μ-Piperidine-κ²N:N′-bis­[(3-nitro­benzoato-κO)silver(I)] monohydrate

The title compound, [Ag₂(C₇H₄NO₄)₂(C₄H₁₀N₂)]·H₂O, has two similar dinuclear Ag^I complex molecules, each with a crystallographic inversion center; the asymmetric unit contains half of each molecule and a molecule of water. Each Ag atom in the compound is coordinated by one O atom from a 3-nitro­benzoate anion and one N atom from a piperidine bridge, in a slightly distorted linear geometry.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.051
• wR factor = 0.115
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT731_ALERT_1_B Bond    Calc     0.84(5), Rep   0.841(10) ......       5.00 su-Rat
              O9   -H1      1.555   1.555
PLAT731_ALERT_1_B Bond    Calc     0.89(5), Rep   0.897(10) ......       5.00 su-Rat
              N4   -H4A     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.89(5), Rep   0.897(10) ......       5.00 su-Rat
              N4   -H4A     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.84(5), Rep   0.841(10) ......       5.00 su-Rat
              O9   -H1      1.555   1.555
PLAT736_ALERT_1_B H...A   Calc     1.91(5), Rep   1.905(12) ......       4.17 su-Rat
              H1   -O6      1.555   1.555

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT731_ALERT_1_C Bond    Calc     0.84(4), Rep   0.841(10) ......       4.00 su-Rat
              O9   -H2      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.90(3), Rep   0.895(10) ......       3.00 su-Rat
              N2   -H2A     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.90(3), Rep   0.895(10) ......       3.00 su-Rat
              N2   -H2A     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(4), Rep   0.841(10) ......       4.00 su-Rat
              O9   -H2      1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.10(5), Rep   2.094(19) ......       2.63 su-Rat
              H4A  -O6      1.555   3.656

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

  10 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

µ-Piperidine-κ²N:N'-bis[(3-nitrobenzoato-κO)silver(I)] monohydrate

Crystal data

[Ag2(C7H4NO4)2(C4H10N2)]·H2O	F(000) = 1288
Mr = 652.12	Dx = 2.052 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.285 (1) Å	Cell parameters from 2560 reflections
b = 24.298 (2) Å	θ = 2.4–25.8°
c = 11.945 (1) Å	µ = 1.92 mm^−1
β = 93.523 (2)°	T = 298 K
V = 2110.4 (4) Å^3	Block, yellow
Z = 4	0.37 × 0.25 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4571 independent reflections
Radiation source: fine-focus sealed tube	3873 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.532, Tmax = 0.767	k = −30→30
17019 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0377P)^2 + 6.6578P] where P = (Fo^2 + 2Fc^2)/3
4571 reflections	(Δ/σ)max < 0.001
314 parameters	Δρmax = 2.03 e Å^−3
5 restraints	Δρmin = −1.90 e Å^−3

