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A novel silver-containing compound, bis(benzylamino)silver(I) benzylcarbamate, with an unusual molecular structure is easily synthesized by the reaction of benzylammonium benzylcarbamate and silver oxide. It crystallizes in the triclinic crystal system with the space group P\bar 1 with a = 5.2006 (5), b = 14.6298 (15), c = 14.7246 (15) Å, α = 68.729 (2), β = 83.507 (2), γ = 85.412 (2)° and Z = 2. In the crystal, one Ag atom coordinates with the two amino groups in two benzylamine molecules, and there are no silver–silver and silver–oxygen interactions. The carboxylate groups take part in balancing the electric charge and forming hydrogen bonds. Both the compound and the starting material benzylammonium benzylcarbamate exhibit room-temperature solid-state emissions with the peaks at 300 and 406 nm, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768112030212/bp5042sup1.cif
Contains datablock I

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112030212/bp5042Isup2.fcf
Contains datablock I

CCDC reference: 898968

Computing details top

Data collection: Bruker SMART; cell refinement: Bruker SMART; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Bruker SHELXTL.

(I) top
Crystal data top
C22H26AgN3O2Z = 2
Mr = 472.33F(000) = 484
Triclinic, P1Dx = 1.514 Mg m3
a = 5.2006 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.6298 (15) ÅCell parameters from 328 reflections
c = 14.7246 (15) Åθ = 2.5–26.0°
α = 68.729 (2)°µ = 0.99 mm1
β = 83.507 (2)°T = 293 K
γ = 85.412 (2)°Block, colourless
V = 1036.37 (18) Å30.32 × 0.28 × 0.26 mm
Data collection top
Bruker
diffractometer
4009 independent reflections
Radiation source: fine-focus sealed tube3622 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Semisphere scansθmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan
SADABS
h = 65
Tmin = 0.741, Tmax = 0.782k = 1716
6094 measured reflectionsl = 1814
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.068 w = 1/[σ2(Fo2) + (0.0323P)2 + 0.2277P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.002
4009 reflectionsΔρmax = 0.33 e Å3
254 parametersΔρmin = 0.51 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0129 (11)
Special details top

