reflections	2305
No. of parameters	191
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23

Computer programs: X-AREA (Stoe, 2008), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), DIAMOND (Brandenburg, 1999), publCIF (Westrip, 2010).

Acknowledgements

The authors would like to thank Inke Jess for collecting the single-crystal data.

References

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Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
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ISSN: 2414-3146

Volume 1| Part 1| January 2016| x160048

doi:10.1107/S2414314616000481

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

Di­methyl­ammonium 2-amino-5-nitro­terephthalate hemihydrate

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

Dimethylammonium 2-amino-5-nitroterephthalate hemihydrate