Tri­aqua(2,6-pyridine­di­carboxyl­ato)copper(II) at 150 K

Blake, A.J.; Felloni, M.; Hubberstey, P.; Wilson, C.; Schröder, M.

doi:10.1107/S160053680102164X

Triaqua(2,6-pyridinedicarboxylato)copper(II) at 150 K

A. J. Blake, M. Felloni, P. Hubberstey, C. Wilson and M. Schröder

The asymmetric unit of the title compound, [Cu(C₇H₃NO₄)(H₂O)₃], comprises a distorted tetragonally elongated octahedral copper(II) centre coordinated equatorially by a tridentate 2,6-pyridinedicarboxylate anion [Cu—N 1.9093 (14), and Cu—O 2.0368 (11) and 2.0397 (11) Å] and a strongly bound water molecule [Cu—O 1.9047 (12) Å] and axially by two weakly bound water molecules [Cu—O 2.3631 (12) and 2.4739 (12) Å]. The extended structure is based on a layered arrangement in which sheets of stacked molecular units are alternately linked by hydrogen-bonding and π–π stacking interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680102164X/om6073sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680102164X/om6073Isup2.hkl Contains datablock I

CCDC reference: 180756

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Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R factor = 0.021
wR factor = 0.061
Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.76
         From the CIF: _reflns_number_total               2308
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         2544
         Completeness (_total/calc)             90.72%
          Alert C: < 95% complete

PLAT_369  Alert C Long   C(sp2)-C(sp2) Bond  C2     -   C7     =       1.53 Ang.

PLAT_369  Alert C Long   C(sp2)-C(sp2) Bond  C6     -   C8     =       1.53 Ang.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT and SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2001).

(I) top

Crystal data top

[Cu(C₇H₃NO₄)(H₂O)₃]	D_x = 1.928 Mg m⁻³
M_r = 282.69	Melting point: unknown K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.4111 (9) Å	Cell parameters from 4778 reflections
b = 23.169 (3) Å	θ = 2.7–28.8°
c = 6.8348 (9) Å	µ = 2.26 mm⁻¹
β = 106.377 (2)°	T = 150 K
V = 974.0 (2) Å³	Block, blue
Z = 4	0.45 × 0.32 × 0.28 mm
F(000) = 572

Data collection top

Bruker SMART 1000 CCD area=detector diffractometer	2308 independent reflections
Radiation source: fine-focus sealed tube	2075 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 28.8°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS: Bruker, 2001)	h = −8→8
T_min = 0.406, T_max = 0.530	k = −30→27
6789 measured reflections	l = −8→6

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier method
Least-squares matrix: full	Hydrogen site location: aromatic H atoms geometrically placed; water H atoms located from ΔF
R[F² > 2σ(F²)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.061	w = 1/[σ²(F_o²) + (0.024P)² + 0.603P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max = 0.001
2248 reflections	Δρ_max = 0.40 e Å⁻³
164 parameters	Δρ_min = −0.48 e Å⁻³
9 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: direct method	Extinction coefficient: 0.0465 (15)

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.

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.