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 (Å2) top
xyzUiso*/Ueq
Ag10.53362 (3)0.873586 (12)0.034393 (13)0.04639 (9)
C10.1886 (4)0.80409 (18)0.09264 (18)0.0475 (5)
H1A0.06770.82620.14260.057*
H1B0.10200.75810.03390.057*
C20.4212 (5)0.75304 (17)0.12702 (17)0.0462 (5)
C30.5345 (6)0.7933 (2)0.2216 (2)0.0594 (7)
H30.46320.85110.26440.071*
C40.7522 (6)0.7489 (3)0.2537 (3)0.0741 (9)
H40.82700.77700.31750.089*
C50.8568 (6)0.6642 (3)0.1918 (3)0.0804 (10)
H51.00300.63420.21330.096*
C60.7476 (7)0.6233 (2)0.0984 (3)0.0844 (11)
H60.81970.56530.05640.101*
C70.5290 (6)0.6676 (2)0.0653 (2)0.0652 (7)
H70.45590.63930.00130.078*
C80.9235 (5)0.75033 (17)0.19255 (18)0.0478 (5)
H8A1.00050.75030.24960.057*
H8B1.06170.73890.14730.057*
C90.7383 (4)0.66834 (16)0.22339 (16)0.0429 (5)
C100.7522 (5)0.60312 (19)0.17517 (19)0.0550 (6)
H100.87910.60920.12370.066*
C110.5795 (6)0.5284 (2)0.2022 (2)0.0629 (7)
H110.59090.48490.16870.075*
C120.3928 (5)0.51837 (19)0.2778 (2)0.0613 (7)
H120.27650.46840.29590.074*
C130.3778 (5)0.5821 (2)0.3268 (2)0.0646 (7)
H130.25180.57520.37870.078*
C140.5484 (5)0.6568 (2)0.2999 (2)0.0561 (6)
H140.53560.70000.33370.067*
C151.0662 (5)0.2159 (2)0.56050 (19)0.0591 (7)
H151.19470.19490.60360.071*
C161.0397 (6)0.3139 (2)0.5046 (2)0.0688 (8)
H161.14940.35830.51040.083*
C170.8519 (6)0.3464 (2)0.4403 (2)0.0678 (8)
H170.83150.41280.40310.081*
C180.6956 (6)0.2800 (3)0.4316 (2)0.0736 (9)
H180.57010.30120.38730.088*
C190.7216 (5)0.1818 (2)0.4878 (2)0.0634 (7)
H190.61310.13760.48110.076*
C200.9076 (4)0.1481 (2)0.55430 (16)0.0482 (6)
C210.9360 (5)0.04127 (19)0.61706 (17)0.0522 (6)
H21A0.78750.00780.61200.063*
H21B1.08910.01270.59170.063*
C220.7457 (4)0.03002 (15)0.78199 (16)0.0380 (5)
N10.2648 (4)0.88914 (13)0.07174 (13)0.0408 (4)
H1C0.11800.91740.05350.049*
H1D0.33040.93250.12890.049*
N20.7950 (4)0.84740 (13)0.14526 (14)0.0421 (4)
H2A0.92160.89030.11890.050*
H2B0.70710.86430.19350.050*
N30.9570 (4)0.02365 (15)0.71937 (13)0.0466 (5)
H3A1.10670.00870.74160.056*
O10.5253 (3)0.04092 (13)0.75078 (12)0.0485 (4)
O20.7879 (3)0.02260 (11)0.86767 (11)0.0427 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.04028 (12)0.04843 (13)0.05196 (13)0.00295 (7)0.01089 (8)0.01752 (9)
C10.0422 (13)0.0505 (13)0.0529 (13)0.0076 (10)0.0076 (10)0.0202 (11)
C20.0457 (13)0.0481 (13)0.0520 (13)0.0058 (10)0.0114 (10)0.0237 (11)
C30.0634 (17)0.0626 (16)0.0565 (15)0.0000 (13)0.0048 (13)0.0271 (13)
C40.0660 (19)0.092 (2)0.082 (2)0.0063 (17)0.0049 (16)0.0550 (19)
C50.0607 (19)0.090 (2)0.123 (3)0.0092 (17)0.021 (2)0.076 (2)
