Bis(3,5-di-tert-butyl-4H-1,2,4-triazol-4-amine-κN1)(nitrato-κO)silver(I) ethanol monosolvate monohydrate

Liu, Y.-M.; Chen, J.-H.; Yang, G.; Ng, S.W.

doi:10.1107/S1600536812019058

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m731

doi:10.1107/S1600536812019058

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Bis(3,5-di-tert-butyl-4H-1,2,4-triazol-4-amine-κN¹)(nitrato-κO)silver(I) ethanol monosolvate monohydrate

Ya-Mei Liu,^a Jing-Huo Chen,^a Guang Yang ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Chemistry, Zhengzhou University, Zhengzhou 450001, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 26 April 2012; accepted 27 April 2012; online 5 May 2012)

The Ag^I atom in the title compound, [Ag(NO₃)(C₁₀H₂₀N₄)₂]·C₂H₅OH·H₂O, is coordinated by the N atoms of two N-heterocycles [N—Ag—N = 151.5 (1)°]; the approximately linear coordination geometry is distorted into a T-shaped geometry owing to a long Ag⋯O_nitrate bond [2.717 (4) Å]. The N atoms of the N-heterocycles that are not involved in coordination point towards the lattice water molecule, which functions as a hydrogen-bond donor. The water molecule itself is a hydrogen-bond acceptor towards the ethanol solvent molecule. Hydrogen bonds of the type N–H⋯O give rise to a layer motif parallel to (001).

Related literature

For the synthesis of the N-heterocycle, see: Yang et al. (2012 ).

Experimental

Crystal data

[Ag(NO₃)(C₁₀H₂₀N₄)₂]·C₂H₆O·H₂O
M_r = 626.56
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.149 (2) Å
b = 14.802 (3) Å
c = 20.405 (4) Å
V = 3065.3 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.70 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.844, T_max = 0.902
11760 measured reflections
6724 independent reflections
5767 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.091
S = 1.15
6724 reflections
363 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.46 e Å⁻³
Absolute structure: Flack (1983 ), 2227 Friedel pairs
Flack parameter: 0.48 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O1w	0.85 (1)	1.94 (2)	2.772 (6)	167 (6)
O1w—H11⋯N2	0.84 (1)	2.16 (2)	2.976 (5)	164 (6)
O1w—H12⋯N6	0.84 (1)	2.08 (2)	2.915 (5)	171 (6)
N4—H41⋯O1ⁱ	0.88 (1)	2.20 (2)	3.008 (6)	153 (4)
N4—H42⋯O4ⁱⁱ	0.88 (1)	2.43 (2)	3.226 (6)	152 (4)
N8—H81⋯O2ⁱⁱⁱ	0.88 (1)	2.27 (1)	3.144 (6)	171 (4)
N8—H82⋯O4^iv	0.88 (1)	2.28 (2)	3.127 (7)	161 (6)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x-1, y, z; (iii) x+1, y, z; (iv) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812019058/xu5525sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019058/xu5525Isup2.hkl

checkCIF report

Comment top

We recently reported the synthesis of di-tert-butyl-4H-1,2,4-triazol-4-amine, a compound that furnishes four isomeric silver(I) thiolatesadducts with silver(I) (Yang et al., 2012). The Ag^I atom in Ag(NO₃)(C₁₀H₂₀N₄)₂^.H₂O^.C₂H₅OH (Scheme I) is coordinated by the the N atoms of two N-heterocycles [N–Ag–N 151.5 (1) °]; the approximately linear coordination geometry is distorted into a T-shaped geometry owing to a long Ag···O_nitrate bond [2.717 (4) Å] (Fig. 1). The N atoms of the N-heterocycles that are not involved in coordination point towards the water molecule, which functions as hydrogen-bond donor. The water molecule itself is hydrogen bond acceptor towards the ethanol molecule. Hydrogen bonds of the type N–H···O give rise to a layer motif (Table 1).

Related literature top

For the synthesis of the N-heterocycle, see: Yang et al. (2012).

