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The title compound, [Cu(C8H5O4)2(C6H9N3)2]·2C6H9N3, is a neutral mononuclear copper(II) complex. The Cu2+ cation lies on an inversion centre, coordinated by the N atoms from two 2-amino-4,6-dimethyl­pyrimidine ligands and four O atoms from two chelating isophthalate ligands, in a distorted octa­hedral configuration. The asymmetric unit also contains a 2-amino-4,6-dimethyl­pyrimidine solvent mol­ecule. The crystal structure is stabilized by a network of O—H...N, N—H...O and N—H...N hydrogen bonds and π–π stacking inter­actions, forming a three-dimensional supra­molecular structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051385/sj2183sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051385/sj2183Isup2.hkl
Contains datablock I

CCDC reference: 622223

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.038
  • wR factor = 0.118
  • Data-to-parameter ratio = 12.8

checkCIF/PLATON results

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Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Cu1 - O2 .. 16.91 su
Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C7 .. 5.75 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O1 .. 6.11 su
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis[(2-amino-4,6-dimethylpyrimidine-κN)(isophthalato-κ2O,O')]copper(II) 2-amino-4,6-dimethylpyrimidine disolvate top
Crystal data top
[Cu(C8H5O4)2(C6H9N3)2]·2C6H9N3Z = 1
Mr = 886.43F(000) = 463
Triclinic, P1Dx = 1.423 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4010 (2) ÅCell parameters from 117 reflections
b = 9.3811 (3) Åθ = 7.5–15°
c = 15.2889 (5) ŵ = 0.60 mm1
α = 101.819 (2)°T = 273 K
β = 93.013 (2)°Block, green
γ = 93.547 (2)°0.33 × 0.21 × 0.15 mm
V = 1034.69 (5) Å3
Data collection top
Bruker SMART APEX-II CCD
diffractometer
3600 independent reflections
Radiation source: fine-focus sealed tube2933 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.828, Tmax = 0.916k = 1111
8817 measured reflectionsl = 1718
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.118 w = 1/[σ2(Fo2) + (0.0754P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
3600 reflectionsΔρmax = 0.41 e Å3
282 parametersΔρmin = 0.54 e Å3
0 restraintsExtinction correction: SHELXL97
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0029 (5)
Special details top

Experimental. Data collection is performed with four batch runs at φ = 0.00 ° (600 frames), at φ = 90.00 ° (600 frames), at φ = 180 ° (600 frames) and at φ = 270 ° (600 frames). Frame width = 0.30 \& in ω. Data is merged, corrected for decay, and treated with multi-scan absorption corrections.