C60.090 (2)0.0589 (18)0.118 (3)0.0236 (17)0.051 (2)0.0405 (19)
C70.0736 (19)0.0557 (16)0.0671 (17)0.0033 (14)0.0224 (15)0.0194 (14)
C80.0394 (12)0.0503 (13)0.0541 (14)0.0004 (10)0.0124 (10)0.0170 (11)
C90.0383 (12)0.0437 (12)0.0446 (12)0.0037 (9)0.0138 (10)0.0114 (10)
C100.0589 (16)0.0533 (15)0.0533 (14)0.0044 (12)0.0027 (12)0.0199 (12)
C110.0725 (19)0.0494 (15)0.0709 (18)0.0042 (13)0.0139 (15)0.0240 (13)
C120.0535 (16)0.0459 (14)0.0745 (18)0.0083 (12)0.0150 (14)0.0056 (13)
C130.0504 (15)0.0660 (18)0.0691 (18)0.0071 (13)0.0057 (13)0.0164 (14)
C140.0517 (15)0.0584 (16)0.0608 (16)0.0029 (12)0.0037 (12)0.0244 (13)
C150.0509 (15)0.0737 (18)0.0482 (14)0.0044 (13)0.0109 (11)0.0141 (13)
C160.0680 (19)0.076 (2)0.0597 (17)0.0122 (15)0.0023 (14)0.0203 (15)
C170.0609 (18)0.0726 (19)0.0554 (16)0.0053 (15)0.0036 (13)0.0097 (14)
C180.0538 (17)0.093 (2)0.0601 (17)0.0114 (16)0.0175 (13)0.0103 (16)
C190.0461 (14)0.086 (2)0.0589 (16)0.0034 (14)0.0118 (12)0.0244 (15)
C200.0380 (12)0.0698 (16)0.0353 (11)0.0021 (11)0.0007 (9)0.0189 (11)
C210.0477 (14)0.0657 (16)0.0452 (13)0.0019 (12)0.0011 (11)0.0239 (12)
C220.0315 (11)0.0367 (11)0.0444 (12)0.0021 (8)0.0026 (9)0.0128 (9)
N10.0351 (9)0.0420 (10)0.0435 (10)0.0008 (8)0.0033 (8)0.0135 (8)
N20.0378 (10)0.0424 (10)0.0497 (11)0.0046 (8)0.0054 (8)0.0198 (8)
N30.0321 (9)0.0639 (12)0.0397 (10)0.0034 (9)0.0036 (8)0.0145 (9)
O10.0299 (8)0.0635 (10)0.0544 (9)0.0016 (7)0.0067 (7)0.0232 (8)
O20.0350 (8)0.0537 (9)0.0405 (8)0.0037 (7)0.0031 (6)0.0179 (7)
Geometric parameters (Å, º) top
Ag1—N22.1504 (19)C12—H120.9300
Ag1—N12.1527 (18)C13—C141.378 (4)
C1—N11.478 (3)C13—H130.9300
C1—C21.506 (3)C14—H140.9300
C1—H1A0.9700C15—C201.373 (4)
C1—H1B0.9700C15—C161.375 (4)
C2—C71.371 (4)C15—H150.9300
C2—C31.382 (4)C16—C171.373 (4)
C3—C41.382 (4)C16—H160.9300
C3—H30.9300C17—C181.364 (5)
C4—C51.359 (5)C17—H170.9300
C4—H40.9300C18—C191.378 (4)
C5—C61.361 (5)C18—H180.9300
C5—H50.9300C19—C201.387 (3)
C6—C71.391 (5)C19—H190.9300
C6—H60.9300C20—C211.505 (4)
C7—H70.9300C21—N31.449 (3)
C8—N21.478 (3)C21—H21A0.9700
C8—C91.504 (3)C21—H21B0.9700
C8—H8A0.9700C22—O11.260 (3)
C8—H8B0.9700C22—O21.269 (3)
C9—C101.374 (4)C22—N31.372 (3)
C9—C141.382 (3)N1—H1C0.9000
C10—C111.386 (4)N1—H1D0.9000
C10—H100.9300N2—H2A0.9000
C11—C121.366 (4)N2—H2B0.9000
C11—H110.9300N3—H3A0.8600
C12—C131.364 (4)
N2—Ag1—N1175.96 (7)C13—C14—C9120.9 (3)
N1—C1—C2111.10 (18)C13—C14—H14119.6
N1—C1—H1A109.4C9—C14—H14119.6
C2—C1—H1A109.4C20—C15—C16121.6 (3)
N1—C1—H1B109.4C20—C15—H15119.2
C2—C1—H1B109.4C16—C15—H15119.2
