Poly[(μ-3,5-dinitro­benzoato)(μ-3,5-dinitro­benzoic acid)rubidium]

Miao, Y.; Fan, T.

doi:10.1107/S160053681102513X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page m1040

doi:10.1107/S160053681102513X

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Poly[(μ-3,5-dinitrobenzoato)(μ-3,5-dinitrobenzoic acid)rubidium]

Yanqing Miao ^a ^* and Tao Fan ^a

^aXi'an Medical University, Department of Pharmacy, Hanguang Road No.137, Xi'an 710021, Shaanxi, People's Republic of China
^*Correspondence e-mail: miaoyanqing66@163.com

(Received 10 May 2011; accepted 26 June 2011; online 6 July 2011)

The asymmetric unit of the title compound, [Rb(C₇H₃N₂O₆)(C₇H₄N₂O₆)]_n, comprises an Rb⁺ cation, a 3,5-dinitrobenzoate anion and a 3,5-dinitrobenzoic acid ligand. The Rb⁺ cation is nine-coordinated by O atoms from four 3,5-dinitrobenzoate anions and three neutral 3,5-dinitrobenzoic acid ligands. The metal atom is firstly linked by four bridging carboxyl groups, forming a binuclear motif, which is further linked by the nitro groups into a two-dimensional framework along the [110] direction. A short O—H⋯O hydrogen bond between two adjacent carboxy/carboxylate groups occurs.

Related literature

For 3,5-dinitrobenzoate complexes, see: Askarinejad et al. (2007 ); Madej et al. (2007 ); Zhu et al. (2001 ). For Rb—O bond lengths, see: Cametti et al. (2005 ).

Experimental

Crystal data

[Rb(C₇H₃N₂O₆)(C₇H₄N₂O₆)]
M_r = 508.71
Triclinic, $[P \overline 1]$
a = 9.4823 (8) Å
b = 9.8136 (8) Å
c = 11.4929 (11) Å
α = 68.425 (1)°
β = 83.821 (1)°
γ = 67.538 (1)°
V = 918.42 (14) Å³
Z = 2
Mo Kα radiation
μ = 2.77 mm⁻¹
T = 293 K
0.40 × 0.31 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.368, T_max = 0.635
4661 measured reflections
3219 independent reflections
2758 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.079
S = 1.08
3219 reflections
284 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H1⋯O1	0.96 (4)	1.52 (4)	2.470 (2)	168 (4)

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681102513X/aa2010sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102513X/aa2010Isup2.hkl

checkCIF report

Comment top

The 3,5-dinitrobenzoic acid is an interesting ligand with one carboxylic and two nitro groups for coordination. In the structural investigation of 3,5-dinitrobenzoic acid complexes, it has been found that the 3,5-dinitrobenzoate moiety functions as a multidentate ligand (Askarinejad et al., 2007; Madej et al., 2007; Zhu et al., 2001) with versatile binding and coordination modes. In this paper, we report the crystal structure of the title compound, a new Rb complex obtained by the reaction of 3,5-dinitrobenzoic acid and RbOH in water.

The asymmetric unit of the title compound (I) comprises a Rb⁺ cation, a 3,5-dinitrobenzoate anion and a 3,5-dinitrobenzoic acid ligand (Fig. 1). The central cation is coordinated to nine O atoms from four 3,5-dinitrobenzoate anions and three neutral 3,5-dinitrobenzoic acid ligands with the Rb—O distances ranging from 2.7973 (19) Å to 3.403 (2) Å, which are well within the range reported in the literature (Cametti et al., 2005). The Rb centre is firstly linked by four bridging carboxylic groups to form a binuclear motif, which is further linked by the nitro groups to give the two-dimensional framework of the title compound (Fig. 2).

Related literature top

For 3,5-dinitrobenzoate complexes, see: Askarinejad et al. (2007); Madej et al. (2007); Zhu et al. (2001). For Rb—O bond lengths, see: Cametti et al. (2005).

