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The title compound, [Cu(C7H3N2O6)2(C12H16N3O3)2(H2O)2], was prepared by the reaction of 4,4,5,5-tetra­methyl-2-(4-pyrid­yl)imidazolin-1-oxyl 3-oxide (nitronyl nitroxide), copper(II) nitrate and 3,5-dinitro­benzoic acid. The CuII ion lies on a crystallographic inversion centre and is in a distorted octa­hedral environment. Two N atoms from two nitronyl nitroxide and two O atoms from two 3,5-dinitro­benzoate ligands form the equatorial plane, while two O atoms from two water mol­ecules occupy axial positions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047131/fi2016sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047131/fi2016Isup2.hkl
Contains datablock I

CCDC reference: 629664

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.052
  • wR factor = 0.104
  • Data-to-parameter ratio = 14.4

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: 0.797 0.929 Tmin(prime) and Tmax expected: 0.897 0.932 RR(prime) = 0.891 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89 PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.55 Ratio PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C13 - C14 ... 1.53 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 3 N1 -CU1 -N1 -C5 10.00 0.00 2.577 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 8 N1 -CU1 -N1 -C1 8.00 0.00 2.577 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 11 O1 -CU1 -O1 -C13 7.00 0.00 2.577 1.555 1.555 1.555
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 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 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); 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) and SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL and WinGX (Farrugia, 1999).

Diaqua(3,5-dinitrobenzoato)bis[4,4,5,5-tetramethyl-2-(4-pyridyl)imidazolin- 1-oxyl 3-oxide]copper(II) top
Crystal data top
[Cu(C7H3N2O6)2(C12H16N3O3)2(H2O)2]Z = 1
Mr = 990.36F(000) = 513
Triclinic, P1Dx = 1.511 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.123 (3) ÅCell parameters from 881 reflections
b = 10.198 (3) Åθ = 2.9–24.1°
c = 10.810 (3) ŵ = 0.59 mm1
α = 78.517 (4)°T = 293 K
β = 85.848 (5)°Block, blue
γ = 85.374 (4)°0.18 × 0.14 × 0.12 mm
V = 1088.2 (5) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
4436 independent reflections
