Poly[diaqua-bis(μ(3)-1H-benzimidazole-5,6-dicarboxyl-ato-κN:O,O:O)bis-(μ(2)-1H,3H-benzimidazolium-5,6-dicarboxyl-ato-κO,O:O)digadolinium(III)].

In the title complex, [Gd(2)(C(9)H(4)N(2)O(4))(2)(C(9)H(5)N(2)O(4))(2)(H(2)O)(2)](n), two of the benzimidazole-5,6-dicarboxyl-ate ligands are pro-ton-ated at the imidazole groups. Each Gd(III) ion is coordinated by six O atoms and one N atom from five ligands and one water mol-ecule, displaying a distorted bicapped trigonal-prismatic geometry. The Gd(III) ions are linked by the carboxyl-ate groups and imidazole N atoms, forming a layer parallel to (001). These layers are further connected by O-H⋯O and N-H⋯O hydrogen bonds into a three-dimensional supra-molecular network.

Related literature

For related structures, see: Gao et al. (2008 ▶); Lo et al. (2007 ▶); Wei et al. (2008 ▶); Yao et al. (2008 ▶).

Experimental

Crystal data

[Gd2(C9H4N2O4)2(C9H5N2O4)2(H2O)2]

M = 1169.12

Monoclinic,

a = 18.7856 (11) Å

b = 12.7745 (7) Å

c = 15.4776 (9) Å

β = 108.010 (1)°

V = 3532.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.82 mm−1

T = 296 K

0.25 × 0.24 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.448, T max = 0.501

24827 measured reflections

6338 independent reflections

5929 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.049

S = 1.08

6338 reflections

595 parameters

13 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.55 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046819/hy2247sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046819/hy2247Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Gd2(C9H4N2O4)2(C9H5N2O4)2(H2O)2]	F(000) = 2264
Mr = 1169.12	Dx = 2.198 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7234 reflections
a = 18.7856 (11) Å	θ = 2.6–28.2°
b = 12.7745 (7) Å	µ = 3.82 mm−1
c = 15.4776 (9) Å	T = 296 K
β = 108.010 (1)°	Block, colorless
V = 3532.3 (3) Å3	0.25 × 0.24 × 0.21 mm
Z = 4

Bruker APEXII CCD diffractometer	6338 independent reflections
Radiation source: fine-focus sealed tube	5929 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→22
Tmin = 0.448, Tmax = 0.501	k = −15→15
24827 measured reflections	l = −18→18