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	0.68212 (6)	0.074743 (16)	0.95235 (4)	0.05264 (14)
Ag2	0.66994 (6)	0.068490 (17)	0.50907 (5)	0.07046 (18)
O1	0.5335 (6)	0.14164 (15)	0.8805 (3)	0.0614 (10)
O2	0.4446 (8)	0.09671 (16)	0.7235 (4)	0.0888 (16)
O3	0.4740 (6)	0.33842 (17)	0.8990 (4)	0.0714 (12)
O4	0.3434 (6)	0.38385 (15)	0.7614 (4)	0.0700 (12)
O5	0.5455 (6)	0.13970 (15)	0.4327 (3)	0.0609 (10)
O6	0.3836 (6)	0.08316 (14)	0.3169 (4)	0.0753 (13)
O7	0.4811 (6)	0.33634 (15)	0.3761 (4)	0.0732 (12)
O8	0.3892 (7)	0.36857 (17)	0.2163 (4)	0.0887 (15)
O9	0.5298 (7)	0.00414 (18)	0.1843 (4)	0.0701 (12)
N1	0.3969 (6)	0.34084 (16)	0.8058 (4)	0.0485 (10)
N2	0.8497 (5)	0.02088 (15)	1.0581 (3)	0.0354 (8)
N3	0.4204 (6)	0.33031 (16)	0.2800 (4)	0.0511 (10)
N4	0.8345 (6)	−0.00314 (17)	0.5585 (4)	0.0504 (10)
C1	0.4602 (7)	0.1386 (2)	0.7824 (5)	0.0513 (12)
C2	0.3922 (6)	0.19242 (18)	0.7321 (4)	0.0363 (9)
C3	0.3108 (6)	0.1945 (2)	0.6249 (4)	0.0434 (11)
H3	0.2912	0.1621	0.5845	0.052*
C4	0.2579 (6)	0.2443 (2)	0.5771 (4)	0.0466 (11)
H4	0.2026	0.2449	0.5048	0.056*
C5	0.2855 (6)	0.2926 (2)	0.6343 (4)	0.0441 (11)
H5	0.2517	0.3262	0.6017	0.053*
C6	0.3655 (6)	0.28982 (18)	0.7424 (4)	0.0350 (9)
C7	0.4178 (6)	0.24085 (18)	0.7927 (4)	0.0348 (9)
H7	0.4693	0.2402	0.8659	0.042*
C8	1.0395 (7)	0.0396 (2)	1.0840 (4)	0.0494 (12)
H8A	1.0975	0.0165	1.1423	0.059*
H8B	1.0385	0.0771	1.1115	0.059*
C9	0.8530 (7)	−0.03679 (19)	1.0184 (5)	0.0482 (12)
H9A	0.7285	−0.0497	1.0010	0.058*
H9B	0.9094	−0.0602	1.0766	0.058*
C10	0.4427 (8)	0.12920 (19)	0.3459 (5)	0.0525 (14)
C11	0.3918 (6)	0.17775 (18)	0.2711 (4)	0.0383 (10)
C12	0.3151 (7)	0.1701 (2)	0.1631 (5)	0.0526 (13)
H12	0.2917	0.1346	0.1368	0.063*
C13	0.2727 (7)	0.2146 (3)	0.0936 (4)	0.0576 (14)
H13	0.2221	0.2087	0.0212	0.069*
C14	0.3047 (7)	0.2672 (2)	0.1308 (4)	0.0487 (12)
H14	0.2751	0.2973	0.0850	0.058*
C15	0.3824 (6)	0.27426 (18)	0.2384 (4)	0.0374 (9)
C16	0.4265 (5)	0.23108 (17)	0.3089 (4)	0.0321 (9)
H16	0.4788	0.2374	0.3808	0.039*
C17	1.0131 (8)	0.01112 (19)	0.6161 (4)	0.0502 (13)
H17A	1.0734	−0.0221	0.6446	0.060*
H17B	0.9935	0.0351	0.6793	0.060*
C18	0.8675 (7)	−0.03935 (18)	0.4627 (5)	0.0497 (12)
H18A	0.7512	−0.0490	0.4238	0.060*
H18B	0.9264	−0.0730	0.4897	0.060*
H1	0.489 (9)	0.0289 (17)	0.225 (4)	0.09 (2)*
H2	0.540 (10)	−0.0251 (13)	0.222 (4)	0.09 (3)*
H2A	0.785 (5)	0.0204 (18)	1.120 (2)	0.032 (12)*
