catena-Poly[[[diaqua-[3-(pyridin-4-yl)benzoato-κ(2)O,O']gadolinium(III)]-bis-[μ-3-(pyridin-4-yl)benzoato-κ(2)O:O']] monohydrate].

In the title coordination polymer, {[Gd(C(12)H(8)NO(2))(3)(H(2)O)(2)]·H(2)O}(n), the Gd(III) ion is ligated by one bidentate carboxyl-ate group, four monodentate bridging carboxyl-ate O atoms and two water mol-ecules. The resulting GdO(8) polyhedron approximates to a square anti-prism. The bridging ligands link the metal ions into a [100] chain, with each pair of adjacent metal ions being bridged by two ligands. Inter-chain O-H⋯O and O-H⋯N hydrogen bonds help to establish the packing.

Related literature

For metal-organic frameworks containing aromatic carb­oxy­lic ligands, see: Li et al. (2010) ▶. For lanthanide metal-organic frameworks based on aromatic carb­oxy­lic ligands, see: Zhang et al. (2010 ▶). For transition metal coordination complexes of 3-pyridin-4-yl­benzo­ate, see: Wu et al. (2011 ▶).

Experimental

Crystal data

[Gd(C12H8NO2)3(H2O)2]·H2O

M = 805.88

Triclinic,

a = 9.7252 (5) Å

b = 13.9535 (6) Å

c = 14.0829 (8) Å

α = 118.019 (5)°

β = 104.240 (5)°

γ = 90.089 (4)°

V = 1619.84 (14) Å3

Z = 2

Mo Kα radiation

μ = 2.11 mm−1

T = 293 K

0.35 × 0.21 × 0.18 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.970, T max = 1.000

12338 measured reflections

5702 independent reflections

4844 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.061

S = 1.05

5702 reflections

460 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.85 e Å−3

Δρmin = −0.66 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812026153/hb6834sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026153/hb6834Isup2.hkl

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

[Gd(C12H8NO2)3(H2O)2]·H2O	Z = 2
Mr = 805.88	F(000) = 806
Triclinic, P1	Dx = 1.652 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7252 (5) Å	Cell parameters from 8413 reflections
b = 13.9535 (6) Å	θ = 2.9–26.3°
c = 14.0829 (8) Å	µ = 2.11 mm−1
α = 118.019 (5)°	T = 293 K
β = 104.240 (5)°	Block, colourless
γ = 90.089 (4)°	0.35 × 0.21 × 0.18 mm
V = 1619.84 (14) Å3

Siemens SMART CCD diffractometer	5702 independent reflections
Radiation source: fine-focus sealed tube	4844 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scan	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.970, Tmax = 1.000	k = −16→16
12338 measured reflections	l = −16→15

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0298P)2 + 0.5641P] where P = (Fo2 + 2Fc2)/3
5702 reflections	(Δ/σ)max = 0.001
460 parameters	Δρmax = 0.85 e Å−3
2 restraints	Δρmin = −0.66 e Å−3

