Poly[[aqua­(μ5-1H-benzimidazole-5,6-dicarboxyl­ato)(μ4-1H-benzimidazole-5,6-dicarboxyl­ato)dibarium] 4.5-hydrate]

Zhang, H.-Q.; Zheng, X.-J.; Zhao, C.-X.; Ng, S.W.

doi:10.1107/S160053681101590X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages m671-m672

doi:10.1107/S160053681101590X

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Poly[[aqua(μ₅-1H-benzimidazole-5,6-dicarboxylato)(μ₄-1H-benzimidazole-5,6-dicarboxylato)dibarium] 4.5-hydrate]

Heng-Qiang Zhang,^a Xiu-Jun Zheng,^b Chun-Xiang Zhao ^c and Seik Weng Ng ^d ^*

^aDepartment of Chemistry, East China Normal University, Shanghai 200062, People's Republic of China, ^bDepartment of Chemical Engineering, Huarui College, Northeast Petroleum University, Harbin 15002, People's Republic of China, ^cDepartment of Chemistry, Zhoukou Normal University, Zhoukou 466001, People's Republic of China, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 19 April 2011; accepted 26 April 2011; online 7 May 2011)

The polymeric title compound, {[Ba₂(C₉H₄N₂O₄)₂(H₂O)]·4.5H₂O}_n, adopts a layer structure parallel to (001) in which adjacent Ba^II atoms are connected by two benzimidazole-5,6-dicarboxylate dianions, one functioning in a μ₄-bridging mode and the other in a μ₅-bridging mode. The Ba atom having water in its coordination environment as well as the Ba atom without water exist in a nine-coordinate polyhedron of O atoms; the geometry is difficult to derive. Lattice water molecules occupy the space between layers and interact with the layers through O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds. ne of the five lattice water molecules is equally disordered around an inversion centre and shows half-occupancy.

Related literature

For the strontium 1H-benzimidazole-5,6-dicarboxylate derivative, see: Song et al. (2009 ).

Experimental

Crystal data

[Ba₂(C₉H₄N₂O₄)₂(H₂O)]·4.5H₂O
M_r = 782.05
Triclinic, $[P \overline 1]$
a = 6.9331 (4) Å
b = 9.5950 (4) Å
c = 18.0179 (7) Å
α = 103.186 (1)°
β = 92.068 (2)°
γ = 93.032 (2)°
V = 1163.94 (9) Å³
Z = 2
Mo Kα radiation
μ = 3.44 mm⁻¹
T = 293 K
0.33 × 0.24 × 0.21 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.396, T_max = 0.532
11398 measured reflections
5246 independent reflections
4749 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.074
S = 1.07
5246 reflections
343 parameters
30 restraints
H-atom parameters constrained
Δρ_max = 1.54 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯O4wⁱ	0.84	1.66	2.49 (1)	170
O1w—H12⋯O2wⁱⁱ	0.84	1.88	2.60 (1)	143
O2w—H21⋯N2	0.84	2.00	2.83 (1)	168
O2w—H22⋯N2ⁱⁱⁱ	0.84	2.28	2.83 (1)	124
O3w—H31⋯N3	0.84	2.34	2.95 (1)	129
O3w—H32⋯O6w^iv	0.84	1.85	2.68 (1)	174
O4w—H41⋯O3w^v	0.84	2.03	2.84 (2)	161
O5w—H51⋯O1w^v	0.84	2.31	2.75 (1)	113
O6w—H61⋯O4^vi	0.84	1.99	2.76 (1)	152
O6w—H62⋯O8	0.84	2.09	2.86 (1)	152
N1—H1⋯O1w	0.88	1.93	2.80 (1)	168
N4—H4⋯O4w	0.88	1.99	2.86 (1)	167
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+2, -z+2; (iii) -x+1, -y+1, -z+2; (iv) x, y+1, z; (v) x, y-1, z; (vi) -x, -y, -z+1.

Data collection: RAPID-AUTO (Rigaku Corporation, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (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/S160053681101590X/jh2280sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101590X/jh2280Isup2.hkl

checkCIF report

Comment top

The 1H-benzimidazole-5,6-dicarboxylate dianion affords a large number of metal salts; most of the crystal structure studies involve rare earth metals. The crystal structures of only few main group derivatives have been reported. The Sr^II derivative exists as a monohydrate; the metal atom is also coordinated by two water ligands in an eight-coordinate square-antiprismatic geometry. The dianion functions in a \m4 bridging mode (Song et al., 2009). The Ba^II analog has 4.5 lattice water molecules (Scheme I). Polymeric Ba₂(H₂O)(C₉H₄NO₄)₂^.4.5H₂O adopts a layer structure in which adjacent Ba^II atoms are connected by two benzimidazole-5,6-dicarboxylate dianions, one functioning in a µ₄ bridging mode and the other in a µ₅ bridging mode. The Ba atom having water in its coordination environment as well as the Ba atom without water exist in a nine-coordinate polyhedron of O atom; the geometry is undefined. Lattice water molecules occupy the space between layers, and interact with the layers through O–H···O and N–H···O hydrogen bonds to generate a three-dimensional network (Table 1).

Related literature top

For the strontium 1H-benzimidazole-5,6-dicarboxylate derivative, see: Song et al. (2009).

Experimental top

Barium chloride (0.0416 g, 0.20 mmol) and 1H-benzimidazole-5,6-dicarboxylic acid (0.0412 g, 0.20 mmol) were placed in water (35 ml); the reactants dissolved upon addition of several drops of dilute sodium hydroxide to a pH of 7. The solution was set aside for the growth of crystals over several weeks; yield 60% based on Ba.

Computing details top

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO (Rigaku Corporation, 1998); data reduction: CrystalStructure (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 a portion of the layer structure of Ba₂(H₂O)(C₉H₄NO₄)₂^.4.5H₂O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry code: (i) -x, -y + 1, -z + 1; (ii) -x + 1, -y + 1, -z + 1; (iii) x, y + 1, z; (iv) x, y - 1, z; (v) -x + 1, -y, -z + 1; (vi) -x, -y, -z + 1.