Experimental top

Analysis grade 3,5-dinitrobenzoic acid and RbOH (purity > 99.5%, Sinopharm Chemical Reagent Co., Ltd., Shanghai, China) were commercially available and used without further purification. To a solution of 20 mmol 3,5-dinitrobenzoic acid in 50 ml bidistilled water, a solution of 10 mmol RbOH in 40 ml bidistilled water was added dropwise at room temperature. After vigorous stirring for 3 h, the resulting solution was then evaporated to a volume of about 20 ml in vacuum and filtered hot. The filtrate was then set aside for crystallization at room temperature. Two weeks later, yellow block crystals of the title compound suitable for X-ray determination were isolated.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), showing the atomic numbering scheme. Non-H atoms are shown with 30% probability displacement ellipsoids. Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 1 + x, - 1 + y, z; (iii) 2 - x, - y, 1 - z; (iv) 1 - x, 1 - y, 1 - z.
	Fig. 2. The two-dimensional framework of (I).

Poly[(µ-3,5-dinitrobenzoato)(µ-3,5-dinitrobenzoic acid)rubidium] top

Crystal data top

[Rb(C₇H₃N₂O₆)(C₇H₄N₂O₆)]	Z = 2
M_r = 508.71	F(000) = 504
Triclinic, P1	D_x = 1.840 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4823 (8) Å	Cell parameters from 2183 reflections
b = 9.8136 (8) Å	θ = 2.3–25.6°
c = 11.4929 (11) Å	µ = 2.77 mm⁻¹
α = 68.425 (1)°	T = 293 K
β = 83.821 (1)°	Block, yellow
γ = 67.538 (1)°	0.40 × 0.31 × 0.20 mm
V = 918.42 (14) Å³

Data collection top

Bruker SMART CCD diffractometer	3219 independent reflections
Radiation source: fine-focus sealed tube	2758 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
phi and ω scans	θ_max = 25.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.368, T_max = 0.635	k = −10→11
4661 measured reflections	l = −13→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0471P)² + 0.0239P] where P = (F_o² + 2F_c²)/3
3219 reflections	(Δ/σ)_max = 0.001
284 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Rb(C₇H₃N₂O₆)(C₇H₄N₂O₆)]	γ = 67.538 (1)°
M_r = 508.71	V = 918.42 (14) Å³
Triclinic, P1	Z = 2
a = 9.4823 (8) Å	Mo Kα radiation
b = 9.8136 (8) Å	µ = 2.77 mm⁻¹
c = 11.4929 (11) Å	T = 293 K
α = 68.425 (1)°	0.40 × 0.31 × 0.20 mm
β = 83.821 (1)°