Experimental top

The N-heterocyclic amine was synthesized as reported (Yang et al., 2012). An acetonitrile solution (1 ml) of silver nitrate (0.05 mmol, 8 mg) was mixed with an ethanol solution (1 ml) of the compound (0.01 mmol, 19 mg). The solution was set aside for the growth of colorless crystals, which were deposited after a week in 30% yield.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Ag(NO₃)(C₁₀H₂₀N₄)₂^.H₂O^.C₂H₅OH at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The long Ag–O bond is denoted by a dashed bond.

Bis(3,5-di-tert-butyl-4H-1,2,4-triazol-4-amine- κN¹)(nitrato-κO)silver(I) ethanol monosolvate monohydrate top

Crystal data top

[Ag(NO₃)(C₁₀H₂₀N₄)₂]·C₂H₆O·H₂O	F(000) = 1320
M_r = 626.56	D_x = 1.358 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 11783 reflections
a = 10.149 (2) Å	θ = 1.7–27.5°
b = 14.802 (3) Å	µ = 0.70 mm⁻¹
c = 20.405 (4) Å	T = 293 K
V = 3065.3 (11) Å³	Prism, colorless
Z = 4	0.25 × 0.20 × 0.15 mm

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	6724 independent reflections
Radiation source: fine-focus sealed tube	5767 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scan	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→13
T_min = 0.844, T_max = 0.902	k = 0→19
11760 measured reflections	l = −26→26

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0195P)² + 2.4088P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max = 0.001
6724 reflections	Δρ_max = 0.28 e Å⁻³
363 parameters	Δρ_min = −0.46 e Å⁻³
7 restraints	Absolute structure: Flack (1983), 2227 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.48 (3)

Crystal data top

[Ag(NO₃)(C₁₀H₂₀N₄)₂]·C₂H₆O·H₂O	V = 3065.3 (11) Å³
M_r = 626.56	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.149 (2) Å	µ = 0.70 mm⁻¹
b = 14.802 (3) Å	T = 293 K
c = 20.405 (4) Å	0.25 × 0.20 × 0.15 mm