Poly[[aqua(µ₅-1H-benzimidazole-5,6-dicarboxylato)(µ₄-1H- benzimidazole-5,6-dicarboxylato)dibarium] 4.5-hydrate] top

Crystal data top

[Ba₂(C₉H₄N₂O₄)₂(H₂O)]·4.5H₂O	Z = 2
M_r = 782.05	F(000) = 750
Triclinic, P1	D_x = 2.231 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9331 (4) Å	Cell parameters from 10107 reflections
b = 9.5950 (4) Å	θ = 3.1–27.5°
c = 18.0179 (7) Å	µ = 3.44 mm⁻¹
α = 103.186 (1)°	T = 293 K
β = 92.068 (2)°	Prism, colorless
γ = 93.032 (2)°	0.33 × 0.24 × 0.21 mm
V = 1163.94 (9) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	5246 independent reflections
Radiation source: fine-focus sealed tube	4749 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 10.000 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→12
T_min = 0.396, T_max = 0.532	l = −23→23
11398 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0388P)² + 1.7294P] where P = (F_o² + 2F_c²)/3
5246 reflections	(Δ/σ)_max = 0.001
343 parameters	Δρ_max = 1.54 e Å⁻³
30 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

[Ba₂(C₉H₄N₂O₄)₂(H₂O)]·4.5H₂O	γ = 93.032 (2)°
M_r = 782.05	V = 1163.94 (9) Å³
Triclinic, P1	Z = 2
a = 6.9331 (4) Å	Mo Kα radiation
b = 9.5950 (4) Å	µ = 3.44 mm⁻¹
c = 18.0179 (7) Å	T = 293 K
α = 103.186 (1)°	0.33 × 0.24 × 0.21 mm
β = 92.068 (2)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5246 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4749 reflections with I > 2σ(I)
T_min = 0.396, T_max = 0.532	R_int = 0.025
11398 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	30 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.07	Δρ_max = 1.54 e Å⁻³
5246 reflections	Δρ_min = −0.68 e Å⁻³
343 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ba1	0.26276 (3)	0.610140 (19)	0.450910 (11)	0.02043 (7)
Ba2	0.26062 (3)	0.078630 (18)	0.581428 (11)	0.01842 (7)
O1	0.1686 (4)	0.8140 (3)	0.60189 (15)	0.0296 (5)
O2	0.0501 (4)	0.5894 (3)	0.57721 (14)	0.0267 (5)
O3	0.3591 (4)	0.3818 (3)	0.61724 (16)	0.0335 (6)
O4	0.0593 (4)	0.3350 (3)	0.64668 (16)	0.0325 (6)
O5	0.4310 (4)	0.3577 (2)	0.43836 (15)	0.0282 (5)
O6	0.4612 (3)	0.1417 (2)	0.46119 (14)	0.0228 (5)
O7	0.1291 (3)	−0.0557 (3)	0.43544 (14)	0.0259 (5)
O8	0.3566 (3)	−0.1786 (3)	0.37175 (15)	0.0262 (5)
O1w	0.3097 (12)	1.1921 (6)	0.8946 (3)	0.128 (2)
H11	0.2025	1.2235	0.9081	0.192*
H12	0.3998	1.2440	0.9213	0.192*
O2w	0.5133 (16)	0.5633 (9)	1.0382 (5)	0.083 (3)	0.50
H21	0.4591	0.5883	1.0013	0.124*	0.50
H22	0.5884	0.4986	1.0218	0.124*	0.50
O3w	0.2112 (15)	0.4994 (10)	0.1075 (5)	0.177 (4)
H31	0.1689	0.4135	0.0922	0.266*
H32	0.2282	0.5210	0.1552	0.266*
O4w	−0.0138 (16)	−0.3037 (13)	0.0517 (7)	0.225 (5)
H41	0.0288	−0.3661	0.0729	0.337*
H42	−0.0152	−0.3286	0.0039	0.337*
O5w	0.3529 (5)	0.1624 (4)	0.74063 (18)	0.0466 (8)
H51	0.2820	0.1137	0.7634	0.070*
H52	0.4694	0.1486	0.7492	0.070*
O6w	0.2361 (6)	−0.4351 (4)	0.2606 (3)	0.0666 (11)
H61	0.1264	−0.4298	0.2790	0.100*
H62	0.3069	−0.3650	0.2855	0.100*
N1	0.3285 (6)	0.9029 (4)	0.8973 (2)	0.0397 (8)
H1	0.3280	0.9966	0.9036	0.048*
N2	0.3607 (6)	0.6883 (4)	0.9229 (2)	0.0424 (9)
N3	0.2152 (6)	0.2189 (5)	0.1479 (2)	0.0434 (9)
N4	0.1238 (6)	−0.0140 (5)	0.1170 (2)	0.0473 (10)
H4	0.0825	−0.0992	0.0897	0.057*
C1	0.1336 (4)	0.6990 (3)	0.62169 (19)	0.0198 (6)
C2	0.1978 (5)	0.6878 (3)	0.70029 (19)	0.0199 (6)
C3	0.2313 (5)	0.8127 (4)	0.7571 (2)	0.0250 (7)
H3A	0.2173	0.9023	0.7467	0.030*
C4	0.2863 (6)	0.7997 (4)	0.8300 (2)	0.0290 (7)
C5	0.3694 (7)	0.8313 (5)	0.9496 (2)	0.0459 (11)
H5	0.4014	0.8757	1.0004	0.055*
C6	0.3078 (6)	0.6659 (4)	0.8458 (2)	0.0305 (8)
C7	0.2809 (6)	0.5397 (4)	0.7887 (2)	0.0294 (8)