H4A	0.767 (7)	−0.022 (2)	0.605 (4)	0.067 (18)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0512 (2)	0.0434 (2)	0.0627 (3)	0.01633 (16)	−0.00099 (18)	0.00906 (17)
Ag2	0.0541 (3)	0.0412 (2)	0.1169 (4)	0.01428 (18)	0.0116 (3)	0.0248 (2)
O1	0.073 (3)	0.048 (2)	0.061 (2)	0.0236 (18)	−0.0126 (19)	0.0036 (17)
O2	0.129 (4)	0.035 (2)	0.098 (3)	0.008 (2)	−0.032 (3)	−0.016 (2)
O3	0.089 (3)	0.054 (2)	0.069 (3)	0.002 (2)	−0.011 (2)	−0.025 (2)
O4	0.099 (3)	0.0325 (19)	0.082 (3)	0.0035 (19)	0.029 (2)	0.0074 (18)
O5	0.078 (3)	0.043 (2)	0.063 (2)	0.0231 (19)	0.015 (2)	0.0131 (18)
O6	0.089 (3)	0.0272 (18)	0.115 (4)	−0.0083 (18)	0.052 (3)	−0.001 (2)
O7	0.095 (3)	0.038 (2)	0.084 (3)	−0.003 (2)	−0.016 (3)	−0.014 (2)
O8	0.121 (4)	0.038 (2)	0.107 (4)	0.007 (2)	0.008 (3)	0.028 (2)
O9	0.084 (3)	0.050 (2)	0.080 (3)	−0.001 (2)	0.036 (2)	−0.005 (2)
N1	0.054 (3)	0.034 (2)	0.059 (3)	−0.0019 (18)	0.019 (2)	−0.0030 (19)
N2	0.0368 (19)	0.0347 (19)	0.0353 (19)	0.0058 (15)	0.0082 (15)	0.0027 (15)
N3	0.049 (2)	0.030 (2)	0.075 (3)	0.0021 (17)	0.010 (2)	0.006 (2)
N4	0.051 (3)	0.034 (2)	0.067 (3)	0.0024 (18)	0.019 (2)	0.0160 (19)
C1	0.047 (3)	0.037 (3)	0.068 (3)	0.005 (2)	−0.004 (2)	−0.001 (2)
C2	0.028 (2)	0.037 (2)	0.043 (2)	0.0018 (17)	−0.0019 (17)	−0.0033 (18)
C3	0.037 (2)	0.051 (3)	0.042 (3)	0.001 (2)	0.0031 (19)	−0.012 (2)
C4	0.035 (2)	0.071 (3)	0.033 (2)	0.004 (2)	−0.0043 (18)	−0.003 (2)
C5	0.036 (2)	0.052 (3)	0.045 (3)	0.008 (2)	0.011 (2)	0.015 (2)
C6	0.031 (2)	0.037 (2)	0.038 (2)	−0.0002 (17)	0.0070 (17)	0.0003 (18)
C7	0.029 (2)	0.039 (2)	0.036 (2)	0.0006 (17)	−0.0019 (17)	0.0004 (17)
C8	0.044 (3)	0.047 (3)	0.057 (3)	0.006 (2)	−0.002 (2)	−0.021 (2)
C9	0.039 (3)	0.032 (2)	0.075 (4)	−0.0015 (19)	0.011 (2)	0.002 (2)
C10	0.058 (3)	0.031 (2)	0.073 (4)	0.008 (2)	0.039 (3)	0.004 (2)
C11	0.035 (2)	0.033 (2)	0.049 (3)	−0.0038 (18)	0.0152 (19)	−0.0028 (19)
C12	0.046 (3)	0.053 (3)	0.059 (3)	−0.020 (2)	0.011 (2)	−0.020 (3)
C13	0.042 (3)	0.091 (4)	0.039 (3)	−0.010 (3)	−0.002 (2)	−0.010 (3)
C14	0.039 (3)	0.063 (3)	0.044 (3)	0.002 (2)	0.001 (2)	0.014 (2)
C15	0.030 (2)	0.036 (2)	0.048 (3)	−0.0008 (17)	0.0065 (18)	0.0033 (19)
C16	0.029 (2)	0.031 (2)	0.036 (2)	−0.0001 (16)	0.0031 (16)	−0.0015 (16)
C17	0.081 (4)	0.032 (2)	0.036 (2)	0.012 (2)	−0.003 (2)	0.0019 (19)
C18	0.050 (3)	0.025 (2)	0.071 (3)	−0.0030 (19)	−0.018 (2)	0.002 (2)