Radiation source: fine-focus sealed tube3069 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 26.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 128
Tmin = 0.797, Tmax = 0.929k = 1212
6388 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0345P)2 + 0.042P]
where P = (Fo2 + 2Fc2)/3
4436 reflections(Δ/σ)max = 0.001
308 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.47 e Å3
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
xyzUiso*/Ueq
Cu10.00001.00001.00000.02820 (16)
N10.1595 (2)1.0610 (2)0.8860 (2)0.0289 (5)
N20.6180 (2)1.1217 (2)0.6498 (2)0.0319 (6)
N30.4913 (2)1.2665 (2)0.5262 (2)0.0325 (6)
N40.1051 (3)0.3492 (3)1.3345 (3)0.0486 (7)
N50.4331 (3)0.3356 (3)0.9801 (3)0.0466 (7)
O10.07705 (19)0.81109 (17)1.04019 (18)0.0347 (5)
O20.1028 (2)0.7495 (2)0.8502 (2)0.0521 (6)
O30.4723 (3)0.3833 (3)0.8733 (3)0.0768 (9)
O40.4863 (3)0.2347 (2)1.0420 (3)0.0717 (8)
O50.1371 (3)0.2314 (2)1.3765 (2)0.0645 (7)
O60.0282 (3)0.4177 (3)1.3894 (3)0.0885 (10)
O70.6563 (2)1.0248 (2)0.7368 (2)0.0549 (7)
O80.3905 (2)1.3361 (2)0.4780 (2)0.0555 (7)
O90.0918 (2)1.0426 (2)1.1770 (2)0.0533 (6)
H9D0.16461.03571.21300.080*
H9E0.04151.10821.19430.080*
C10.2832 (3)1.0221 (3)0.9187 (3)0.0314 (7)
H10.29540.96730.99730.038*
C20.3936 (3)1.0590 (3)0.8419 (3)0.0326 (7)
H20.47811.03030.86890.039*
C30.3775 (3)1.1399 (3)0.7230 (3)0.0272 (6)
C40.2489 (3)1.1818 (3)0.6899 (3)0.0371 (7)
H40.23351.23790.61260.045*
C50.1444 (3)1.1395 (3)0.7730 (3)0.0373 (8)
H50.05861.16720.74890.045*
C60.4918 (3)1.1758 (3)0.6358 (3)0.0279 (6)
C70.7149 (3)1.1989 (3)0.5565 (3)0.0327 (7)
C80.6216 (3)1.2627 (3)0.4514 (3)0.0332 (7)
C90.7675 (3)1.2989 (3)0.6265 (3)0.0544 (10)
H9A0.69581.35970.64720.082*
H9B0.83401.34840.57340.082*
H9C0.80571.25110.70270.082*
C100.8276 (3)1.1067 (3)0.5156 (3)0.0530 (9)
H10A0.88531.07670.58390.079*
H10B0.87691.15430.44380.079*
H10C0.79201.03060.49340.079*
C110.6525 (3)1.4028 (3)0.3837 (3)0.0576 (10)
H11A0.58691.43700.32340.086*
H11B0.73861.39980.34060.086*
H11C0.65141.46030.44420.086*
C120.6060 (4)1.1733 (4)0.3568 (3)0.0583 (10)
H12A0.58751.08490.40150.087*
H12B0.68651.16860.30480.087*
H12C0.53401.21000.30450.087*
C130.1095 (3)0.7306 (3)0.9663 (3)0.0326 (7)
C140.1646 (3)0.5927 (3)1.0334 (3)0.0298 (7)
C150.1134 (3)0.5358 (3)1.1519 (3)0.0349 (7)
H150.04560.58131.19250.042*
C160.1640 (3)0.4105 (3)1.2097 (3)0.0360 (7)
C170.2678 (3)0.3416 (3)1.1563 (3)0.0366 (7)
H170.30240.25841.19740.044*
C180.3178 (3)0.4021 (3)1.0388 (3)0.0344 (7)