Data collection top

Bruker SMART CCD diffractometer	3219 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2758 reflections with I > 2σ(I)
T_min = 0.368, T_max = 0.635	R_int = 0.015
4661 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.33 e Å⁻³
3219 reflections	Δρ_min = −0.38 e Å⁻³
284 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
Rb1	0.60363 (3)	0.23726 (3)	0.63137 (2)	0.04777 (12)
O1	0.6222 (2)	0.5041 (3)	0.74637 (18)	0.0566 (5)
O2	0.4151 (2)	0.5791 (2)	0.62901 (18)	0.0501 (5)
O3	−0.0505 (2)	0.9948 (3)	0.6899 (2)	0.0726 (7)
O4	−0.0484 (3)	1.1013 (3)	0.8223 (2)	0.0801 (7)
O5	0.3968 (3)	0.9004 (3)	1.0902 (2)	0.0794 (7)
O6	0.5892 (3)	0.6992 (3)	1.0817 (2)	0.0817 (7)
O7	0.7938 (2)	0.4276 (2)	0.58487 (18)	0.0465 (4)
H1	0.717 (5)	0.463 (5)	0.640 (4)	0.108 (14)*
O8	0.6987 (2)	0.6736 (2)	0.44553 (19)	0.0532 (5)
O9	0.9040 (3)	0.7679 (3)	0.0193 (2)	0.0801 (7)
O10	1.1097 (3)	0.5933 (3)	−0.0103 (2)	0.0751 (7)
O11	1.3434 (3)	0.1010 (3)	0.3122 (2)	0.0779 (7)
O12	1.2396 (3)	0.0396 (3)	0.4887 (2)	0.0705 (6)
C1	0.3944 (3)	0.6901 (3)	0.7846 (2)	0.0369 (5)
C2	0.2455 (3)	0.7921 (3)	0.7486 (2)	0.0382 (6)
H2	0.1956	0.7907	0.6839	0.046*
C3	0.1717 (3)	0.8963 (3)	0.8101 (2)	0.0402 (6)
C4	0.2396 (3)	0.9027 (3)	0.9064 (2)	0.0443 (6)
H3	0.1888	0.9745	0.9461	0.053*
C5	0.3874 (3)	0.7969 (3)	0.9414 (2)	0.0403 (6)
C6	0.4654 (3)	0.6916 (3)	0.8829 (2)	0.0385 (6)
H4	0.5650	0.6222	0.9091	0.046*
C7	0.4807 (3)	0.5831 (3)	0.7125 (2)	0.0423 (6)
C8	0.9000 (3)	0.4805 (3)	0.3865 (2)	0.0366 (5)
C9	0.8963 (3)	0.5842 (3)	0.2643 (2)	0.0407 (6)
H5	0.8216	0.6852	0.2370	0.049*
C10	1.0068 (3)	0.5329 (3)	0.1847 (2)	0.0418 (6)
C11	1.1200 (3)	0.3858 (3)	0.2214 (2)	0.0425 (6)
H6	1.1936	0.3540	0.1666	0.051*
C12	1.1197 (3)	0.2878 (3)	0.3423 (2)	0.0387 (6)
C13	1.0115 (3)	0.3310 (3)	0.4255 (2)	0.0381 (6)
H7	1.0136	0.2606	0.5066	0.046*
C14	0.7854 (3)	0.5361 (3)	0.4767 (3)	0.0411 (6)
N1	0.0124 (3)	1.0057 (3)	0.7712 (2)	0.0519 (6)
N2	0.4643 (3)	0.7987 (3)	1.0451 (2)	0.0549 (6)
N3	1.0066 (3)	0.6400 (3)	0.0554 (2)	0.0546 (6)
N4	1.2440 (3)	0.1311 (3)	0.3850 (2)	0.0516 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Rb1	0.04757 (17)	0.04046 (16)	0.04939 (18)	−0.00983 (12)	−0.00575 (11)	−0.01423 (12)
O1	0.0394 (10)	0.0773 (15)	0.0520 (12)	−0.0082 (10)	0.0055 (9)	−0.0366 (11)