H7	0.2983	0.4506	0.7992	0.035*
C8	0.2277 (5)	0.5522 (3)	0.71628 (19)	0.0208 (6)
C9	0.2134 (5)	0.4149 (3)	0.6539 (2)	0.0241 (7)
C10	0.4047 (4)	0.2236 (3)	0.41961 (19)	0.0198 (6)
C11	0.3099 (5)	0.1562 (3)	0.34209 (19)	0.0201 (6)
C12	0.3057 (5)	0.2372 (4)	0.2876 (2)	0.0271 (7)
H12A	0.3482	0.3337	0.2999	0.033*
C13	0.2370 (5)	0.1713 (4)	0.2147 (2)	0.0306 (8)
C14	0.1482 (8)	0.1045 (6)	0.0937 (3)	0.0517 (12)
H14	0.1213	0.1093	0.0434	0.062*
C15	0.1772 (6)	0.0235 (4)	0.1942 (2)	0.0312 (8)
C16	0.1771 (5)	−0.0567 (4)	0.2494 (2)	0.0285 (7)
H16	0.1342	−0.1530	0.2371	0.034*
C17	0.2418 (5)	0.0098 (3)	0.32264 (19)	0.0206 (6)
C18	0.2422 (5)	−0.0791 (3)	0.38180 (19)	0.0201 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ba1	0.01885 (11)	0.01795 (11)	0.02441 (11)	−0.00112 (7)	−0.00104 (7)	0.00554 (8)
Ba2	0.01508 (11)	0.01541 (10)	0.02374 (11)	−0.00021 (7)	0.00126 (7)	0.00261 (8)
O1	0.0343 (14)	0.0228 (12)	0.0336 (14)	−0.0030 (10)	0.0009 (11)	0.0118 (11)
O2	0.0294 (13)	0.0237 (12)	0.0247 (12)	−0.0051 (10)	−0.0022 (10)	0.0027 (10)
O3	0.0334 (15)	0.0224 (12)	0.0429 (16)	0.0048 (10)	0.0116 (12)	0.0014 (11)
O4	0.0310 (14)	0.0199 (12)	0.0433 (15)	−0.0043 (10)	−0.0035 (11)	0.0024 (11)
O5	0.0296 (14)	0.0170 (11)	0.0360 (14)	0.0010 (10)	−0.0055 (11)	0.0032 (10)
O6	0.0206 (12)	0.0219 (11)	0.0260 (12)	−0.0023 (9)	−0.0012 (9)	0.0066 (10)
O7	0.0189 (12)	0.0325 (13)	0.0245 (12)	−0.0055 (10)	0.0009 (9)	0.0042 (10)
O8	0.0210 (12)	0.0212 (11)	0.0377 (14)	0.0022 (9)	0.0004 (10)	0.0096 (11)
O1w	0.250 (7)	0.084 (3)	0.052 (3)	0.056 (4)	−0.013 (4)	0.010 (3)
O2w	0.115 (7)	0.066 (5)	0.070 (5)	0.018 (5)	−0.021 (5)	0.024 (4)
O3w	0.222 (8)	0.179 (7)	0.139 (6)	0.058 (6)	0.037 (6)	0.036 (5)
O4w	0.220 (9)	0.245 (8)	0.216 (9)	0.008 (7)	0.022 (7)	0.067 (7)
O5w	0.049 (2)	0.0500 (18)	0.0395 (17)	0.0039 (15)	0.0036 (14)	0.0080 (15)
O6w	0.058 (2)	0.046 (2)	0.089 (3)	0.0012 (17)	0.014 (2)	0.002 (2)
N1	0.051 (2)	0.0288 (16)	0.0326 (17)	0.0046 (15)	−0.0052 (15)	−0.0057 (14)
N2	0.059 (2)	0.042 (2)	0.0234 (16)	−0.0016 (17)	−0.0061 (15)	0.0048 (15)
N3	0.039 (2)	0.062 (2)	0.0366 (19)	0.0035 (18)	−0.0018 (15)	0.0271 (19)
N4	0.052 (2)	0.061 (2)	0.0265 (17)	0.0011 (19)	−0.0085 (16)	0.0065 (18)
C1	0.0138 (14)	0.0201 (15)	0.0252 (16)	0.0012 (11)	0.0034 (12)	0.0045 (13)
C2	0.0161 (15)	0.0184 (14)	0.0244 (16)	0.0021 (11)	0.0013 (12)	0.0031 (13)
C3	0.0246 (17)	0.0189 (15)	0.0304 (18)	0.0025 (13)	0.0012 (14)	0.0028 (14)
C4	0.0298 (19)	0.0263 (17)	0.0259 (17)	0.0017 (14)	−0.0002 (14)	−0.0044 (14)
C5	0.059 (3)	0.049 (3)	0.0234 (19)	0.002 (2)	−0.0075 (18)	−0.0030 (18)
C6	0.035 (2)	0.0309 (18)	0.0237 (17)	−0.0003 (15)	−0.0015 (14)	0.0036 (15)
C7	0.037 (2)	0.0222 (16)	0.0284 (18)	0.0018 (14)	−0.0023 (15)	0.0061 (14)
C8	0.0197 (16)	0.0163 (14)	0.0248 (16)	−0.0008 (12)	0.0001 (12)	0.0021 (13)
C9	0.0289 (18)	0.0157 (14)	0.0276 (17)	0.0026 (13)	−0.0018 (13)	0.0052 (13)
C10	0.0135 (14)	0.0200 (14)	0.0258 (16)	0.0013 (11)	0.0014 (12)	0.0048 (13)
C11	0.0155 (15)	0.0179 (14)	0.0272 (16)	0.0033 (11)	0.0017 (12)	0.0051 (13)
C12	0.0228 (17)	0.0273 (17)	0.0342 (19)	0.0011 (13)	0.0021 (14)	0.0128 (15)
C13	0.0247 (18)	0.041 (2)	0.0309 (19)	0.0055 (15)	0.0008 (14)	0.0178 (17)
C14	0.049 (3)	0.079 (4)	0.030 (2)	0.004 (3)	−0.0050 (19)	0.022 (2)
C15	0.0285 (19)	0.038 (2)	0.0248 (17)	0.0024 (15)	−0.0037 (14)	0.0022 (16)
C16	0.0274 (18)	0.0265 (17)	0.0292 (18)	0.0013 (14)	−0.0015 (14)	0.0019 (15)
C17	0.0166 (15)	0.0202 (15)	0.0248 (16)	0.0026 (12)	0.0006 (12)	0.0044 (13)
C18	0.0157 (15)	0.0176 (14)	0.0258 (16)	−0.0047 (11)	−0.0032 (12)	0.0044 (13)

