Tris(μ-1,6-di­amino­hexane)­diterephthalatotetrasilver(I) dihydrate

The title compound, [Ag₄(C₈H₄O₄)₂{H₂N(CH₂)₆}₃]·2H₂O, is an Ag^I tetranuclear complex. Four Ag^I atoms, three hexa­methyl­enedi­amine mol­ecules, and two terephthalate dianions constitute a chain-like tetranuclear silver(I) complex. The complex lies on a center of symmetry, located at the mid-point of the central C—C bond. The two different kinds of Ag^I atoms are both in a linear environment. One kind of Ag atom is coordinated by two N atoms from different amine ligands, and the other is coordinated by an O atom from a carboxyl­ate group and by a N atom from an amine ligand. Adjacent complexes are joined together by weak Ag...Ag interactions to form ladder-like ribbons, which are further linked by hydrogen bonds to form a three-dimensional structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.037
• wR factor = 0.093
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.97

Alert level B
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....        C14

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT213_ALERT_2_C Atom N2      has ADP max/min Ratio .............       3.50 prolat
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       3.01 Ratio
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.31
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2A    ...          ?
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          9
            N3  -AG1 -N1  -C9    -49.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         11
            N1  -AG1 -N3  -C15  -131.00  3.00   1.555   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT804_ALERT_4_C ARU-Pack Problem in PLATON Analysis ............          !

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  11 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
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

Tris(1,6-diaminohexane)diterephthalatotetrasilver(I) dihydrate

Crystal data

[Ag4(C8H4O4)2(C6H14N2)3]·2H2O	Z = 2
Mr = 572.18	F(000) = 574
Triclinic, P1	Dx = 1.893 Mg m^−3
a = 7.220 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.928 (2) Å	Cell parameters from 4208 reflections
c = 13.919 (3) Å	θ = 2.8–25.9°
α = 110.08 (3)°	µ = 1.98 mm^−1
β = 98.73 (3)°	T = 293 K
γ = 96.31 (3)°	Rod, colorless
V = 1003.9 (3) Å^3	0.38 × 0.38 × 0.30 mm

Data collection

Siemens SMART CCD area-detector diffractometer	3814 independent reflections
Radiation source: fine-focus sealed tube	3353 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
φ and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→6
Tmin = 0.490, Tmax = 0.552	k = −12→13
4537 measured reflections	l = −17→17

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)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.0429P)^2 + 1.1362P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
3814 reflections	Δρmax = 0.93 e Å^−3
245 parameters	Δρmin = −0.95 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0038 (6)