C190.2660 (3)0.5243 (3)0.9752 (3)0.0342 (7)
H190.29900.56010.89400.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0224 (3)0.0246 (3)0.0337 (3)0.0020 (2)0.0039 (2)0.0004 (2)
N10.0228 (13)0.0293 (12)0.0317 (14)0.0022 (10)0.0002 (10)0.0016 (11)
N20.0238 (13)0.0338 (13)0.0334 (15)0.0026 (11)0.0010 (11)0.0038 (11)
N30.0306 (14)0.0334 (13)0.0292 (14)0.0002 (11)0.0009 (11)0.0026 (11)
N40.068 (2)0.0387 (16)0.0375 (18)0.0187 (15)0.0059 (15)0.0003 (14)
N50.0471 (17)0.0358 (15)0.052 (2)0.0101 (13)0.0012 (14)0.0035 (14)
O10.0361 (12)0.0268 (10)0.0372 (13)0.0070 (9)0.0040 (9)0.0028 (9)
O20.0683 (17)0.0448 (13)0.0367 (14)0.0216 (12)0.0039 (12)0.0024 (11)
O30.078 (2)0.0727 (18)0.0599 (19)0.0325 (15)0.0239 (15)0.0094 (15)
O40.0752 (19)0.0485 (14)0.076 (2)0.0333 (14)0.0010 (15)0.0075 (14)
O50.091 (2)0.0433 (14)0.0510 (16)0.0139 (14)0.0010 (14)0.0132 (12)
O60.127 (3)0.0596 (17)0.068 (2)0.0117 (18)0.0534 (18)0.0049 (15)
O70.0285 (12)0.0652 (15)0.0520 (15)0.0092 (11)0.0046 (10)0.0275 (12)
O80.0424 (14)0.0621 (15)0.0479 (15)0.0104 (12)0.0000 (11)0.0166 (12)
O90.0427 (14)0.0615 (14)0.0611 (17)0.0134 (12)0.0218 (12)0.0247 (12)
C10.0265 (16)0.0349 (15)0.0281 (17)0.0010 (13)0.0001 (12)0.0031 (13)
C20.0220 (15)0.0398 (16)0.0328 (18)0.0004 (13)0.0021 (13)0.0004 (14)
C30.0230 (15)0.0268 (14)0.0307 (17)0.0023 (12)0.0008 (12)0.0038 (12)
C40.0293 (17)0.0422 (17)0.0335 (18)0.0009 (14)0.0033 (13)0.0077 (14)
C50.0256 (16)0.0428 (17)0.0377 (19)0.0027 (14)0.0038 (14)0.0046 (15)
C60.0251 (15)0.0275 (14)0.0296 (17)0.0022 (12)0.0019 (12)0.0019 (12)
C70.0281 (16)0.0371 (16)0.0307 (17)0.0084 (13)0.0052 (13)0.0011 (13)
C80.0349 (17)0.0356 (16)0.0259 (17)0.0047 (14)0.0050 (13)0.0004 (13)
C90.044 (2)0.076 (2)0.048 (2)0.0266 (19)0.0016 (17)0.0178 (19)
C100.040 (2)0.057 (2)0.053 (2)0.0024 (17)0.0125 (16)0.0058 (18)
C110.054 (2)0.053 (2)0.052 (2)0.0058 (18)0.0084 (18)0.0187 (18)
C120.054 (2)0.086 (3)0.041 (2)0.009 (2)0.0034 (17)0.027 (2)
C130.0255 (16)0.0293 (15)0.0384 (19)0.0020 (13)0.0036 (13)0.0009 (14)
C140.0318 (16)0.0228 (14)0.0338 (18)0.0019 (12)0.0027 (13)0.0030 (13)
C150.0375 (18)0.0283 (15)0.0385 (19)0.0065 (14)0.0048 (14)0.0061 (14)
C160.0449 (19)0.0309 (16)0.0314 (18)0.0141 (14)0.0033 (14)0.0006 (14)
C170.0436 (19)0.0253 (15)0.0382 (19)0.0011 (14)0.0079 (15)0.0016 (14)
C180.0374 (18)0.0276 (15)0.0366 (19)0.0056 (13)0.0034 (14)0.0048 (14)