Geometric parameters (Å, º) top

Ba1—O1	3.080 (3)	O3w—H31	0.8400
Ba1—O2	2.795 (2)	O3w—H32	0.8400
Ba1—O2ⁱ	2.769 (2)	O4w—H41	0.8401
Ba1—O3ⁱⁱ	2.940 (3)	O4w—H42	0.8400
Ba1—O4ⁱ	2.936 (3)	O5w—H51	0.8401
Ba1—O5	2.711 (2)	O5w—H52	0.8400
Ba1—O5ⁱⁱ	2.816 (3)	O6w—H61	0.8401
Ba1—O6ⁱⁱ	3.069 (2)	O6w—H62	0.8400
Ba1—O8ⁱⁱⁱ	2.795 (2)	N1—C5	1.318 (6)
Ba2—O1^iv	2.695 (2)	N1—C4	1.389 (5)
Ba2—O3	2.871 (3)	N1—H1	0.8800
Ba2—O4	2.923 (3)	N2—C5	1.343 (6)
Ba2—O6	2.778 (2)	N2—C6	1.389 (5)
Ba2—O6^v	2.928 (2)	N3—C14	1.342 (7)
Ba2—O7^vi	2.700 (2)	N3—C13	1.387 (5)
Ba2—O7	2.751 (2)	N4—C14	1.304 (7)
Ba2—O8^v	2.806 (2)	N4—C15	1.386 (5)
Ba2—O5w	2.836 (3)	N4—H4	0.8800
O1—C1	1.249 (4)	C1—C2	1.498 (5)
O1—Ba2ⁱⁱⁱ	2.695 (2)	C2—C3	1.390 (5)
O2—C1	1.266 (4)	C2—C8	1.419 (4)
O2—Ba1ⁱ	2.769 (2)	C3—C4	1.389 (5)
O3—C9	1.242 (4)	C3—H3A	0.9300
O3—Ba1ⁱⁱ	2.940 (3)	C4—C6	1.392 (5)
O4—C9	1.266 (4)	C5—H5	0.9300
O4—Ba1ⁱ	2.936 (3)	C6—C7	1.398 (5)
O5—C10	1.255 (4)	C7—C8	1.376 (5)
O5—Ba1ⁱⁱ	2.816 (3)	C7—H7	0.9300
O6—C10	1.270 (4)	C8—C9	1.521 (5)
O6—Ba2^v	2.928 (2)	C10—C11	1.509 (5)
O6—Ba1ⁱⁱ	3.069 (2)	C10—Ba1ⁱⁱ	3.290 (3)
O7—C18	1.254 (4)	C11—C12	1.384 (5)
O7—Ba2^vi	2.700 (2)	C11—C17	1.419 (4)
O8—C18	1.259 (4)	C12—C13	1.377 (5)
O8—Ba1^iv	2.795 (2)	C12—H12A	0.9300
O8—Ba2^v	2.806 (2)	C13—C15	1.417 (6)
O1w—H11	0.8400	C14—H14	0.9300
O1w—H12	0.8400	C15—C16	1.388 (6)
O2w—O2w^vii	1.613 (18)	C16—C17	1.377 (5)
O2w—H21	0.8400	C16—H16	0.9300
O2w—H22	0.8400	C17—C18	1.510 (4)