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.021P)2 + 3.3986P] where P = (Fo2 + 2Fc2)/3
6338 reflections	(Δ/σ)max = 0.002
595 parameters	Δρmax = 0.63 e Å−3
13 restraints	Δρmin = −0.55 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Gd1	0.028568 (8)	0.296570 (11)	0.225244 (9)	0.01343 (5)
Gd2	0.524307 (8)	−0.054993 (10)	0.209686 (9)	0.01317 (5)
N6	0.10953 (14)	0.1586 (2)	0.17264 (18)	0.0208 (6)
N5	0.12241 (15)	0.0250 (2)	0.08627 (19)	0.0251 (6)
H5A	0.111 (2)	−0.029 (3)	0.056 (2)	0.030*
C23	0.07832 (18)	0.0751 (2)	0.1265 (2)	0.0218 (7)
H23	0.0302	0.0529	0.1222	0.026*
C25	0.24026 (17)	0.2316 (2)	0.1949 (2)	0.0220 (7)
H25	0.2367	0.2863	0.2331	0.026*
C21	0.25303 (17)	0.0637 (2)	0.0817 (2)	0.0215 (7)
H21	0.2569	0.0077	0.0449	0.026*
C24	0.18074 (16)	0.1631 (2)	0.1607 (2)	0.0181 (6)
C22	0.18850 (17)	0.0794 (2)	0.1059 (2)	0.0197 (6)
C20	0.31133 (16)	0.1340 (2)	0.11398 (19)	0.0166 (6)
C26	0.30518 (17)	0.2172 (2)	0.1711 (2)	0.0178 (6)
N3	0.36219 (16)	0.1575 (2)	0.4264 (2)	0.0312 (7)
H3A	0.375 (2)	0.212 (3)	0.453 (3)	0.037*
C13	0.28840 (17)	0.0294 (2)	0.3540 (2)	0.0199 (7)
N4	0.35934 (15)	0.0200 (2)	0.3445 (2)	0.0256 (6)
H4A	0.372 (2)	−0.029 (3)	0.316 (2)	0.031*
C15	0.29033 (17)	0.1190 (2)	0.4058 (2)	0.0195 (6)
C14	0.40105 (19)	0.0970 (3)	0.3890 (2)	0.0334 (8)
H14	0.4511	0.1073	0.3934	0.040*
C27	0.36712 (17)	0.2947 (2)	0.2069 (2)	0.0207 (7)
C19	0.38033 (17)	0.1168 (2)	0.0861 (2)	0.0181 (6)
O11	0.41746 (14)	0.30726 (19)	0.17120 (17)	0.0342 (6)
O10	0.37957 (14)	0.15189 (19)	0.01034 (16)	0.0338 (6)
C17	0.16278 (17)	0.0978 (2)	0.39339 (19)	0.0163 (6)
C12	0.22389 (17)	−0.0299 (2)	0.3229 (2)	0.0206 (7)
H12	0.2230	−0.0912	0.2902	0.025*
C16	0.22774 (17)	0.1551 (2)	0.4263 (2)	0.0199 (7)
H16	0.2295	0.2153	0.4607	0.024*
C11	0.16054 (17)	0.0050 (2)	0.3421 (2)	0.0177 (6)
C10	0.08996 (17)	−0.0570 (2)	0.3073 (2)	0.0185 (7)
C18	0.09517 (16)	0.1407 (2)	0.41501 (19)	0.0161 (6)
O8	0.05302 (12)	0.20217 (15)	0.35883 (14)	0.0207 (5)
O7	0.08767 (13)	0.11675 (18)	0.48980 (14)	0.0269 (5)
O5	0.08938 (12)	−0.13723 (16)	0.25772 (16)	0.0266 (5)
O6	0.03295 (12)	−0.03134 (16)	0.32721 (15)	0.0246 (5)
O12	0.36722 (13)	0.3474 (2)	0.27665 (18)	0.0391 (7)
C36	0.40339 (17)	−0.1991 (2)	0.1826 (2)	0.0185 (6)
C33	0.20968 (17)	−0.2999 (2)	0.1476 (2)	0.0192 (6)
C35	0.33593 (17)	−0.2677 (2)	0.1548 (2)	0.0175 (6)
C34	0.27150 (17)	−0.2345 (2)	0.1727 (2)	0.0200 (7)
H34	0.2699	−0.1705	0.2006	0.024*
O16	0.40712 (12)	−0.12307 (16)	0.23682 (15)	0.0246 (5)
O15	0.45572 (13)	−0.21597 (18)	0.15068 (17)	0.0320 (6)
O9	0.43302 (13)	0.06471 (18)	0.13734 (16)	0.0294 (5)
N7	0.14022 (15)	−0.2953 (2)	0.16138 (19)	0.0242 (6)
H7A	0.127 (2)	−0.248 (3)	0.184 (2)	0.029*
C28	0.40817 (17)	−0.4085 (2)	0.09601 (19)	0.0163 (6)
C29	0.33774 (16)	−0.3652 (2)	0.11096 (19)	0.0159 (6)
C32	0.10256 (17)	−0.3811 (3)	0.1275 (2)	0.0233 (7)
H32	0.0547	−0.3968	0.1292	0.028*
O14	0.41716 (12)	−0.40122 (17)	0.02045 (14)	0.0237 (5)
N8	0.14248 (15)	−0.4412 (2)	0.09098 (19)	0.0219 (6)
H8A	0.126 (2)	−0.495 (3)	0.066 (2)	0.026*
C31	0.21123 (16)	−0.3943 (2)	0.1031 (2)	0.0168 (6)
C30	0.27505 (17)	−0.4281 (2)	0.0840 (2)	0.0192 (6)
H30	0.2755	−0.4911	0.0539	0.023*
C1	0.13784 (17)	0.4457 (2)	0.3037 (2)	0.0188 (7)
C2	0.19826 (17)	0.5268 (2)	0.3348 (2)	0.0176 (6)
O2	0.09162 (12)	0.42965 (17)	0.34523 (15)	0.0249 (5)
O1	0.13579 (12)	0.39355 (17)	0.23230 (16)	0.0287 (5)
C8	0.18820 (16)	0.6163 (2)	0.38430 (19)	0.0158 (6)
C7	0.24484 (17)	0.6887 (2)	0.4144 (2)	0.0185 (6)
H7	0.2389	0.7474	0.4471	0.022*
C4	0.32222 (16)	0.5828 (2)	0.3467 (2)	0.0175 (6)
C6	0.31138 (16)	0.6714 (2)	0.39437 (19)	0.0172 (6)
C3	0.26477 (16)	0.5098 (2)	0.3167 (2)	0.0193 (7)
H3	0.2711	0.4506	0.2849	0.023*
N1	0.39340 (14)	0.5868 (2)	0.33531 (17)	0.0190 (5)
N2	0.37599 (15)	0.7294 (2)	0.41004 (18)	0.0217 (6)
H2A	0.385 (2)	0.785 (3)	0.437 (2)	0.026*
C5	0.42138 (17)	0.6759 (2)	0.3735 (2)	0.0208 (7)
H5	0.4685	0.6999	0.3752	0.025*
C9	0.11320 (17)	0.6424 (2)	0.3956 (2)	0.0165 (6)
O4	0.10804 (12)	0.64817 (17)	0.47426 (14)	0.0242 (5)
O13	0.45307 (12)	−0.45613 (17)	0.16304 (14)	0.0247 (5)
O3	0.06077 (11)	0.66278 (16)	0.32358 (14)	0.0203 (5)
O1W	−0.00880 (13)	0.30447 (17)	0.06416 (14)	0.0264 (5)
H1W	0.0184	0.3242	0.0331	0.040*
H2W	−0.0314	0.2519	0.0407	0.040*
O2W	0.51762 (14)	−0.0852 (2)	0.05540 (15)	0.0346 (6)
H3W	0.5544	−0.1080	0.0390	0.052*
H4WA	0.4879	−0.1341	0.0480	0.052*	0.50
H4WB	0.5025	−0.0331	0.0237	0.052*	0.50