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Gd1	0.252518 (15)	−0.002199 (12)	0.002647 (12)	0.01875 (6)
O1	0.2075 (2)	0.17870 (18)	0.15035 (19)	0.0298 (5)
O2	0.3835 (2)	0.18197 (17)	0.07980 (19)	0.0290 (5)
O3	0.4213 (2)	0.03112 (19)	0.17419 (19)	0.0307 (5)
O4	0.6183 (2)	0.02697 (19)	0.12145 (18)	0.0284 (5)
O5	−0.0958 (2)	0.04584 (19)	−0.0786 (2)	0.0310 (5)
O6	0.1155 (2)	0.08726 (18)	−0.0915 (2)	0.0295 (5)
O7	0.0774 (2)	−0.1512 (2)	−0.1568 (2)	0.0312 (6)
O8	0.3516 (3)	−0.17299 (19)	−0.0343 (2)	0.0333 (6)
O9	0.3749 (6)	0.2281 (5)	−0.1164 (5)	0.1291 (19)
N1	0.1269 (4)	0.6874 (3)	0.6483 (3)	0.0487 (9)
N2	1.3290 (4)	0.2014 (3)	0.5396 (4)	0.0674 (11)
N3	0.2287 (4)	0.6204 (3)	−0.0892 (3)	0.0560 (10)
C1	0.3436 (3)	0.3525 (3)	0.2204 (3)	0.0268 (7)
C2	0.2774 (3)	0.4068 (3)	0.3048 (3)	0.0285 (7)
H2	0.2038	0.3674	0.3114	0.034*
C3	0.3178 (4)	0.5181 (3)	0.3797 (3)	0.0320 (8)
C4	0.4266 (4)	0.5753 (3)	0.3694 (3)	0.0384 (9)
H4	0.4578	0.6507	0.4217	0.046*
C5	0.4884 (4)	0.5218 (3)	0.2832 (3)	0.0441 (10)
H5	0.5597	0.5613	0.2746	0.053*
C6	0.4478 (4)	0.4114 (3)	0.2092 (3)	0.0349 (8)
H6	0.4914	0.3755	0.1503	0.042*
C7	0.2509 (4)	0.5773 (3)	0.4722 (3)	0.0343 (8)
C8	0.3328 (5)	0.6354 (3)	0.5820 (3)	0.0514 (11)
H8	0.4341	0.6393	0.5998	0.062*
C9	0.2673 (5)	0.6879 (4)	0.6658 (4)	0.0609 (13)
H9	0.3263	0.7268	0.7408	0.073*
C10	0.0485 (5)	0.6331 (3)	0.5419 (4)	0.0509 (11)
H10	−0.0522	0.6332	0.5267	0.061*
C11	0.1031 (4)	0.5768 (3)	0.4523 (3)	0.0444 (10)
H11	0.0413	0.5384	0.3782	0.053*
C12	0.3088 (3)	0.2315 (3)	0.1464 (3)	0.0246 (7)
C13	0.6422 (3)	0.0531 (3)	0.3047 (3)	0.0264 (7)
C14	0.7906 (3)	0.0751 (3)	0.3354 (3)	0.0276 (7)
H14	0.8363	0.0731	0.2823	0.033*
C15	0.8737 (3)	0.0999 (3)	0.4416 (3)	0.0299 (8)
C16	0.8041 (4)	0.0999 (4)	0.5168 (3)	0.0477 (11)