O2	0.0509 (11)	0.0616 (12)	0.0454 (11)	−0.0191 (10)	0.0037 (9)	−0.0297 (10)
O3	0.0460 (12)	0.0759 (16)	0.0887 (17)	−0.0075 (11)	−0.0183 (11)	−0.0315 (14)
O4	0.0614 (14)	0.0672 (15)	0.0889 (18)	0.0102 (12)	−0.0024 (12)	−0.0369 (14)
O5	0.0976 (18)	0.0906 (18)	0.0631 (15)	−0.0270 (15)	0.0006 (13)	−0.0492 (14)
O6	0.0751 (16)	0.0908 (19)	0.0759 (17)	−0.0125 (15)	−0.0291 (13)	−0.0365 (14)
O7	0.0445 (10)	0.0532 (12)	0.0453 (11)	−0.0170 (9)	0.0116 (9)	−0.0251 (10)
O8	0.0423 (10)	0.0490 (12)	0.0665 (13)	−0.0068 (10)	0.0019 (9)	−0.0293 (10)
O9	0.113 (2)	0.0466 (14)	0.0556 (14)	−0.0148 (14)	−0.0025 (13)	−0.0045 (11)
O10	0.1009 (18)	0.0685 (15)	0.0537 (14)	−0.0412 (14)	0.0285 (13)	−0.0160 (12)
O11	0.0647 (14)	0.0471 (13)	0.0999 (19)	−0.0078 (11)	0.0371 (13)	−0.0251 (12)
O12	0.0735 (15)	0.0445 (12)	0.0622 (14)	−0.0041 (11)	0.0064 (11)	−0.0044 (11)
C1	0.0396 (13)	0.0394 (14)	0.0306 (13)	−0.0163 (11)	0.0077 (10)	−0.0113 (11)
C2	0.0401 (14)	0.0439 (15)	0.0319 (13)	−0.0202 (12)	0.0038 (10)	−0.0107 (11)
C3	0.0370 (13)	0.0360 (14)	0.0389 (14)	−0.0106 (11)	0.0036 (11)	−0.0076 (11)
C4	0.0529 (16)	0.0398 (15)	0.0389 (15)	−0.0154 (13)	0.0085 (12)	−0.0164 (12)
C5	0.0459 (15)	0.0440 (15)	0.0310 (13)	−0.0175 (12)	0.0036 (11)	−0.0130 (11)
C6	0.0348 (13)	0.0448 (15)	0.0316 (13)	−0.0128 (12)	0.0035 (10)	−0.0114 (11)
C7	0.0425 (15)	0.0494 (16)	0.0353 (14)	−0.0182 (13)	0.0079 (11)	−0.0159 (12)
C8	0.0341 (12)	0.0391 (14)	0.0417 (14)	−0.0148 (11)	0.0015 (10)	−0.0188 (12)
C9	0.0399 (14)	0.0374 (14)	0.0460 (15)	−0.0111 (12)	−0.0031 (11)	−0.0182 (12)
C10	0.0515 (15)	0.0395 (14)	0.0374 (14)	−0.0224 (13)	0.0017 (12)	−0.0111 (11)
C11	0.0454 (14)	0.0424 (15)	0.0454 (15)	−0.0203 (13)	0.0146 (12)	−0.0211 (12)
C12	0.0372 (13)	0.0319 (13)	0.0478 (15)	−0.0125 (11)	0.0048 (11)	−0.0161 (11)
C13	0.0411 (13)	0.0380 (14)	0.0384 (14)	−0.0187 (12)	0.0040 (11)	−0.0137 (11)
C14	0.0314 (13)	0.0476 (16)	0.0524 (17)	−0.0141 (12)	0.0014 (11)	−0.0271 (14)
N1	0.0431 (13)	0.0441 (14)	0.0543 (15)	−0.0085 (11)	0.0039 (11)	−0.0105 (12)
N2	0.0658 (17)	0.0629 (17)	0.0408 (13)	−0.0243 (14)	−0.0014 (12)	−0.0223 (12)
N3	0.0771 (18)	0.0437 (15)	0.0466 (14)	−0.0293 (14)	0.0058 (13)	−0.0138 (12)
N4	0.0479 (14)	0.0381 (13)	0.0643 (17)	−0.0123 (11)	0.0093 (12)	−0.0192 (12)