	U11	U22	U33	U12	U13	U23
Gd1	0.01015 (8)	0.01374 (8)	0.01696 (8)	−0.00059 (5)	0.00501 (6)	0.00056 (5)
Gd2	0.01062 (8)	0.01412 (8)	0.01541 (8)	−0.00007 (5)	0.00497 (6)	−0.00022 (5)
N6	0.0124 (13)	0.0236 (14)	0.0276 (14)	−0.0025 (11)	0.0079 (11)	−0.0044 (11)
N5	0.0183 (15)	0.0242 (14)	0.0323 (16)	−0.0062 (12)	0.0071 (12)	−0.0130 (12)
C23	0.0146 (16)	0.0244 (16)	0.0278 (17)	−0.0023 (13)	0.0084 (14)	−0.0022 (13)
C25	0.0183 (17)	0.0186 (15)	0.0294 (17)	−0.0016 (13)	0.0077 (14)	−0.0101 (13)
C21	0.0188 (17)	0.0214 (16)	0.0252 (17)	−0.0004 (13)	0.0080 (14)	−0.0090 (13)
C24	0.0115 (15)	0.0204 (15)	0.0233 (16)	0.0007 (12)	0.0067 (12)	−0.0028 (12)
C22	0.0152 (16)	0.0202 (15)	0.0232 (16)	−0.0026 (12)	0.0052 (13)	−0.0044 (13)
C20	0.0123 (15)	0.0210 (15)	0.0155 (14)	0.0035 (12)	0.0029 (12)	0.0036 (12)
C26	0.0141 (16)	0.0166 (15)	0.0235 (16)	−0.0007 (12)	0.0067 (13)	−0.0023 (12)
N3	0.0182 (16)	0.0345 (17)	0.0425 (18)	−0.0092 (13)	0.0116 (13)	−0.0153 (14)
C13	0.0139 (16)	0.0242 (16)	0.0230 (16)	0.0032 (13)	0.0077 (13)	−0.0003 (13)
N4	0.0163 (15)	0.0311 (16)	0.0328 (16)	0.0008 (12)	0.0126 (12)	−0.0051 (13)
C15	0.0126 (16)	0.0225 (16)	0.0221 (16)	−0.0037 (12)	0.0036 (13)	−0.0016 (13)
C14	0.0156 (18)	0.043 (2)	0.044 (2)	−0.0055 (15)	0.0122 (16)	−0.0085 (17)
C27	0.0136 (16)	0.0185 (15)	0.0300 (18)	0.0017 (12)	0.0068 (14)	−0.0032 (13)
C19	0.0158 (16)	0.0151 (14)	0.0239 (16)	0.0016 (12)	0.0066 (13)	−0.0024 (12)
O11	0.0307 (14)	0.0418 (15)	0.0373 (14)	−0.0177 (11)	0.0211 (12)	−0.0165 (11)
O10	0.0385 (15)	0.0404 (14)	0.0280 (13)	0.0139 (12)	0.0184 (11)	0.0108 (11)
C17	0.0162 (16)	0.0181 (15)	0.0153 (14)	0.0015 (12)	0.0059 (12)	0.0001 (12)
C12	0.0199 (17)	0.0171 (15)	0.0272 (17)	−0.0006 (13)	0.0108 (14)	−0.0045 (13)
C16	0.0193 (17)	0.0188 (15)	0.0232 (16)	−0.0021 (12)	0.0090 (13)	−0.0043 (13)
C11	0.0144 (16)	0.0189 (15)	0.0205 (15)	−0.0001 (12)	0.0065 (13)	0.0003 (12)
C10	0.0178 (17)	0.0150 (15)	0.0227 (16)	−0.0015 (12)	0.0062 (13)	0.0010 (12)
C18	0.0144 (16)	0.0163 (14)	0.0185 (15)	−0.0019 (12)	0.0062 (12)	−0.0018 (12)
O8	0.0202 (12)	0.0202 (11)	0.0221 (11)	0.0063 (9)	0.0070 (9)	0.0064 (9)
O7	0.0288 (13)	0.0343 (13)	0.0225 (12)	0.0150 (10)	0.0151 (10)	0.0088 (10)
O5	0.0197 (12)	0.0208 (11)	0.0433 (14)	−0.0069 (9)	0.0155 (11)	−0.0133 (10)
O6	0.0162 (12)	0.0223 (11)	0.0380 (13)	−0.0038 (9)	0.0124 (10)	−0.0065 (10)
O12	0.0252 (14)	0.0405 (15)	0.0588 (17)	−0.0157 (11)	0.0233 (13)	−0.0302 (13)
C36	0.0173 (17)	0.0195 (15)	0.0186 (15)	−0.0020 (12)	0.0054 (13)	0.0015 (12)
