The crystal structure of the title compound, [Cu(C7H4NO4)2(C6H12N2)(H2O)]n, contains a one-dimensional polymeric chain running along the a axis. Both p-nitrobenzoate groups are monodentate ligands and dabco (1,4-diazabicyclo[2.2.2]octane) acts as an end-to-end bridging ligand. The Cu atom has a slightly distorted square-pyramidal (SQP) coordination involving two N atoms of the dabco ligand, two O atoms from the carboxylate group of the p-nitrobenzoate anions and one water ligand. The point symmetry of the copper(II) polyhedron with the p-nitrobenzoate anion ligands is mm, these ligands lying on mirror planes. The chains are crosslinked by hydrogen bonds involving the coordinated water molecule to form layers parallel to (101).
Supporting information
CCDC reference: 258653
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.012 Å
- R factor = 0.074
- wR factor = 0.164
- Data-to-parameter ratio = 9.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.91
PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 2.54 Ratio
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.10 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.32
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXLTL (Bruker, 1997); molecular graphics: SHELXLTL.
catena-poly[[aquabis(
p-nitrobenzoate-
κO)copper(II)]-
µ-1,4-diazabicyclo[2.2.2]octane-
κ2N:
N']
top
Crystal data top
[Cu(C7H4NO4)2(C6H12N2)(H2O)] | F(000) = 542 |
Mr = 525.96 | Dx = 1.652 Mg m−3 |
Orthorhombic, Pmmn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ab 2a | Cell parameters from 1000 reflections |
a = 6.8202 (14) Å | θ = 2.5–24.4° |
b = 25.024 (5) Å | µ = 1.10 mm−1 |
c = 6.1958 (12) Å | T = 293 K |
V = 1057.4 (4) Å3 | Block, green |
Z = 2 | 0.41 × 0.30 × 0.26 mm |
Data collection top
Bruker APEX CCD area-detector diffractometer | 1041 independent reflections |
Radiation source: fine-focus sealed tube | 1000 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
Detector resolution: 0 pixels mm-1 | θmax = 25.0°, θmin = 3.1° |
φ and ω scans | h = −8→7 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −29→29 |
Tmin = 0.700, Tmax = 0.750 | l = −6→7 |
4939 measured reflections | |
Refinement top
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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.38 | w = 1/[σ2(Fo2) + (0.0227P)2 + 7.5254P] where P = (Fo2 + 2Fc2)/3 |
1041 reflections | (Δ/σ)max = 0.001 |
105 parameters | Δρmax = 0.94 e Å−3 |
0 restraints | Δρmin = −0.91 e Å−3 |
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 | Uiso*/Ueq | Occ. (<1) |
Cu1 | 0.2500 | 0.7500 | 0.2341 (2) | 0.0185 (4) | |
C9 | −0.1373 (8) | 0.7019 (2) | 0.3560 (11) | 0.0313 (15) | |
H9A | −0.0900 | 0.7021 | 0.5036 | 0.038* | |
H9B | −0.0900 | 0.6696 | 0.2870 | 0.038* | |
C1 | 0.2500 | 0.5834 (3) | 0.0675 (15) | 0.0278 (19) | |