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	6724 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	5767 reflections with I > 2σ(I)
T_min = 0.844, T_max = 0.902	R_int = 0.044
11760 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	Δρ_max = 0.28 e Å⁻³
S = 1.15	Δρ_min = −0.46 e Å⁻³
6724 reflections	Absolute structure: Flack (1983), 2227 Friedel pairs
363 parameters	Absolute structure parameter: 0.48 (3)
7 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ag1	0.66379 (3)	0.80143 (2)	0.790672 (16)	0.04839 (10)
O1	0.6035 (3)	0.6499 (3)	0.8596 (2)	0.0729 (11)
O2	0.4161 (4)	0.7157 (3)	0.8614 (2)	0.0849 (13)
O3	0.4257 (4)	0.5733 (3)	0.8692 (3)	0.0876 (14)
O4	0.9653 (4)	0.9402 (3)	0.59873 (19)	0.0669 (10)
O1W	0.8036 (4)	0.7982 (4)	0.63591 (19)	0.0729 (11)
N1	0.5190 (3)	0.8688 (2)	0.73091 (16)	0.0391 (8)
N2	0.5237 (3)	0.8422 (2)	0.66564 (17)	0.0389 (8)
N3	0.3520 (3)	0.9287 (2)	0.68103 (15)	0.0322 (7)
N4	0.2395 (4)	0.9833 (3)	0.6723 (2)	0.0467 (10)
N5	0.8624 (3)	0.7531 (2)	0.80776 (15)	0.0361 (8)
N6	0.9183 (3)	0.7150 (3)	0.75210 (16)	0.0382 (9)
N7	1.0358 (3)	0.6783 (2)	0.83740 (15)	0.0334 (8)
N8	1.1297 (4)	0.6390 (3)	0.8800 (2)	0.0484 (11)
N9	0.4821 (4)	0.6455 (3)	0.8638 (2)	0.0462 (9)
C1	0.4162 (4)	0.9210 (3)	0.7396 (2)	0.0334 (9)
C2	0.3745 (4)	0.9642 (3)	0.80379 (19)	0.0378 (10)
C3	0.4758 (5)	0.9436 (4)	0.8568 (2)	0.0581 (14)
H3A	0.5599	0.9676	0.8441	0.087*
H3B	0.4828	0.8794	0.8625	0.087*
H3C	0.4486	0.9708	0.8973	0.087*
C4	0.2405 (5)	0.9256 (4)	0.8252 (3)	0.0625 (15)
H4A	0.2471	0.8612	0.8297	0.094*
H4B	0.1751	0.9400	0.7929	0.094*
H4C	0.2156	0.9516	0.8665	0.094*
C5	0.3651 (5)	1.0677 (3)	0.7967 (3)	0.0591 (13)
H5A	0.4491	1.0913	0.7835	0.089*
H5B	0.3402	1.0938	0.8379	0.089*
H5C	0.3002	1.0825	0.7642	0.089*
C6	0.4225 (4)	0.8794 (3)	0.6363 (2)	0.0362 (10)
C7	0.3900 (4)	0.8649 (3)	0.5646 (2)	0.0403 (10)
C8	0.5029 (5)	0.8112 (5)	0.5332 (2)	0.0709 (16)
H8A	0.5136	0.7548	0.5559	0.106*
H8B	0.5831	0.8454	0.5362	0.106*
H8C	0.4829	0.7997	0.4880	0.106*
C9	0.3738 (7)	0.9540 (4)	0.5276 (3)	0.077 (2)
H9A	0.3036	0.9883	0.5470	0.115*
H9B	0.3533	0.9418	0.4825	0.115*
H9C	0.4543	0.9879	0.5301	0.115*
C10	0.2645 (5)	0.8078 (4)	0.5584 (2)	0.0627 (14)