C33	0.0130 (16)	0.0244 (16)	0.0213 (16)	0.0017 (12)	0.0066 (13)	−0.0002 (13)
C35	0.0150 (16)	0.0185 (15)	0.0189 (15)	−0.0016 (12)	0.0053 (13)	−0.0006 (12)
C34	0.0199 (17)	0.0160 (15)	0.0249 (16)	−0.0002 (12)	0.0083 (14)	−0.0042 (12)
O16	0.0219 (12)	0.0203 (11)	0.0351 (13)	−0.0064 (9)	0.0136 (10)	−0.0118 (10)
O15	0.0281 (14)	0.0341 (13)	0.0422 (15)	−0.0139 (11)	0.0232 (12)	−0.0182 (11)
O9	0.0184 (13)	0.0341 (13)	0.0370 (14)	0.0092 (10)	0.0106 (11)	0.0128 (11)
N7	0.0180 (15)	0.0282 (16)	0.0287 (16)	0.0006 (12)	0.0104 (12)	−0.0061 (12)
C28	0.0180 (16)	0.0127 (14)	0.0181 (15)	−0.0019 (12)	0.0052 (13)	−0.0002 (12)
C29	0.0155 (16)	0.0190 (15)	0.0146 (14)	−0.0001 (12)	0.0069 (12)	0.0003 (12)
C32	0.0122 (16)	0.0313 (18)	0.0259 (17)	−0.0018 (13)	0.0053 (13)	0.0008 (14)
O14	0.0258 (13)	0.0289 (12)	0.0184 (11)	0.0076 (10)	0.0097 (10)	0.0039 (9)
N8	0.0121 (14)	0.0244 (15)	0.0276 (15)	−0.0051 (11)	0.0039 (12)	−0.0046 (12)
C31	0.0120 (15)	0.0181 (15)	0.0187 (15)	−0.0029 (12)	0.0024 (12)	0.0000 (12)
C30	0.0177 (17)	0.0180 (15)	0.0216 (16)	−0.0004 (12)	0.0055 (13)	−0.0032 (12)
C1	0.0121 (16)	0.0158 (15)	0.0268 (17)	0.0017 (12)	0.0033 (13)	−0.0022 (12)
C2	0.0141 (16)	0.0158 (15)	0.0229 (16)	0.0003 (12)	0.0057 (13)	0.0001 (12)
O2	0.0235 (13)	0.0260 (12)	0.0282 (12)	−0.0070 (9)	0.0122 (10)	−0.0035 (10)
O1	0.0207 (13)	0.0270 (12)	0.0441 (14)	−0.0100 (10)	0.0186 (11)	−0.0172 (11)
C8	0.0141 (16)	0.0158 (14)	0.0165 (14)	0.0027 (12)	0.0033 (12)	0.0010 (11)
C7	0.0179 (16)	0.0194 (15)	0.0186 (15)	0.0029 (12)	0.0064 (13)	−0.0032 (12)
C4	0.0117 (16)	0.0212 (15)	0.0188 (15)	0.0003 (12)	0.0035 (12)	−0.0029 (12)
C6	0.0144 (16)	0.0192 (15)	0.0166 (15)	−0.0001 (12)	0.0029 (12)	−0.0004 (12)
C3	0.0138 (16)	0.0159 (15)	0.0276 (17)	0.0003 (12)	0.0057 (13)	−0.0060 (12)
N1	0.0104 (13)	0.0228 (13)	0.0229 (13)	−0.0027 (10)	0.0038 (11)	−0.0038 (11)
N2	0.0166 (14)	0.0196 (14)	0.0282 (15)	−0.0033 (11)	0.0060 (12)	−0.0092 (12)
C5	0.0154 (16)	0.0241 (16)	0.0240 (16)	−0.0015 (13)	0.0075 (13)	−0.0015 (13)
C9	0.0161 (16)	0.0110 (14)	0.0235 (16)	0.0036 (11)	0.0077 (13)	0.0013 (12)
O4	0.0261 (13)	0.0288 (12)	0.0214 (11)	0.0088 (10)	0.0128 (10)	0.0055 (9)
O13	0.0208 (12)	0.0322 (13)	0.0224 (12)	0.0071 (10)	0.0084 (10)	0.0112 (10)
O3	0.0131 (11)	0.0248 (11)	0.0218 (11)	0.0054 (9)	0.0038 (9)	0.0013 (9)
O1W	0.0313 (14)	0.0279 (12)	0.0216 (12)	−0.0129 (10)	0.0108 (10)	0.0001 (9)
O2W	0.0307 (14)	0.0532 (16)	0.0215 (12)	−0.0001 (12)	0.0108 (11)	−0.0028 (11)

