Crystal structure of a mixed-ligand silver(I) complex of the non-steroidal anti-inflammatory drug diclofenac and pyrimidine

The coordination polymeric silver(I)–diclofenac complex including pyrimidine is based on a centrosymmetric carboxyl­ate O:O′-bridged dinuclear unit which is extended through N-atom donors of the pyrimidine ligand into a two-dimensional layered structure

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.039
• wR factor = 0.095
• Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         O2 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C14 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      5.187 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          7 Report
PLAT976_ALERT_2_C Check Calcd Residual Density  0.85A From      N1      -0.46 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on      H1      -0.46 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density           0 Note

Alert level G
PLAT004_ALERT_5_G Polymeric Structure Found with Maximum Dimension          2 Info
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ag1    --  N3_d    ..        6.9 s.u.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         23 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) within WinGX (Farrugia, 2012); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Poly[{µ₂-2-[2-(2,6-dichloroanilino)phenyl]acetato-κ²O:O'}(µ₂-pyrimidine-κ²N¹:N³)silver(I)]

Crystal data

[Ag(C14H10Cl2NO2)(C4H4N2)]	F(000) = 960
Mr = 483.09	Dx = 1.806 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.5886 (4) Å	Cell parameters from 13681 reflections
b = 9.3071 (4) Å	θ = 2.0–29.1°
c = 10.6646 (8) Å	µ = 1.45 mm^−1
β = 105.644 (3)°	T = 293 K
V = 1776.69 (16) Å^3	Prism, colorless
Z = 4	0.60 × 0.46 × 0.27 mm

Data collection

Stoe IPDS2 diffractometer	3672 reflections with I > 2σ(I)
ω–scan rotation method	Rint = 0.088
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	θmax = 28.7°, θmin = 2.3°
Tmin = 0.471, Tmax = 0.693	h = −24→24
13090 measured reflections	k = −12→12
4538 independent reflections	l = −14→14