Geometric parameters (Å, º) top

Rb1—O8ⁱ	2.7973 (19)	O12—N4	1.208 (3)
Rb1—O2ⁱ	2.853 (2)	O12—Rb1ⁱⁱⁱ	3.274 (2)
Rb1—O7	2.9421 (19)	C1—C2	1.381 (3)
Rb1—O5ⁱⁱ	2.981 (2)	C1—C6	1.384 (4)
Rb1—O11ⁱⁱⁱ	2.984 (2)	C1—C7	1.515 (3)
Rb1—O2	3.132 (2)	C2—C3	1.383 (4)
Rb1—O3^iv	3.195 (2)	C2—H2	0.9300
Rb1—O12ⁱⁱⁱ	3.274 (2)	C3—C4	1.371 (4)
Rb1—O1	3.403 (2)	C3—N1	1.479 (3)
O1—C7	1.284 (3)	C4—C5	1.381 (4)
O2—C7	1.218 (3)	C4—H3	0.9300
O2—Rb1ⁱ	2.853 (2)	C5—C6	1.373 (4)
O3—N1	1.217 (3)	C5—N2	1.472 (3)
O3—Rb1^v	3.195 (2)	C6—H4	0.9300
O4—N1	1.215 (3)	C8—C13	1.379 (3)
O5—N2	1.223 (3)	C8—C9	1.394 (4)
O5—Rb1ⁱⁱ	2.981 (2)	C8—C14	1.508 (3)
O6—N2	1.206 (3)	C9—C10	1.385 (4)
O7—C14	1.292 (3)	C9—H5	0.9300
O7—H1	0.96 (4)	C10—C11	1.371 (4)
O8—C14	1.219 (3)	C10—N3	1.471 (3)
O8—Rb1ⁱ	2.7973 (19)	C11—C12	1.369 (4)
O9—N3	1.210 (3)	C11—H6	0.9300
O10—N3	1.220 (3)	C12—C13	1.379 (3)
O11—N4	1.215 (3)	C12—N4	1.476 (3)
O11—Rb1ⁱⁱⁱ	2.984 (2)	C13—H7	0.9300