H16	0.8584	0.1169	0.5901	0.057*
C17	0.6570 (4)	0.0754 (4)	0.4861 (3)	0.0563 (12)
H17	0.6113	0.0735	0.5377	0.068*
C18	0.5758 (4)	0.0535 (3)	0.3811 (3)	0.0404 (9)
H18	0.4744	0.0387	0.3614	0.048*
C19	1.0316 (4)	0.1321 (3)	0.4756 (3)	0.0341 (8)
C20	1.1051 (4)	0.1240 (3)	0.3992 (4)	0.0446 (10)
H20	1.0552	0.0931	0.3220	0.053*
C21	1.2497 (4)	0.1605 (4)	0.4350 (4)	0.0548 (11)
H21	1.2952	0.1559	0.3808	0.066*
C22	1.2615 (5)	0.2065 (4)	0.6113 (4)	0.0720 (15)
H22	1.3162	0.2343	0.6871	0.086*
C23	1.1152 (4)	0.1742 (4)	0.5848 (4)	0.0566 (12)
H23	1.0733	0.1812	0.6416	0.068*
C24	0.5544 (3)	0.0352 (3)	0.1922 (3)	0.0236 (7)
C25	−0.0766 (3)	0.1751 (3)	−0.1399 (3)	0.0234 (7)
C26	0.0122 (3)	0.2600 (3)	−0.1274 (3)	0.0268 (7)
H26	0.1128	0.2649	−0.0993	0.032*
C27	−0.0424 (4)	0.3386 (3)	−0.1553 (3)	0.0314 (8)
C28	−0.1895 (4)	0.3258 (3)	−0.2000 (4)	0.0465 (10)
H28	−0.2296	0.3774	−0.2209	0.056*
C29	−0.2787 (4)	0.2405 (3)	−0.2148 (4)	0.0463 (10)
H29	−0.3789	0.2332	−0.2466	0.056*
C30	−0.2230 (4)	0.1656 (3)	−0.1837 (3)	0.0316 (8)
H30	−0.2848	0.1077	−0.1922	0.038*
C31	0.0522 (4)	0.4346 (3)	−0.1337 (3)	0.0349 (8)
C32	−0.0024 (5)	0.5242 (3)	−0.1383 (3)	0.0491 (11)
H32	−0.1030	0.5246	−0.1565	0.059*
C33	0.0871 (6)	0.6126 (3)	−0.1170 (4)	0.0559 (12)
H33	0.0448	0.6718	−0.1224	0.067*
C34	0.2818 (5)	0.5352 (4)	−0.0836 (5)	0.0685 (14)
H34	0.3830	0.5385	−0.0628	0.082*
C35	0.2005 (5)	0.4419 (3)	−0.1060 (4)	0.0586 (13)
H35	0.2459	0.3830	−0.1024	0.070*
C36	−0.0144 (3)	0.0968 (2)	−0.1011 (2)	0.0203 (7)
H7A	0.004 (4)	−0.156 (3)	−0.158 (3)	0.030*
H8A	0.318 (4)	−0.235 (3)	−0.047 (3)	0.030*
H7B	0.088 (3)	−0.207 (3)	−0.219 (3)	0.030*
H8B	0.422 (4)	−0.181 (3)	−0.048 (3)	0.030*
H9B	0.450 (3)	0.198 (3)	−0.132 (3)	0.030*
H9A	0.359 (4)	0.189 (3)	−0.087 (3)	0.030*