Special details

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
Ag1	0.45582 (5)	0.47516 (3)	0.32966 (2)	0.04479 (13)
Ag2	0.13054 (6)	0.37910 (4)	0.13754 (3)	0.06196 (16)
O3	0.0277 (5)	0.1945 (3)	0.1412 (3)	0.0552 (8)
O2	−0.0853 (5)	−0.3665 (3)	0.3071 (3)	0.0609 (9)
C10	0.5037 (6)	0.1375 (4)	0.2084 (3)	0.0357 (8)
H10A	0.4043	0.1649	0.2453	0.080*
H10B	0.6118	0.1381	0.2582	0.080*
C5	−0.0281 (5)	0.0475 (4)	0.2278 (3)	0.0362 (8)
C4	−0.0158 (6)	0.0247 (4)	0.3207 (3)	0.0398 (9)
H4A	0.0182	0.0984	0.3861	0.080*
C13	0.3548 (6)	−0.2465 (4)	0.0998 (3)	0.0418 (9)
H13A	0.4556	−0.2673	0.0624	0.080*
H13B	0.2420	−0.2539	0.0503	0.080*
N1	0.6357 (5)	0.3690 (3)	0.2367 (3)	0.0425 (8)
H1A	0.7361	0.3622	0.2804	0.080*
H1B	0.6807	0.4189	0.2028	0.080*
N3	0.2685 (5)	0.5793 (3)	0.4171 (3)	0.0450 (8)
H3B	0.2205	0.5298	0.4504	0.080*
H3C	0.1708	0.5859	0.3716	0.080*
C6	−0.0808 (6)	−0.0600 (4)	0.1339 (3)	0.0393 (9)
H6A	−0.0897	−0.0457	0.0692	0.080*
C7	−0.1220 (6)	−0.1863 (4)	0.1337 (3)	0.0396 (9)
H7A	−0.1616	−0.2594	0.0682	0.080*
C3	−0.0523 (6)	−0.1025 (4)	0.3196 (3)	0.0389 (9)
H3A	−0.0405	−0.1167	0.3844	0.080*
C12	0.4085 (6)	−0.1061 (4)	0.1781 (3)	0.0376 (9)
H12A	0.5242	−0.0985	0.2256	0.080*
H12B	0.3104	−0.0877	0.2177	0.080*
C16	0.4073 (6)	0.8096 (4)	0.4454 (3)	0.0440 (10)
H16A	0.5097	0.7819	0.4113	0.080*
H16B	0.3027	0.8085	0.3933	0.080*
O1	−0.2176 (6)	−0.4402 (3)	0.1402 (2)	0.0682 (10)
C17	0.4709 (7)	0.9501 (4)	0.5241 (3)	0.0482 (10)
H17A	0.5776	0.9512	0.5749	0.080*
H17B	0.3697	0.9762	0.5598	0.080*
C2	−0.1057 (5)	−0.2098 (4)	0.2257 (3)	0.0348 (8)
C9	0.5581 (6)	0.2347 (4)	0.1580 (3)	0.0399 (9)
H9A	0.4479	0.2386	0.1116	0.080*
H9B	0.6514	0.2042	0.1173	0.080*
C8	0.0173 (6)	0.1861 (4)	0.2290 (4)	0.0425 (9)
C15	0.3453 (7)	0.7136 (4)	0.4955 (3)	0.0471 (10)
H15A	0.4530	0.7088	0.5431	0.080*
H15B	0.2510	0.7457	0.5349	0.080*
O4	0.0377 (6)	0.2814 (3)	0.3106 (3)	0.0660 (10)
C11	0.4361 (6)	−0.0031 (4)	0.1285 (3)	0.0382 (9)
H11A	0.5276	−0.0251	0.0848	0.080*
H11B	0.3178	−0.0061	0.0849	0.080*
C14	0.3193 (7)	−0.3442 (4)	0.1527 (3)	0.0471 (10)
H14A	0.2141	−0.3248	0.1867	0.080*
H14B	0.4294	−0.3303	0.2059	0.080*
C1	−0.1397 (6)	−0.3493 (4)	0.2246 (3)	0.0416 (9)