C190.0380 (18)0.0289 (15)0.0316 (18)0.0005 (13)0.0003 (13)0.0019 (13)
Geometric parameters (Å, º) top
Cu1—O1i1.9954 (18)C4—C51.376 (4)
Cu1—O11.9954 (18)C4—H40.9300
Cu1—N12.020 (2)C5—H50.9300
Cu1—N1i2.020 (2)C7—C101.517 (4)
Cu1—O9i2.317 (2)C7—C91.532 (4)
Cu1—O92.317 (2)C7—C81.539 (4)
N1—C51.333 (3)C8—C111.515 (4)
N1—C11.333 (3)C8—C121.523 (4)
N2—O71.277 (3)C9—H9A0.9600
N2—C61.356 (3)C9—H9B0.9600
N2—C71.505 (3)C9—H9C0.9600
N3—O81.277 (3)C10—H10A0.9600
N3—C61.350 (3)C10—H10B0.9600
N3—C81.498 (4)C10—H10C0.9600
N4—O61.207 (4)C11—H11A0.9600
N4—O51.223 (3)C11—H11B0.9600
N4—C161.475 (4)C11—H11C0.9600
N5—O31.212 (3)C12—H12A0.9600
N5—O41.218 (3)C12—H12B0.9600
N5—C181.470 (4)C12—H12C0.9600
O1—C131.264 (3)C13—C141.530 (4)
O2—C131.238 (3)C14—C151.379 (4)
O9—H9D0.8500C14—C191.379 (4)
O9—H9E0.8499C15—C161.381 (4)
C1—C21.374 (4)C15—H150.9300
C1—H10.9300C16—C171.373 (4)
C2—C31.396 (4)C17—C181.377 (4)
C2—H20.9300C17—H170.9300
C3—C41.386 (4)C18—C191.380 (4)
C3—C61.461 (4)C19—H190.9300
O1i—Cu1—O1180.000 (1)N2—C7—C8100.0 (2)
O1i—Cu1—N187.47 (8)C10—C7—C8114.4 (3)
O1—Cu1—N192.53 (8)C9—C7—C8114.5 (2)
O1i—Cu1—N1i92.53 (8)N3—C8—C11110.3 (2)
O1—Cu1—N1i87.47 (8)N3—C8—C12105.8 (2)
N1—Cu1—N1i180.000 (1)C11—C8—C12110.7 (3)
O1i—Cu1—O9i89.46 (8)N3—C8—C7100.7 (2)
O1—Cu1—O9i90.54 (8)C11—C8—C7114.9 (3)
N1—Cu1—O9i87.41 (9)C12—C8—C7113.6 (3)
N1i—Cu1—O9i92.59 (9)C7—C9—H9A109.5
O1i—Cu1—O990.54 (8)C7—C9—H9B109.5
O1—Cu1—O989.46 (8)H9A—C9—H9B109.5
N1—Cu1—O992.59 (9)C7—C9—H9C109.5
N1i—Cu1—O987.41 (9)H9A—C9—H9C109.5
O9i—Cu1—O9180.000 (1)H9B—C9—H9C109.5
C5—N1—C1117.4 (2)C7—C10—H10A109.5
C5—N1—Cu1120.73 (18)C7—C10—H10B109.5
C1—N1—Cu1121.87 (19)H10A—C10—H10B109.5
O7—N2—C6126.2 (2)C7—C10—H10C109.5
O7—N2—C7121.9 (2)H10A—C10—H10C109.5
C6—N2—C7111.7 (2)H10B—C10—H10C109.5
O8—N3—C6126.6 (2)C8—C11—H11A109.5
O8—N3—C8120.6 (2)C8—C11—H11B109.5
C6—N3—C8112.1 (2)H11A—C11—H11B109.5
O6—N4—O5123.7 (3)C8—C11—H11C109.5
O6—N4—C16118.3 (3)H11A—C11—H11C109.5
O5—N4—C16117.9 (3)H11B—C11—H11C109.5
O3—N5—O4122.6 (3)C8—C12—H12A109.5
O3—N5—C18119.1 (2)C8—C12—H12B109.5
O4—N5—C18118.3 (3)H12A—C12—H12B109.5
C13—O1—Cu1129.02 (18)C8—C12—H12C109.5
Cu1—O9—H9D142.2H12A—C12—H12C109.5
Cu1—O9—H9E102.3H12B—C12—H12C109.5
H9D—O9—H9E111.3O2—C13—O1128.8 (3)
N1—C1—C2123.3 (3)O2—C13—C14117.6 (3)
N1—C1—H1118.4O1—C13—C14113.6 (3)
C2—C1—H1118.4C15—C14—C19119.6 (2)
C1—C2—C3119.3 (3)C15—C14—C13120.5 (3)
C1—C2—H2120.4C19—C14—C13119.9 (3)
C3—C2—H2120.4C14—C15—C16119.3 (3)
