Dimethyl-ammonium diaqua-(pyridine-2,4-dicarboxyl-ato-κN,O)cuprate(II).

The asymmetric unit of the title compound, (C(2)H(8)N)(2)[Cu(C(7)H(3)NO(4))(2)(H(2)O)(2)], contains one-half of a mononuclear [Cu(C(7)H(3)NO(4))(2)(H(2)O)(2)](2-) anion, one dimethyl-ammonium cation and one aqua ligand. The Cu(II) atom, lying on an inversion center, is coordinated by two symmetry-related N atoms and two O atoms from one pyridine-2,4-dicarboxyl-ate ligand and two symmetry-related aqua ligands and exhibits a distorted octa-hedral trans-[CuN(2)O(4)] coordination geometry. Multiple crystallographically independent O-H⋯O and N-H⋯O hydrogen bonds form a three-dimensional network in the crystal structure.

Related literature

For the structural diversity and potential applications of coordination polymers constructed from metal ions and bridging ligands, see: Eddaoudi et al. (2001 ▶); Kitagawa et al. (2004 ▶). For general background to metal complexes of pyridine-2,4-dicarboxyl­ates, see: Mahata & Natarajan (2005 ▶); Bai et al. (2008 ▶); Chen & Beatty (2008 ▶). For similar structures, see: Zou et al. (2008 ▶); Noro et al. (2005 ▶). For comparative bond lengths and angles, see: Chutia et al. (2009 ▶); Klein et al. (1982 ▶).

Experimental

Crystal data

(C2H8N)2[Cu(C7H3NO4)2(H2O)2]

M = 521.98

Monoclinic,

a = 7.9854 (7) Å

b = 9.4648 (8) Å

c = 14.9380 (12) Å

β = 103.540 (1)°

V = 1097.64 (16) Å3

Z = 2

Mo Kα radiation

μ = 1.06 mm−1

T = 293 K

0.31 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.732, T max = 0.849

5508 measured reflections

2160 independent reflections

1992 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.079

S = 1.06

2160 reflections

159 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002497/bx2257sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002497/bx2257Isup2.hkl

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

(C2H8N)2[Cu(C7H3NO4)2(H2O)2]	F(000) = 542
Mr = 521.98	Dx = 1.579 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3343 reflections
a = 7.9854 (7) Å	θ = 2.6–26.0°
b = 9.4648 (8) Å	µ = 1.06 mm−1
c = 14.9380 (12) Å	T = 293 K
β = 103.540 (1)°	Block, green
V = 1097.64 (16) Å3	0.31 × 0.16 × 0.16 mm
Z = 2

Bruker SMART APEX CCD diffractometer	2160 independent reflections
Radiation source: sealed tube	1992 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.732, Tmax = 0.849	k = −7→11
5508 measured reflections	l = −12→18

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0456P)2 + 0.427P] where P = (Fo2 + 2Fc2)/3
2160 reflections	(Δ/σ)max = 0.001
159 parameters	Δρmax = 0.35 e Å−3
2 restraints	Δρmin = −0.26 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.0000	0.5000	1.0000	0.02668 (12)
N1	0.15726 (18)	0.55054 (15)	0.92027 (9)	0.0235 (3)
N2	0.7815 (2)	0.47684 (16)	0.59707 (11)	0.0302 (3)
H2A	0.6957	0.4670	0.6264	0.036*
H2B	0.8078	0.3904	0.5793	0.036*
O1	0.15272 (15)	0.33417 (12)	1.02961 (8)	0.0291 (3)
O2	0.38987 (16)	0.24074 (13)	0.99920 (9)	0.0337 (3)
O3	0.57116 (18)	0.46822 (17)	0.72146 (10)	0.0393 (3)
O4	0.4794 (2)	0.68865 (19)	0.68723 (12)	0.0618 (5)
O1W	0.18306 (19)	0.62993 (16)	1.12457 (10)	0.0400 (3)
H1WA	0.126 (3)	0.687 (2)	1.1473 (16)	0.048*
H1WB	0.250 (2)	0.594 (2)	1.1680 (12)	0.048*
C1	0.2761 (2)	0.33162 (18)	0.98819 (11)	0.0253 (3)
C2	0.2792 (2)	0.45160 (18)	0.92182 (11)	0.0223 (3)
C3	0.3928 (2)	0.45788 (18)	0.86496 (11)	0.0234 (3)
H3	0.4755	0.3880	0.8674	0.028*
C4	0.3812 (2)	0.57093 (18)	0.80377 (11)	0.0249 (3)
C5	0.2608 (2)	0.67552 (18)	0.80637 (11)	0.0277 (4)
H5	0.2545	0.7549	0.7690	0.033*
C6	0.1501 (2)	0.66179 (18)	0.86455 (11)	0.0269 (4)
H6	0.0686	0.7319	0.8649	0.032*
C7	0.4887 (2)	0.5772 (2)	0.73205 (12)	0.0337 (4)
C8	0.9339 (3)	0.5361 (3)	0.66186 (15)	0.0414 (5)
H8A	1.0242	0.5513	0.6303	0.062*
H8B	0.9728	0.4712	0.7118	0.062*
H8C	0.9037	0.6244	0.6856	0.062*
C9	0.7204 (3)	0.5659 (2)	0.51421 (13)	0.0409 (5)
H9A	0.6653	0.6490	0.5306	0.061*
H9B	0.6396	0.5134	0.4686	0.061*
H9C	0.8166	0.5931	0.4898	0.061*