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0488P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.095	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.57 e Å^−3
4538 reflections	Δρmin = −1.14 e Å^−3
236 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0206 (11)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	0.17222 (14)	0.3200 (3)	0.6246 (3)	0.0419 (6)
C2	0.12206 (16)	0.2364 (3)	0.5353 (3)	0.0496 (7)
H2	0.1387	0.1695	0.4847	0.060*
C3	0.04629 (16)	0.2541 (4)	0.5223 (4)	0.0546 (8)
H3	0.0116	0.2009	0.4607	0.065*
C4	0.02263 (15)	0.3495 (4)	0.5995 (3)	0.0505 (7)
H4	−0.0282	0.3603	0.5912	0.061*
C5	0.07381 (14)	0.4302 (3)	0.6904 (3)	0.0406 (6)
C6	0.15110 (13)	0.4220 (3)	0.7029 (3)	0.0381 (5)
C7	0.19762 (12)	0.6542 (3)	0.8068 (3)	0.0377 (5)
C8	0.15520 (14)	0.7377 (3)	0.7067 (3)	0.0451 (6)
H8	0.1312	0.6953	0.6275	0.054*
C9	0.14820 (16)	0.8839 (4)	0.7235 (4)	0.0529 (8)
H9	0.1197	0.9397	0.6558	0.063*
C10	0.18355 (17)	0.9463 (3)	0.8408 (4)	0.0573 (9)
H10	0.1785	1.0443	0.8535	0.069*
C11	0.22657 (15)	0.8624 (3)	0.9396 (4)	0.0501 (7)
H11	0.2502	0.9054	1.0187	0.060*
C12	0.23575 (12)	0.7165 (3)	0.9249 (3)	0.0391 (6)
C13	0.28437 (13)	0.6294 (4)	1.0340 (3)	0.0437 (6)
H13A	0.2575	0.5429	1.0448	0.052*
H13B	0.2930	0.6843	1.1140	0.052*
C14	0.36042 (13)	0.5857 (3)	1.0147 (3)	0.0367 (5)
C15	0.44153 (16)	0.3069 (3)	0.5812 (3)	0.0444 (6)
H15	0.4577	0.2251	0.6310	0.053*
C16	0.40626 (15)	0.4123 (3)	0.3828 (3)	0.0461 (6)
H16	0.3968	0.4080	0.2926	0.055*
C17	0.39630 (16)	0.5399 (4)	0.4394 (3)	0.0489 (7)
H17	0.3807	0.6220	0.3899	0.059*
C18	0.41040 (15)	0.5417 (3)	0.5740 (3)	0.0461 (6)
H18	0.4038	0.6266	0.6154	0.055*
Ag1	0.46373 (2)	0.43353 (3)	0.87652 (2)	0.04354 (10)
Cl1	0.26694 (4)	0.29612 (9)	0.63922 (10)	0.0610 (2)
Cl2	0.03984 (4)	0.54045 (9)	0.79226 (9)	0.05280 (19)
N1	0.20327 (12)	0.5025 (3)	0.7931 (3)	0.0443 (5)
H1	0.2409	0.4588	0.8434	0.053*
N2	0.43318 (12)	0.4245 (3)	0.6450 (2)	0.0425 (5)
N3	0.42916 (13)	0.2935 (3)	0.4527 (2)	0.0457 (5)
O1	0.41252 (11)	0.5735 (3)	1.1157 (2)	0.0586 (6)
O2	0.36494 (11)	0.5641 (3)	0.9022 (2)	0.0590 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0374 (11)	0.0372 (13)	0.0497 (15)	0.0009 (10)	0.0092 (11)	0.0018 (13)
C2	0.0522 (15)	0.0425 (15)	0.0518 (17)	−0.0023 (12)	0.0097 (13)	−0.0065 (14)
C3	0.0458 (14)	0.0469 (16)	0.063 (2)	−0.0076 (12)	0.0001 (13)	−0.0057 (16)
C4	0.0350 (12)	0.0496 (17)	0.062 (2)	−0.0056 (11)	0.0045 (12)	0.0027 (15)
C5	0.0362 (11)	0.0378 (13)	0.0472 (15)	0.0012 (10)	0.0104 (11)	0.0046 (12)
C6	0.0341 (10)	0.0344 (12)	0.0430 (14)	0.0025 (9)	0.0055 (10)	0.0047 (11)
C7	0.0293 (10)	0.0376 (13)	0.0472 (14)	0.0020 (9)	0.0119 (10)	0.0004 (12)
C8	0.0339 (11)	0.0495 (15)	0.0504 (16)	0.0006 (11)	0.0090 (11)	0.0030 (14)
C9	0.0402 (13)	0.0480 (16)	0.072 (2)	0.0062 (12)	0.0182 (14)	0.0166 (17)
C10	0.0468 (15)	0.0384 (15)	0.089 (3)	0.0036 (12)	0.0230 (16)	−0.0026 (17)
C11	0.0383 (12)	0.0468 (16)	0.067 (2)	−0.0010 (11)	0.0167 (13)	−0.0129 (15)
C12	0.0267 (10)	0.0422 (14)	0.0502 (15)	0.0005 (9)	0.0135 (10)	−0.0046 (12)
C13	0.0319 (11)	0.0561 (17)	0.0432 (15)	0.0005 (11)	0.0102 (10)	−0.0061 (14)
C14	0.0303 (10)	0.0338 (12)	0.0445 (14)	0.0008 (9)	0.0074 (10)	−0.0019 (11)
C15	0.0539 (14)	0.0419 (14)	0.0395 (14)	0.0020 (12)	0.0159 (12)	0.0026 (13)
C16	0.0441 (13)	0.0577 (18)	0.0356 (13)	−0.0024 (12)	0.0094 (11)	0.0018 (13)
C17	0.0451 (13)	0.0503 (16)	0.0493 (16)	0.0086 (12)	0.0096 (12)	0.0110 (14)
C18	0.0404 (12)	0.0432 (15)	0.0522 (17)	0.0056 (11)	0.0084 (12)	−0.0035 (13)
Ag1	0.04020 (13)	0.05477 (15)	0.03712 (13)	0.00513 (8)	0.01297 (8)	−0.00042 (10)
Cl1	0.0401 (3)	0.0555 (4)	0.0877 (6)	0.0068 (3)	0.0176 (3)	−0.0087 (5)
Cl2	0.0458 (3)	0.0534 (4)	0.0647 (5)	0.0013 (3)	0.0243 (3)	−0.0020 (4)
N1	0.0344 (10)	0.0402 (12)	0.0504 (14)	0.0065 (9)	−0.0019 (9)	−0.0026 (11)
N2	0.0401 (10)	0.0500 (14)	0.0375 (11)	0.0031 (9)	0.0104 (9)	−0.0026 (11)
N3	0.0534 (13)	0.0460 (13)	0.0392 (12)	−0.0014 (10)	0.0149 (10)	−0.0015 (11)
O1	0.0334 (9)	0.0967 (19)	0.0426 (11)	0.0109 (10)	0.0049 (8)	0.0071 (12)
O2	0.0412 (10)	0.0880 (18)	0.0456 (12)	0.0186 (10)	0.0080 (9)	−0.0133 (12)