N2	0.2714 (12)	−0.4793 (4)	0.0868 (4)	0.127 (3)
H2A	0.3834	−0.5044	0.0758	0.080*
H2B	0.2041	−0.4862	0.0246	0.080*
O1W	−0.2084 (5)	−0.3810 (4)	0.4810 (3)	0.0776 (11)
H1WA	−0.1693	−0.3764	0.4172	0.080*
H1WB	−0.1662	−0.3273	0.5476	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0578 (2)	0.03001 (19)	0.0447 (2)	0.00802 (14)	0.01112 (15)	0.01095 (14)
Ag2	0.0913 (3)	0.0387 (2)	0.0553 (2)	−0.00989 (18)	0.0051 (2)	0.02711 (18)
O3	0.071 (2)	0.0385 (17)	0.060 (2)	−0.0016 (15)	0.0111 (16)	0.0273 (15)
O2	0.082 (2)	0.0466 (19)	0.058 (2)	−0.0028 (16)	−0.0015 (17)	0.0349 (16)
C10	0.041 (2)	0.0270 (19)	0.038 (2)	0.0019 (15)	0.0110 (16)	0.0105 (16)
C5	0.0336 (19)	0.031 (2)	0.046 (2)	0.0040 (15)	0.0081 (16)	0.0171 (17)
C4	0.046 (2)	0.033 (2)	0.040 (2)	0.0087 (17)	0.0093 (17)	0.0121 (17)
C13	0.058 (3)	0.029 (2)	0.040 (2)	0.0010 (18)	0.0128 (19)	0.0162 (17)
N1	0.049 (2)	0.0255 (17)	0.051 (2)	0.0006 (14)	0.0140 (16)	0.0113 (15)
N3	0.052 (2)	0.0355 (19)	0.046 (2)	0.0046 (15)	0.0109 (16)	0.0124 (16)
C6	0.045 (2)	0.036 (2)	0.040 (2)	0.0041 (17)	0.0075 (17)	0.0193 (18)
C7	0.047 (2)	0.032 (2)	0.039 (2)	−0.0026 (17)	0.0053 (17)	0.0150 (17)
C3	0.048 (2)	0.038 (2)	0.036 (2)	0.0095 (17)	0.0114 (17)	0.0183 (17)
C12	0.046 (2)	0.030 (2)	0.037 (2)	0.0056 (16)	0.0095 (17)	0.0125 (16)
C16	0.058 (3)	0.032 (2)	0.039 (2)	0.0072 (18)	0.0113 (19)	0.0090 (17)
O1	0.119 (3)	0.0326 (17)	0.0449 (18)	−0.0114 (18)	0.0104 (19)	0.0144 (15)
C17	0.062 (3)	0.034 (2)	0.042 (2)	0.0029 (19)	0.011 (2)	0.0083 (19)
C2	0.036 (2)	0.030 (2)	0.041 (2)	0.0044 (15)	0.0088 (16)	0.0159 (17)
C9	0.051 (2)	0.027 (2)	0.041 (2)	0.0023 (17)	0.0129 (18)	0.0121 (17)
C8	0.039 (2)	0.035 (2)	0.056 (3)	0.0073 (17)	0.0064 (18)	0.022 (2)
C15	0.063 (3)	0.034 (2)	0.039 (2)	0.0050 (19)	0.014 (2)	0.0071 (18)
O4	0.103 (3)	0.0320 (17)	0.057 (2)	0.0030 (17)	0.0073 (19)	0.0154 (16)
C11	0.049 (2)	0.027 (2)	0.038 (2)	0.0033 (16)	0.0090 (17)	0.0113 (16)
C14	0.065 (3)	0.031 (2)	0.051 (3)	0.0056 (19)	0.020 (2)	0.0185 (19)
C1	0.048 (2)	0.033 (2)	0.046 (2)	0.0029 (17)	0.0124 (19)	0.0170 (19)
N2	0.288 (9)	0.034 (3)	0.050 (3)	−0.028 (4)	0.052 (4)	0.012 (2)
O1W	0.081 (3)	0.091 (3)	0.050 (2)	−0.019 (2)	0.0043 (18)	0.026 (2)

