catena-Poly[[[aqua­(2-amino-4,6-dimethyl­pyrimidine-κN¹)copper(II)]-μ-benzene-1,3-dicarboxyl­ato-κ²O¹:O³] 2-amino-4,6-dimethyl­pyrimidine solvate]

In the title polymer, {[Cu(C₈H₄O₄)(C₆H₉N₃)(H₂O)]·C₆H₉N₃}_n, the Cu^II ion approximates a distorted square-pyramidal geometry defined by an NO₄ donor set. Adjacent Cu^II ions are bridged by isophthalate dianions to form a one-dimensional chain. Chains inter­act through π–π stacking inter­actions of 2-amino-4,6-dimethyl­pyrimidine rings and hydrogen bonds, to build a three-dimensional crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.045
• wR factor = 0.149
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT731_ALERT_1_B Bond    Calc     0.84(5), Rep   0.843(10) ......       5.00 su-Ra
              O5   -H5E     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.84(5), Rep   0.843(10) ......       5.00 su-Ra
              O5   -H5E     1.555   1.555

Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N6     -   H6B    ...          ?
PLAT731_ALERT_1_C Bond    Calc     0.84(4), Rep   0.846(10) ......       4.00 su-Ra
              O5   -H5F     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(4), Rep   0.846(10) ......       4.00 su-Ra
              O5   -H5F     1.555   1.555

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL(Bruker, 2005); software used to prepare material for publication: SHELXTL.

catena-Poly[[[aqua(2-amino-4,6-dimethylpyrimidine-κN¹)copper(II)]- µ-benzene-1,3-dicarboxylato-κ²O¹:O³] 2-amino-4,6-dimethylpyrimidine solvate]

Crystal data

[Cu(C8H4O4)(C6H9N3)(H2O)]·C6H9N3	F(000) = 1020
Mr = 491.99	Dx = 1.489 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3900 reflections
a = 7.8409 (2) Å	θ = 2.8–25.0°
b = 21.4009 (7) Å	µ = 1.04 mm^−1
c = 13.1791 (3) Å	T = 296 K
β = 97.195 (2)°	Block, green
V = 2194.07 (10) Å^3	0.38 × 0.25 × 0.13 mm
Z = 4