C6 | 0.2500 | 0.5666 (3) | 0.2823 (17) | 0.048 (3) | |
H6A | 0.2500 | 0.5923 | 0.3971 | 0.080* | |
C7 | 0.2500 | 0.6428 (3) | 0.0155 (19) | 0.034 (2) | |
C2 | 0.2500 | 0.5462 (3) | −0.0936 (16) | 0.036 (2) | |
H2A | 0.2500 | 0.5581 | −0.2410 | 0.080* | |
C8 | −0.1376 (11) | 0.7500 | 0.0177 (13) | 0.0257 (18) | |
H8B | −0.0906 | 0.7186 | −0.0585 | 0.039* | 0.50 |
H8C | −0.0906 | 0.7814 | −0.0585 | 0.039* | 0.50 |
C3 | 0.2500 | 0.4920 (3) | −0.0488 (16) | 0.037 (2) | |
H3A | 0.2500 | 0.4662 | −0.1634 | 0.080* | |
C4 | 0.2500 | 0.4756 (3) | 0.1603 (16) | 0.033 (2) | |
C5 | 0.2500 | 0.5118 (4) | 0.3258 (16) | 0.051 (3) | |
H5A | 0.2500 | 0.4994 | 0.4725 | 0.080* | |
N2 | −0.0581 (9) | 0.7500 | 0.2380 (11) | 0.0198 (14) | |
N1 | 0.2500 | 0.4185 (3) | 0.2125 (17) | 0.050 (2) | |
O1 | 0.2500 | 0.6727 (2) | 0.1808 (10) | 0.0292 (15) | |
O1W | 0.2500 | 0.7500 | 0.5969 (15) | 0.029 (2) | |
O2 | 0.2500 | 0.6574 (3) | −0.1725 (12) | 0.056 (2) | |
O3 | 0.2500 | 0.4055 (3) | 0.4022 (18) | 0.090 (4) | |
O4 | 0.2500 | 0.3862 (3) | 0.0653 (15) | 0.066 (3) | |
H1W | 0.2500 | 0.722 (4) | 0.657 (17) | 0.05 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0164 (7) | 0.0183 (7) | 0.0208 (8) | 0.000 | 0.000 | 0.000 |
C9 | 0.021 (3) | 0.022 (3) | 0.051 (4) | −0.001 (2) | 0.000 (3) | 0.014 (3) |
C1 | 0.024 (4) | 0.023 (4) | 0.037 (5) | 0.000 | 0.000 | 0.002 (4) |
C6 | 0.086 (8) | 0.019 (4) | 0.040 (6) | 0.000 | 0.000 | −0.004 (4) |
C7 | 0.019 (4) | 0.020 (4) | 0.064 (7) | 0.000 | 0.000 | −0.001 (5) |
C2 | 0.046 (6) | 0.025 (4) | 0.035 (5) | 0.000 | 0.000 | 0.001 (4) |
C8 | 0.017 (4) | 0.036 (4) | 0.025 (4) | 0.000 | 0.000 (4) | 0.000 |
C3 | 0.052 (6) | 0.021 (4) | 0.039 (6) | 0.000 | 0.000 | −0.006 (4) |
C4 | 0.033 (5) | 0.019 (4) | 0.049 (6) | 0.000 | 0.000 | 0.001 (4) |
C5 | 0.094 (9) | 0.030 (5) | 0.028 (5) | 0.000 | 0.000 | 0.007 (4) |
N2 | 0.017 (3) | 0.018 (3) | 0.024 (3) | 0.000 | 0.001 (3) | 0.000 |
N1 | 0.059 (6) | 0.023 (4) | 0.069 (7) | 0.000 | 0.000 | 0.001 (5) |
O1 | 0.020 (3) | 0.016 (3) | 0.051 (4) | 0.000 | 0.000 | −0.007 (3) |
O1W | 0.035 (5) | 0.022 (5) | 0.030 (5) | 0.000 | 0.000 | 0.000 |
O2 | 0.100 (7) | 0.028 (3) | 0.041 (4) | 0.000 | 0.000 | 0.011 (3) |
O3 | 0.154 (11) | 0.030 (4) | 0.086 (7) | 0.000 | 0.000 | 0.028 (5) |
O4 | 0.099 (7) | 0.018 (3) | 0.080 (6) | 0.000 | 0.000 | −0.006 (4) |
Geometric parameters (Å, º) top
Cu1—O1i | 1.962 (5) | C2—C3 | 1.384 (12) |
Cu1—O1 | 1.962 (5) | C2—H2A | 0.9600 |
Cu1—N2i | 2.101 (6) | C8—N2 | 1.469 (10) |
Cu1—N2 | 2.101 (6) | C8—C8iii | 1.534 (16) |
Cu1—O1W | 2.248 (10) | C8—H8B | 0.9700 |
C9—N2 | 1.508 (7) | C8—H8C | 0.9700 |
C9—C9ii | 1.537 (11) | C3—C4 | 1.359 (14) |
C9—H9A | 0.9700 | C3—H3A | 0.9601 |
C9—H9B | 0.9700 | C4—C5 | 1.368 (13) |
C1—C2 | 1.365 (13) | C4—N1 | 1.466 (11) |