Geometric parameters (Å, º)

Ag1—N3	2.120 (4)	C3—C2	1.388 (5)
Ag1—N1	2.125 (3)	C3—H3A	0.9600
Ag1—Ag2	3.0646 (14)	C12—C11	1.518 (5)
Ag2—O3	2.092 (3)	C12—H12A	0.9600
Ag2—N2^i	2.133 (4)	C12—H12B	0.9600
O3—C8	1.269 (5)	C16—C15	1.510 (6)
O2—C1	1.240 (5)	C16—C17	1.518 (6)
C10—C9	1.510 (5)	C16—H16A	0.9600
C10—C11	1.527 (5)	C16—H16B	0.9600
C10—H10A	0.9600	O1—C1	1.247 (5)
C10—H10B	0.9600	C17—C17^ii	1.517 (8)
C5—C6	1.389 (5)	C17—H17A	0.9600
C5—C4	1.390 (6)	C17—H17B	0.9600
C5—C8	1.508 (5)	C2—C1	1.511 (5)
C4—C3	1.381 (6)	C9—H9A	0.9600
C4—H4A	0.9600	C9—H9B	0.9600
C13—C12	1.512 (5)	C8—O4	1.225 (5)
C13—C14	1.512 (5)	C15—H15A	0.9601
C13—H13A	0.9600	C15—H15B	0.9600
C13—H13B	0.9600	C11—H11A	0.9600
N1—C9	1.483 (5)	C11—H11B	0.9600
N1—H1A	0.8999	C14—N2	1.415 (6)
N1—H1B	0.9000	C14—H14A	0.9600
N3—C15	1.480 (5)	C14—H14B	0.9600
N3—H3B	0.9001	N2—Ag2^iii	2.133 (4)
N3—H3C	0.9000	N2—H2A	0.9000
C6—C7	1.378 (5)	N2—H2B	0.9000
C6—H6A	0.9600	O1W—H1WA	0.9876
C7—C2	1.382 (5)	O1W—H1WB	0.8931
C7—H7A	0.9600
N3—Ag1—N1	177.80 (13)	C15—C16—C17	112.4 (3)
N3—Ag1—Ag2	87.93 (10)	C15—C16—H16A	109.4
N1—Ag1—Ag2	89.89 (10)	C17—C16—H16A	109.3
O3—Ag2—N2^i	158.96 (18)	C15—C16—H16B	108.9
O3—Ag2—Ag1	98.98 (10)	C17—C16—H16B	108.8
N2^i—Ag2—Ag1	87.55 (18)	H16A—C16—H16B	108.0
C8—O3—Ag2	118.5 (3)	C17^ii—C17—C16	113.8 (4)
C9—C10—C11	112.2 (3)	C17^ii—C17—H17A	108.4
C9—C10—H10A	109.2	C16—C17—H17A	108.4
C11—C10—H10A	109.3	C17^ii—C17—H17B	109.3
C9—C10—H10B	109.1	C16—C17—H17B	108.9
C11—C10—H10B	109.0	H17A—C17—H17B	107.8
H10A—C10—H10B	108.0	C7—C2—C3	118.5 (3)
C6—C5—C4	118.7 (4)	C7—C2—C1	120.9 (4)
C6—C5—C8	120.7 (4)	C3—C2—C1	120.6 (3)
C4—C5—C8	120.6 (4)	N1—C9—C10	111.8 (3)
C3—C4—C5	120.6 (4)	N1—C9—H9A	109.2
C3—C4—H4A	119.9	C10—C9—H9A	109.1
C5—C4—H4A	119.5	N1—C9—H9B	109.5
C12—C13—C14	111.5 (3)	C10—C9—H9B	109.2
C12—C13—H13A	109.2	H9A—C9—H9B	108.0
C14—C13—H13A	109.4	O4—C8—O3	124.3 (4)
C12—C13—H13B	109.4	O4—C8—C5	120.2 (4)
C14—C13—H13B	109.2	O3—C8—C5	115.5 (4)
H13A—C13—H13B	108.1	N3—C15—C16	111.9 (3)
C9—N1—Ag1	119.4 (3)	N3—C15—H15A	108.7
C9—N1—H1A	107.4	C16—C15—H15A	108.9
Ag1—N1—H1A	107.5	N3—C15—H15B	109.9
C9—N1—H1B	107.4	C16—C15—H15B	109.3
Ag1—N1—H1B	107.5	H15A—C15—H15B	108.0
H1A—N1—H1B	107.0	C12—C11—C10	113.3 (3)