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

	x	y	z	U_iso*/U_eq
Cu	−0.00531 (3)	0.185504 (7)	0.26660 (3)	0.01235 (10)
N1	−0.00377 (17)	0.10313 (6)	0.25952 (17)	0.0121 (3)
C2	0.1832 (2)	0.07556 (6)	0.3430 (2)	0.0129 (3)
C3	0.1924 (2)	0.01573 (7)	0.3373 (2)	0.0160 (3)
H3	0.3255	−0.0043	0.3920	0.019*
C4	−0.0005 (2)	−0.01411 (7)	0.2486 (2)	0.0171 (3)
H4	0.0006	−0.0551	0.2447	0.020*
C5	−0.1952 (2)	0.01569 (7)	0.1653 (2)	0.0157 (3)
H5	−0.3272	−0.0044	0.1067	0.019*
C6	−0.1894 (2)	0.07558 (7)	0.1711 (2)	0.0130 (3)
C7	0.3675 (2)	0.11741 (6)	0.4402 (2)	0.0137 (3)
O1	0.55342 (17)	0.09934 (5)	0.51778 (18)	0.0193 (2)
O2	0.30812 (17)	0.17066 (5)	0.43291 (17)	0.0157 (2)
C8	−0.3753 (2)	0.11753 (6)	0.0816 (2)	0.0134 (3)
O3	−0.56128 (17)	0.09975 (5)	0.00236 (18)	0.0187 (2)
O4	−0.31722 (17)	0.17102 (5)	0.09691 (17)	0.0155 (2)
O1W	−0.00441 (18)	0.26771 (5)	0.26412 (16)	0.0193 (3)
H1WA	0.051 (3)	0.2864 (8)	0.366 (2)	0.029*
H1WB	−0.047 (3)	0.2877 (8)	0.163 (2)	0.029*
O2W	−0.13958 (19)	0.19273 (5)	0.55411 (18)	0.0184 (2)
H2WA	−0.229 (3)	0.1678 (7)	0.545 (3)	0.028*
H2WB	−0.057 (3)	0.1931 (9)	0.6691 (18)	0.028*
O3W	0.12943 (18)	0.19374 (5)	−0.03765 (18)	0.0181 (2)
H3WA	0.193 (3)	0.2247 (5)	−0.019 (3)	0.027*
H3WB	0.221 (3)	0.1685 (6)	−0.022 (3)	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.01152 (12)	0.00718 (12)	0.01579 (13)	0.00012 (6)	−0.00031 (8)	−0.00026 (6)
N1	0.0122 (6)	0.0103 (6)	0.0130 (6)	0.0004 (4)	0.0021 (5)	0.0000 (4)
C2	0.0127 (6)	0.0116 (7)	0.0137 (7)	0.0002 (5)	0.0026 (5)	0.0005 (5)
C3	0.0144 (7)	0.0129 (7)	0.0193 (7)	0.0025 (5)	0.0022 (6)	0.0007 (6)
C4	0.0199 (8)	0.0094 (7)	0.0207 (8)	0.0003 (5)	0.0038 (6)	−0.0005 (5)
C5	0.0146 (7)	0.0118 (7)	0.0189 (7)	−0.0026 (5)	0.0017 (6)	−0.0012 (5)
C6	0.0119 (6)	0.0138 (7)	0.0128 (7)	−0.0001 (5)	0.0025 (5)	−0.0001 (5)
C7	0.0150 (7)	0.0113 (7)	0.0138 (7)	−0.0011 (5)	0.0027 (5)	−0.0005 (5)
O1	0.0130 (5)	0.0155 (6)	0.0255 (6)	0.0015 (4)	−0.0010 (4)	0.0011 (4)
O2	0.0138 (5)	0.0114 (5)	0.0185 (5)	−0.0002 (4)	−0.0007 (4)	−0.0008 (4)
C8	0.0139 (6)	0.0123 (7)	0.0133 (7)	0.0005 (5)	0.0028 (5)	−0.0001 (5)
O3	0.0131 (5)	0.0148 (5)	0.0248 (6)	−0.0017 (4)	−0.0005 (4)	−0.0017 (4)
O4	0.0136 (5)	0.0107 (5)	0.0189 (5)	0.0002 (4)	−0.0008 (4)	0.0009 (4)
O1W	0.0303 (7)	0.0094 (6)	0.0137 (5)	−0.0001 (4)	−0.0012 (5)	0.0003 (4)
O2W	0.0174 (5)	0.0206 (6)	0.0163 (6)	−0.0037 (4)	0.0033 (4)	−0.0003 (4)
O3W	0.0152 (5)	0.0176 (6)	0.0212 (6)	−0.0003 (4)	0.0047 (5)	0.0006 (4)

Geometric parameters (Å, º) top

Cu—N1	1.9093 (14)	C7—O1	1.2333 (18)
Cu—O2	2.0397 (11)	C7—O2	1.2880 (19)
Cu—O4	2.0368 (11)	C8—O3	1.2332 (18)
Cu—O1W	1.9047 (12)	C8—O4	1.2897 (19)
Cu—O2W	2.3631 (12)	O1W—H1WA	0.813 (9)
Cu—O3W	2.4739 (12)	O1W—H1WB	0.813 (9)
N1—C6	1.3352 (18)	O2W—H2WA	0.804 (9)
N1—C2	1.3362 (18)	O2W—H2WB	0.815 (9)
C2—C3	1.388 (2)	C3—H3	0.9500
C2—C7	1.528 (2)	C4—H4	0.9500
C3—C4	1.397 (2)	C5—H5	0.9500
C4—C5	1.399 (2)	O3W—H3WA	0.817 (9)
C5—C6	1.389 (2)	O3W—H3WB	0.815 (9)
C6—C8	1.526 (2)