H1A—C1—H1B108.0C17—C16—C15120.2 (3)
C7—C2—C3118.6 (3)C17—C16—H16119.9
C7—C2—C1121.3 (2)C15—C16—H16119.9
C3—C2—C1120.1 (2)C18—C17—C16119.1 (3)
C4—C3—C2121.0 (3)C18—C17—H17120.5
C4—C3—H3119.5C16—C17—H17120.5
C2—C3—H3119.5C17—C18—C19120.7 (3)
C5—C4—C3119.8 (3)C17—C18—H18119.7
C5—C4—H4120.1C19—C18—H18119.7
C3—C4—H4120.1C18—C19—C20120.9 (3)
C4—C5—C6120.1 (3)C18—C19—H19119.6
C4—C5—H5120.0C20—C19—H19119.6
C6—C5—H5120.0C15—C20—C19117.5 (3)
C5—C6—C7120.5 (3)C15—C20—C21121.1 (2)
C5—C6—H6119.7C19—C20—C21121.4 (3)
C7—C6—H6119.7N3—C21—C20114.1 (2)
C2—C7—C6120.0 (3)N3—C21—H21A108.7
C2—C7—H7120.0C20—C21—H21A108.7
C6—C7—H7120.0N3—C21—H21B108.7
N2—C8—C9112.28 (18)C20—C21—H21B108.7
N2—C8—H8A109.1H21A—C21—H21B107.6
C9—C8—H8A109.1O1—C22—O2125.1 (2)
N2—C8—H8B109.1O1—C22—N3117.7 (2)
C9—C8—H8B109.1O2—C22—N3117.16 (19)
H8A—C8—H8B107.9C1—N1—Ag1121.93 (14)
C10—C9—C14118.1 (2)C1—N1—H1C106.8
C10—C9—C8120.6 (2)Ag1—N1—H1C106.8
C14—C9—C8121.3 (2)C1—N1—H1D106.8
C9—C10—C11120.9 (3)Ag1—N1—H1D106.8
C9—C10—H10119.6H1C—N1—H1D106.7
C11—C10—H10119.6C8—N2—Ag1122.49 (14)
C12—C11—C10120.2 (3)C8—N2—H2A106.7
C12—C11—H11119.9Ag1—N2—H2A106.7
C10—C11—H11119.9C8—N2—H2B106.7
C13—C12—C11119.6 (3)Ag1—N2—H2B106.7
C13—C12—H12120.2H2A—N2—H2B106.6
C11—C12—H12120.2C22—N3—C21122.13 (19)
C12—C13—C14120.4 (3)C22—N3—H3A118.9
C12—C13—H13119.8C21—N3—H3A118.9
C14—C13—H13119.8
N1—C1—C2—C7101.7 (3)C8—C9—C14—C13179.2 (2)
N1—C1—C2—C376.7 (3)C20—C15—C16—C170.2 (4)
C7—C2—C3—C40.2 (4)C15—C16—C17—C181.1 (4)
C1—C2—C3—C4178.2 (2)C16—C17—C18—C191.3 (5)
C2—C3—C4—C50.3 (5)C17—C18—C19—C200.2 (5)
C3—C4—C5—C60.1 (5)C16—C15—C20—C191.3 (4)
C4—C5—C6—C70.1 (5)C16—C15—C20—C21179.0 (2)
C3—C2—C7—C60.0 (4)C18—C19—C20—C151.0 (4)
C1—C2—C7—C6178.5 (3)C18—C19—C20—C21179.2 (3)
C5—C6—C7—C20.2 (5)C15—C20—C21—N347.1 (3)
N2—C8—C9—C10109.3 (2)C19—C20—C21—N3133.2 (2)
N2—C8—C9—C1470.1 (3)C2—C1—N1—Ag158.7 (2)
C14—C9—C10—C110.4 (4)N2—Ag1—N1—C123.4 (10)
C8—C9—C10—C11179.0 (2)C9—C8—N2—Ag146.1 (3)
C9—C10—C11—C120.2 (4)N1—Ag1—N2—C829.8 (10)
C10—C11—C12—C130.2 (4)O1—C22—N3—C217.9 (3)
C11—C12—C13—C140.5 (4)O2—C22—N3—C21173.4 (2)
C12—C13—C14—C90.3 (4)C20—C21—N3—C2277.1 (3)
C10—C9—C14—C130.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O1i0.862.293.087 (2)154
N2—H2B···O1ii0.902.102.931 (2)154
N2—H2A···O2iii0.902.122.943 (2)151
N1—H1D···O1iv0.902.123.011 (2)171
N1—H1C···O2v0.902.323.037 (2)136
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z+1; (iii) x+2, y+1, z+1; (iv) x, y+1, z1; (v) x1, y+1, z1.
 

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