	U11	U22	U33	U12	U13	U23
Gd1	0.01859 (9)	0.01705 (9)	0.02183 (9)	0.00224 (6)	0.00914 (6)	0.00871 (7)
O1	0.0271 (12)	0.0209 (12)	0.0364 (14)	0.0000 (10)	0.0167 (11)	0.0063 (11)
O2	0.0239 (12)	0.0224 (12)	0.0353 (14)	0.0021 (10)	0.0154 (11)	0.0065 (11)
O3	0.0215 (12)	0.0426 (15)	0.0293 (13)	0.0027 (10)	0.0080 (10)	0.0181 (12)
O4	0.0270 (12)	0.0393 (14)	0.0239 (12)	0.0062 (10)	0.0126 (10)	0.0164 (11)
O5	0.0294 (13)	0.0361 (14)	0.0416 (15)	0.0049 (11)	0.0149 (11)	0.0274 (13)
O6	0.0198 (12)	0.0311 (14)	0.0434 (15)	0.0055 (10)	0.0073 (11)	0.0234 (12)
O7	0.0210 (13)	0.0284 (14)	0.0306 (14)	0.0001 (11)	0.0099 (12)	0.0023 (11)
O8	0.0273 (14)	0.0206 (13)	0.0557 (17)	0.0068 (11)	0.0211 (13)	0.0170 (13)
O9	0.155 (5)	0.143 (5)	0.166 (5)	0.077 (4)	0.082 (4)	0.117 (4)
N1	0.067 (3)	0.035 (2)	0.044 (2)	0.0145 (18)	0.029 (2)	0.0121 (17)
N2	0.037 (2)	0.074 (3)	0.074 (3)	−0.008 (2)	0.010 (2)	0.025 (2)
N3	0.078 (3)	0.032 (2)	0.068 (3)	−0.0022 (19)	0.033 (2)	0.0253 (19)
C1	0.0235 (17)	0.0210 (18)	0.0311 (19)	0.0030 (14)	0.0040 (15)	0.0107 (15)
C2	0.0273 (18)	0.0241 (18)	0.0302 (19)	0.0036 (14)	0.0093 (15)	0.0096 (16)
C3	0.0324 (19)	0.0254 (19)	0.032 (2)	0.0078 (15)	0.0069 (16)	0.0101 (16)
C4	0.046 (2)	0.0195 (19)	0.037 (2)	−0.0030 (16)	0.0090 (18)	0.0049 (17)
C5	0.047 (2)	0.028 (2)	0.055 (3)	−0.0019 (17)	0.022 (2)	0.014 (2)
C6	0.037 (2)	0.0244 (19)	0.042 (2)	0.0016 (16)	0.0195 (18)	0.0117 (17)
C7	0.043 (2)	0.0203 (18)	0.033 (2)	0.0084 (16)	0.0128 (17)	0.0071 (16)
C8	0.052 (3)	0.050 (3)	0.036 (2)	0.022 (2)	0.012 (2)	0.008 (2)
C9	0.081 (4)	0.050 (3)	0.035 (2)	0.022 (3)	0.013 (2)	0.009 (2)
C10	0.053 (3)	0.036 (2)	0.058 (3)	0.009 (2)	0.029 (2)	0.012 (2)
C11	0.045 (2)	0.034 (2)	0.039 (2)	−0.0008 (18)	0.0153 (19)	0.0045 (18)
C12	0.0183 (16)	0.0211 (17)	0.0310 (19)	0.0031 (13)	0.0070 (14)	0.0098 (15)
C13	0.0256 (18)	0.0285 (19)	0.0255 (18)	0.0029 (14)	0.0093 (15)	0.0124 (15)
C14	0.0267 (18)	0.0315 (19)	0.0283 (19)	0.0052 (15)	0.0116 (15)	0.0156 (16)
C15	0.0251 (18)	0.033 (2)	0.0283 (19)	0.0023 (15)	0.0048 (15)	0.0136 (16)
C16	0.040 (2)	0.077 (3)	0.032 (2)	−0.002 (2)	0.0036 (18)	0.033 (2)
C17	0.039 (2)	0.103 (4)	0.037 (2)	−0.003 (2)	0.0124 (19)	0.041 (3)
C18	0.0252 (19)	0.067 (3)	0.032 (2)	−0.0013 (18)	0.0079 (16)	0.026 (2)
C19	0.0296 (19)	0.033 (2)	0.036 (2)	0.0032 (16)	0.0070 (17)	0.0143 (17)
C20	0.027 (2)	0.055 (3)	0.050 (3)	0.0052 (18)	0.0067 (18)	0.026 (2)
C21	0.034 (2)	0.067 (3)	0.066 (3)	0.006 (2)	0.016 (2)	0.034 (3)
C22	0.040 (3)	0.086 (4)	0.051 (3)	−0.009 (3)	−0.011 (2)	0.014 (3)
C23	0.037 (2)	0.079 (3)	0.037 (2)	−0.004 (2)	0.0046 (19)	0.017 (2)
C24	0.0217 (17)	0.0223 (17)	0.0269 (18)	0.0034 (13)	0.0084 (14)	0.0112 (15)
C25	0.0238 (17)	0.0247 (18)	0.0242 (17)	0.0043 (14)	0.0076 (14)	0.0134 (15)
C26	0.0243 (17)	0.0266 (18)	0.0304 (19)	0.0049 (14)	0.0065 (15)	0.0151 (16)
C27	0.038 (2)	0.0240 (19)	0.036 (2)	0.0067 (15)	0.0121 (17)	0.0170 (17)
C28	0.043 (2)	0.045 (3)	0.064 (3)	0.0128 (19)	0.008 (2)	0.039 (2)
C29	0.025 (2)	0.053 (3)	0.069 (3)	0.0071 (18)	0.0040 (19)	0.041 (2)
C30	0.0281 (19)	0.032 (2)	0.037 (2)	0.0001 (15)	0.0078 (16)	0.0185 (17)
C31	0.050 (2)	0.028 (2)	0.035 (2)	0.0037 (17)	0.0189 (18)	0.0182 (17)
C32	0.060 (3)	0.037 (2)	0.057 (3)	0.003 (2)	0.010 (2)	0.031 (2)
C33	0.095 (4)	0.031 (2)	0.051 (3)	0.007 (2)	0.021 (3)	0.027 (2)
C34	0.059 (3)	0.048 (3)	0.112 (4)	0.001 (2)	0.036 (3)	0.044 (3)
C35	0.055 (3)	0.041 (3)	0.101 (4)	0.010 (2)	0.033 (3)	0.046 (3)
C36	0.0264 (18)	0.0155 (16)	0.0164 (16)	−0.0001 (13)	0.0068 (13)	0.0054 (13)