Geometric parameters (Å, º)

C1—C2	1.379 (4)	C12—C13	1.504 (4)
C1—C6	1.390 (4)	C13—C14	1.537 (3)
C1—Cl1	1.739 (3)	C13—H13A	0.9700
C2—C3	1.387 (4)	C13—H13B	0.9700
C2—H2	0.9300	C14—O2	1.242 (4)
C3—C4	1.362 (5)	C14—O1	1.244 (3)
C3—H3	0.9300	C15—N2	1.320 (4)
C4—C5	1.382 (4)	C15—N3	1.333 (4)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.409 (3)	C16—N3	1.338 (4)
C5—Cl2	1.733 (3)	C16—C17	1.367 (5)
C6—N1	1.387 (3)	C16—H16	0.9300
C7—C8	1.382 (4)	C17—C18	1.388 (5)
C7—C12	1.394 (4)	C17—H17	0.9300
C7—N1	1.426 (4)	C18—N2	1.330 (4)
C8—C9	1.383 (5)	C18—H18	0.9300
C8—H8	0.9300	Ag1—O2	2.279 (2)
C9—C10	1.375 (6)	Ag1—O1^i	2.280 (2)
C9—H9	0.9300	Ag1—N2	2.381 (3)
C10—C11	1.380 (5)	Ag1—N3^ii	2.412 (3)
C10—H10	0.9300	Ag1—Ag1^i	2.8931 (5)
C11—C12	1.383 (4)	N1—H1	0.8600
C11—H11	0.9300
C2—C1—C6	123.5 (2)	C12—C13—H13B	108.5
C2—C1—Cl1	118.0 (2)	C14—C13—H13B	108.5
C6—C1—Cl1	118.5 (2)	H13A—C13—H13B	107.5
C1—C2—C3	118.8 (3)	O2—C14—O1	125.6 (2)
C1—C2—H2	120.6	O2—C14—C13	118.5 (2)
C3—C2—H2	120.6	O1—C14—C13	115.9 (3)
C4—C3—C2	120.1 (3)	N2—C15—N3	126.6 (3)
C4—C3—H3	119.9	N2—C15—H15	116.7
C2—C3—H3	119.9	N3—C15—H15	116.7
C3—C4—C5	120.3 (3)	N3—C16—C17	122.1 (3)
C3—C4—H4	119.9	N3—C16—H16	118.9
C5—C4—H4	119.9	C17—C16—H16	118.9
C4—C5—C6	122.0 (3)	C16—C17—C18	117.2 (3)
C4—C5—Cl2	117.6 (2)	C16—C17—H17	121.4
C6—C5—Cl2	120.5 (2)	C18—C17—H17	121.4
N1—C6—C1	121.9 (2)	N2—C18—C17	121.4 (3)
N1—C6—C5	122.8 (3)	N2—C18—H18	119.3
C1—C6—C5	115.2 (2)	C17—C18—H18	119.3
C8—C7—C12	120.6 (3)	O2—Ag1—O1^i	148.04 (10)
C8—C7—N1	121.4 (3)	O2—Ag1—N2	99.71 (8)
C12—C7—N1	118.1 (2)	O1^i—Ag1—N2	89.58 (8)
C7—C8—C9	120.5 (3)	O2—Ag1—N3^ii	97.48 (9)
C7—C8—H8	119.8	O1^i—Ag1—N3^ii	108.69 (9)
C9—C8—H8	119.8	N2—Ag1—N3^ii	107.93 (9)
C10—C9—C8	119.7 (3)	O2—Ag1—Ag1^i	81.70 (6)
C10—C9—H9	120.2	O1^i—Ag1—Ag1^i	76.19 (6)
C8—C9—H9	120.2	N2—Ag1—Ag1^i	151.80 (6)
C9—C10—C11	119.4 (3)	N3^ii—Ag1—Ag1^i	99.73 (6)