H10A	0.2756	0.7522	0.5819	0.094*
H10B	0.2481	0.7949	0.5130	0.094*
H10C	0.1913	0.8406	0.5763	0.094*
C11	0.9341 (4)	0.7314 (3)	0.8586 (2)	0.0321 (9)
C12	0.9110 (4)	0.7612 (3)	0.9293 (2)	0.0375 (10)
C13	0.7894 (5)	0.8214 (3)	0.9327 (2)	0.0550 (14)
H13A	0.7137	0.7881	0.9181	0.083*
H13B	0.8019	0.8732	0.9051	0.083*
H13C	0.7761	0.8408	0.9771	0.083*
C14	0.8880 (5)	0.6789 (3)	0.9731 (2)	0.0546 (13)
H14A	0.8130	0.6458	0.9574	0.082*
H14B	0.8721	0.6986	1.0172	0.082*
H14C	0.9644	0.6407	0.9721	0.082*
C15	1.0301 (5)	0.8155 (4)	0.9531 (2)	0.0621 (15)
H15A	1.0158	0.8343	0.9976	0.093*
H15B	1.0413	0.8678	0.9258	0.093*
H15C	1.1077	0.7786	0.9508	0.093*
C16	1.0224 (4)	0.6699 (3)	0.77094 (18)	0.0321 (9)
C17	1.1144 (4)	0.6206 (3)	0.7243 (2)	0.0407 (11)
C18	1.0508 (5)	0.6196 (4)	0.6563 (2)	0.0567 (14)
H18A	1.0353	0.6805	0.6421	0.085*
H18B	0.9686	0.5876	0.6583	0.085*
H18C	1.1085	0.5900	0.6259	0.085*
C19	1.2451 (4)	0.6716 (4)	0.7205 (3)	0.0661 (17)
H19A	1.2855	0.6729	0.7630	0.099*
H19B	1.2293	0.7323	0.7059	0.099*
H19C	1.3027	0.6417	0.6901	0.099*
C21	0.9561 (6)	0.9340 (5)	0.5300 (3)	0.0750 (17)
H21A	0.9795	0.8732	0.5168	0.090*
H21B	1.0200	0.9749	0.5107	0.090*
C22	0.8266 (7)	0.9553 (5)	0.5036 (3)	0.093 (2)
H22A	0.8286	0.9502	0.4567	0.139*
H22B	0.8029	1.0158	0.5157	0.139*
H22C	0.7629	0.9138	0.5210	0.139*
C30	1.1378 (6)	0.5227 (4)	0.7462 (3)	0.0721 (17)
H30A	1.1784	0.5223	0.7887	0.108*
H30B	1.1945	0.4930	0.7153	0.108*
H30C	1.0550	0.4914	0.7483	0.108*
H4	0.918 (5)	0.900 (3)	0.616 (3)	0.07 (2)*
H11	0.728 (3)	0.806 (4)	0.652 (3)	0.08 (2)*
H12	0.844 (5)	0.775 (3)	0.6672 (19)	0.08 (2)*
H41	0.267 (4)	1.032 (2)	0.652 (2)	0.053 (16)*
H42	0.182 (3)	0.954 (2)	0.6480 (18)	0.047 (13)*
H81	1.209 (2)	0.658 (3)	0.870 (2)	0.040 (14)*
H82	1.118 (6)	0.5800 (10)	0.880 (3)	0.09 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.04155 (16)	0.0608 (2)	0.04285 (16)	0.02041 (17)	−0.00957 (16)	−0.0024 (2)
O1	0.0377 (19)	0.094 (3)	0.087 (3)	−0.0074 (19)	0.0054 (19)	−0.010 (2)
O2	0.091 (3)	0.050 (2)	0.113 (4)	0.018 (2)	−0.032 (3)	−0.009 (2)
O3	0.053 (2)	0.059 (2)	0.151 (4)	−0.010 (2)	−0.013 (3)	0.028 (3)
O4	0.069 (3)	0.080 (3)	0.052 (2)	−0.010 (2)	−0.006 (2)	−0.005 (2)