C4—C3—C2117.4 (3)C14—C15—H15120.4
C4—C3—C6121.6 (3)C16—C15—H15120.4
C2—C3—C6121.1 (2)C17—C16—C15122.7 (3)
C5—C4—C3119.2 (3)C17—C16—N4118.7 (3)
C5—C4—H4120.4C15—C16—N4118.6 (3)
C3—C4—H4120.4C16—C17—C18116.5 (3)
N1—C5—C4123.5 (3)C16—C17—H17121.7
N1—C5—H5118.3C18—C17—H17121.7
C4—C5—H5118.3C17—C18—C19122.6 (3)
N3—C6—N2107.6 (2)C17—C18—N5118.7 (3)
N3—C6—C3126.6 (2)C19—C18—N5118.7 (3)
N2—C6—C3125.8 (2)C14—C19—C18119.2 (3)
N2—C7—C10111.2 (2)C14—C19—H19120.4
N2—C7—C9105.2 (3)C18—C19—H19120.4
C10—C7—C9110.6 (3)
O1i—Cu1—N1—C545.7 (2)C6—N2—C7—C824.8 (3)
O1—Cu1—N1—C5134.3 (2)O8—N3—C8—C1144.8 (4)
N1i—Cu1—N1—C5103 (100)C6—N3—C8—C11144.3 (3)
O9i—Cu1—N1—C543.9 (2)O8—N3—C8—C1275.1 (3)
O9—Cu1—N1—C5136.1 (2)C6—N3—C8—C1295.9 (3)
O1i—Cu1—N1—C1136.1 (2)O8—N3—C8—C7166.5 (2)
O1—Cu1—N1—C143.9 (2)C6—N3—C8—C722.6 (3)
N1i—Cu1—N1—C175 (100)N2—C7—C8—N326.1 (3)
O9i—Cu1—N1—C1134.3 (2)C10—C7—C8—N3145.0 (2)
O9—Cu1—N1—C145.7 (2)C9—C7—C8—N385.9 (3)
O1i—Cu1—O1—C1369 (100)N2—C7—C8—C11144.5 (3)
N1—Cu1—O1—C1360.9 (2)C10—C7—C8—C1196.6 (3)
N1i—Cu1—O1—C13119.1 (2)C9—C7—C8—C1132.6 (4)
O9i—Cu1—O1—C1326.5 (2)N2—C7—C8—C1286.6 (3)
O9—Cu1—O1—C13153.5 (2)C10—C7—C8—C1232.3 (4)
C5—N1—C1—C20.0 (4)C9—C7—C8—C12161.5 (3)
Cu1—N1—C1—C2178.2 (2)Cu1—O1—C13—O20.9 (4)
N1—C1—C2—C30.7 (5)Cu1—O1—C13—C14179.47 (16)
C1—C2—C3—C41.6 (4)O2—C13—C14—C15143.9 (3)
C1—C2—C3—C6176.9 (3)O1—C13—C14—C1536.3 (4)
C2—C3—C4—C51.7 (4)O2—C13—C14—C1936.0 (4)
C6—C3—C4—C5176.7 (3)O1—C13—C14—C19143.8 (3)
C1—N1—C5—C40.2 (4)C19—C14—C15—C160.6 (4)
Cu1—N1—C5—C4178.4 (2)C13—C14—C15—C16179.3 (2)
C3—C4—C5—N11.1 (5)C14—C15—C16—C172.8 (4)
O8—N3—C6—N2178.0 (3)C14—C15—C16—N4177.9 (2)
C8—N3—C6—N27.7 (3)O6—N4—C16—C17169.0 (3)
O8—N3—C6—C31.0 (5)O5—N4—C16—C1711.0 (4)
C8—N3—C6—C3171.3 (3)O6—N4—C16—C1510.2 (4)
O7—N2—C6—N3174.2 (3)O5—N4—C16—C15169.7 (3)
C7—N2—C6—N311.7 (3)C15—C16—C17—C181.8 (4)
O7—N2—C6—C34.8 (5)N4—C16—C17—C18178.9 (3)
C7—N2—C6—C3169.3 (3)C16—C17—C18—C191.4 (4)
C4—C3—C6—N311.0 (5)C16—C17—C18—N5177.1 (3)
C2—C3—C6—N3170.7 (3)O3—N5—C18—C17175.0 (3)
C4—C3—C6—N2167.8 (3)O4—N5—C18—C175.6 (4)
C2—C3—C6—N210.5 (5)O3—N5—C18—C196.4 (4)
O7—N2—C7—C1039.5 (4)O4—N5—C18—C19172.9 (3)
C6—N2—C7—C10146.0 (3)C15—C14—C19—C182.4 (4)
O7—N2—C7—C980.3 (3)C13—C14—C19—C18177.7 (3)
C6—N2—C7—C994.2 (3)C17—C18—C19—C143.5 (4)
O7—N2—C7—C8160.8 (3)N5—C18—C19—C14175.0 (3)
Symmetry code: (i) x, y+2, z+2.
 

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