Data collection

Bruker SMART APEX-II area-detector diffractometer	3900 independent reflections
Radiation source: fine-focus sealed tube	2923 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 25.1°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.693, Tmax = 0.877	k = −22→25
9167 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0981P)^2] where P = (Fo^2 + 2Fc^2)/3
3900 reflections	(Δ/σ)max = 0.001
301 parameters	Δρmax = 0.41 e Å^−3
2 restraints	Δρmin = −0.54 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.56712 (5)	0.09899 (2)	0.66860 (3)	0.03712 (19)
C1	0.2411 (4)	0.21107 (16)	0.7969 (2)	0.0326 (7)
C2	0.2750 (4)	0.25289 (16)	0.8778 (2)	0.0332 (8)
H2	0.3878	0.2595	0.9069	0.040*
C3	0.1438 (4)	0.28457 (16)	0.9151 (2)	0.0326 (8)
C4	−0.0248 (5)	0.27449 (19)	0.8724 (3)	0.0429 (9)
H4	−0.1142	0.2951	0.8987	0.052*
C5	−0.0605 (5)	0.2336 (2)	0.7903 (3)	0.0491 (10)
H5	−0.1733	0.2274	0.7608	0.059*
C6	0.0720 (5)	0.20242 (18)	0.7531 (3)	0.0421 (9)
H6	0.0483	0.1753	0.6981	0.051*
C7	0.3838 (4)	0.17441 (17)	0.7599 (3)	0.0367 (8)
C8	0.1854 (5)	0.32871 (17)	1.0033 (3)	0.0390 (8)
C12	0.4664 (4)	−0.02542 (17)	0.7290 (2)	0.0369 (8)
C10	0.5874 (5)	−0.07974 (18)	0.8781 (3)	0.0427 (9)
N2	0.6616 (4)	−0.02807 (15)	0.9154 (2)	0.0421 (7)
C9	0.6375 (4)	0.02455 (17)	0.8607 (2)	0.0368 (8)
C13	0.6167 (7)	−0.1377 (2)	0.9390 (3)	0.0638 (12)
H13A	0.7022	−0.1301	0.9965	0.096*
H13B	0.6557	−0.1701	0.8971	0.096*
H13C	0.5113	−0.1504	0.9629	0.096*
N3	0.7086 (5)	0.07697 (15)	0.8994 (2)	0.0514 (9)
H3A	0.7689	0.0767	0.9586	0.062*
H3B	0.6945	0.1112	0.8653	0.062*
C15	0.9360 (5)	0.02829 (18)	0.1679 (3)	0.0409 (9)
C16	1.0695 (5)	0.08408 (19)	0.3043 (3)	0.0416 (9)
C17	1.0308 (5)	0.13806 (19)	0.2519 (3)	0.0463 (9)
H17	1.0612	0.1766	0.2813	0.056*
C18	0.9445 (5)	0.13412 (18)	0.1533 (3)	0.0425 (9)
C19	0.8990 (7)	0.1917 (2)	0.0906 (3)	0.0650 (13)
H19A	0.9437	0.1881	0.0262	0.097*
H19B	0.9481	0.2277	0.1266	0.097*
H19C	0.7763	0.1960	0.0787	0.097*
C20	1.1605 (6)	0.0833 (2)	0.4116 (3)	0.0602 (12)
H20A	1.1147	0.0504	0.4495	0.090*
H20B	1.1439	0.1227	0.4439	0.090*
H20C	1.2811	0.0764	0.4099	0.090*
N1	0.5485 (4)	0.02706 (13)	0.76478 (19)	0.0334 (6)
C11	0.4813 (5)	−0.07939 (19)	0.7839 (3)	0.0465 (10)
H11	0.4227	−0.1152	0.7597	0.056*
C14	0.3609 (5)	−0.0202 (2)	0.6267 (3)	0.0506 (10)
H14A	0.2787	0.0129	0.6281	0.076*
H14B	0.3015	−0.0589	0.6106	0.076*
H14C	0.4347	−0.0114	0.5756	0.076*
N4	0.8973 (4)	0.07929 (15)	0.1114 (2)	0.0401 (7)
N5	1.0254 (4)	0.02806 (15)	0.2635 (2)	0.0426 (8)
N6	0.8844 (5)	−0.02695 (17)	0.1279 (3)	0.0617 (10)
H6A	0.8282	−0.0288	0.0676	0.074*
H6B	0.9074	−0.0606	0.1624	0.074*
O1	0.3448 (3)	0.13265 (12)	0.69321 (18)	0.0420 (6)