O8ⁱ—Rb1—O2ⁱ	74.83 (6)	C3—C2—H2	120.5
O8ⁱ—Rb1—O7	130.02 (6)	C4—C3—C2	122.9 (2)
O2ⁱ—Rb1—O7	70.65 (5)	C4—C3—N1	118.1 (2)
O8ⁱ—Rb1—O5ⁱⁱ	104.14 (7)	C2—C3—N1	119.0 (2)
O2ⁱ—Rb1—O5ⁱⁱ	169.95 (6)	C3—C4—C5	116.3 (2)
O7—Rb1—O5ⁱⁱ	103.80 (6)	C3—C4—H3	121.8
O8ⁱ—Rb1—O11ⁱⁱⁱ	90.51 (7)	C5—C4—H3	121.8
O2ⁱ—Rb1—O11ⁱⁱⁱ	114.53 (6)	C6—C5—C4	122.9 (2)
O7—Rb1—O11ⁱⁱⁱ	136.55 (6)	C6—C5—N2	118.9 (2)
O5ⁱⁱ—Rb1—O11ⁱⁱⁱ	75.35 (7)	C4—C5—N2	118.2 (2)
O8ⁱ—Rb1—O2	70.73 (5)	C5—C6—C1	119.3 (2)
O2ⁱ—Rb1—O2	78.03 (5)	C5—C6—H4	120.4
O7—Rb1—O2	67.61 (5)	C1—C6—H4	120.4
O5ⁱⁱ—Rb1—O2	92.15 (6)	O2—C7—O1	125.6 (2)
O11ⁱⁱⁱ—Rb1—O2	154.45 (6)	O2—C7—C1	119.8 (2)
O8ⁱ—Rb1—O3^iv	152.21 (6)	O1—C7—C1	114.6 (2)
O2ⁱ—Rb1—O3^iv	105.72 (6)	C13—C8—C9	120.1 (2)
O7—Rb1—O3^iv	73.40 (6)	C13—C8—C14	120.6 (2)
O5ⁱⁱ—Rb1—O3^iv	79.97 (7)	C9—C8—C14	119.2 (2)
O11ⁱⁱⁱ—Rb1—O3^iv	63.58 (7)	C10—C9—C8	118.2 (2)
O2—Rb1—O3^iv	137.02 (6)	C10—C9—H5	120.9
O8ⁱ—Rb1—O12ⁱⁱⁱ	97.66 (6)	C8—C9—H5	120.9
O2ⁱ—Rb1—O12ⁱⁱⁱ	78.90 (6)	C11—C10—C9	122.9 (2)
O7—Rb1—O12ⁱⁱⁱ	109.61 (6)	C11—C10—N3	117.6 (2)
O5ⁱⁱ—Rb1—O12ⁱⁱⁱ	111.08 (6)	C9—C10—N3	119.5 (2)
O11ⁱⁱⁱ—Rb1—O12ⁱⁱⁱ	39.61 (6)	C12—C11—C10	117.0 (2)
O2—Rb1—O12ⁱⁱⁱ	156.22 (6)	C12—C11—H6	121.5
O3^iv—Rb1—O12ⁱⁱⁱ	56.26 (6)	C10—C11—H6	121.5
O8ⁱ—Rb1—O1	108.63 (5)	C11—C12—C13	122.9 (2)
O2ⁱ—Rb1—O1	98.35 (5)	C11—C12—N4	117.8 (2)
O7—Rb1—O1	45.08 (5)	C13—C12—N4	119.3 (2)
O5ⁱⁱ—Rb1—O1	72.34 (6)	C12—C13—C8	118.9 (2)
O11ⁱⁱⁱ—Rb1—O1	145.53 (6)	C12—C13—H7	120.6
O2—Rb1—O1	39.54 (5)	C8—C13—H7	120.6
O3^iv—Rb1—O1	98.85 (6)	O8—C14—O7	126.1 (2)
O12ⁱⁱⁱ—Rb1—O1	151.95 (5)	O8—C14—C8	120.0 (3)
C7—O1—Rb1	87.28 (15)	O7—C14—C8	113.8 (2)
C7—O2—Rb1ⁱ	127.37 (18)	O4—N1—O3	123.7 (3)
C7—O2—Rb1	101.53 (17)	O4—N1—C3	118.1 (3)
Rb1ⁱ—O2—Rb1	101.97 (5)	O3—N1—C3	118.2 (2)
N1—O3—Rb1^v	112.76 (17)	O6—N2—O5	123.7 (3)
N2—O5—Rb1ⁱⁱ	111.6 (2)	O6—N2—C5	118.4 (2)
C14—O7—Rb1	119.78 (15)	O5—N2—C5	117.9 (3)
C14—O7—H1	113 (3)	O6—N2—Rb1ⁱⁱ	86.28 (17)
Rb1—O7—H1	74 (3)	O5—N2—Rb1ⁱⁱ	50.10 (15)
C14—O8—Rb1ⁱ	120.61 (16)	C5—N2—Rb1ⁱⁱ	137.66 (17)
N4—O11—Rb1ⁱⁱⁱ	100.05 (17)	O9—N3—O10	123.6 (3)
N4—O12—Rb1ⁱⁱⁱ	86.09 (16)	O9—N3—C10	118.7 (2)
C2—C1—C6	119.5 (2)	O10—N3—C10	117.7 (3)
C2—C1—C7	119.8 (2)	O12—N4—O11	123.8 (2)
C6—C1—C7	120.6 (2)	O12—N4—C12	118.5 (2)
C1—C2—C3	119.0 (2)	O11—N4—C12	117.7 (2)
C1—C2—H2	120.5

