Bis(2-amino-4,6-dimethyl­pyrimidine-κN)bis(isophthalato-κ²O,O′)copper(II) 2-amino-4,6-dimethyl­pyrimidine disolvate

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.

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

No syntax errors found



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

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Computing details

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

Crystal data

[Cu(C8H5O4)2(C6H9N3)2]·2C6H9N3	Z = 1
Mr = 886.43	F(000) = 463
Triclinic, P1	Dx = 1.423 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4010 (2) Å	Cell parameters from 117 reflections
b = 9.3811 (3) Å	θ = 7.5–15°
c = 15.2889 (5) Å	µ = 0.60 mm^−1
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) Å^3

Data collection

Bruker SMART APEX-II CCD diffractometer	3600 independent reflections
Radiation source: fine-focus sealed tube	2933 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.828, Tmax = 0.916	k = −11→11
8817 measured reflections	l = −17→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0754P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
3600 reflections	Δρmax = 0.41 e Å^−3
282 parameters	Δρmin = −0.54 e Å^−3
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0029 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.0000	0.5000	1.0000	0.03557 (17)
O1	−0.0023 (2)	0.34415 (19)	0.88873 (12)	0.0453 (4)
O2	−0.2689 (2)	0.4349 (2)	0.88448 (13)	0.0521 (5)
O3	0.1327 (3)	−0.0765 (2)	0.63678 (14)	0.0634 (6)
O4	−0.0903 (3)	−0.1523 (2)	0.53031 (13)	0.0566 (5)
H4	−0.0241	−0.2183	0.5141	0.085*
N1	0.1078 (2)	0.6486 (2)	0.93513 (13)	0.0377 (5)
N2	0.3729 (3)	0.7445 (2)	0.87789 (16)	0.0489 (5)
N3	0.3581 (3)	0.5141 (3)	0.90618 (17)	0.0561 (6)
H3A	0.4656	0.5051	0.8880	0.067*
H3B	0.3021	0.4433	0.9241	0.067*
N4	0.6834 (3)	0.5235 (2)	0.58598 (14)	0.0414 (5)
N5	0.9256 (3)	0.3668 (2)	0.55658 (14)	0.0397 (5)
N6	0.6632 (3)	0.3314 (2)	0.46544 (16)	0.0533 (6)
H6A	0.5569	0.3552	0.4512	0.064*
H6B	0.7077	0.2574	0.4331	0.064*
C1	−0.2099 (3)	0.2405 (2)	0.76473 (16)	0.0357 (5)
C2	−0.0925 (3)	0.1393 (2)	0.72593 (16)	0.0370 (5)
H2	0.0209	0.1360	0.7544	0.044*
C3	−0.1426 (3)	0.0429 (2)	0.64515 (17)	0.0384 (6)
C4	−0.3150 (4)	0.0482 (3)	0.60402 (18)	0.0490 (7)
H4A	−0.3504	−0.0155	0.5499	0.059*
C5	−0.4313 (4)	0.1457 (3)	0.6425 (2)	0.0548 (8)
H5	−0.5461	0.1470	0.6150	0.066*
C6	−0.3798 (3)	0.2431 (3)	0.72222 (18)	0.0458 (6)
H6	−0.4594	0.3104	0.7474	0.055*
C7	−0.1592 (3)	0.3474 (3)	0.85152 (17)	0.0396 (6)
C8	−0.0186 (3)	−0.0671 (3)	0.60379 (18)	0.0453 (6)
C9	0.0233 (3)	0.7705 (3)	0.92694 (17)	0.0401 (6)
C10	0.1100 (4)	0.8785 (3)	0.89419 (19)	0.0487 (7)
H10	0.0507	0.9602	0.8866	0.058*
C11	0.2895 (4)	0.8645 (3)	0.87219 (19)	0.0520 (7)
C12	0.2775 (3)	0.6390 (3)	0.90668 (17)	0.0399 (6)
C13	−0.1667 (3)	0.7795 (3)	0.9537 (2)	0.0505 (7)
H13A	−0.2401	0.6957	0.9210	0.076*
H13B	−0.2135	0.8667	0.9408	0.076*
H13C	−0.1690	0.7821	1.0168	0.076*
C14	0.3957 (5)	0.9840 (4)	0.8413 (3)	0.0776 (10)
H14A	0.5199	0.9890	0.8638	0.116*