	U11	U22	U33	U12	U13	U23
Cu1	0.03408 (19)	0.02407 (18)	0.02744 (19)	0.00826 (11)	0.01843 (13)	0.00608 (11)
N1	0.0288 (7)	0.0230 (7)	0.0207 (6)	0.0025 (6)	0.0095 (5)	0.0003 (6)
N2	0.0352 (8)	0.0289 (8)	0.0295 (8)	−0.0024 (6)	0.0136 (7)	−0.0061 (6)
O1	0.0363 (7)	0.0269 (6)	0.0297 (6)	0.0071 (5)	0.0190 (5)	0.0078 (5)
O2	0.0357 (7)	0.0289 (7)	0.0411 (7)	0.0097 (5)	0.0183 (6)	0.0119 (6)
O3	0.0368 (7)	0.0531 (8)	0.0329 (7)	0.0035 (6)	0.0183 (6)	0.0039 (6)
O4	0.0617 (10)	0.0642 (11)	0.0720 (11)	0.0089 (8)	0.0411 (9)	0.0378 (9)
O1W	0.0444 (8)	0.0413 (8)	0.0345 (7)	0.0109 (6)	0.0095 (6)	−0.0020 (6)
C1	0.0304 (8)	0.0230 (8)	0.0242 (8)	0.0016 (7)	0.0097 (7)	0.0016 (6)
C2	0.0258 (8)	0.0208 (8)	0.0209 (7)	−0.0009 (6)	0.0070 (6)	−0.0010 (6)
C3	0.0236 (8)	0.0235 (8)	0.0240 (8)	0.0001 (6)	0.0074 (6)	−0.0001 (7)
C4	0.0245 (8)	0.0276 (9)	0.0228 (8)	−0.0058 (6)	0.0062 (6)	0.0009 (7)
C5	0.0333 (9)	0.0245 (9)	0.0250 (8)	−0.0027 (7)	0.0063 (7)	0.0059 (7)
C6	0.0320 (8)	0.0231 (8)	0.0260 (8)	0.0043 (7)	0.0079 (7)	0.0026 (7)
C7	0.0277 (9)	0.0459 (12)	0.0287 (9)	−0.0047 (8)	0.0090 (7)	0.0085 (8)
C8	0.0349 (10)	0.0507 (12)	0.0376 (11)	−0.0059 (9)	0.0066 (8)	−0.0036 (10)
C9	0.0472 (11)	0.0445 (12)	0.0319 (10)	0.0041 (9)	0.0110 (8)	0.0005 (9)