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
Cu10.00000.50001.00000.03557 (17)
O10.0023 (2)0.34415 (19)0.88873 (12)0.0453 (4)
O20.2689 (2)0.4349 (2)0.88448 (13)0.0521 (5)
O30.1327 (3)0.0765 (2)0.63678 (14)0.0634 (6)
O40.0903 (3)0.1523 (2)0.53031 (13)0.0566 (5)
H40.02410.21830.51410.085*
N10.1078 (2)0.6486 (2)0.93513 (13)0.0377 (5)
N20.3729 (3)0.7445 (2)0.87789 (16)0.0489 (5)
N30.3581 (3)0.5141 (3)0.90618 (17)0.0561 (6)
H3A0.46560.50510.88800.067*
H3B0.30210.44330.92410.067*
N40.6834 (3)0.5235 (2)0.58598 (14)0.0414 (5)
N50.9256 (3)0.3668 (2)0.55658 (14)0.0397 (5)
N60.6632 (3)0.3314 (2)0.46544 (16)0.0533 (6)
H6A0.55690.35520.45120.064*
H6B0.70770.25740.43310.064*
C10.2099 (3)0.2405 (2)0.76473 (16)0.0357 (5)
C20.0925 (3)0.1393 (2)0.72593 (16)0.0370 (5)
H20.02090.13600.75440.044*
C30.1426 (3)0.0429 (2)0.64515 (17)0.0384 (6)
C40.3150 (4)0.0482 (3)0.60402 (18)0.0490 (7)
H4A0.35040.01550.54990.059*
C50.4313 (4)0.1457 (3)0.6425 (2)0.0548 (8)
H50.54610.14700.61500.066*
C60.3798 (3)0.2431 (3)0.72222 (18)0.0458 (6)
H60.45940.31040.74740.055*
C70.1592 (3)0.3474 (3)0.85152 (17)0.0396 (6)
C80.0186 (3)0.0671 (3)0.60379 (18)0.0453 (6)
C90.0233 (3)0.7705 (3)0.92694 (17)0.0401 (6)
C100.1100 (4)0.8785 (3)0.89419 (19)0.0487 (7)
H100.05070.96020.88660.058*
C110.2895 (4)0.8645 (3)0.87219 (19)0.0520 (7)
C120.2775 (3)0.6390 (3)0.90668 (17)0.0399 (6)
C130.1667 (3)0.7795 (3)0.9537 (2)0.0505 (7)
H13A0.24010.69570.92100.076*
H13B0.21350.86670.94080.076*
H13C0.16900.78211.01680.076*
C140.3957 (5)0.9840 (4)0.8413 (3)0.0776 (10)
H14A0.51990.98900.86380.116*
H14B0.34551.07550.86310.116*
H14C0.38970.96410.77700.116*
C151.0218 (3)0.4455 (3)0.62923 (17)0.0414 (6)
C160.9539 (4)0.5638 (3)0.68137 (18)0.0465 (6)
H161.02130.61870.73130.056*
C170.7805 (3)0.5999 (3)0.65754 (17)0.0420 (6)
C180.7589 (3)0.4090 (3)0.53761 (17)0.0407 (6)
C190.6937 (4)0.7242 (3)0.7134 (2)0.0552 (7)
H19A0.63010.77620.67500.083*
H19B0.78560.78910.75050.083*
H19C0.60980.68680.75050.083*
C201.2051 (4)0.3970 (3)0.6502 (2)0.0554 (7)
H20A1.19160.30450.66760.083*
H20B1.26740.46800.69820.083*
H20C1.27400.38740.59810.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0276 (2)0.0436 (3)0.0310 (3)0.00802 (16)0.00161 (16)0.00330 (17)
O10.0386 (10)0.0540 (10)0.0372 (10)0.0070 (8)0.0026 (8)0.0042 (8)
O20.0438 (10)0.0561 (11)0.0475 (12)0.0139 (9)0.0025 (9)0.0126 (9)
O30.0496 (12)0.0706 (12)0.0605 (14)0.0286 (10)0.0130 (10)0.0117 (10)