H14B	0.3455	1.0755	0.8631	0.116*
H14C	0.3897	0.9641	0.7770	0.116*
C15	1.0218 (3)	0.4455 (3)	0.62923 (17)	0.0414 (6)
C16	0.9539 (4)	0.5638 (3)	0.68137 (18)	0.0465 (6)
H16	1.0213	0.6187	0.7313	0.056*
C17	0.7805 (3)	0.5999 (3)	0.65754 (17)	0.0420 (6)
C18	0.7589 (3)	0.4090 (3)	0.53761 (17)	0.0407 (6)
C19	0.6937 (4)	0.7242 (3)	0.7134 (2)	0.0552 (7)
H19A	0.6301	0.7762	0.6750	0.083*
H19B	0.7856	0.7891	0.7505	0.083*
H19C	0.6098	0.6868	0.7505	0.083*
C20	1.2051 (4)	0.3970 (3)	0.6502 (2)	0.0554 (7)
H20A	1.1916	0.3045	0.6676	0.083*
H20B	1.2674	0.4680	0.6982	0.083*
H20C	1.2740	0.3874	0.5981	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0276 (2)	0.0436 (3)	0.0310 (3)	0.00802 (16)	−0.00161 (16)	−0.00330 (17)
O1	0.0386 (10)	0.0540 (10)	0.0372 (10)	0.0070 (8)	−0.0026 (8)	−0.0042 (8)
O2	0.0438 (10)	0.0561 (11)	0.0475 (12)	0.0139 (9)	0.0025 (9)	−0.0126 (9)
O3	0.0496 (12)	0.0706 (12)	0.0605 (14)	0.0286 (10)	−0.0130 (10)	−0.0117 (10)
O4	0.0533 (11)	0.0557 (11)	0.0510 (12)	0.0258 (9)	−0.0088 (9)	−0.0154 (9)
N1	0.0288 (10)	0.0470 (11)	0.0343 (12)	0.0089 (8)	−0.0003 (8)	0.0003 (9)
N2	0.0400 (12)	0.0572 (13)	0.0496 (14)	0.0070 (10)	0.0075 (10)	0.0092 (11)
N3	0.0376 (12)	0.0638 (14)	0.0740 (18)	0.0202 (10)	0.0187 (11)	0.0226 (13)
N4	0.0381 (11)	0.0444 (11)	0.0415 (13)	0.0147 (9)	−0.0001 (9)	0.0058 (10)
N5	0.0378 (11)	0.0411 (10)	0.0392 (12)	0.0148 (9)	−0.0007 (9)	0.0037 (9)
N6	0.0477 (13)	0.0557 (13)	0.0493 (14)	0.0220 (11)	−0.0129 (11)	−0.0070 (11)
C1	0.0367 (13)	0.0370 (11)	0.0316 (13)	0.0034 (10)	0.0005 (10)	0.0034 (10)
C2	0.0329 (12)	0.0402 (12)	0.0366 (14)	0.0051 (10)	−0.0055 (10)	0.0068 (10)
C3	0.0389 (13)	0.0387 (12)	0.0366 (14)	0.0110 (10)	−0.0020 (11)	0.0039 (10)
C4	0.0481 (15)	0.0514 (14)	0.0392 (15)	0.0137 (12)	−0.0151 (12)	−0.0081 (12)
C5	0.0414 (15)	0.0615 (16)	0.0526 (18)	0.0193 (13)	−0.0160 (13)	−0.0084 (13)
C6	0.0401 (14)	0.0473 (14)	0.0450 (16)	0.0130 (11)	−0.0045 (12)	−0.0030 (12)
C7	0.0337 (13)	0.0469 (13)	0.0367 (14)	0.0014 (11)	0.0001 (11)	0.0058 (11)
C8	0.0461 (15)	0.0438 (13)	0.0444 (16)	0.0119 (11)	−0.0019 (12)	0.0041 (12)
C9	0.0338 (12)	0.0472 (13)	0.0338 (14)	0.0085 (10)	−0.0039 (10)	−0.0047 (11)
C10	0.0467 (15)	0.0467 (14)	0.0517 (17)	0.0105 (12)	−0.0014 (13)	0.0067 (13)
C11	0.0512 (17)	0.0540 (15)	0.0486 (17)	0.0042 (13)	0.0042 (13)	0.0054 (13)
C12	0.0313 (12)	0.0532 (14)	0.0327 (14)	0.0095 (11)	−0.0002 (10)	0.0020 (11)
C13	0.0337 (13)	0.0536 (15)	0.0625 (19)	0.0129 (11)	0.0012 (12)	0.0055 (13)
C14	0.071 (2)	0.071 (2)	0.098 (3)	0.0078 (17)	0.028 (2)	0.027 (2)
C15	0.0386 (13)	0.0457 (13)	0.0405 (15)	0.0072 (11)	−0.0026 (11)	0.0103 (11)
C16	0.0438 (14)	0.0502 (14)	0.0419 (16)	0.0088 (11)	−0.0049 (12)	0.0013 (12)
C17	0.0469 (14)	0.0409 (12)	0.0384 (15)	0.0109 (11)	0.0036 (12)	0.0064 (11)
C18	0.0385 (13)	0.0422 (13)	0.0418 (15)	0.0121 (10)	−0.0031 (11)	0.0082 (11)
C19	0.0545 (17)	0.0565 (16)	0.0512 (18)	0.0166 (13)	0.0033 (14)	0.0000 (13)
C20	0.0457 (15)	0.0610 (17)	0.0578 (19)	0.0170 (13)	−0.0076 (14)	0.0069 (14)