Gd1—O1	2.338 (2)	C16—H16	0.9300
Gd1—O2	2.526 (2)	C11—C10	1.495 (4)
Gd1—O3i	2.350 (2)	C10—O6	1.247 (4)
Gd1—O5ii	2.461 (2)	C10—O5	1.278 (4)
Gd1—O6ii	2.499 (2)	C18—O7	1.247 (4)
Gd1—O8	2.314 (2)	C18—O8	1.255 (3)
Gd1—N6	2.617 (3)	C36—O15	1.248 (4)
Gd1—O1W	2.374 (2)	C36—O16	1.271 (4)
Gd2—O9	2.312 (2)	C36—C35	1.491 (4)
Gd2—O11iii	2.539 (2)	C33—C34	1.385 (4)
Gd2—O12iii	2.342 (2)	C33—N7	1.387 (4)
Gd2—O13iv	2.267 (2)	C33—C31	1.393 (4)
Gd2—O15	2.449 (2)	C35—C34	1.388 (4)
Gd2—O16	2.520 (2)	C35—C29	1.424 (4)
Gd2—N1iii	2.612 (3)	C34—H34	0.9300
Gd2—O2W	2.384 (2)	N7—C32	1.323 (4)
N6—C23	1.316 (4)	N7—H7A	0.77 (4)
N6—C24	1.407 (4)	C28—O14	1.236 (4)
N5—C23	1.343 (4)	C28—O13	1.272 (4)
N5—C22	1.372 (4)	C28—C29	1.516 (4)
N5—H5A	0.83 (4)	C29—C30	1.380 (4)
C23—H23	0.9300	C32—N8	1.316 (4)
C25—C24	1.389 (4)	C32—H32	0.9300
C25—C26	1.391 (4)	N8—C31	1.382 (4)
C25—H25	0.9300	N8—H8A	0.80 (4)
C21—C20	1.385 (4)	C31—C30	1.390 (4)
C21—C22	1.390 (4)	C30—H30	0.9300
C21—H21	0.9300	C1—O2	1.247 (4)
C24—C22	1.400 (4)	C1—O1	1.281 (4)
C20—C26	1.411 (4)	C1—C2	1.502 (4)
C20—C19	1.504 (4)	C2—C3	1.380 (4)
C26—C27	1.498 (4)	C2—C8	1.420 (4)
N3—C14	1.314 (4)	C8—C7	1.378 (4)
N3—C15	1.378 (4)	C8—C9	1.510 (4)
N3—H3A	0.81 (4)	C7—C6	1.396 (4)
C13—C12	1.383 (4)	C7—H7	0.9300
C13—N4	1.391 (4)	C4—C3	1.392 (4)
C13—C15	1.392 (4)	C4—C6	1.400 (4)
N4—C14	1.313 (4)	C4—N1	1.403 (4)
N4—H4A	0.84 (4)	C6—N2	1.378 (4)
C15—C16	1.387 (4)	C3—H3	0.9300
C14—H14	0.9300	N1—C5	1.315 (4)
C27—O11	1.245 (4)	N2—C5	1.345 (4)
C27—O12	1.270 (4)	N2—H2A	0.82 (4)
C19—O10	1.251 (4)	C5—H5	0.9300
C19—O9	1.251 (4)	C9—O4	1.252 (4)
O11—Gd2iv	2.539 (2)	C9—O3	1.266 (4)
C17—C16	1.378 (4)	O1W—H1W	0.84
C17—C11	1.420 (4)	O1W—H2W	0.82
C17—C18	1.513 (4)	O2W—H3W	0.86
C12—C11	1.386 (4)	O2W—H4WA	0.82
C12—H12	0.9300	O2W—H4WB	0.82
O8—Gd1—O1	107.71 (8)	N3—C14—H14	124.8
O8—Gd1—O3i	80.39 (7)	O11—C27—O12	120.5 (3)
O1—Gd1—O3i	156.84 (7)	O11—C27—C26	122.0 (3)
O8—Gd1—O1W	150.83 (7)	O12—C27—C26	117.5 (3)
O1—Gd1—O1W	89.84 (8)	O11—C27—Gd2iv	64.70 (17)
O3i—Gd1—O1W	75.13 (7)	O12—C27—Gd2iv	55.80 (16)
O8—Gd1—O5ii	91.14 (7)	C26—C27—Gd2iv	173.3 (2)
O1—Gd1—O5ii	127.16 (7)	O10—C19—O9	124.2 (3)
O3i—Gd1—O5ii	72.98 (7)	O10—C19—C20	117.1 (3)
O1W—Gd1—O5ii	96.56 (8)	O9—C19—C20	118.6 (3)