O8ⁱ—Rb1—O1—C7	−4.89 (16)	Rb1—O1—C7—C1	155.4 (2)
O2ⁱ—Rb1—O1—C7	71.84 (15)	Rb1—O1—C7—Rb1ⁱ	−67.82 (12)
O7—Rb1—O1—C7	123.58 (17)	C2—C1—C7—O2	−5.5 (4)
O5ⁱⁱ—Rb1—O1—C7	−104.28 (16)	C6—C1—C7—O2	177.5 (2)
O11ⁱⁱⁱ—Rb1—O1—C7	−125.39 (16)	C2—C1—C7—O1	173.8 (2)
O2—Rb1—O1—C7	12.30 (14)	C6—C1—C7—O1	−3.3 (4)
O3^iv—Rb1—O1—C7	179.29 (15)	C2—C1—C7—Rb1ⁱ	36.6 (3)
O12ⁱⁱⁱ—Rb1—O1—C7	153.88 (15)	C6—C1—C7—Rb1ⁱ	−140.5 (2)
N4ⁱⁱⁱ—Rb1—O1—C7	−163.41 (14)	C13—C8—C9—C10	−0.1 (4)
C14ⁱ—Rb1—O1—C7	2.46 (15)	C14—C8—C9—C10	177.2 (2)
N2ⁱⁱ—Rb1—O1—C7	−92.20 (16)	C8—C9—C10—C11	−0.7 (4)
O8ⁱ—Rb1—O2—C7	149.51 (17)	C8—C9—C10—N3	−179.6 (2)
O2ⁱ—Rb1—O2—C7	−132.57 (18)	C9—C10—C11—C12	0.5 (4)
O7—Rb1—O2—C7	−58.77 (16)	N3—C10—C11—C12	179.4 (2)
O5ⁱⁱ—Rb1—O2—C7	45.28 (17)	C10—C11—C12—C13	0.5 (4)
O11ⁱⁱⁱ—Rb1—O2—C7	104.7 (2)	C10—C11—C12—N4	−177.8 (2)
O3^iv—Rb1—O2—C7	−32.3 (2)	C11—C12—C13—C8	−1.3 (4)
O12ⁱⁱⁱ—Rb1—O2—C7	−146.79 (17)	N4—C12—C13—C8	177.0 (2)
O1—Rb1—O2—C7	−13.23 (15)	C9—C8—C13—C12	1.0 (4)
C14ⁱ—Rb1—O2—C7	154.64 (18)	C14—C8—C13—C12	−176.2 (2)
N2ⁱⁱ—Rb1—O2—C7	45.08 (16)	Rb1ⁱ—O8—C14—O7	−81.4 (3)
O8ⁱ—Rb1—O2—Rb1ⁱ	−77.92 (6)	Rb1ⁱ—O8—C14—C8	100.6 (2)
O2ⁱ—Rb1—O2—Rb1ⁱ	0.0	Rb1—O7—C14—O8	89.7 (3)
O7—Rb1—O2—Rb1ⁱ	73.80 (6)	Rb1—O7—C14—C8	−92.2 (2)
O5ⁱⁱ—Rb1—O2—Rb1ⁱ	177.84 (7)	Rb1—O7—C14—Rb1ⁱ	44.33 (18)
O11ⁱⁱⁱ—Rb1—O2—Rb1ⁱ	−122.72 (14)	C13—C8—C14—O8	171.6 (2)
O3^iv—Rb1—O2—Rb1ⁱ	100.29 (9)	C9—C8—C14—O8	−5.6 (4)
O12ⁱⁱⁱ—Rb1—O2—Rb1ⁱ	−14.22 (17)	C13—C8—C14—O7	−6.6 (3)
O1—Rb1—O2—Rb1ⁱ	119.33 (9)	C9—C8—C14—O7	176.2 (2)
C14ⁱ—Rb1—O2—Rb1ⁱ	−72.80 (7)	C13—C8—C14—Rb1ⁱ	−139.52 (19)
N2ⁱⁱ—Rb1—O2—Rb1ⁱ	177.65 (7)	C9—C8—C14—Rb1ⁱ	43.2 (3)
O8ⁱ—Rb1—O7—C14	−39.1 (2)	Rb1^v—O3—N1—O4	−1.9 (4)
O2ⁱ—Rb1—O7—C14	9.82 (17)	Rb1^v—O3—N1—C3	178.04 (16)
O5ⁱⁱ—Rb1—O7—C14	−161.43 (18)	C4—C3—N1—O4	3.4 (4)
O11ⁱⁱⁱ—Rb1—O7—C14	115.44 (19)	C2—C3—N1—O4	−176.7 (3)
O2—Rb1—O7—C14	−74.83 (18)	C4—C3—N1—O3	−176.5 (3)
O3^iv—Rb1—O7—C14	123.67 (18)	C2—C3—N1—O3	3.4 (4)
O12ⁱⁱⁱ—Rb1—O7—C14	79.84 (18)	Rb1ⁱⁱ—O5—N2—O6	−48.8 (4)
O1—Rb1—O7—C14	−114.75 (19)	Rb1ⁱⁱ—O5—N2—C5	130.3 (2)
N4ⁱⁱⁱ—Rb1—O7—C14	99.53 (18)	C6—C5—N2—O6	−5.8 (4)
C14ⁱ—Rb1—O7—C14	−45.6 (2)	C4—C5—N2—O6	174.8 (3)
N2ⁱⁱ—Rb1—O7—C14	−144.50 (18)	C6—C5—N2—O5	175.1 (3)
C6—C1—C2—C3	1.4 (4)	C4—C5—N2—O5	−4.3 (4)