Gd1—O5i	2.290 (2)	C9—H9	0.9500
Gd1—O4ii	2.295 (2)	C10—C11	1.375 (5)
Gd1—O3	2.395 (2)	C10—H10	0.9500
Gd1—O6	2.405 (2)	C11—H11	0.9500
Gd1—O8	2.443 (2)	C13—C18	1.382 (4)
Gd1—O7	2.447 (2)	C13—C14	1.389 (4)
Gd1—O2	2.468 (2)	C13—C24	1.505 (4)
Gd1—O1	2.532 (2)	C14—C15	1.388 (4)
O1—C12	1.257 (4)	C14—H14	0.9500
O2—C12	1.270 (4)	C15—C16	1.390 (5)
O3—C24	1.252 (3)	C15—C19	1.491 (5)
O4—C24	1.261 (3)	C16—C17	1.381 (5)
O4—Gd1ii	2.295 (2)	C16—H16	0.9500
O5—C36	1.252 (3)	C17—C18	1.379 (5)
O5—Gd1i	2.290 (2)	C17—H17	0.9500
O6—C36	1.251 (3)	C18—H18	0.9500
O7—H7A	0.71 (3)	C19—C23	1.380 (5)
O7—H7B	0.89 (4)	C19—C20	1.395 (5)
O8—H8A	0.84 (4)	C20—C21	1.378 (5)
O8—H8B	0.75 (3)	C20—H20	0.9500
O9—H9B	0.872 (10)	C21—H21	0.9500
O9—H9A	0.868 (10)	C22—C23	1.394 (6)
N1—C9	1.325 (5)	C22—H22	0.9500
N1—C10	1.331 (5)	C23—H23	0.9500
N2—C22	1.310 (6)	C25—C26	1.381 (4)
N2—C21	1.320 (6)	C25—C30	1.384 (4)
N3—C33	1.325 (6)	C25—C36	1.502 (4)
N3—C34	1.325 (5)	C26—C27	1.394 (4)
C1—C6	1.387 (4)	C26—H26	0.9500
C1—C2	1.390 (4)	C27—C28	1.387 (5)
C1—C12	1.490 (4)	C27—C31	1.486 (5)
C2—C3	1.391 (5)	C28—C29	1.373 (5)
C2—H2	0.9500	C28—H28	0.9500
C3—C4	1.398 (5)	C29—C30	1.376 (5)
C3—C7	1.488 (5)	C29—H29	0.9500
C4—C5	1.380 (5)	C30—H30	0.9500
C4—H4	0.9500	C31—C32	1.382 (5)
C5—C6	1.379 (5)	C31—C35	1.389 (5)
C5—H5	0.9500	C32—C33	1.374 (6)
C6—H6	0.9500	C32—H32	0.9500
C7—C8	1.377 (5)	C33—H33	0.9500
C7—C11	1.394 (5)	C34—C35	1.381 (5)
C8—C9	1.376 (5)	C34—H34	0.9500
C8—H8	0.9500	C35—H35	0.9500
O5i—Gd1—O4ii	158.30 (9)	O1—C12—C1	120.5 (3)
O5i—Gd1—O3	82.32 (8)	O2—C12—C1	119.3 (3)
O4ii—Gd1—O3	106.79 (7)	O1—C12—Gd1	61.50 (16)
O5i—Gd1—O6	103.62 (7)	O2—C12—Gd1	58.66 (16)
O4ii—Gd1—O6	81.10 (7)	C1—C12—Gd1	177.8 (2)
O3—Gd1—O6	143.19 (8)	C18—C13—C14	119.1 (3)
O5i—Gd1—O8	89.77 (8)	C18—C13—C24	120.3 (3)
O4ii—Gd1—O8	74.67 (8)	C14—C13—C24	120.5 (3)
O3—Gd1—O8	73.33 (9)	C15—C14—C13	121.8 (3)
O6—Gd1—O8	141.74 (9)	C15—C14—H14	119.1