Cu1—O1	1.9733 (11)	O1W—H1WB	0.815 (10)
Cu1—O1i	1.9733 (11)	C1—C2	1.512 (2)
Cu1—N1i	1.9810 (14)	C2—C3	1.381 (2)
Cu1—N1	1.9810 (14)	C3—C4	1.396 (2)
Cu1—O1Wi	2.4162 (15)	C3—H3	0.9300
Cu1—O1W	2.4162 (15)	C4—C5	1.387 (2)
N1—C6	1.335 (2)	C4—C7	1.523 (2)
N1—C2	1.347 (2)	C5—C6	1.383 (2)
N2—C8	1.477 (3)	C5—H5	0.9300
N2—C9	1.483 (3)	C6—H6	0.9300
N2—H2A	0.9000	C8—H8A	0.9600
N2—H2B	0.9000	C8—H8B	0.9600
O1—C1	1.281 (2)	C8—H8C	0.9600
O2—C1	1.234 (2)	C9—H9A	0.9600
O3—C7	1.253 (2)	C9—H9B	0.9600
O4—C7	1.242 (2)	C9—H9C	0.9600
O1W—H1WA	0.832 (10)
O1—Cu1—O1i	179.998 (1)	N1—C2—C3	122.38 (15)
O1—Cu1—N1i	96.81 (5)	N1—C2—C1	114.25 (14)
O1i—Cu1—N1i	83.18 (5)	C3—C2—C1	123.33 (15)
O1—Cu1—N1	83.19 (5)	C2—C3—C4	118.89 (16)
O1i—Cu1—N1	96.81 (5)	C2—C3—H3	120.6
N1i—Cu1—N1	180.00 (5)	C4—C3—H3	120.6
O1—Cu1—O1Wi	89.92 (5)	C5—C4—C3	117.97 (15)
O1i—Cu1—O1Wi	90.08 (5)	C5—C4—C7	120.04 (15)
N1i—Cu1—O1Wi	89.18 (5)	C3—C4—C7	121.90 (16)
N1—Cu1—O1Wi	90.82 (5)	C6—C5—C4	119.98 (15)
O1—Cu1—O1W	90.08 (5)	C6—C5—H5	120.0
O1i—Cu1—O1W	89.91 (5)	C4—C5—H5	120.0
N1i—Cu1—O1W	90.82 (5)	N1—C6—C5	121.69 (15)
N1—Cu1—O1W	89.18 (5)	N1—C6—H6	119.2
O1Wi—Cu1—O1W	180.00 (5)	C5—C6—H6	119.2
C6—N1—C2	118.96 (14)	O4—C7—O3	126.71 (18)
C6—N1—Cu1	128.65 (12)	O4—C7—C4	116.09 (18)
C2—N1—Cu1	112.29 (11)	O3—C7—C4	117.13 (16)
C8—N2—C9	113.01 (16)	N2—C8—H8A	109.5
C8—N2—H2A	109.0	N2—C8—H8B	109.5
C9—N2—H2A	109.0	H8A—C8—H8B	109.5
C8—N2—H2B	109.0	N2—C8—H8C	109.5
C9—N2—H2B	109.0	H8A—C8—H8C	109.5
H2A—N2—H2B	107.8	H8B—C8—H8C	109.5
C1—O1—Cu1	114.32 (10)	N2—C9—H9A	109.5
Cu1—O1W—H1WA	110.7 (17)	N2—C9—H9B	109.5
Cu1—O1W—H1WB	124.4 (18)	H9A—C9—H9B	109.5
H1WA—O1W—H1WB	106 (2)	N2—C9—H9C	109.5
O2—C1—O1	125.07 (15)	H9A—C9—H9C	109.5
O2—C1—C2	119.13 (14)	H9B—C9—H9C	109.5
O1—C1—C2	115.80 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O4ii	0.83 (2)	1.85 (2)	2.680 (2)	174
O1W—H1Wb···O3iii	0.812 (18)	2.002 (17)	2.809 (2)	172
N2—H2A···O3	0.90	1.92	2.783 (2)	161
N2—H2B···O2iv	0.90	1.94	2.778 (2)	154

Table 1

Selected bond lengths (Å)

Cu1—O1	1.9733 (11)
Cu1—N1	1.9810 (14)
Cu1—O1W	2.4162 (15)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O4i	0.83 (2)	1.85 (2)	2.680 (2)	174
O1W—H1Wb⋯O3ii	0.81 (2)	2.00 (2)	2.809 (2)	172
N2—H2A⋯O3	0.90	1.92	2.783 (2)	161
N2—H2B⋯O2iii	0.90	1.94	2.778 (2)	154

Symmetry codes: (i) ; (ii) ; (iii) .