O8—Gd1—O6ii	133.85 (7)	C27—O11—Gd2iv	88.98 (18)
O1—Gd1—O6ii	81.62 (8)	C16—C17—C11	121.3 (3)
O3i—Gd1—O6ii	108.82 (7)	C16—C17—C18	115.8 (3)
O1W—Gd1—O6ii	70.40 (8)	C11—C17—C18	123.0 (3)
O5ii—Gd1—O6ii	52.51 (7)	C13—C12—C11	117.9 (3)
O8—Gd1—O2	77.02 (7)	C13—C12—H12	121.1
O1—Gd1—O2	53.69 (7)	C11—C12—H12	121.1
O3i—Gd1—O2	148.38 (7)	C17—C16—C15	117.1 (3)
O1W—Gd1—O2	131.50 (7)	C17—C16—H16	121.4
O5ii—Gd1—O2	85.58 (8)	C15—C16—H16	121.4
O6ii—Gd1—O2	73.23 (7)	C12—C11—C17	120.6 (3)
O8—Gd1—N6	87.31 (8)	C12—C11—C10	118.5 (3)
O1—Gd1—N6	78.24 (8)	C17—C11—C10	120.9 (3)
O3i—Gd1—N6	80.57 (8)	O6—C10—O5	120.7 (3)
O1W—Gd1—N6	73.35 (8)	O6—C10—C11	120.3 (3)
O5ii—Gd1—N6	153.38 (8)	O5—C10—C11	118.9 (3)
O6ii—Gd1—N6	138.26 (8)	O6—C10—Gd1i	61.93 (15)
O2—Gd1—N6	119.76 (8)	O5—C10—Gd1i	60.23 (15)
O8—Gd1—C10ii	115.53 (8)	C11—C10—Gd1i	167.3 (2)
O1—Gd1—C10ii	106.09 (8)	O7—C18—O8	124.7 (3)
O3i—Gd1—C10ii	88.80 (8)	O7—C18—C17	117.4 (3)
O1W—Gd1—C10ii	79.89 (8)	O8—C18—C17	117.8 (3)
O5ii—Gd1—C10ii	26.78 (8)	C18—O8—Gd1	148.6 (2)
O6ii—Gd1—C10ii	26.11 (8)	C10—O5—Gd1i	92.99 (18)
O2—Gd1—C10ii	81.39 (8)	C10—O6—Gd1i	91.96 (17)
N6—Gd1—C10ii	152.92 (8)	C27—O12—Gd2iv	97.54 (19)
O13iv—Gd2—O9	87.94 (8)	O15—C36—O16	120.3 (3)
O13iv—Gd2—O12iii	107.11 (9)	O15—C36—C35	119.2 (3)
O9—Gd2—O12iii	152.90 (8)	O16—C36—C35	120.5 (3)
O13iv—Gd2—O2W	153.97 (8)	C34—C33—N7	132.7 (3)
O9—Gd2—O2W	79.66 (9)	C34—C33—C31	121.1 (3)
O12iii—Gd2—O2W	77.24 (9)	N7—C33—C31	106.1 (3)
O13iv—Gd2—O15	136.70 (8)	C34—C35—C29	120.9 (3)
O9—Gd2—O15	98.56 (8)	C34—C35—C36	118.6 (3)
O12iii—Gd2—O15	85.94 (9)	C29—C35—C36	120.6 (3)
O2W—Gd2—O15	68.38 (8)	C33—C34—C35	117.8 (3)
O13iv—Gd2—O16	89.20 (7)	C33—C34—H34	121.1
O9—Gd2—O16	75.74 (8)	C35—C34—H34	121.1
O12iii—Gd2—O16	125.56 (8)	C36—O16—Gd2	91.50 (18)
O2W—Gd2—O16	109.44 (8)	C36—O15—Gd2	95.47 (18)
O15—Gd2—O16	52.14 (7)	C19—O9—Gd2	168.9 (2)
O13iv—Gd2—O11iii	80.34 (8)	C32—N7—C33	108.5 (3)
O9—Gd2—O11iii	153.99 (8)	C32—N7—H7A	129 (3)
O12iii—Gd2—O11iii	52.97 (8)	C33—N7—H7A	123 (3)
O2W—Gd2—O11iii	119.51 (8)	O14—C28—O13	123.9 (3)
O15—Gd2—O11iii	75.38 (9)	O14—C28—C29	119.9 (3)
O16—Gd2—O11iii	80.92 (8)	O13—C28—C29	116.1 (3)
O13iv—Gd2—N1iii	82.99 (8)	C30—C29—C35	120.7 (3)
O9—Gd2—N1iii	79.84 (8)	C30—C29—C28	116.4 (3)