O5—Ba1—O2ⁱ	77.01 (8)	C10—O6—Ba2	124.7 (2)
O5—Ba1—O2	95.97 (8)	C10—O6—Ba2^v	125.3 (2)
O2ⁱ—Ba1—O2	64.13 (8)	Ba2—O6—Ba2^v	107.25 (7)
O5—Ba1—O8ⁱⁱⁱ	126.34 (8)	C10—O6—Ba1ⁱⁱ	88.47 (18)
O2ⁱ—Ba1—O8ⁱⁱⁱ	127.94 (7)	Ba2—O6—Ba1ⁱⁱ	99.88 (7)
O2—Ba1—O8ⁱⁱⁱ	136.76 (7)	Ba2^v—O6—Ba1ⁱⁱ	99.38 (7)
O5—Ba1—O5ⁱⁱ	70.23 (8)	C18—O7—Ba2^vi	125.1 (2)
O2ⁱ—Ba1—O5ⁱⁱ	128.53 (7)	C18—O7—Ba2	121.1 (2)
O2—Ba1—O5ⁱⁱ	80.81 (8)	Ba2^vi—O7—Ba2	112.68 (8)
O8ⁱⁱⁱ—Ba1—O5ⁱⁱ	103.49 (7)	C18—O8—Ba1^iv	113.3 (2)
O5—Ba1—O4ⁱ	126.10 (7)	C18—O8—Ba2^v	112.42 (19)
O2ⁱ—Ba1—O4ⁱ	63.11 (7)	Ba1^iv—O8—Ba2^v	106.20 (8)
O2—Ba1—O4ⁱ	97.43 (8)	H11—O1w—H12	110.0
O8ⁱⁱⁱ—Ba1—O4ⁱ	66.63 (7)	O2w^vii—O2w—H21	66.4
O5ⁱⁱ—Ba1—O4ⁱ	163.60 (7)	O2w^vii—O2w—H22	51.6
O5—Ba1—O3ⁱⁱ	68.84 (7)	H21—O2w—H22	109.5
O2ⁱ—Ba1—O3ⁱⁱ	132.66 (7)	H31—O3w—H32	110.7
O2—Ba1—O3ⁱⁱ	148.68 (8)	H41—O4w—H42	112.7
O8ⁱⁱⁱ—Ba1—O3ⁱⁱ	60.17 (7)	Ba2—O5w—H51	109.4
O5ⁱⁱ—Ba1—O3ⁱⁱ	68.41 (8)	Ba2—O5w—H52	109.5
O4ⁱ—Ba1—O3ⁱⁱ	113.72 (8)	H51—O5w—H52	109.5
O5—Ba1—O6ⁱⁱ	110.03 (7)	H61—O6w—H62	107.7
O2ⁱ—Ba1—O6ⁱⁱ	158.74 (6)	C5—N1—C4	105.7 (4)
O2—Ba1—O6ⁱⁱ	94.83 (7)	C5—N1—H1	127.1
O8ⁱⁱⁱ—Ba1—O6ⁱⁱ	64.97 (7)	C4—N1—H1	127.1
O5ⁱⁱ—Ba1—O6ⁱⁱ	44.11 (6)	C5—N2—C6	105.2 (4)
O4ⁱ—Ba1—O6ⁱⁱ	120.42 (7)	C14—N3—C13	106.3 (4)
O3ⁱⁱ—Ba1—O6ⁱⁱ	67.22 (7)	C14—N4—C15	105.0 (4)
O5—Ba1—O1	125.39 (7)	C14—N4—H4	127.5
O2ⁱ—Ba1—O1	103.10 (7)	C15—N4—H4	127.5
O2—Ba1—O1	43.78 (6)	O1—C1—O2	122.6 (3)
O8ⁱⁱⁱ—Ba1—O1	97.04 (7)	O1—C1—C2	119.2 (3)
O5ⁱⁱ—Ba1—O1	68.40 (7)	O2—C1—C2	118.2 (3)
O4ⁱ—Ba1—O1	98.98 (7)	C3—C2—C8	120.4 (3)
O3ⁱⁱ—Ba1—O1	123.17 (7)	C3—C2—C1	118.9 (3)
O6ⁱⁱ—Ba1—O1	56.15 (6)	C8—C2—C1	120.7 (3)
O1^iv—Ba2—O7^vi	76.72 (8)	C4—C3—C2	118.0 (3)
O1^iv—Ba2—O7	80.25 (8)	C4—C3—H3A	121.0
O7^vi—Ba2—O7	67.32 (8)	C2—C3—H3A	121.0
O1^iv—Ba2—O6	125.88 (8)	C3—C4—N1	131.1 (4)
O7^vi—Ba2—O6	116.89 (7)	C3—C4—C6	121.1 (3)
O7—Ba2—O6	62.22 (7)	N1—C4—C6	107.7 (3)
O1^iv—Ba2—O8^v	113.68 (8)	N1—C5—N2	113.9 (4)
O7^vi—Ba2—O8^v	163.12 (8)	N1—C5—H5	123.1
O7—Ba2—O8^v	126.06 (7)	N2—C5—H5	123.1
O6—Ba2—O8^v	68.87 (7)	N2—C6—C4	107.4 (3)
O1^iv—Ba2—O5w	87.21 (9)	N2—C6—C7	131.1 (4)
O7^vi—Ba2—O5w	106.45 (9)	C4—C6—C7	121.4 (3)
O7—Ba2—O5w	166.97 (8)	C8—C7—C6	117.6 (3)
O6—Ba2—O5w	129.48 (9)	C8—C7—H7	121.2
O8^v—Ba2—O5w	62.57 (9)	C6—C7—H7	121.2
O1^iv—Ba2—O3	159.72 (8)	C7—C8—C2	121.4 (3)
O7^vi—Ba2—O3	104.58 (8)	C7—C8—C9	116.6 (3)
O7—Ba2—O3	119.27 (8)	C2—C8—C9	121.9 (3)
O6—Ba2—O3	72.16 (7)	O3—C9—O4	123.7 (3)
O8^v—Ba2—O3	60.90 (8)	O3—C9—C8	118.1 (3)
O5w—Ba2—O3	72.92 (9)	O4—C9—C8	118.0 (3)
O1^iv—Ba2—O4	124.90 (8)	O5—C10—O6	123.3 (3)
O7^vi—Ba2—O4	63.37 (7)	O5—C10—C11	118.2 (3)
O7—Ba2—O4	113.76 (8)	O6—C10—C11	118.4 (3)
O6—Ba2—O4	106.09 (7)	O5—C10—Ba1ⁱⁱ	57.20 (18)
O8^v—Ba2—O4	100.03 (7)	O6—C10—Ba1ⁱⁱ	68.83 (18)
O5w—Ba2—O4	70.81 (9)	C11—C10—Ba1ⁱⁱ	159.4 (2)
O3—Ba2—O4	44.87 (7)	C12—C11—C17	120.1 (3)
O1^iv—Ba2—O6^v	61.79 (7)	C12—C11—C10	118.3 (3)
O7^vi—Ba2—O6^v	129.53 (7)	C17—C11—C10	121.3 (3)
O7—Ba2—O6^v	77.96 (7)	C13—C12—C11	118.3 (3)
O6—Ba2—O6^v	72.75 (7)	C13—C12—H12A	120.9
O8^v—Ba2—O6^v	66.84 (7)	C11—C12—H12A	120.9
O5w—Ba2—O6^v	99.26 (8)	C12—C13—N3	133.1 (4)
O3—Ba2—O6^v	124.42 (7)	C12—C13—C15	121.7 (3)
O4—Ba2—O6^v	166.54 (7)	N3—C13—C15	105.1 (4)
C1—O1—Ba2ⁱⁱⁱ	171.4 (2)	N4—C14—N3	114.6 (4)
C1—O1—Ba1	82.76 (19)	N4—C14—H14	122.7
Ba2ⁱⁱⁱ—O1—Ba1	104.56 (8)	N3—C14—H14	122.7
C1—O2—Ba1ⁱ	147.4 (2)	N4—C15—C16	131.3 (4)
C1—O2—Ba1	95.42 (19)	N4—C15—C13	108.9 (4)
Ba1ⁱ—O2—Ba1	115.87 (8)	C16—C15—C13	119.9 (3)
C9—O3—Ba2	95.3 (2)	C17—C16—C15	118.4 (3)
C9—O3—Ba1ⁱⁱ	163.6 (2)	C17—C16—H16	120.8
Ba2—O3—Ba1ⁱⁱ	100.86 (8)	C15—C16—H16	120.8
C9—O4—Ba2	92.3 (2)	C16—C17—C11	121.5 (3)
C9—O4—Ba1ⁱ	118.6 (2)	C16—C17—C18	117.8 (3)
Ba2—O4—Ba1ⁱ	114.25 (9)	C11—C17—C18	120.7 (3)
C10—O5—Ba1	145.3 (2)	O7—C18—O8	123.6 (3)
C10—O5—Ba1ⁱⁱ	100.8 (2)	O7—C18—C17	120.6 (3)
Ba1—O5—Ba1ⁱⁱ	109.77 (8)	O8—C18—C17	115.8 (3)