C9—C10—H10	120.3	C6—N1—C7	123.3 (2)
C11—C10—H10	120.3	C6—N1—H1	118.4
C10—C11—C12	122.2 (3)	C7—N1—H1	118.4
C10—C11—H11	118.9	C15—N2—C18	116.7 (3)
C12—C11—H11	118.9	C15—N2—Ag1	122.4 (2)
C11—C12—C7	117.6 (3)	C18—N2—Ag1	120.8 (2)
C11—C12—C13	120.6 (3)	C15—N3—C16	115.9 (3)
C7—C12—C13	121.9 (2)	C15—N3—Ag1^iii	116.2 (2)
C12—C13—C14	114.9 (2)	C16—N3—Ag1^iii	127.6 (2)
C12—C13—H13A	108.5	C14—O1—Ag1^i	125.2 (2)
C14—C13—H13A	108.5	C14—O2—Ag1	117.96 (17)
C6—C1—C2—C3	−0.1 (5)	N1—C7—C12—C13	2.6 (4)
Cl1—C1—C2—C3	−180.0 (3)	C11—C12—C13—C14	−105.3 (3)
C1—C2—C3—C4	−2.0 (5)	C7—C12—C13—C14	75.6 (3)
C2—C3—C4—C5	0.7 (5)	C12—C13—C14—O2	−31.7 (4)
C3—C4—C5—C6	2.7 (5)	C12—C13—C14—O1	149.1 (3)
C3—C4—C5—Cl2	−175.9 (3)	N3—C16—C17—C18	−0.5 (4)
C2—C1—C6—N1	179.0 (3)	C16—C17—C18—N2	0.5 (4)
Cl1—C1—C6—N1	−1.2 (4)	C1—C6—N1—C7	133.5 (3)
C2—C1—C6—C5	3.2 (4)	C5—C6—N1—C7	−51.1 (4)
Cl1—C1—C6—C5	−176.9 (2)	C8—C7—N1—C6	−21.6 (4)
C4—C5—C6—N1	179.8 (3)	C12—C7—N1—C6	157.8 (3)
Cl2—C5—C6—N1	−1.6 (4)	N3—C15—N2—C18	−0.3 (4)
C4—C5—C6—C1	−4.5 (4)	N3—C15—N2—Ag1	−176.8 (2)
Cl2—C5—C6—C1	174.0 (2)	C17—C18—N2—C15	−0.1 (4)
C12—C7—C8—C9	−1.8 (4)	C17—C18—N2—Ag1	176.4 (2)
N1—C7—C8—C9	177.6 (3)	N2—C15—N3—C16	0.3 (4)
C7—C8—C9—C10	−0.2 (4)	N2—C15—N3—Ag1^iii	173.7 (2)
C8—C9—C10—C11	1.0 (5)	C17—C16—N3—C15	0.2 (4)
C9—C10—C11—C12	0.2 (5)	C17—C16—N3—Ag1^iii	−172.4 (2)
C10—C11—C12—C7	−2.1 (4)	O2—C14—O1—Ag1^i	17.1 (4)
C10—C11—C12—C13	178.7 (3)	C13—C14—O1—Ag1^i	−163.8 (2)
C8—C7—C12—C11	3.0 (4)	O1—C14—O2—Ag1	18.3 (4)
N1—C7—C12—C11	−176.5 (2)	C13—C14—O2—Ag1	−160.8 (2)
C8—C7—C12—C13	−177.9 (2)

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

Hydrogen-bond geometry (Å, º)

Cg6 is the centroid of the [please define] ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.43	2.971 (3)	122
C16—H16···O1^iv	0.93	2.51	3.248 (4)	136
C13—H13B···Cg6^iii	0.97	3.30	3.983 (3)	129

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