Geometric parameters (Å, º)

Cu1—O1^i	2.002 (2)	C3—C4	1.401 (3)
Cu1—O1	2.002 (2)	C3—C8	1.489 (4)
Cu1—N1^i	2.019 (2)	C4—C5	1.362 (4)
Cu1—N1	2.019 (2)	C4—H4A	0.9300
Cu1—O2	2.548 (2)	C5—C6	1.384 (4)
O1—C7	1.271 (3)	C5—H5	0.9300
O2—C7	1.242 (3)	C6—H6	0.9300
O3—C8	1.219 (3)	C9—C10	1.360 (4)
O4—C8	1.303 (3)	C9—C13	1.487 (4)
O4—H4	0.8200	C10—C11	1.395 (4)
N1—C12	1.353 (3)	C10—H10	0.9300
N1—C9	1.362 (3)	C11—C14	1.498 (4)
N2—C11	1.333 (3)	C13—H13A	0.9600
N2—C12	1.340 (3)	C13—H13B	0.9600
N3—C12	1.346 (3)	C13—H13C	0.9600
N3—H3A	0.8600	C14—H14A	0.9600
N3—H3B	0.8600	C14—H14B	0.9600
N4—C17	1.327 (3)	C14—H14C	0.9600
N4—C18	1.343 (3)	C15—C16	1.367 (4)
N5—C15	1.342 (3)	C15—C20	1.497 (3)
N5—C18	1.354 (3)	C16—C17	1.396 (3)
N6—C18	1.332 (3)	C16—H16	0.9300
N6—H6A	0.8600	C17—C19	1.498 (4)
N6—H6B	0.8600	C19—H19A	0.9600
C1—C6	1.389 (3)	C19—H19B	0.9600
C1—C2	1.391 (3)	C19—H19C	0.9600
C1—C7	1.504 (3)	C20—H20A	0.9600
C2—C3	1.391 (3)	C20—H20B	0.9600
C2—H2	0.9300	C20—H20C	0.9600
O1^i—Cu1—O1	180.0	N1—C9—C13	117.6 (2)
O1^i—Cu1—N1^i	90.44 (8)	C9—C10—C11	118.7 (2)
O1—Cu1—N1^i	89.56 (8)	C9—C10—H10	120.6
O1^i—Cu1—N1	89.56 (8)	C11—C10—H10	120.6
O1—Cu1—N1	90.44 (8)	N2—C11—C10	121.3 (2)
N1^i—Cu1—N1	180.000 (1)	N2—C11—C14	117.6 (3)
C7—O1—Cu1	103.04 (15)	C10—C11—C14	121.2 (3)
C8—O4—H4	109.5	N2—C12—N3	116.7 (2)
C12—N1—C9	116.9 (2)	N2—C12—N1	125.0 (2)
C12—N1—Cu1	120.69 (16)	N3—C12—N1	118.3 (2)
C9—N1—Cu1	122.02 (17)	C9—C13—H13A	109.5
C11—N2—C12	117.1 (2)	C9—C13—H13B	109.5
C12—N3—H3A	120.0	H13A—C13—H13B	109.5
C12—N3—H3B	120.0	C9—C13—H13C	109.5