O1W	0.050 (2)	0.110 (3)	0.059 (2)	0.016 (3)	0.0067 (18)	0.034 (3)
N1	0.0349 (18)	0.052 (2)	0.0309 (18)	0.0102 (17)	−0.0017 (14)	0.0019 (16)
N2	0.0382 (19)	0.047 (2)	0.0313 (18)	0.0093 (17)	−0.0015 (15)	−0.0042 (16)
N3	0.0285 (17)	0.0348 (17)	0.0332 (16)	0.0089 (16)	−0.0051 (15)	0.0004 (13)
N4	0.034 (2)	0.054 (3)	0.052 (3)	0.0135 (19)	−0.0080 (18)	−0.001 (2)
N5	0.0316 (18)	0.0479 (19)	0.0288 (17)	0.0124 (15)	−0.0002 (13)	0.0030 (14)
N6	0.0296 (16)	0.054 (2)	0.0314 (18)	0.0076 (17)	0.0007 (13)	0.0006 (17)
N7	0.0283 (16)	0.046 (2)	0.0255 (16)	0.0053 (15)	−0.0027 (13)	0.0033 (15)
N8	0.036 (2)	0.072 (3)	0.037 (2)	0.017 (2)	−0.0061 (16)	0.008 (2)
N9	0.048 (2)	0.053 (3)	0.038 (2)	0.004 (2)	−0.0045 (19)	−0.0014 (19)
C1	0.030 (2)	0.034 (2)	0.036 (2)	0.0032 (18)	0.0022 (17)	0.0019 (18)
C2	0.039 (2)	0.044 (2)	0.030 (2)	0.0069 (17)	0.0020 (17)	−0.0018 (18)
C3	0.068 (4)	0.072 (4)	0.034 (3)	0.010 (3)	−0.007 (3)	−0.008 (2)
C4	0.054 (3)	0.075 (4)	0.059 (3)	0.000 (3)	0.019 (3)	−0.001 (3)
C5	0.070 (3)	0.050 (3)	0.057 (3)	0.012 (2)	−0.006 (3)	−0.006 (3)
C6	0.033 (2)	0.035 (2)	0.041 (2)	−0.0013 (18)	0.0003 (18)	0.0038 (19)
C7	0.043 (2)	0.046 (3)	0.033 (2)	0.000 (2)	−0.0061 (18)	−0.001 (2)
C8	0.064 (3)	0.106 (5)	0.043 (3)	0.013 (4)	0.005 (2)	−0.018 (3)
C9	0.131 (6)	0.062 (3)	0.038 (3)	−0.001 (4)	−0.012 (3)	0.011 (2)
C10	0.061 (3)	0.075 (4)	0.053 (3)	−0.009 (3)	−0.010 (2)	−0.012 (3)
C11	0.0282 (19)	0.040 (2)	0.028 (2)	−0.0015 (17)	0.0000 (16)	0.0019 (17)
C12	0.035 (2)	0.048 (3)	0.029 (2)	0.002 (2)	0.0000 (17)	−0.0012 (19)
C13	0.072 (3)	0.058 (3)	0.035 (2)	0.022 (3)	0.007 (2)	−0.008 (2)
C14	0.067 (3)	0.056 (3)	0.041 (2)	0.009 (3)	0.015 (2)	0.009 (2)
C15	0.059 (3)	0.080 (4)	0.047 (3)	−0.023 (3)	0.005 (2)	−0.018 (3)
C16	0.0276 (19)	0.040 (2)	0.029 (2)	0.0008 (16)	0.0030 (15)	−0.0007 (16)
C17	0.034 (2)	0.056 (3)	0.032 (2)	0.0082 (19)	0.0064 (17)	−0.004 (2)
C18	0.053 (3)	0.086 (4)	0.031 (2)	0.001 (3)	0.010 (2)	−0.011 (2)
C19	0.037 (2)	0.111 (5)	0.051 (3)	−0.005 (3)	0.010 (2)	−0.009 (3)
C21	0.082 (4)	0.079 (4)	0.064 (4)	0.006 (3)	−0.003 (3)	−0.002 (3)
C22	0.086 (5)	0.111 (5)	0.081 (4)	−0.008 (5)	−0.023 (4)	0.012 (4)
C30	0.091 (5)	0.065 (3)	0.060 (3)	0.032 (3)	0.012 (3)	−0.005 (3)