C1—C6 | 1.396 (14) | C5—H5A | 0.9600 |
C1—C7 | 1.519 (11) | N2—C9iv | 1.508 (7) |
C6—C5 | 1.398 (13) | N1—O3 | 1.219 (14) |
C6—H6A | 0.9599 | N1—O4 | 1.220 (12) |
C7—O2 | 1.221 (12) | O1W—H1W | 0.78 (9) |
C7—O1 | 1.269 (12) | | |
| | | |
O1i—Cu1—O1 | 160.6 (4) | C3—C2—H2A | 119.5 |
O1i—Cu1—N2i | 90.11 (4) | N2—C8—C8iii | 111.7 (4) |
O1—Cu1—N2i | 90.11 (4) | N2—C8—H8B | 109.3 |
O1i—Cu1—N2 | 90.11 (4) | C8iii—C8—H8B | 109.3 |
O1—Cu1—N2 | 90.11 (4) | N2—C8—H8C | 109.3 |
N2i—Cu1—N2 | 178.7 (4) | C8iii—C8—H8C | 109.3 |
O1i—Cu1—O1W | 99.68 (19) | H8B—C8—H8C | 108.0 |
O1—Cu1—O1W | 99.68 (19) | C4—C3—C2 | 119.2 (9) |
N2i—Cu1—O1W | 89.3 (2) | C4—C3—H3A | 120.1 |
N2—Cu1—O1W | 89.3 (2) | C2—C3—H3A | 120.7 |
N2—C9—C9ii | 111.0 (3) | C3—C4—C5 | 121.0 (8) |
N2—C9—H9A | 109.4 | C3—C4—N1 | 120.4 (9) |
C9ii—C9—H9A | 109.4 | C5—C4—N1 | 118.6 (9) |
N2—C9—H9B | 109.4 | C4—C5—C6 | 120.3 (9) |
C9ii—C9—H9B | 109.4 | C4—C5—H5A | 119.8 |
H9A—C9—H9B | 108.0 | C6—C5—H5A | 119.9 |
C2—C1—C6 | 119.4 (8) | C8—N2—C9iv | 108.5 (4) |
C2—C1—C7 | 120.7 (9) | C8—N2—C9 | 108.5 (4) |
C6—C1—C7 | 119.9 (8) | C9iv—N2—C9 | 105.9 (6) |
C1—C6—C5 | 118.7 (9) | C8—N2—Cu1 | 111.0 (5) |
C1—C6—H6A | 120.2 | C9iv—N2—Cu1 | 111.3 (3) |
C5—C6—H6A | 121.1 | C9—N2—Cu1 | 111.3 (3) |
O2—C7—O1 | 126.3 (8) | O3—N1—O4 | 122.9 (9) |
O2—C7—C1 | 119.7 (9) | O3—N1—C4 | 118.2 (9) |
O1—C7—C1 | 113.9 (9) | O4—N1—C4 | 118.8 (10) |
C1—C2—C3 | 121.4 (9) | C7—O1—Cu1 | 135.9 (6) |
C1—C2—H2A | 119.1 | Cu1—O1W—H1W | 118 (8) |
| | | |
C2—C1—C6—C5 | 0.000 (7) | O1i—Cu1—N2—C8 | 80.32 (19) |
C7—C1—C6—C5 | 180.000 (5) | O1—Cu1—N2—C8 | −80.32 (19) |
C2—C1—C7—O2 | 0.000 (7) | O1W—Cu1—N2—C8 | 180.0 |
C6—C1—C7—O2 | 180.000 (5) | O1i—Cu1—N2—C9iv | −40.7 (5) |
C2—C1—C7—O1 | 180.000 (5) | O1—Cu1—N2—C9iv | 158.6 (5) |
C6—C1—C7—O1 | 0.000 (6) | O1W—Cu1—N2—C9iv | 59.0 (4) |
C6—C1—C2—C3 | 0.000 (6) | O1i—Cu1—N2—C9 | −158.6 (5) |
C7—C1—C2—C3 | 180.000 (5) | O1—Cu1—N2—C9 | 40.7 (5) |
C1—C2—C3—C4 | 0.000 (6) | O1W—Cu1—N2—C9 | −59.0 (4) |
C2—C3—C4—C5 | 0.000 (6) | C3—C4—N1—O3 | 180.000 (6) |
C2—C3—C4—N1 | 180.000 (5) | C5—C4—N1—O3 | 0.000 (7) |
C3—C4—C5—C6 | 0.000 (7) | C3—C4—N1—O4 | 0.000 (6) |
N1—C4—C5—C6 | 180.000 (5) | C5—C4—N1—O4 | 180.000 (5) |
C1—C6—C5—C4 | 0.000 (7) | O2—C7—O1—Cu1 | 0.000 (8) |
C8iii—C8—N2—C9iv | −57.3 (4) | C1—C7—O1—Cu1 | 180.000 (4) |
C8iii—C8—N2—C9 | 57.3 (4) | O1i—Cu1—O1—C7 | 0.000 (10) |
C8iii—C8—N2—Cu1 | 180.0 | N2i—Cu1—O1—C7 | −90.66 (19) |
C9ii—C9—N2—C8 | −56.9 (5) | N2—Cu1—O1—C7 | 90.66 (19) |
C9ii—C9—N2—C9iv | 59.5 (6) | O1W—Cu1—O1—C7 | 180.000 (7) |
Symmetry codes: (i) −x+1/2, −y+3/2, z; (ii) −x−1/2, y, z; (iii) −x−1/2, −y+3/2, z; (iv) x, −y+3/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O2v | 0.78 (9) | 1.94 (10) | 2.722 (8) | 175 (11) |
Symmetry code: (v) x, y, z+1. |