C15—N3—Ag1	118.1 (3)	C12—C11—H11A	108.8
C15—N3—H3B	107.6	C10—C11—H11A	109.0
Ag1—N3—H3B	107.8	C12—C11—H11B	108.9
C15—N3—H3C	107.8	C10—C11—H11B	108.9
Ag1—N3—H3C	107.8	H11A—C11—H11B	107.9
H3B—N3—H3C	107.2	N2—C14—C13	116.3 (4)
C7—C6—C5	120.2 (4)	N2—C14—H14A	106.0
C7—C6—H6A	120.2	C13—C14—H14A	108.3
C5—C6—H6A	119.6	N2—C14—H14B	110.3
C6—C7—C2	121.3 (4)	C13—C14—H14B	108.0
C6—C7—H7A	119.3	H14A—C14—H14B	107.5
C2—C7—H7A	119.4	O2—C1—O1	124.2 (4)
C4—C3—C2	120.6 (4)	O2—C1—C2	117.8 (4)
C4—C3—H3A	119.6	O1—C1—C2	118.0 (4)
C2—C3—H3A	119.8	C14—N2—Ag2^iii	120.5 (3)
C13—C12—C11	113.6 (3)	C14—N2—H2A	104.9
C13—C12—H12A	108.9	Ag2^iii—N2—H2A	105.9
C11—C12—H12A	108.8	C14—N2—H2B	109.0
C13—C12—H12B	108.7	Ag2^iii—N2—H2B	108.7
C11—C12—H12B	108.8	H2A—N2—H2B	107.2
H12A—C12—H12B	107.8	H1WA—O1W—H1WB	129.7
N3—Ag1—Ag2—O3	−96.44 (14)	C4—C3—C2—C7	−0.2 (6)
N1—Ag1—Ag2—O3	83.88 (13)	C4—C3—C2—C1	178.1 (4)
N3—Ag1—Ag2—N2^i	103.7 (2)	Ag1—N1—C9—C10	−65.5 (4)
N1—Ag1—Ag2—N2^i	−76.0 (2)	C11—C10—C9—N1	−176.2 (3)
N2^i—Ag2—O3—C8	147.7 (6)	Ag2—O3—C8—O4	10.9 (6)
Ag1—Ag2—O3—C8	40.8 (3)	Ag2—O3—C8—C5	−170.7 (2)
C6—C5—C4—C3	1.1 (6)	C6—C5—C8—O4	169.8 (4)
C8—C5—C4—C3	−178.2 (4)	C4—C5—C8—O4	−11.0 (6)
N3—Ag1—N1—C9	−49 (3)	C6—C5—C8—O3	−8.7 (6)
Ag2—Ag1—N1—C9	−41.2 (3)	C4—C5—C8—O3	170.6 (4)
N1—Ag1—N3—C15	−131 (3)	Ag1—N3—C15—C16	64.9 (4)
Ag2—Ag1—N3—C15	−139.6 (3)	C17—C16—C15—N3	175.2 (4)
C4—C5—C6—C7	0.7 (6)	C13—C12—C11—C10	−176.0 (3)
C8—C5—C6—C7	180.0 (4)	C9—C10—C11—C12	171.4 (3)
C5—C6—C7—C2	−2.3 (6)	C12—C13—C14—N2	−178.8 (5)
C5—C4—C3—C2	−1.3 (6)	C7—C2—C1—O2	165.2 (4)
C14—C13—C12—C11	−177.1 (4)	C3—C2—C1—O2	−13.0 (6)
C15—C16—C17—C17^ii	−178.4 (5)	C7—C2—C1—O1	−13.6 (6)
C6—C7—C2—C3	2.0 (6)	C3—C2—C1—O1	168.2 (4)
C6—C7—C2—C1	−176.3 (4)	C13—C14—N2—Ag2^iii	−159.7 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4^iv	0.90	2.47	3.283 (5)	151
N1—H1B···O1^v	0.90	2.13	3.023 (5)	172
N1—H1B···O2^v	0.90	2.55	3.090 (5)	119
N3—H3B···O1W^vi	0.90	2.15	2.998 (5)	157
N3—H3C···O2^i	0.90	2.13	2.997 (5)	163
N2—H2B···O1^vii	0.90	2.18	2.924 (6)	140
O1W—H1WA···O2	0.99	1.76	2.749 (5)	177
O1W—H1WB···O4^vi	0.89	1.92	2.751 (5)	155

Symmetry codes: (i) x, y+1, z; (iv) x+1, y, z; (v) x+1, y+1, z; (vi) −x, −y, −z+1; (vii) −x, −y−1, −z.