Geometric parameters (Å, º)

Ag1—O1	2.107 (3)	C4—H4	0.9300
Ag1—N2	2.147 (4)	C5—C6	1.386 (6)
Ag2—O5	2.132 (3)	C5—H5	0.9300
Ag2—N4	2.174 (4)	C6—C7	1.376 (6)
O1—C1	1.259 (6)	C7—H7	0.9300
O2—C1	1.239 (6)	C8—C9^i	1.494 (7)
O3—N1	1.218 (6)	C8—H8A	0.9700
O4—N1	1.225 (5)	C8—H8B	0.9700
O5—C10	1.267 (7)	C9—C8^i	1.494 (7)
O6—C10	1.240 (6)	C9—H9A	0.9700
O7—N3	1.213 (6)	C9—H9B	0.9700
O8—N3	1.214 (6)	C10—C11	1.513 (7)
O9—H1	0.841 (10)	C11—C12	1.387 (7)
O9—H2	0.841 (10)	C11—C16	1.391 (6)
N1—C6	1.463 (6)	C12—C13	1.388 (8)
N2—C8	1.470 (6)	C12—H12	0.9300
N2—C9	1.480 (6)	C13—C14	1.366 (8)
N2—H2A	0.895 (10)	C13—H13	0.9300
N3—C15	1.470 (6)	C14—C15	1.383 (7)
N4—C18	1.475 (7)	C14—H14	0.9300
N4—C17	1.475 (7)	C15—C16	1.371 (6)
N4—H4A	0.897 (10)	C16—H16	0.9300
C1—C2	1.510 (6)	C17—C18^ii	1.488 (7)
C2—C3	1.378 (6)	C17—H17A	0.9700
C2—C7	1.388 (6)	C17—H17B	0.9700
C3—C4	1.383 (7)	C18—C17^ii	1.488 (7)
C3—H3	0.9300	C18—H18A	0.9700
C4—C5	1.367 (7)	C18—H18B	0.9700
O1—Ag1—N2	165.85 (15)	N2—C8—H8A	109.6
O5—Ag2—N4	168.12 (16)	C9^i—C8—H8A	109.6
C1—O1—Ag1	120.8 (3)	N2—C8—H8B	109.6
C10—O5—Ag2	113.6 (3)	C9^i—C8—H8B	109.6
H1—O9—H2	108 (3)	H8A—C8—H8B	108.1
O3—N1—O4	123.6 (5)	N2—C9—C8^i	109.0 (4)
O3—N1—C6	118.7 (4)	N2—C9—H9A	109.9
O4—N1—C6	117.6 (4)	C8^i—C9—H9A	109.9
C8—N2—C9	109.0 (3)	N2—C9—H9B	109.9
C8—N2—Ag1	115.4 (3)	C8^i—C9—H9B	109.9
C9—N2—Ag1	114.1 (3)	H9A—C9—H9B	108.3
C8—N2—H2A	111 (3)	O6—C10—O5	126.0 (5)
C9—N2—H2A	106 (3)	O6—C10—C11	118.0 (6)
Ag1—N2—H2A	101 (3)	O5—C10—C11	116.0 (4)
O7—N3—O8	123.0 (5)	C12—C11—C16	118.9 (4)
O7—N3—C15	118.8 (4)	C12—C11—C10	121.0 (4)
O8—N3—C15	118.2 (5)	C16—C11—C10	120.1 (4)
C18—N4—C17	108.7 (4)	C11—C12—C13	120.9 (5)
C18—N4—Ag2	112.3 (3)	C11—C12—H12	119.5
C17—N4—Ag2	113.2 (3)	C13—C12—H12	119.5
C18—N4—H4A	107 (4)	C14—C13—C12	120.5 (5)
C17—N4—H4A	110 (4)	C14—C13—H13	119.8
Ag2—N4—H4A	105 (4)	C12—C13—H13	119.8
O2—C1—O1	126.5 (5)	C13—C14—C15	118.1 (5)
O2—C1—C2	118.0 (5)	C13—C14—H14	121.0
O1—C1—C2	115.5 (4)	C15—C14—H14	121.0
C3—C2—C7	119.3 (4)	C16—C15—C14	122.9 (4)
C3—C2—C1	120.9 (4)	C16—C15—N3	118.0 (4)
C7—C2—C1	119.8 (4)	C14—C15—N3	119.2 (4)
C2—C3—C4	120.6 (4)	C15—C16—C11	118.8 (4)