O40.0533 (11)0.0557 (11)0.0510 (12)0.0258 (9)0.0088 (9)0.0154 (9)
N10.0288 (10)0.0470 (11)0.0343 (12)0.0089 (8)0.0003 (8)0.0003 (9)
N20.0400 (12)0.0572 (13)0.0496 (14)0.0070 (10)0.0075 (10)0.0092 (11)
N30.0376 (12)0.0638 (14)0.0740 (18)0.0202 (10)0.0187 (11)0.0226 (13)
N40.0381 (11)0.0444 (11)0.0415 (13)0.0147 (9)0.0001 (9)0.0058 (10)
N50.0378 (11)0.0411 (10)0.0392 (12)0.0148 (9)0.0007 (9)0.0037 (9)
N60.0477 (13)0.0557 (13)0.0493 (14)0.0220 (11)0.0129 (11)0.0070 (11)
C10.0367 (13)0.0370 (11)0.0316 (13)0.0034 (10)0.0005 (10)0.0034 (10)
C20.0329 (12)0.0402 (12)0.0366 (14)0.0051 (10)0.0055 (10)0.0068 (10)
C30.0389 (13)0.0387 (12)0.0366 (14)0.0110 (10)0.0020 (11)0.0039 (10)
C40.0481 (15)0.0514 (14)0.0392 (15)0.0137 (12)0.0151 (12)0.0081 (12)
C50.0414 (15)0.0615 (16)0.0526 (18)0.0193 (13)0.0160 (13)0.0084 (13)
C60.0401 (14)0.0473 (14)0.0450 (16)0.0130 (11)0.0045 (12)0.0030 (12)
C70.0337 (13)0.0469 (13)0.0367 (14)0.0014 (11)0.0001 (11)0.0058 (11)
C80.0461 (15)0.0438 (13)0.0444 (16)0.0119 (11)0.0019 (12)0.0041 (12)
C90.0338 (12)0.0472 (13)0.0338 (14)0.0085 (10)0.0039 (10)0.0047 (11)
C100.0467 (15)0.0467 (14)0.0517 (17)0.0105 (12)0.0014 (13)0.0067 (13)
C110.0512 (17)0.0540 (15)0.0486 (17)0.0042 (13)0.0042 (13)0.0054 (13)
C120.0313 (12)0.0532 (14)0.0327 (14)0.0095 (11)0.0002 (10)0.0020 (11)
C130.0337 (13)0.0536 (15)0.0625 (19)0.0129 (11)0.0012 (12)0.0055 (13)
C140.071 (2)0.071 (2)0.098 (3)0.0078 (17)0.028 (2)0.027 (2)
C150.0386 (13)0.0457 (13)0.0405 (15)0.0072 (11)0.0026 (11)0.0103 (11)
C160.0438 (14)0.0502 (14)0.0419 (16)0.0088 (11)0.0049 (12)0.0013 (12)
C170.0469 (14)0.0409 (12)0.0384 (15)0.0109 (11)0.0036 (12)0.0064 (11)
C180.0385 (13)0.0422 (13)0.0418 (15)0.0121 (10)0.0031 (11)0.0082 (11)
C190.0545 (17)0.0565 (16)0.0512 (18)0.0166 (13)0.0033 (14)0.0000 (13)
C200.0457 (15)0.0610 (17)0.0578 (19)0.0170 (13)0.0076 (14)0.0069 (14)
Geometric parameters (Å, º) top
Cu1—O1i2.002 (2)C3—C41.401 (3)
Cu1—O12.002 (2)C3—C81.489 (4)
Cu1—N1i2.019 (2)C4—C51.362 (4)
Cu1—N12.019 (2)C4—H4A0.9300
Cu1—O22.548 (2)C5—C61.384 (4)
O1—C71.271 (3)C5—H50.9300
O2—C71.242 (3)C6—H60.9300
O3—C81.219 (3)C9—C101.360 (4)
O4—C81.303 (3)C9—C131.487 (4)
O4—H40.8200C10—C111.395 (4)
N1—C121.353 (3)C10—H100.9300
N1—C91.362 (3)C11—C141.498 (4)
N2—C111.333 (3)C13—H13A0.9600
N2—C121.340 (3)C13—H13B0.9600
N3—C121.346 (3)C13—H13C0.9600
N3—H3A0.8600C14—H14A0.9600