Geometric parameters (Å, º) top

Ag1—N1	2.154 (3)	C7—C8	1.535 (7)
Ag1—N5	2.167 (3)	C8—H8A	0.9600
Ag1—O1	2.717 (4)	C8—H8B	0.9600
O1—N9	1.236 (5)	C8—H8C	0.9600
O2—N9	1.238 (5)	C9—H9A	0.9600
O3—N9	1.217 (5)	C9—H9B	0.9600
O4—C21	1.409 (7)	C9—H9C	0.9600
O4—H4	0.845 (10)	C10—H10A	0.9600
O1W—H11	0.836 (10)	C10—H10B	0.9600
O1W—H12	0.838 (10)	C10—H10C	0.9600
N1—C1	1.311 (5)	C11—C12	1.525 (6)
N1—N2	1.390 (5)	C12—C13	1.523 (6)
N2—C6	1.310 (5)	C12—C14	1.529 (6)
N3—C1	1.366 (5)	C12—C15	1.531 (6)
N3—C6	1.370 (5)	C13—H13A	0.9600
N3—N4	1.410 (5)	C13—H13B	0.9600
N4—H41	0.878 (10)	C13—H13C	0.9600
N4—H42	0.879 (10)	C14—H14A	0.9600
N5—C11	1.308 (5)	C14—H14B	0.9600
N5—N6	1.389 (4)	C14—H14C	0.9600
N6—C16	1.307 (5)	C15—H15A	0.9600
N7—C11	1.368 (5)	C15—H15B	0.9600
N7—C16	1.369 (5)	C15—H15C	0.9600
N7—N8	1.416 (5)	C16—C17	1.520 (5)
N8—H81	0.882 (10)	C17—C19	1.528 (6)
N8—H82	0.881 (10)	C17—C18	1.531 (6)
C1—C2	1.518 (6)	C17—C30	1.535 (7)
C2—C3	1.524 (6)	C18—H18A	0.9600
C2—C4	1.538 (6)	C18—H18B	0.9600
C2—C5	1.542 (6)	C18—H18C	0.9600
C3—H3A	0.9600	C19—H19A	0.9600
C3—H3B	0.9600	C19—H19B	0.9600
C3—H3C	0.9600	C19—H19C	0.9600
C4—H4A	0.9600	C21—C22	1.454 (8)
C4—H4B	0.9600	C21—H21A	0.9700
C4—H4C	0.9600	C21—H21B	0.9700
C5—H5A	0.9600	C22—H22A	0.9600
C5—H5B	0.9600	C22—H22B	0.9600
C5—H5C	0.9600	C22—H22C	0.9600
C6—C7	1.516 (6)	C30—H30A	0.9600
C7—C9	1.529 (7)	C30—H30B	0.9600
C7—C10	1.533 (6)	C30—H30C	0.9600