O12iii—Gd2—N1iii	79.83 (8)	C35—C29—C28	122.8 (3)
O2W—Gd2—N1iii	72.39 (8)	N8—C32—N7	110.4 (3)
O15—Gd2—N1iii	140.32 (8)	N8—C32—H32	124.8
O16—Gd2—N1iii	154.59 (7)	N7—C32—H32	124.8
O11iii—Gd2—N1iii	121.11 (8)	C32—N8—C31	108.8 (3)
O13iv—Gd2—C27iii	93.85 (9)	C32—N8—H8A	122 (3)
O9—Gd2—C27iii	178.09 (9)	C31—N8—H8A	130 (3)
O12iii—Gd2—C27iii	26.65 (9)	N8—C31—C30	131.9 (3)
O2W—Gd2—C27iii	98.94 (9)	N8—C31—C33	106.3 (3)
O15—Gd2—C27iii	79.68 (9)	C30—C31—C33	121.7 (3)
O16—Gd2—C27iii	103.62 (8)	C29—C30—C31	117.8 (3)
O11iii—Gd2—C27iii	26.32 (8)	C29—C30—H30	121.1
N1iii—Gd2—C27iii	101.01 (8)	C31—C30—H30	121.1
C23—N6—C24	104.1 (3)	O2—C1—O1	121.3 (3)
C23—N6—Gd1	120.7 (2)	O2—C1—C2	121.7 (3)
C24—N6—Gd1	132.91 (19)	O1—C1—C2	117.0 (3)
C23—N5—C22	107.6 (3)	C3—C2—C8	121.1 (3)
C23—N5—H5A	126 (3)	C3—C2—C1	117.9 (3)
C22—N5—H5A	127 (3)	C8—C2—C1	121.0 (3)
N6—C23—N5	113.7 (3)	C1—O2—Gd1	88.55 (18)
N6—C23—H23	123.1	C1—O1—Gd1	96.42 (18)
N5—C23—H23	123.1	C7—C8—C2	120.3 (3)
C24—C25—C26	119.0 (3)	C7—C8—C9	117.6 (3)
C24—C25—H25	120.5	C2—C8—C9	121.6 (3)
C26—C25—H25	120.5	C8—C7—C6	118.0 (3)
C20—C21—C22	117.9 (3)	C8—C7—H7	121.0
C20—C21—H21	121.1	C6—C7—H7	121.0
C22—C21—H21	121.1	C3—C4—C6	119.5 (3)
C25—C24—C22	119.3 (3)	C3—C4—N1	130.8 (3)
C25—C24—N6	131.4 (3)	C6—C4—N1	109.6 (3)
C22—C24—N6	109.2 (3)	N2—C6—C7	132.6 (3)
N5—C22—C21	132.2 (3)	N2—C6—C4	105.3 (3)
N5—C22—C24	105.3 (3)	C7—C6—C4	122.1 (3)
C21—C22—C24	122.4 (3)	C2—C3—C4	118.9 (3)
C21—C20—C26	120.4 (3)	C2—C3—H3	120.5
C21—C20—C19	117.2 (3)	C4—C3—H3	120.5
C26—C20—C19	122.3 (3)	C5—N1—C4	103.9 (2)
C25—C26—C20	120.9 (3)	C5—N1—Gd2iv	122.2 (2)
C25—C26—C27	117.3 (3)	C4—N1—Gd2iv	132.34 (19)
C20—C26—C27	121.7 (3)	C5—N2—C6	106.9 (3)
C14—N3—C15	109.0 (3)	C5—N2—H2A	127 (3)
C14—N3—H3A	128 (3)	C6—N2—H2A	126 (3)
C15—N3—H3A	123 (3)	N1—C5—N2	114.3 (3)
C12—C13—N4	132.9 (3)	N1—C5—H5	122.9
C12—C13—C15	121.0 (3)	N2—C5—H5	122.9
N4—C13—C15	106.1 (3)	O4—C9—O3	124.8 (3)
C14—N4—C13	108.4 (3)	O4—C9—C8	118.8 (3)
C14—N4—H4A	127 (3)	O3—C9—C8	116.3 (3)
C13—N4—H4A	124 (3)	C28—O13—Gd2iii	151.0 (2)
N3—C15—C16	131.9 (3)	C9—O3—Gd1ii	135.77 (18)
N3—C15—C13	106.0 (3)	H1W—O1W—H2W	108
C16—C15—C13	122.1 (3)	H3W—O2W—H4WA	106
N4—C14—N3	110.4 (3)	H3W—O2W—H4WB	105
N4—C14—H14	124.8