N3—H3B0.8600C14—H14B0.9600
N4—C171.327 (3)C14—H14C0.9600
N4—C181.343 (3)C15—C161.367 (4)
N5—C151.342 (3)C15—C201.497 (3)
N5—C181.354 (3)C16—C171.396 (3)
N6—C181.332 (3)C16—H160.9300
N6—H6A0.8600C17—C191.498 (4)
N6—H6B0.8600C19—H19A0.9600
C1—C61.389 (3)C19—H19B0.9600
C1—C21.391 (3)C19—H19C0.9600
C1—C71.504 (3)C20—H20A0.9600
C2—C31.391 (3)C20—H20B0.9600
C2—H20.9300C20—H20C0.9600
O1i—Cu1—O1180.0N1—C9—C13117.6 (2)
O1i—Cu1—N1i90.44 (8)C9—C10—C11118.7 (2)
O1—Cu1—N1i89.56 (8)C9—C10—H10120.6
O1i—Cu1—N189.56 (8)C11—C10—H10120.6
O1—Cu1—N190.44 (8)N2—C11—C10121.3 (2)
N1i—Cu1—N1180.000 (1)N2—C11—C14117.6 (3)
C7—O1—Cu1103.04 (15)C10—C11—C14121.2 (3)
C8—O4—H4109.5N2—C12—N3116.7 (2)
C12—N1—C9116.9 (2)N2—C12—N1125.0 (2)
C12—N1—Cu1120.69 (16)N3—C12—N1118.3 (2)
C9—N1—Cu1122.02 (17)C9—C13—H13A109.5
C11—N2—C12117.1 (2)C9—C13—H13B109.5
C12—N3—H3A120.0H13A—C13—H13B109.5
C12—N3—H3B120.0C9—C13—H13C109.5
H3A—N3—H3B120.0H13A—C13—H13C109.5
C17—N4—C18117.0 (2)H13B—C13—H13C109.5
C15—N5—C18117.3 (2)C11—C14—H14A109.5
C18—N6—H6A120.0C11—C14—H14B109.5
C18—N6—H6B120.0H14A—C14—H14B109.5
H6A—N6—H6B120.0C11—C14—H14C109.5
C6—C1—C2119.0 (2)H14A—C14—H14C109.5
C6—C1—C7118.8 (2)H14B—C14—H14C109.5
C2—C1—C7122.2 (2)N5—C15—C16121.1 (2)
C3—C2—C1120.8 (2)N5—C15—C20116.9 (2)
C3—C2—H2119.6C16—C15—C20122.1 (2)
C1—C2—H2119.6C15—C16—C17118.2 (2)
C2—C3—C4118.7 (2)C15—C16—H16120.9
C2—C3—C8121.1 (2)C17—C16—H16120.9
C4—C3—C8120.2 (2)N4—C17—C16121.6 (2)
C5—C4—C3120.6 (2)N4—C17—C19117.1 (2)
C5—C4—H4A119.7C16—C17—C19121.3 (2)
C3—C4—H4A119.7N6—C18—N4117.7 (2)
C4—C5—C6120.5 (2)N6—C18—N5117.4 (2)
C4—C5—H5119.7N4—C18—N5124.8 (2)
C6—C5—H5119.7C17—C19—H19A109.5
C5—C6—C1120.3 (2)C17—C19—H19B109.5
C5—C6—H6119.9H19A—C19—H19B109.5
C1—C6—H6119.9C17—C19—H19C109.5
O2—C7—O1122.2 (2)H19A—C19—H19C109.5
O2—C7—C1120.2 (2)H19B—C19—H19C109.5
O1—C7—C1117.7 (2)C15—C20—H20A109.5
O3—C8—O4124.3 (2)C15—C20—H20B109.5
O3—C8—C3122.8 (2)H20A—C20—H20B109.5
O4—C8—C3112.9 (2)C15—C20—H20C109.5
C10—C9—N1120.7 (2)H20A—C20—H20C109.5
C10—C9—C13121.7 (2)H20B—C20—H20C109.5
Symmetry code: (i) x, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···N5ii0.821.802.585 (3)160
N3—H3A···O2iii0.862.112.921 (3)157
N3—H3B···O10.862.372.992 (3)129
N6—H6A···N4iv0.862.283.116 (3)165
N6—H6B···O3ii0.862.253.099 (3)170
Symmetry codes: (ii) x+1, y, z+1; (iii) x+1, y, z; (iv) x+1, y+1, z+1.
 

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