N1—Ag1—N5	151.45 (12)	H9A—C9—H9C	109.5
N1—Ag1—O1	121.43 (13)	H9B—C9—H9C	109.5
N5—Ag1—O1	81.58 (12)	C7—C10—H10A	109.5
N9—O1—Ag1	107.7 (3)	C7—C10—H10B	109.5
C21—O4—H4	109 (4)	H10A—C10—H10B	109.5
H11—O1W—H12	102 (6)	C7—C10—H10C	109.5
C1—N1—N2	108.9 (3)	H10A—C10—H10C	109.5
C1—N1—Ag1	137.7 (3)	H10B—C10—H10C	109.5
N2—N1—Ag1	112.8 (2)	N5—C11—N7	108.0 (3)
C6—N2—N1	107.0 (3)	N5—C11—C12	126.4 (4)
C1—N3—C6	106.8 (3)	N7—C11—C12	125.5 (3)
C1—N3—N4	123.0 (3)	C13—C12—C11	109.7 (3)
C6—N3—N4	130.1 (3)	C13—C12—C14	108.3 (4)
N3—N4—H41	106 (3)	C11—C12—C14	110.3 (4)
N3—N4—H42	109 (3)	C13—C12—C15	108.5 (4)
H41—N4—H42	110 (4)	C11—C12—C15	109.3 (3)
C11—N5—N6	108.8 (3)	C14—C12—C15	110.7 (4)
C11—N5—Ag1	136.6 (3)	C12—C13—H13A	109.5
N6—N5—Ag1	112.5 (2)	C12—C13—H13B	109.5
C16—N6—N5	107.3 (3)	H13A—C13—H13B	109.5
C11—N7—C16	106.9 (3)	C12—C13—H13C	109.5
C11—N7—N8	123.3 (3)	H13A—C13—H13C	109.5
C16—N7—N8	129.7 (4)	H13B—C13—H13C	109.5
N7—N8—H81	110 (3)	C12—C14—H14A	109.5
N7—N8—H82	108 (4)	C12—C14—H14B	109.5
H81—N8—H82	116 (5)	H14A—C14—H14B	109.5
O3—N9—O1	121.4 (4)	C12—C14—H14C	109.5
O3—N9—O2	119.1 (4)	H14A—C14—H14C	109.5
O1—N9—O2	119.5 (5)	H14B—C14—H14C	109.5
N1—C1—N3	108.1 (3)	C12—C15—H15A	109.5
N1—C1—C2	125.9 (4)	C12—C15—H15B	109.5
N3—C1—C2	125.9 (3)	H15A—C15—H15B	109.5
C1—C2—C3	109.9 (3)	C12—C15—H15C	109.5
C1—C2—C4	109.6 (4)	H15A—C15—H15C	109.5
C3—C2—C4	108.7 (4)	H15B—C15—H15C	109.5
C1—C2—C5	110.7 (4)	N6—C16—N7	109.0 (3)
C3—C2—C5	107.9 (4)	N6—C16—C17	123.9 (3)
C4—C2—C5	109.9 (4)	N7—C16—C17	127.0 (4)
C2—C3—H3A	109.5	C16—C17—C19	109.2 (4)
C2—C3—H3B	109.5	C16—C17—C18	108.2 (3)
H3A—C3—H3B	109.5	C19—C17—C18	108.9 (4)
C2—C3—H3C	109.5	C16—C17—C30	111.5 (4)
H3A—C3—H3C	109.5	C19—C17—C30	110.3 (4)
H3B—C3—H3C	109.5	C18—C17—C30	108.6 (4)
C2—C4—H4A	109.5	C17—C18—H18A	109.5
C2—C4—H4B	109.5	C17—C18—H18B	109.5
H4A—C4—H4B	109.5	H18A—C18—H18B	109.5
C2—C4—H4C	109.5	C17—C18—H18C	109.5
H4A—C4—H4C	109.5	H18A—C18—H18C	109.5
H4B—C4—H4C	109.5	H18B—C18—H18C	109.5
C2—C5—H5A	109.5	C17—C19—H19A	109.5
C2—C5—H5B	109.5	C17—C19—H19B	109.5
H5A—C5—H5B	109.5	H19A—C19—H19B	109.5
C2—C5—H5C	109.5	C17—C19—H19C	109.5
H5A—C5—H5C	109.5	H19A—C19—H19C	109.5
H5B—C5—H5C	109.5	H19B—C19—H19C	109.5
N2—C6—N3	109.2 (4)	O4—C21—C22	114.5 (6)
N2—C6—C7	123.5 (4)	O4—C21—H21A	108.6
N3—C6—C7	127.2 (4)	C22—C21—H21A	108.6
C6—C7—C9	112.1 (4)	O4—C21—H21B	108.6
C6—C7—C10	109.8 (4)	C22—C21—H21B	108.6
C9—C7—C10	110.2 (4)	H21A—C21—H21B	107.6
C6—C7—C8	108.2 (4)	C21—C22—H22A	109.5
C9—C7—C8	108.8 (4)	C21—C22—H22B	109.5
C10—C7—C8	107.5 (4)	H22A—C22—H22B	109.5
C7—C8—H8A	109.5	C21—C22—H22C	109.5
C7—C8—H8B	109.5	H22A—C22—H22C	109.5
H8A—C8—H8B	109.5	H22B—C22—H22C	109.5
C7—C8—H8C	109.5	C17—C30—H30A	109.5
H8A—C8—H8C	109.5	C17—C30—H30B	109.5
H8B—C8—H8C	109.5	H30A—C30—H30B	109.5
C7—C9—H9A	109.5	C17—C30—H30C	109.5
C7—C9—H9B	109.5	H30A—C30—H30C	109.5
H9A—C9—H9B	109.5	H30B—C30—H30C	109.5
C7—C9—H9C	109.5