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O7v	0.84	1.80	2.629 (3)	167
O1W—H2W···O4i	0.82	1.92	2.670 (3)	153
O2W—H3W···O10vi	0.86	1.74	2.590 (3)	172
O2W—H4WA···O15	0.82	2.14	2.716 (5)	127
O2W—H4WB···O2Wvi	0.82	1.91	2.723 (4)	170
N2—H2A···O14vii	0.82 (4)	1.94 (4)	2.742 (3)	169 (3)
N3—H3A···O10vii	0.81 (4)	1.94 (4)	2.731 (4)	166 (4)
N4—H4A···O16	0.84 (4)	1.97 (4)	2.801 (4)	170 (4)
N5—H5A···O4v	0.83 (4)	1.96 (4)	2.772 (3)	165 (4)
N7—H7A···O5	0.77 (4)	2.08 (4)	2.845 (3)	171 (4)
N8—H8A···O7viii	0.80 (4)	1.95 (4)	2.747 (3)	172 (4)

Table 1

Selected bond lengths (Å)

Gd1—O1	2.338 (2)
Gd1—O2	2.526 (2)
Gd1—O3i	2.350 (2)
Gd1—O5ii	2.461 (2)
Gd1—O6ii	2.499 (2)
Gd1—O8	2.314 (2)
Gd1—N6	2.617 (3)
Gd1—O1W	2.374 (2)
Gd2—O9	2.312 (2)
Gd2—O11iii	2.539 (2)
Gd2—O12iii	2.342 (2)
Gd2—O13iv	2.267 (2)
Gd2—O15	2.449 (2)
Gd2—O16	2.520 (2)
Gd2—N1iii	2.612 (3)
Gd2—O2W	2.384 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O7v	0.84	1.80	2.629 (3)	167
O1W—H2W⋯O4i	0.82	1.92	2.670 (3)	153
O2W—H3W⋯O10vi	0.86	1.74	2.590 (3)	172
O2W—H4WA⋯O15	0.82	2.14	2.716 (5)	127
O2W—H4WB⋯O2W vi	0.82	1.91	2.723 (4)	170
N2—H2A⋯O14vii	0.82 (4)	1.94 (4)	2.742 (3)	169 (3)
N3—H3A⋯O10vii	0.81 (4)	1.94 (4)	2.731 (4)	166 (4)
N4—H4A⋯O16	0.84 (4)	1.97 (4)	2.801 (4)	170 (4)
N5—H5A⋯O4v	0.83 (4)	1.96 (4)	2.772 (3)	165 (4)
N7—H7A⋯O5	0.77 (4)	2.08 (4)	2.845 (3)	171 (4)
N8—H8A⋯O7viii	0.80 (4)	1.95 (4)	2.747 (3)	172 (4)

Symmetry codes: (i) ; (v) ; (vi) ; (vii) ; (viii) .