O5—Ba1—O1—C1	−35.8 (2)	O3—Ba2—O7—C18	74.1 (3)
O2ⁱ—Ba1—O1—C1	47.5 (2)	O4—Ba2—O7—C18	124.3 (2)
O2—Ba1—O1—C1	20.40 (18)	O6^v—Ba2—O7—C18	−48.8 (2)
O8ⁱⁱⁱ—Ba1—O1—C1	179.1 (2)	O1^iv—Ba2—O7—Ba2^vi	79.59 (10)
O5ⁱⁱ—Ba1—O1—C1	−79.1 (2)	O7^vi—Ba2—O7—Ba2^vi	0.0
O4ⁱ—Ba1—O1—C1	111.8 (2)	O6—Ba2—O7—Ba2^vi	−140.71 (12)
O3ⁱⁱ—Ba1—O1—C1	−122.06 (19)	O8^v—Ba2—O7—Ba2^vi	−168.15 (7)
O6ⁱⁱ—Ba1—O1—C1	−127.5 (2)	O5w—Ba2—O7—Ba2^vi	63.6 (4)
O5—Ba1—O1—Ba2ⁱⁱⁱ	139.56 (8)	O3—Ba2—O7—Ba2^vi	−94.51 (10)
O2ⁱ—Ba1—O1—Ba2ⁱⁱⁱ	−137.20 (9)	O4—Ba2—O7—Ba2^vi	−44.37 (11)
O2—Ba1—O1—Ba2ⁱⁱⁱ	−164.28 (15)	O6^v—Ba2—O7—Ba2^vi	142.60 (10)
O8ⁱⁱⁱ—Ba1—O1—Ba2ⁱⁱⁱ	−5.53 (9)	Ba1—O1—C1—O2	−39.2 (3)
O5ⁱⁱ—Ba1—O1—Ba2ⁱⁱⁱ	96.23 (9)	Ba1—O1—C1—C2	138.9 (3)
O4ⁱ—Ba1—O1—Ba2ⁱⁱⁱ	−72.88 (9)	Ba1ⁱ—O2—C1—O1	−120.1 (4)
O3ⁱⁱ—Ba1—O1—Ba2ⁱⁱⁱ	53.27 (12)	Ba1—O2—C1—O1	44.0 (3)
O6ⁱⁱ—Ba1—O1—Ba2ⁱⁱⁱ	47.87 (8)	Ba1ⁱ—O2—C1—C2	61.8 (5)
O5—Ba1—O2—C1	117.0 (2)	Ba1—O2—C1—C2	−134.1 (2)
O2ⁱ—Ba1—O2—C1	−170.5 (3)	O1—C1—C2—C3	22.3 (5)
O8ⁱⁱⁱ—Ba1—O2—C1	−51.7 (2)	O2—C1—C2—C3	−159.5 (3)
O5ⁱⁱ—Ba1—O2—C1	48.2 (2)	O1—C1—C2—C8	−156.5 (3)
O4ⁱ—Ba1—O2—C1	−115.3 (2)	O2—C1—C2—C8	21.7 (5)
O3ⁱⁱ—Ba1—O2—C1	58.8 (3)	C8—C2—C3—C4	−2.7 (5)
O6ⁱⁱ—Ba1—O2—C1	6.3 (2)	C1—C2—C3—C4	178.5 (3)
O1—Ba1—O2—C1	−20.05 (18)	C2—C3—C4—N1	−179.8 (4)
O5—Ba1—O2—Ba1ⁱ	−72.43 (10)	C2—C3—C4—C6	0.2 (6)
O2ⁱ—Ba1—O2—Ba1ⁱ	0.0	C5—N1—C4—C3	179.1 (4)
O8ⁱⁱⁱ—Ba1—O2—Ba1ⁱ	118.81 (11)	C5—N1—C4—C6	−0.9 (5)
O5ⁱⁱ—Ba1—O2—Ba1ⁱ	−141.24 (11)	C4—N1—C5—N2	0.8 (6)
O4ⁱ—Ba1—O2—Ba1ⁱ	55.24 (10)	C6—N2—C5—N1	−0.4 (6)
O3ⁱⁱ—Ba1—O2—Ba1ⁱ	−130.67 (12)	C5—N2—C6—C4	−0.3 (5)
O6ⁱⁱ—Ba1—O2—Ba1ⁱ	176.81 (9)	C5—N2—C6—C7	178.3 (5)
O1—Ba1—O2—Ba1ⁱ	150.49 (16)	C3—C4—C6—N2	−179.3 (4)
O1^iv—Ba2—O3—C9	−57.0 (4)	N1—C4—C6—N2	0.7 (5)
O7^vi—Ba2—O3—C9	34.1 (2)	C3—C4—C6—C7	2.0 (6)
O7—Ba2—O3—C9	106.0 (2)	N1—C4—C6—C7	−178.0 (4)
O6—Ba2—O3—C9	148.1 (2)	N2—C6—C7—C8	−179.9 (4)
O8^v—Ba2—O3—C9	−136.6 (2)	C4—C6—C7—C8	−1.5 (6)
O5w—Ba2—O3—C9	−69.0 (2)	C6—C7—C8—C2	−1.1 (5)
O4—Ba2—O3—C9	10.7 (2)	C6—C7—C8—C9	175.7 (3)
O6^v—Ba2—O3—C9	−158.6 (2)	C3—C2—C8—C7	3.2 (5)
O1^iv—Ba2—O3—Ba1ⁱⁱ	120.0 (2)	C1—C2—C8—C7	−178.0 (3)
O7^vi—Ba2—O3—Ba1ⁱⁱ	−148.87 (8)	C3—C2—C8—C9	−173.4 (3)
O7—Ba2—O3—Ba1ⁱⁱ	−76.98 (10)	C1—C2—C8—C9	5.4 (5)
O6—Ba2—O3—Ba1ⁱⁱ	−34.84 (8)	Ba2—O3—C9—O4	−21.3 (4)
O8^v—Ba2—O3—Ba1ⁱⁱ	40.43 (8)	Ba1ⁱⁱ—O3—C9—O4	169.0 (7)
O5w—Ba2—O3—Ba1ⁱⁱ	108.05 (11)	Ba2—O3—C9—C8	152.6 (3)
O4—Ba2—O3—Ba1ⁱⁱ	−172.25 (15)	Ba1ⁱⁱ—O3—C9—C8	−17.2 (11)
O6^v—Ba2—O3—Ba1ⁱⁱ	18.42 (12)	Ba2—O4—C9—O3	20.8 (4)
O1^iv—Ba2—O4—C9	146.5 (2)	Ba1ⁱ—O4—C9—O3	−98.5 (4)
O7^vi—Ba2—O4—C9	−165.0 (2)	Ba2—O4—C9—C8	−153.0 (3)
O7—Ba2—O4—C9	−118.8 (2)	Ba1ⁱ—O4—C9—C8	87.6 (3)
O6—Ba2—O4—C9	−52.6 (2)	C7—C8—C9—O3	−91.7 (4)
O8^v—Ba2—O4—C9	18.2 (2)	C2—C8—C9—O3	85.1 (4)
O5w—Ba2—O4—C9	74.3 (2)	C7—C8—C9—O4	82.5 (4)
O3—Ba2—O4—C9	−10.4 (2)	C2—C8—C9—O4	−100.7 (4)
O6^v—Ba2—O4—C9	30.6 (4)	Ba1—O5—C10—O6	−131.3 (3)
O1^iv—Ba2—O4—Ba1ⁱ	−90.55 (11)	Ba1ⁱⁱ—O5—C10—O6	20.4 (4)
O7^vi—Ba2—O4—Ba1ⁱ	−42.08 (8)	Ba1—O5—C10—C11	51.7 (5)
O7—Ba2—O4—Ba1ⁱ	4.13 (11)	Ba1ⁱⁱ—O5—C10—C11	−156.6 (2)
O6—Ba2—O4—Ba1ⁱ	70.37 (10)	Ba1—O5—C10—Ba1ⁱⁱ	−151.7 (4)
O8^v—Ba2—O4—Ba1ⁱ	141.10 (9)	Ba2—O6—C10—O5	82.7 (4)