N1—Ag1—O1—N9	−17.7 (4)	C1—N3—C6—C7	178.5 (4)
N5—Ag1—O1—N9	−179.6 (3)	N4—N3—C6—C7	−5.4 (7)
N5—Ag1—N1—C1	−145.1 (4)	N2—C6—C7—C9	−126.9 (5)
O1—Ag1—N1—C1	75.1 (5)	N3—C6—C7—C9	55.8 (6)
N5—Ag1—N1—N2	44.9 (5)	N2—C6—C7—C10	110.1 (5)
O1—Ag1—N1—N2	−94.9 (3)	N3—C6—C7—C10	−67.1 (6)
C1—N1—N2—C6	−0.1 (5)	N2—C6—C7—C8	−7.0 (6)
Ag1—N1—N2—C6	172.9 (3)	N3—C6—C7—C8	175.8 (4)
N1—Ag1—N5—C11	157.9 (4)	N6—N5—C11—N7	−0.9 (4)
O1—Ag1—N5—C11	−55.9 (4)	Ag1—N5—C11—N7	160.4 (3)
N1—Ag1—N5—N6	−41.2 (4)	N6—N5—C11—C12	178.1 (4)
O1—Ag1—N5—N6	105.0 (3)	Ag1—N5—C11—C12	−20.6 (7)
C11—N5—N6—C16	0.8 (4)	C16—N7—C11—N5	0.7 (4)
Ag1—N5—N6—C16	−165.4 (3)	N8—N7—C11—N5	−177.0 (4)
Ag1—O1—N9—O3	152.1 (4)	C16—N7—C11—C12	−178.3 (4)
Ag1—O1—N9—O2	−26.7 (5)	N8—N7—C11—C12	4.0 (6)
N2—N1—C1—N3	0.6 (5)	N5—C11—C12—C13	0.0 (6)
Ag1—N1—C1—N3	−169.7 (3)	N7—C11—C12—C13	178.8 (4)
N2—N1—C1—C2	179.6 (4)	N5—C11—C12—C14	119.2 (5)
Ag1—N1—C1—C2	9.3 (7)	N7—C11—C12—C14	−61.9 (5)
C6—N3—C1—N1	−0.9 (5)	N5—C11—C12—C15	−118.8 (5)
N4—N3—C1—N1	−177.4 (4)	N7—C11—C12—C15	60.0 (5)
C6—N3—C1—C2	−179.9 (4)	N5—N6—C16—N7	−0.3 (5)
N4—N3—C1—C2	3.6 (6)	N5—N6—C16—C17	−177.8 (4)
N1—C1—C2—C3	4.1 (6)	C11—N7—C16—N6	−0.2 (5)
N3—C1—C2—C3	−177.1 (4)	N8—N7—C16—N6	177.3 (4)
N1—C1—C2—C4	−115.3 (5)	C11—N7—C16—C17	177.2 (4)
N3—C1—C2—C4	63.5 (6)	N8—N7—C16—C17	−5.3 (7)
N1—C1—C2—C5	123.2 (5)	N6—C16—C17—C19	108.7 (5)
N3—C1—C2—C5	−58.0 (6)	N7—C16—C17—C19	−68.4 (6)
N1—N2—C6—N3	−0.5 (5)	N6—C16—C17—C18	−9.8 (6)
N1—N2—C6—C7	−178.2 (4)	N7—C16—C17—C18	173.1 (4)
C1—N3—C6—N2	0.9 (5)	N6—C16—C17—C30	−129.2 (5)
N4—N3—C6—N2	177.0 (4)	N7—C16—C17—C30	53.8 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1w	0.85 (1)	1.94 (2)	2.772 (6)	167 (6)
O1w—H11···N2	0.84 (1)	2.16 (2)	2.976 (5)	164 (6)
O1w—H12···N6	0.84 (1)	2.08 (2)	2.915 (5)	171 (6)
N4—H41···O1ⁱ	0.88 (1)	2.20 (2)	3.008 (6)	153 (4)
N4—H42···O4ⁱⁱ	0.88 (1)	2.43 (2)	3.226 (6)	152 (4)
N8—H81···O2ⁱⁱⁱ	0.88 (1)	2.27 (1)	3.144 (6)	171 (4)
N8—H82···O4^iv	0.88 (1)	2.28 (2)	3.127 (7)	161 (6)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, y, z; (iii) x+1, y, z; (iv) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Ag(NO₃)(C₁₀H₂₀N₄)₂]·C₂H₆O·H₂O
M_r	626.56
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	10.149 (2), 14.802 (3), 20.405 (4)
V (Å³)	3065.3 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.844, 0.902
No. of measured, independent and observed [I > 2σ(I)] reflections	11760, 6724, 5767
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.091, 1.15
No. of reflections	6724
No. of parameters	363
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.46
Absolute structure	Flack (1983), 2227 Friedel pairs
Absolute structure parameter	0.48 (3)

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1w	0.85 (1)	1.94 (2)	2.772 (6)	167 (6)
O1w—H11···N2	0.84 (1)	2.16 (2)	2.976 (5)	164 (6)
O1w—H12···N6	0.84 (1)	2.08 (2)	2.915 (5)	171 (6)
N4—H41···O1ⁱ	0.88 (1)	2.20 (2)	3.008 (6)	153 (4)
N4—H42···O4ⁱⁱ	0.88 (1)	2.43 (2)	3.226 (6)	152 (4)
N8—H81···O2ⁱⁱⁱ	0.88 (1)	2.27 (1)	3.144 (6)	171 (4)
N8—H82···O4^iv	0.88 (1)	2.28 (2)	3.127 (7)	161 (6)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, y, z; (iii) x+1, y, z; (iv) −x+2, y−1/2, −z+3/2.

Acknowledgements

We thank Zhengzhou University of China and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, G., Duan, P.-C., Shi, K.-G. & Raptis, R. G. (2012). Cryst. Growth Des. 12, 1882–1889. Web of Science CSD CrossRef CAS Google Scholar

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