N1—Cu—O2	80.46 (4)	N1—C6—C8	111.88 (13)
N1—Cu—O4	80.34 (4)	C5—C6—C8	127.84 (13)
N1—Cu—O1W	177.86 (5)	O1—C7—O2	125.53 (14)
N1—Cu—O2W	95.60 (4)	O1—C7—C2	120.44 (13)
N1—Cu—O3W	92.88 (4)	O2—C7—C2	114.04 (12)
O2—Cu—O4	160.79 (5)	C7—O2—Cu	114.65 (9)
O2—Cu—O1W	99.71 (5)	O3—C8—O4	125.30 (14)
O2—Cu—O2W	94.66 (4)	O3—C8—C6	120.84 (13)
O2—Cu—O3W	87.64 (4)	O4—C8—C6	113.86 (12)
O4—Cu—O1W	99.47 (4)	C8—O4—Cu	114.78 (9)
O4—Cu—O2W	87.47 (4)	Cu—O1W—H1WA	121.8 (14)
O4—Cu—O3W	93.07 (4)	Cu—O1W—H1WB	125.2 (14)
O1W—Cu—O2W	86.52 (5)	H1WA—O1W—H1WB	113 (2)
O1W—Cu—O3W	84.99 (4)	Cu—O2W—H2WA	107.6 (16)
O2W—Cu—O3W	171.47 (4)	Cu—O2W—H2WB	120.8 (15)
C6—N1—C2	122.86 (14)	H2WA—O2W—H2WB	109.9 (17)
C6—N1—Cu	118.61 (10)	C2—C3—H3	121.1
C2—N1—Cu	118.52 (10)	C4—C3—H3	121.1
N1—C2—C3	120.34 (13)	C3—C4—H4	119.6
N1—C2—C7	111.90 (13)	C5—C4—H4	119.6
C3—C2—C7	127.75 (13)	C6—C5—H5	121.1
C2—C3—C4	117.85 (14)	C4—C5—H5	121.1
C3—C4—C5	120.74 (15)	Cu—O3W—H3WA	102.2 (15)
C6—C5—C4	117.89 (14)	Cu—O3W—H3WB	104.2 (16)
N1—C6—C5	120.26 (13)	H3WA—O3W—H3WB	107.4 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O4ⁱ	0.81 (1)	1.85 (1)	2.6627 (15)	179 (2)
O1W—H1WB···O2ⁱⁱ	0.81 (1)	1.86 (1)	2.6596 (15)	170 (2)
O2W—H2WA···O1ⁱⁱⁱ	0.80 (1)	2.09 (1)	2.8883 (16)	176 (2)
O2W—H2WB···O3W^iv	0.82 (1)	2.02 (1)	2.8367 (19)	176 (2)
O3W—H3WA···O2W^v	0.82 (1)	2.18 (1)	2.9969 (19)	176 (2)
O3W—H3WB···O3^vi	0.82 (1)	2.09 (1)	2.9056 (17)	176 (2)

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

Co-ordination distances (Cu—N and Cu—O, Å) for the [dipic]^2- anion and the H₂dipic molecule in [Cu(dipic)(OH₂)_n] (n = 2 or 3) and [Cu(dipic)(H₂dipic)].nH₂O (n = 1 or 3). top

Compound	Cu—N(1)	Cu—O(1)	Cu—O(2)
anionic [dipic]^2-
[Cu(dipic)(OH₂)₃]^a	1.9093 (14)	2.0368 (11)	2.0397 (11)
monoclinic-[Cu(dipic)(OH₂)₂]^b	1.898 (4)	2.037 (3)	2.050 (4)
triclinic-[Cu(dipic)(OH₂)₂]^b	1.901 (6)	2.005 (6)	2.018 (5)
[Cu(dipic)(H₂dipic)].H₂O^c	1.911 (4)	2.008 (3)	2.008 (3)
[Cu(dipic)(H₂dipic)].3H₂O^c	1.907 (7)	2.027 (8)	2.063 (8)
[Cu(dipic)(H₂dipic)].3H₂O^c	1.901 (7)	2.048 (7)	2.056 (7)
molecular H₂dipic
[Cu(dipic)(H₂dipic)].H₂O^c	2.011 (4)	2.425 (3)	2.425 (3)
[Cu(dipic)(H₂dipic)].3H₂O^c	2.003 (8)	2.310 (8)	2.465 (8)
[Cu(dipic)(H₂dipic)].3H₂O^c	1.995 (8)	2.302 (8)	2.379 (8)

^a This work; ^b Sarchet et al. (1973); ^c Sileo et al. (1996)

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