Bis(dimethyl­ammonium) bis­(pyridine-2,5-dicarboxyl­ato)copper(II)

In the title compound, (C₂H₈N)₂[Cu(C₇H₃NO₄)₂], the Cu^II atom lies on an inversion centre and is coordinated in a slightly deformed square-planar geometry by two N and two O atoms from pyridine-2,5-dicarboxyl­ate ligands. The complex anions are linked via weak coordination of an O atom of the 2-carboxyl­ate group to the Cu atom of a neighbouring complex, forming chains along the a axis. There are N—H...O hydrogen bonds between dimethyl­ammonium cations and the 5-carboxyl­ate group of the ligand.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.092
• Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.655     1.000
            Tmin(prime) and Tmax expected:      0.750     0.889
            RR(prime) =      0.777
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.77
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.89
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.15
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C5     -   C7     ...       1.53 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            O1  -CU1 -O1  -C1      9.00  0.00   2.775   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          6
            N1  -CU1 -N1  -C6      4.00  0.00   2.775   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          9
            N1  -CU1 -N1  -C2     14.00  0.00   2.775   1.555   1.555   1.555

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.889
            Tmax scaled      0.889 Tmin scaled      0.582
PLAT804_ALERT_5_G ARU-Pack Problem in PLATON Analysis ............          1 Times

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker,1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis(dimethylammonium) bis(pyridine-2,5-dicarboxylato)copper(II)

Crystal data

(C2H8N)2[Cu(C7H3NO4)2]	Z = 1
Mr = 485.94	F(000) = 251
Triclinic, P1	Dx = 1.661 Mg m^−3
a = 5.2516 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.216 (2) Å	Cell parameters from 1119 reflections
c = 12.290 (3) Å	θ = 2.8–26.3°
α = 103.232 (4)°	µ = 1.18 mm^−1
β = 92.484 (4)°	T = 294 K
γ = 108.439 (4)°	Block, blue
V = 485.8 (2) Å^3	0.24 × 0.14 × 0.10 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	1715 independent reflections
Radiation source: fine-focus sealed tube	1450 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→4
Tmin = 0.655, Tmax = 1.000	k = −8→9
2504 measured reflections	l = −11→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0491P)^2 + 0.0557P] where P = (Fo^2 + 2Fc^2)/3
1715 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

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.