O5w—Ba2—O4—Ba1ⁱ	−162.74 (12)	Ba2^v—O6—C10—O5	−118.7 (3)
O3—Ba2—O4—Ba1ⁱ	112.48 (14)	Ba1ⁱⁱ—O6—C10—O5	−18.3 (3)
O6^v—Ba2—O4—Ba1ⁱ	153.5 (2)	Ba2—O6—C10—C11	−100.4 (3)
O2ⁱ—Ba1—O5—C10	10.7 (4)	Ba2^v—O6—C10—C11	58.2 (3)
O2—Ba1—O5—C10	72.3 (4)	Ba1ⁱⁱ—O6—C10—C11	158.7 (3)
O8ⁱⁱⁱ—Ba1—O5—C10	−117.2 (4)	Ba2—O6—C10—Ba1ⁱⁱ	100.96 (18)
O5ⁱⁱ—Ba1—O5—C10	150.3 (5)	Ba2^v—O6—C10—Ba1ⁱⁱ	−100.42 (18)
O4ⁱ—Ba1—O5—C10	−31.4 (4)	O5—C10—C11—C12	17.9 (5)
O3ⁱⁱ—Ba1—O5—C10	−136.0 (4)	O6—C10—C11—C12	−159.2 (3)
O6ⁱⁱ—Ba1—O5—C10	169.7 (4)	Ba1ⁱⁱ—C10—C11—C12	−53.5 (7)
O1—Ba1—O5—C10	107.6 (4)	O5—C10—C11—C17	−167.7 (3)
O2ⁱ—Ba1—O5—Ba1ⁱⁱ	−139.66 (10)	O6—C10—C11—C17	15.2 (5)
O2—Ba1—O5—Ba1ⁱⁱ	−77.98 (9)	Ba1ⁱⁱ—C10—C11—C17	121.0 (5)
O8ⁱⁱⁱ—Ba1—O5—Ba1ⁱⁱ	92.48 (11)	C17—C11—C12—C13	−1.0 (5)
O5ⁱⁱ—Ba1—O5—Ba1ⁱⁱ	0.0	C10—C11—C12—C13	173.5 (3)
O4ⁱ—Ba1—O5—Ba1ⁱⁱ	178.30 (8)	C11—C12—C13—N3	−179.2 (4)
O3ⁱⁱ—Ba1—O5—Ba1ⁱⁱ	73.73 (10)	C11—C12—C13—C15	−2.0 (6)
O6ⁱⁱ—Ba1—O5—Ba1ⁱⁱ	19.40 (11)	C14—N3—C13—C12	177.3 (5)
O1—Ba1—O5—Ba1ⁱⁱ	−42.68 (12)	C14—N3—C13—C15	−0.2 (5)
O1^iv—Ba2—O6—C10	128.5 (2)	C15—N4—C14—N3	0.6 (6)
O7^vi—Ba2—O6—C10	35.7 (3)	C13—N3—C14—N4	−0.2 (6)
O7—Ba2—O6—C10	76.6 (2)	C14—N4—C15—C16	178.2 (5)
O8^v—Ba2—O6—C10	−126.9 (3)	C14—N4—C15—C13	−0.7 (5)
O5w—Ba2—O6—C10	−110.3 (3)	C12—C13—C15—N4	−177.3 (4)
O3—Ba2—O6—C10	−62.0 (2)	N3—C13—C15—N4	0.6 (5)
O4—Ba2—O6—C10	−32.2 (3)	C12—C13—C15—C16	3.6 (6)
O6^v—Ba2—O6—C10	161.8 (3)	N3—C13—C15—C16	−178.5 (4)
O1^iv—Ba2—O6—Ba2^v	−33.33 (12)	N4—C15—C16—C17	179.1 (4)
O7^vi—Ba2—O6—Ba2^v	−126.14 (8)	C13—C15—C16—C17	−2.1 (6)
O7—Ba2—O6—Ba2^v	−85.22 (9)	C15—C16—C17—C11	−0.8 (5)
O8^v—Ba2—O6—Ba2^v	71.25 (8)	C15—C16—C17—C18	−179.5 (3)
O5w—Ba2—O6—Ba2^v	87.86 (12)	C12—C11—C17—C16	2.4 (5)
O3—Ba2—O6—Ba2^v	136.20 (10)	C10—C11—C17—C16	−171.9 (3)
O4—Ba2—O6—Ba2^v	165.99 (7)	C12—C11—C17—C18	−178.9 (3)
O6^v—Ba2—O6—Ba2^v	0.0	C10—C11—C17—C18	6.8 (5)
O1^iv—Ba2—O6—Ba1ⁱⁱ	−136.47 (8)	Ba2^vi—O7—C18—O8	−115.8 (3)
O7^vi—Ba2—O6—Ba1ⁱⁱ	130.72 (7)	Ba2—O7—C18—O8	77.0 (4)
O7—Ba2—O6—Ba1ⁱⁱ	171.65 (10)	Ba2^vi—O7—C18—C17	61.7 (4)
O8^v—Ba2—O6—Ba1ⁱⁱ	−31.89 (7)	Ba2—O7—C18—C17	−105.5 (3)
O5w—Ba2—O6—Ba1ⁱⁱ	−15.28 (13)	Ba1^iv—O8—C18—O7	17.2 (4)
O3—Ba2—O6—Ba1ⁱⁱ	33.06 (8)	Ba2^v—O8—C18—O7	−103.3 (3)
O4—Ba2—O6—Ba1ⁱⁱ	62.86 (8)	Ba1^iv—O8—C18—C17	−160.4 (2)
O6^v—Ba2—O6—Ba1ⁱⁱ	−103.13 (9)	Ba2^v—O8—C18—C17	79.1 (3)
O1^iv—Ba2—O7—C18	−111.8 (3)	C16—C17—C18—O7	−112.0 (4)
O7^vi—Ba2—O7—C18	168.6 (3)	C11—C17—C18—O7	69.3 (4)
O6—Ba2—O7—C18	27.9 (2)	C16—C17—C18—O8	65.7 (4)
O8^v—Ba2—O7—C18	0.5 (3)	C11—C17—C18—O8	−113.0 (3)
O5w—Ba2—O7—C18	−127.7 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O4wⁱ	0.84	1.66	2.49 (1)	170
O1w—H12···O2w^viii	0.84	1.88	2.60 (1)	143
O2w—H21···N2	0.84	2.00	2.83 (1)	168
O2w—H22···N2^vii	0.84	2.28	2.83 (1)	124
O3w—H31···N3	0.84	2.34	2.95 (1)	129
O3w—H32···O6wⁱⁱⁱ	0.84	1.85	2.68 (1)	174
O4w—H41···O3w^iv	0.84	2.03	2.84 (2)	161
O5w—H51···O1w^iv	0.84	2.31	2.75 (1)	113
O6w—H61···O4^vi	0.84	1.99	2.76 (1)	152
O6w—H62···O8	0.84	2.09	2.86 (1)	152
N1—H1···O1w	0.88	1.93	2.80 (1)	168
N4—H4···O4w	0.88	1.99	2.86 (1)	167