C2—C3—H3	119.7	C15—C16—H16	120.6
C4—C3—H3	119.7	C11—C16—H16	120.6
C5—C4—C3	121.1 (4)	N4—C17—C18^ii	110.3 (4)
C5—C4—H4	119.5	N4—C17—H17A	109.6
C3—C4—H4	119.5	C18^ii—C17—H17A	109.6
C4—C5—C6	117.7 (4)	N4—C17—H17B	109.6
C4—C5—H5	121.1	C18^ii—C17—H17B	109.6
C6—C5—H5	121.1	H17A—C17—H17B	108.1
C7—C6—C5	122.5 (4)	N4—C18—C17^ii	110.2 (4)
C7—C6—N1	118.5 (4)	N4—C18—H18A	109.6
C5—C6—N1	119.0 (4)	C17^ii—C18—H18A	109.6
C6—C7—C2	118.8 (4)	N4—C18—H18B	109.6
C6—C7—H7	120.6	C17^ii—C18—H18B	109.6
C2—C7—H7	120.6	H18A—C18—H18B	108.1
N2—C8—C9^i	110.3 (4)
N2—Ag1—O1—C1	173.1 (5)	Ag1—N2—C8—C9^i	−69.6 (4)
N4—Ag2—O5—C10	76.8 (10)	C8—N2—C9—C8^i	−59.5 (6)
O1—Ag1—N2—C8	−58.6 (7)	Ag1—N2—C9—C8^i	71.1 (4)
O1—Ag1—N2—C9	174.0 (6)	Ag2—O5—C10—O6	14.7 (7)
O5—Ag2—N4—C18	−45.0 (10)	Ag2—O5—C10—C11	−164.2 (3)
O5—Ag2—N4—C17	78.6 (10)	O6—C10—C11—C12	−13.2 (7)
Ag1—O1—C1—O2	9.7 (9)	O5—C10—C11—C12	165.8 (4)
Ag1—O1—C1—C2	−167.9 (3)	O6—C10—C11—C16	168.6 (4)
O2—C1—C2—C3	1.7 (8)	O5—C10—C11—C16	−12.3 (6)
O1—C1—C2—C3	179.5 (5)	C16—C11—C12—C13	−0.2 (7)
O2—C1—C2—C7	−175.9 (5)	C10—C11—C12—C13	−178.4 (5)
O1—C1—C2—C7	1.9 (7)	C11—C12—C13—C14	−0.5 (8)
C7—C2—C3—C4	1.2 (7)	C12—C13—C14—C15	0.9 (8)
C1—C2—C3—C4	−176.5 (4)	C13—C14—C15—C16	−0.6 (7)
C2—C3—C4—C5	0.3 (7)	C13—C14—C15—N3	179.2 (4)
C3—C4—C5—C6	−1.0 (7)	O7—N3—C15—C16	−3.3 (7)
C4—C5—C6—C7	0.4 (7)	O8—N3—C15—C16	176.8 (5)
C4—C5—C6—N1	180.0 (4)	O7—N3—C15—C14	176.8 (5)
O3—N1—C6—C7	2.5 (6)	O8—N3—C15—C14	−3.1 (7)
O4—N1—C6—C7	−177.4 (4)	C14—C15—C16—C11	−0.1 (7)
O3—N1—C6—C5	−177.1 (5)	N3—C15—C16—C11	−179.9 (4)
O4—N1—C6—C5	3.0 (6)	C12—C11—C16—C15	0.5 (6)
C5—C6—C7—C2	1.1 (6)	C10—C11—C16—C15	178.7 (4)
N1—C6—C7—C2	−178.5 (4)	C18—N4—C17—C18^ii	59.1 (5)
C3—C2—C7—C6	−1.8 (6)	Ag2—N4—C17—C18^ii	−66.5 (4)
C1—C2—C7—C6	175.9 (4)	C17—N4—C18—C17^ii	−59.1 (5)
C9—N2—C8—C9^i	60.4 (6)	Ag2—N4—C18—C17^ii	67.1 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O6^iii	0.90 (1)	2.09 (2)	2.968 (5)	165 (5)
N2—H2A···O9^iv	0.90 (1)	2.10 (3)	2.881 (6)	146 (4)
O9—H2···O2^iii	0.84 (1)	1.86 (2)	2.688 (6)	168 (6)
O9—H1···O6	0.84 (1)	1.91 (1)	2.745 (6)	177 (7)

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