CCDC number: 620909.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	1.0000	1.0000	0.0000	0.0275 (2)
O1	1.2263 (4)	0.8976 (3)	−0.09590 (17)	0.0315 (5)
O2	1.4979 (5)	0.7359 (3)	−0.09340 (18)	0.0402 (6)
O3	0.9241 (4)	0.5701 (3)	0.39638 (19)	0.0384 (6)
O4	0.7079 (5)	0.7585 (3)	0.3789 (2)	0.0466 (6)
N1	1.0489 (4)	0.8428 (3)	0.09188 (19)	0.0221 (5)
C1	1.3254 (6)	0.7966 (4)	−0.0557 (2)	0.0256 (6)
C2	1.2137 (5)	0.7537 (4)	0.0504 (2)	0.0218 (6)
C3	1.2705 (6)	0.6339 (4)	0.1009 (2)	0.0270 (7)
H3	1.3837	0.5729	0.0708	0.032*
C4	1.1566 (6)	0.6056 (4)	0.1973 (2)	0.0277 (7)
H4	1.1924	0.5248	0.2324	0.033*
C5	0.9893 (5)	0.6978 (4)	0.2412 (2)	0.0219 (6)
C6	0.9386 (5)	0.8153 (4)	0.1853 (2)	0.0233 (6)
H6	0.8244	0.8769	0.2135	0.028*
C7	0.8623 (6)	0.6727 (4)	0.3482 (2)	0.0275 (7)
N2	0.5206 (5)	0.2761 (3)	0.4280 (2)	0.0299 (6)
H2A	0.4629	0.2766	0.4960	0.036*
H2B	0.6663	0.3740	0.4362	0.036*
C8	0.3058 (7)	0.2813 (5)	0.3497 (3)	0.0454 (9)
H8A	0.3715	0.2902	0.2789	0.068*
H8B	0.2529	0.3824	0.3806	0.068*
H8C	0.1526	0.1749	0.3385	0.068*
C9	0.5987 (7)	0.1174 (4)	0.3880 (3)	0.0432 (9)
H9A	0.4474	0.0129	0.3850	0.065*
H9B	0.7465	0.1222	0.4388	0.065*
H9C	0.6530	0.1139	0.3142	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0384 (3)	0.0341 (3)	0.0234 (3)	0.0210 (2)	0.0156 (2)	0.0181 (2)
O1	0.0403 (12)	0.0404 (12)	0.0273 (11)	0.0227 (10)	0.0170 (9)	0.0196 (10)
O2	0.0487 (14)	0.0519 (14)	0.0363 (13)	0.0315 (12)	0.0253 (11)	0.0182 (11)
O3	0.0469 (13)	0.0459 (14)	0.0369 (13)	0.0203 (11)	0.0158 (11)	0.0300 (11)
O4	0.0646 (16)	0.0630 (16)	0.0406 (14)	0.0429 (14)	0.0330 (12)	0.0325 (12)
N1	0.0237 (12)	0.0237 (12)	0.0218 (12)	0.0096 (10)	0.0086 (10)	0.0082 (10)
C1	0.0267 (16)	0.0269 (16)	0.0233 (16)	0.0081 (13)	0.0080 (13)	0.0070 (13)
C2	0.0222 (14)	0.0231 (15)	0.0203 (15)	0.0083 (12)	0.0060 (11)	0.0043 (12)
C3	0.0287 (16)	0.0293 (16)	0.0290 (16)	0.0161 (13)	0.0069 (13)	0.0094 (13)
C4	0.0327 (16)	0.0270 (16)	0.0293 (16)	0.0125 (13)	0.0047 (13)	0.0147 (13)
C5	0.0219 (15)	0.0225 (14)	0.0207 (15)	0.0052 (12)	0.0040 (12)	0.0073 (12)
C6	0.0259 (15)	0.0258 (15)	0.0216 (15)	0.0102 (12)	0.0099 (12)	0.0095 (12)
C7	0.0290 (16)	0.0324 (17)	0.0229 (16)	0.0087 (13)	0.0072 (13)	0.0124 (13)
N2	0.0369 (15)	0.0296 (14)	0.0280 (14)	0.0130 (11)	0.0156 (11)	0.0119 (11)
C8	0.055 (2)	0.062 (2)	0.0321 (19)	0.0350 (19)	0.0122 (17)	0.0148 (17)
C9	0.044 (2)	0.041 (2)	0.049 (2)	0.0207 (17)	0.0126 (17)	0.0110 (17)

Geometric parameters (Å, º)