H3A—N3—H3B	120.0	H13A—C13—H13C	109.5
C17—N4—C18	117.0 (2)	H13B—C13—H13C	109.5
C15—N5—C18	117.3 (2)	C11—C14—H14A	109.5
C18—N6—H6A	120.0	C11—C14—H14B	109.5
C18—N6—H6B	120.0	H14A—C14—H14B	109.5
H6A—N6—H6B	120.0	C11—C14—H14C	109.5
C6—C1—C2	119.0 (2)	H14A—C14—H14C	109.5
C6—C1—C7	118.8 (2)	H14B—C14—H14C	109.5
C2—C1—C7	122.2 (2)	N5—C15—C16	121.1 (2)
C3—C2—C1	120.8 (2)	N5—C15—C20	116.9 (2)
C3—C2—H2	119.6	C16—C15—C20	122.1 (2)
C1—C2—H2	119.6	C15—C16—C17	118.2 (2)
C2—C3—C4	118.7 (2)	C15—C16—H16	120.9
C2—C3—C8	121.1 (2)	C17—C16—H16	120.9
C4—C3—C8	120.2 (2)	N4—C17—C16	121.6 (2)
C5—C4—C3	120.6 (2)	N4—C17—C19	117.1 (2)
C5—C4—H4A	119.7	C16—C17—C19	121.3 (2)
C3—C4—H4A	119.7	N6—C18—N4	117.7 (2)
C4—C5—C6	120.5 (2)	N6—C18—N5	117.4 (2)
C4—C5—H5	119.7	N4—C18—N5	124.8 (2)
C6—C5—H5	119.7	C17—C19—H19A	109.5
C5—C6—C1	120.3 (2)	C17—C19—H19B	109.5
C5—C6—H6	119.9	H19A—C19—H19B	109.5
C1—C6—H6	119.9	C17—C19—H19C	109.5
O2—C7—O1	122.2 (2)	H19A—C19—H19C	109.5
O2—C7—C1	120.2 (2)	H19B—C19—H19C	109.5
O1—C7—C1	117.7 (2)	C15—C20—H20A	109.5
O3—C8—O4	124.3 (2)	C15—C20—H20B	109.5
O3—C8—C3	122.8 (2)	H20A—C20—H20B	109.5
O4—C8—C3	112.9 (2)	C15—C20—H20C	109.5
C10—C9—N1	120.7 (2)	H20A—C20—H20C	109.5
C10—C9—C13	121.7 (2)	H20B—C20—H20C	109.5

Symmetry code: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···N5^ii	0.82	1.80	2.585 (3)	160
N3—H3A···O2^iii	0.86	2.11	2.921 (3)	157
N3—H3B···O1	0.86	2.37	2.992 (3)	129
N6—H6A···N4^iv	0.86	2.28	3.116 (3)	165
N6—H6B···O3^ii	0.86	2.25	3.099 (3)	170

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