O2	0.5372 (3)	0.18595 (12)	0.7953 (2)	0.0457 (6)
O3	0.3390 (3)	0.34437 (15)	1.0266 (2)	0.0614 (9)
O4	0.0599 (3)	0.34829 (13)	1.04698 (19)	0.0452 (6)
O5	0.8004 (4)	0.07415 (18)	0.6585 (3)	0.0730 (10)
H5E	0.880 (6)	0.048 (2)	0.662 (5)	0.12 (2)*
H5F	0.847 (6)	0.091 (2)	0.611 (3)	0.070 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0409 (3)	0.0352 (3)	0.0354 (3)	0.00296 (19)	0.00530 (19)	0.00232 (19)
C1	0.0371 (18)	0.0296 (19)	0.0310 (17)	0.0024 (14)	0.0043 (14)	0.0015 (14)
C2	0.0319 (17)	0.0301 (19)	0.0366 (18)	−0.0008 (14)	0.0007 (14)	0.0029 (14)
C3	0.0387 (19)	0.0285 (19)	0.0305 (17)	−0.0027 (14)	0.0036 (14)	0.0027 (14)
C4	0.039 (2)	0.045 (2)	0.046 (2)	0.0041 (17)	0.0101 (16)	−0.0029 (18)
C5	0.0299 (19)	0.062 (3)	0.054 (2)	−0.0020 (18)	−0.0001 (16)	−0.013 (2)
C6	0.043 (2)	0.041 (2)	0.042 (2)	−0.0009 (17)	0.0005 (16)	−0.0083 (17)
C7	0.041 (2)	0.034 (2)	0.0346 (18)	0.0035 (16)	0.0042 (15)	0.0055 (16)
C8	0.050 (2)	0.032 (2)	0.0351 (18)	0.0031 (17)	0.0054 (16)	0.0008 (15)
C12	0.0413 (19)	0.038 (2)	0.0327 (17)	0.0003 (16)	0.0106 (15)	−0.0020 (16)
C10	0.053 (2)	0.037 (2)	0.041 (2)	0.0013 (18)	0.0146 (18)	0.0056 (17)
N2	0.0507 (18)	0.0401 (19)	0.0353 (16)	0.0051 (15)	0.0040 (14)	0.0068 (14)
C9	0.0420 (19)	0.037 (2)	0.0313 (17)	0.0029 (16)	0.0046 (15)	0.0037 (15)
C13	0.090 (3)	0.040 (3)	0.062 (3)	0.006 (2)	0.013 (2)	0.018 (2)
N3	0.073 (2)	0.0374 (19)	0.0383 (17)	−0.0027 (17)	−0.0165 (16)	0.0022 (15)
C15	0.0419 (19)	0.039 (2)	0.041 (2)	0.0028 (16)	−0.0001 (16)	0.0010 (17)
C16	0.0347 (19)	0.053 (3)	0.0371 (19)	0.0024 (17)	0.0036 (16)	−0.0023 (17)
C17	0.053 (2)	0.042 (2)	0.043 (2)	−0.0036 (18)	0.0019 (18)	−0.0040 (18)
C18	0.0406 (19)	0.042 (2)	0.045 (2)	0.0018 (17)	0.0059 (16)	0.0043 (18)
C19	0.092 (3)	0.041 (3)	0.059 (3)	−0.003 (2)	−0.007 (2)	0.014 (2)
C20	0.063 (3)	0.071 (3)	0.042 (2)	0.003 (2)	−0.010 (2)	−0.004 (2)
N1	0.0383 (15)	0.0329 (16)	0.0287 (14)	0.0013 (13)	0.0035 (12)	0.0032 (12)
C11	0.053 (2)	0.038 (2)	0.049 (2)	−0.0097 (18)	0.0091 (19)	−0.0030 (18)
C14	0.057 (2)	0.050 (3)	0.042 (2)	−0.0105 (19)	−0.0034 (18)	−0.0062 (18)
N4	0.0447 (18)	0.0377 (18)	0.0370 (16)	0.0028 (14)	0.0016 (13)	0.0058 (14)
N5	0.0465 (17)	0.0435 (19)	0.0362 (16)	0.0063 (15)	−0.0004 (14)	0.0057 (14)
N6	0.087 (3)	0.038 (2)	0.052 (2)	0.0028 (18)	−0.0219 (19)	0.0045 (16)
O1	0.0439 (14)	0.0387 (15)	0.0434 (14)	0.0035 (12)	0.0053 (11)	−0.0104 (12)
O2	0.0330 (13)	0.0427 (16)	0.0604 (16)	0.0031 (11)	0.0021 (12)	−0.0038 (13)
O3	0.0417 (16)	0.076 (2)	0.0653 (19)	0.0009 (15)	0.0026 (13)	−0.0326 (17)
O4	0.0452 (14)	0.0489 (17)	0.0433 (14)	−0.0055 (12)	0.0123 (12)	−0.0128 (12)
O5	0.0519 (18)	0.075 (2)	0.098 (3)	0.0258 (17)	0.0311 (18)	0.050 (2)