Cu1—N1	1.965 (2)	C4—C5	1.383 (4)
Cu1—N1^i	1.965 (2)	C4—H4	0.9300
Cu1—O1^i	1.952 (2)	C5—C6	1.388 (4)
Cu1—O1	1.952 (2)	C5—C7	1.526 (4)
Cu1—O2^ii	2.821 (2)	C6—H6	0.9300
Cu1—O2^iii	2.821 (2)	N2—C8	1.468 (4)
O1—C1	1.282 (3)	N2—C9	1.474 (4)
O2—C1	1.225 (3)	N2—H2A	0.9000
O3—C7	1.246 (3)	N2—H2B	0.9000
O4—C7	1.250 (4)	C8—H8A	0.9600
N1—C6	1.341 (3)	C8—H8B	0.9600
N1—C2	1.347 (4)	C8—H8C	0.9600
C1—C2	1.521 (4)	C9—H9A	0.9600
C2—C3	1.375 (4)	C9—H9B	0.9600
C3—C4	1.383 (4)	C9—H9C	0.9600
C3—H3	0.9300
O1^i—Cu1—O1	180.0	C5—C4—H4	120.1
O1^i—Cu1—N1	96.56 (9)	C3—C4—H4	120.1
O1—Cu1—N1	83.44 (9)	C4—C5—C6	118.2 (3)
O1^i—Cu1—N1^i	83.44 (9)	C4—C5—C7	121.6 (3)
O1—Cu1—N1^i	96.56 (9)	C6—C5—C7	120.2 (2)
N1—Cu1—N1^i	180.0	N1—C6—C5	122.1 (3)
O1—Cu1—O2^ii	97.55 (8)	N1—C6—H6	119.0
O1—Cu1—O2^iii	82.45 (8)	C5—C6—H6	119.0
O2^ii—Cu1—N1	86.99 (8)	O3—C7—O4	126.7 (3)
O2^iii—Cu1—N1	93.01 (8)	O3—C7—C5	116.9 (3)
O1^i—Cu1—O2^ii	82.45 (8)	O4—C7—C5	116.4 (2)
O2^ii—Cu1—N1^i	93.01 (8)	C8—N2—C9	111.8 (3)
O2^ii—Cu1—O2^iii	180.00	C8—N2—H2A	109.2
O1^i—Cu1—O2^iii	97.55 (8)	C9—N2—H2A	109.2
O2^iii—Cu1—N1^i	86.99 (8)	C8—N2—H2B	109.2
C1—O1—Cu1	114.99 (18)	C9—N2—H2B	109.2
C6—N1—C2	119.3 (2)	H2A—N2—H2B	107.9
C6—N1—Cu1	128.35 (19)	N2—C8—H8A	109.5
C2—N1—Cu1	112.37 (18)	N2—C8—H8B	109.5
O2—C1—O1	126.6 (3)	H8A—C8—H8B	109.5
O2—C1—C2	119.0 (3)	N2—C8—H8C	109.5
O1—C1—C2	114.4 (2)	H8A—C8—H8C	109.5
N1—C2—C3	121.7 (3)	H8B—C8—H8C	109.5
N1—C2—C1	114.1 (2)	N2—C9—H9A	109.5
C3—C2—C1	124.2 (3)	N2—C9—H9B	109.5
C2—C3—C4	119.0 (3)	H9A—C9—H9B	109.5
C2—C3—H3	120.5	N2—C9—H9C	109.5
C4—C3—H3	120.5	H9A—C9—H9C	109.5
C5—C4—C3	119.8 (3)	H9B—C9—H9C	109.5
O1^i—Cu1—O1—C1	−94 (100)	C6—N1—C2—C1	180.0 (2)
N1—Cu1—O1—C1	−6.8 (2)	Cu1—N1—C2—C1	0.8 (3)
N1^i—Cu1—O1—C1	173.2 (2)	O2—C1—C2—N1	172.8 (3)
O1^i—Cu1—N1—C6	3.8 (3)	O1—C1—C2—N1	−6.4 (4)
O1—Cu1—N1—C6	−176.2 (3)	O2—C1—C2—C3	−7.7 (4)
N1^i—Cu1—N1—C6	−39 (100)	O1—C1—C2—C3	173.1 (3)
O1^i—Cu1—N1—C2	−177.08 (19)	N1—C2—C3—C4	−0.5 (4)
O1—Cu1—N1—C2	2.92 (19)	C1—C2—C3—C4	−179.9 (3)
N1^i—Cu1—N1—C2	140 (100)	C2—C3—C4—C5	−0.2 (4)
O2^ii—Cu1—O1—C1	−92.9 (2)	C3—C4—C5—C6	0.8 (4)
O2^iii—Cu1—O1—C1	87.1 (2)	C3—C4—C5—C7	−179.2 (3)
O2^ii—Cu1—N1—C2	100.88 (19)	C2—N1—C6—C5	0.2 (4)
O2^iii—Cu1—N1—C2	−79.12 (19)	Cu1—N1—C6—C5	179.3 (2)
O2^ii—Cu1—N1—C6	−78.2 (2)	C4—C5—C6—N1	−0.9 (4)
O2^iii—Cu1—N1—C6	101.8 (2)	C7—C5—C6—N1	179.2 (2)
Cu1—O1—C1—O2	−170.3 (2)	C4—C5—C7—O3	2.6 (4)
Cu1—O1—C1—C2	8.8 (3)	C6—C5—C7—O3	−177.5 (3)
C6—N1—C2—C3	0.5 (4)	C4—C5—C7—O4	−178.0 (3)
Cu1—N1—C2—C3	−178.7 (2)	C6—C5—C7—O4	2.0 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O3	0.90	1.92	2.782 (3)	159
N2—H2A···O4^iv	0.90	1.85	2.737 (3)	170

Symmetry code: (iv) −x+1, −y+1, −z+1.