C7—C1—C2—C3	−175.7 (2)	C6—C5—N2—Rb1ⁱⁱ	−124.7 (2)
C1—C2—C3—C4	−0.3 (4)	C4—C5—N2—Rb1ⁱⁱ	55.9 (4)
C1—C2—C3—N1	179.8 (2)	C11—C10—N3—O9	176.9 (3)
C2—C3—C4—C5	−0.9 (4)	C9—C10—N3—O9	−4.2 (4)
N1—C3—C4—C5	178.9 (2)	C11—C10—N3—O10	−2.2 (4)
C3—C4—C5—C6	1.1 (4)	C9—C10—N3—O10	176.8 (3)
C3—C4—C5—N2	−179.5 (2)	Rb1ⁱⁱⁱ—O12—N4—O11	−32.7 (3)
C4—C5—C6—C1	−0.1 (4)	Rb1ⁱⁱⁱ—O12—N4—C12	145.8 (2)
N2—C5—C6—C1	−179.4 (2)	Rb1ⁱⁱⁱ—O11—N4—O12	36.9 (3)
C2—C1—C6—C5	−1.2 (4)	Rb1ⁱⁱⁱ—O11—N4—C12	−141.63 (19)
C7—C1—C6—C5	175.9 (2)	C11—C12—N4—O12	−175.2 (3)
Rb1ⁱ—O2—C7—O1	−86.6 (3)	C13—C12—N4—O12	6.5 (4)
Rb1—O2—C7—O1	28.4 (3)	C11—C12—N4—O11	3.4 (4)
Rb1ⁱ—O2—C7—C1	92.5 (3)	C13—C12—N4—O11	−174.9 (3)
Rb1—O2—C7—C1	−152.5 (2)	C11—C12—N4—Rb1ⁱⁱⁱ	−72.2 (4)
Rb1—O2—C7—Rb1ⁱ	114.97 (17)	C13—C12—N4—Rb1ⁱⁱⁱ	109.5 (3)
Rb1—O1—C7—O2	−25.4 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H1···O1	0.96 (4)	1.52 (4)	2.470 (2)	168 (4)

Experimental details

Crystal data
Chemical formula	[Rb(C₇H₃N₂O₆)(C₇H₄N₂O₆)]
M_r	508.71
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.4823 (8), 9.8136 (8), 11.4929 (11)
α, β, γ (°)	68.425 (1), 83.821 (1), 67.538 (1)
V (Å³)	918.42 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.77
Crystal size (mm)	0.40 × 0.31 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.368, 0.635
No. of measured, independent and observed [I > 2σ(I)] reflections	4661, 3219, 2758
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.079, 1.08
No. of reflections	3219
No. of parameters	284
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.38

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H1···O1	0.96 (4)	1.52 (4)	2.470 (2)	168 (4)

Acknowledgements

This work was supported financially by grants from the Scientific Research Plan Projects of Shaanxi Province Department of Health (2010D54), the Natural Science Research Plan Projects of Shaanxi Science and Technology Department (SJ08B19) and the Scientific Research Plan Projects of Shaanxi Education Department (09 J K709). Chunye Liu is thanked for the data collection and Lining Yang for the structure solution and refinement.

References

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