Geometric parameters (Å, º)

Cu1—O5	1.926 (3)	C13—H13A	0.9600
Cu1—O1	1.950 (2)	C13—H13B	0.9600
Cu1—O4^i	1.955 (2)	C13—H13C	0.9600
Cu1—N1	2.011 (3)	N3—H3A	0.8600
Cu1—O2	2.530 (3)	N3—H3B	0.8600
C1—C6	1.391 (5)	C15—N4	1.334 (5)
C1—C2	1.391 (5)	C15—N6	1.336 (5)
C1—C7	1.497 (5)	C15—N5	1.363 (4)
C2—C3	1.374 (5)	C16—N5	1.342 (5)
C2—H2	0.9300	C16—C17	1.361 (5)
C3—C4	1.388 (5)	C16—C20	1.502 (5)
C3—C8	1.501 (5)	C17—C18	1.390 (5)
C4—C5	1.392 (5)	C17—H17	0.9300
C4—H4	0.9300	C18—N4	1.330 (5)
C5—C6	1.377 (5)	C18—C19	1.501 (6)
C5—H5	0.9300	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C7—O2	1.258 (4)	C19—H19C	0.9600
C7—O1	1.264 (4)	C20—H20A	0.9600
C8—O3	1.251 (5)	C20—H20B	0.9600
C8—O4	1.272 (4)	C20—H20C	0.9600
C12—N1	1.350 (4)	C11—H11	0.9300
C12—C11	1.360 (5)	C14—H14A	0.9600
C12—C14	1.496 (5)	C14—H14B	0.9600
C10—N2	1.316 (5)	C14—H14C	0.9600
C10—C11	1.405 (5)	N6—H6A	0.8600
C10—C13	1.479 (5)	N6—H6B	0.8600
N2—C9	1.338 (5)	O4—Cu1^ii	1.955 (2)
C9—N3	1.326 (5)	O5—H5E	0.843 (10)
C9—N1	1.366 (4)	O5—H5F	0.846 (10)
O5—Cu1—O1	171.91 (15)	C9—N3—H3A	120.0
O5—Cu1—O4^i	91.88 (12)	C9—N3—H3B	120.0
O1—Cu1—O4^i	89.34 (11)	H3A—N3—H3B	120.0
O5—Cu1—N1	88.67 (13)	N4—C15—N6	117.9 (3)
O1—Cu1—N1	92.35 (11)	N4—C15—N5	125.0 (3)
O4^i—Cu1—N1	164.05 (11)	N6—C15—N5	117.2 (3)
O5—Cu1—O2	114.60 (15)	N5—C16—C17	121.7 (3)
O1—Cu1—O2	57.32 (9)	N5—C16—C20	115.9 (4)
O4^i—Cu1—O2	96.94 (10)	C17—C16—C20	122.4 (4)
N1—Cu1—O2	97.31 (10)	C16—C17—C18	118.3 (4)
C6—C1—C2	118.9 (3)	C16—C17—H17	120.8
C6—C1—C7	120.5 (3)	C18—C17—H17	120.8
C2—C1—C7	120.5 (3)	N4—C18—C17	121.3 (4)
C3—C2—C1	120.8 (3)	N4—C18—C19	117.4 (3)
C3—C2—H2	119.6	C17—C18—C19	121.3 (4)
C1—C2—H2	119.6	C18—C19—H19A	109.5
C2—C3—C4	119.7 (3)	C18—C19—H19B	109.5
C2—C3—C8	119.2 (3)	H19A—C19—H19B	109.5
C4—C3—C8	121.0 (3)	C18—C19—H19C	109.5
C3—C4—C5	120.1 (3)	H19A—C19—H19C	109.5
C3—C4—H4	119.9	H19B—C19—H19C	109.5
C5—C4—H4	119.9	C16—C20—H20A	109.5
C6—C5—C4	119.6 (3)	C16—C20—H20B	109.5
C6—C5—H5	120.2	H20A—C20—H20B	109.5
C4—C5—H5	120.2	C16—C20—H20C	109.5
C5—C6—C1	120.7 (3)	H20A—C20—H20C	109.5
C5—C6—H6	119.6	H20B—C20—H20C	109.5
C1—C6—H6	119.6	C12—N1—C9	117.1 (3)
O2—C7—O1	122.2 (3)	C12—N1—Cu1	119.1 (2)
O2—C7—C1	119.7 (3)	C9—N1—Cu1	123.0 (2)
O1—C7—C1	118.1 (3)	C12—C11—C10	118.5 (4)
O3—C8—O4	125.2 (3)	C12—C11—H11	120.8
O3—C8—C3	117.9 (3)	C10—C11—H11	120.8
O4—C8—C3	116.9 (3)	C12—C14—H14A	109.5
N1—C12—C11	121.0 (3)	C12—C14—H14B	109.5
N1—C12—C14	116.0 (3)	H14A—C14—H14B	109.5
C11—C12—C14	122.9 (3)	C12—C14—H14C	109.5
N2—C10—C11	120.7 (3)	H14A—C14—H14C	109.5
N2—C10—C13	118.0 (3)	H14B—C14—H14C	109.5
C11—C10—C13	121.2 (4)	C18—N4—C15	117.3 (3)
C10—N2—C9	118.7 (3)	C16—N5—C15	116.4 (3)
N3—C9—N2	118.7 (3)	C15—N6—H6A	120.0
N3—C9—N1	117.6 (3)	C15—N6—H6B	120.0
N2—C9—N1	123.6 (3)	H6A—N6—H6B	120.0
C10—C13—H13A	109.5	C7—O1—Cu1	103.5 (2)
C10—C13—H13B	109.5	C7—O2—Cu1	77.0 (2)
H13A—C13—H13B	109.5	C8—O4—Cu1^ii	128.1 (2)
C10—C13—H13C	109.5	Cu1—O5—H5E	152 (5)
H13A—C13—H13C	109.5	Cu1—O5—H5F	115 (4)
H13B—C13—H13C	109.5	H5E—O5—H5F	87 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N4^iii	0.86	2.14	2.994 (4)	175
N6—H6A···N2^iv	0.86	2.25	3.109 (4)	175
N3—H3B···O2	0.86	2.16	2.944 (4)	152
O5—H5E···N5^v	0.84 (1)	1.98 (4)	2.712 (4)	144 (6)
O5—H5F···O3^i	0.85 (1)	1.76 (3)	2.507 (4)	145 (5)

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