Symmetry codes: (i) −x, −y+1, −z+1; (iii) x, y+1, z; (iv) x, y−1, z; (vi) −x, −y, −z+1; (vii) −x+1, −y+1, −z+2; (viii) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	[Ba₂(C₉H₄N₂O₄)₂(H₂O)]·4.5H₂O
M_r	782.05
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.9331 (4), 9.5950 (4), 18.0179 (7)
α, β, γ (°)	103.186 (1), 92.068 (2), 93.032 (2)
V (Å³)	1163.94 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.44
Crystal size (mm)	0.33 × 0.24 × 0.21

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.396, 0.532
No. of measured, independent and observed [I > 2σ(I)] reflections	11398, 5246, 4749
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.074, 1.07
No. of reflections	5246
No. of parameters	343
No. of restraints	30
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.54, −0.68

Computer programs: RAPID-AUTO (Rigaku Corporation, 1998), CrystalStructure (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
O1w—H11···O4wⁱ	0.84	1.66	2.49 (1)	170
O1w—H12···O2wⁱⁱ	0.84	1.88	2.60 (1)	143
O2w—H21···N2	0.84	2.00	2.83 (1)	168
O2w—H22···N2ⁱⁱⁱ	0.84	2.28	2.83 (1)	124
O3w—H31···N3	0.84	2.34	2.95 (1)	129
O3w—H32···O6w^iv	0.84	1.85	2.68 (1)	174
O4w—H41···O3w^v	0.84	2.03	2.84 (2)	161
O5w—H51···O1w^v	0.84	2.31	2.75 (1)	113
O6w—H61···O4^vi	0.84	1.99	2.76 (1)	152
O6w—H62···O8	0.84	2.09	2.86 (1)	152
N1—H1···O1w	0.88	1.93	2.80 (1)	168
N4—H4···O4w	0.88	1.99	2.86 (1)	167

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

Acknowledgements

We thank the Scientific Research Foundation of the Education Department of Heilongjiang Province (No. 11544005), the Scientific Research Innovation Foundation for young teachers of Zhoukou Normal University (No. zknuqn201044B) and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku Corporation (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
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Song, W.-D., Wang, H., Liu, J.-H., Ma, X.-T. & Ng, S. W. (2009). Acta Cryst. E65, m1643–m1644. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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