O5i—Gd1—O7	74.87 (9)	C13—C14—H14	119.1
O4ii—Gd1—O7	85.95 (8)	C14—C15—C16	117.9 (3)
O3—Gd1—O7	138.81 (8)	C14—C15—C19	120.8 (3)
O6—Gd1—O7	76.44 (8)	C16—C15—C19	121.2 (3)
O8—Gd1—O7	72.76 (9)	C17—C16—C15	120.7 (3)
O5i—Gd1—O2	125.02 (8)	C17—C16—H16	119.6
O4ii—Gd1—O2	76.66 (8)	C15—C16—H16	119.6
O3—Gd1—O2	74.77 (8)	C18—C17—C16	120.5 (4)
O6—Gd1—O2	72.28 (8)	C18—C17—H17	119.7
O8—Gd1—O2	127.98 (8)	C16—C17—H17	119.7
O7—Gd1—O2	146.07 (9)	C17—C18—C13	119.9 (3)
O5i—Gd1—O1	74.17 (8)	C17—C18—H18	120.1
O4ii—Gd1—O1	126.86 (7)	C13—C18—H18	120.1
O3—Gd1—O1	74.94 (8)	C23—C19—C20	115.1 (3)
O6—Gd1—O1	72.06 (8)	C23—C19—C15	122.8 (3)
O8—Gd1—O1	146.02 (9)	C20—C19—C15	122.1 (3)
O7—Gd1—O1	128.36 (7)	C21—C20—C19	120.4 (4)
O2—Gd1—O1	51.95 (7)	C21—C20—H20	119.8
C12—O1—Gd1	92.62 (18)	C19—C20—H20	119.8
C12—O2—Gd1	95.27 (18)	N2—C21—C20	124.2 (4)
C24—O3—Gd1	126.2 (2)	N2—C21—H21	117.9
C24—O4—Gd1ii	174.8 (2)	C20—C21—H21	117.9
C36—O5—Gd1i	163.6 (2)	N2—C22—C23	124.8 (4)
C36—O6—Gd1	125.31 (18)	N2—C22—H22	117.6
Gd1—O7—H7A	121 (3)	C23—C22—H22	117.6
Gd1—O7—H7B	131 (2)	C19—C23—C22	119.7 (4)
H7A—O7—H7B	108 (4)	C19—C23—H23	120.2
Gd1—O8—H8A	134 (2)	C22—C23—H23	120.2
Gd1—O8—H8B	120 (3)	O3—C24—O4	123.2 (3)
H8A—O8—H8B	105 (3)	O3—C24—C13	118.2 (3)
H9B—O9—H9A	93 (3)	O4—C24—C13	118.5 (3)
C9—N1—C10	115.9 (4)	C26—C25—C30	119.6 (3)
C22—N2—C21	115.7 (4)	C26—C25—C36	119.8 (3)
C33—N3—C34	115.4 (4)	C30—C25—C36	120.5 (3)
C6—C1—C2	119.2 (3)	C25—C26—C27	121.5 (3)
C6—C1—C12	120.2 (3)	C25—C26—H26	119.3
C2—C1—C12	120.6 (3)	C27—C26—H26	119.3
C1—C2—C3	120.7 (3)	C28—C27—C26	117.2 (3)
C1—C2—H2	119.6	C28—C27—C31	121.4 (3)
C3—C2—H2	119.6	C26—C27—C31	121.4 (3)
C2—C3—C4	119.2 (3)	C29—C28—C27	121.9 (3)
C2—C3—C7	121.6 (3)	C29—C28—H28	119.1
C4—C3—C7	119.2 (3)	C27—C28—H28	119.1
C5—C4—C3	119.8 (3)	C28—C29—C30	120.0 (3)
C5—C4—H4	120.1	C28—C29—H29	120.0
C3—C4—H4	120.1	C30—C29—H29	120.0
C6—C5—C4	120.7 (3)	C29—C30—C25	119.8 (3)
C6—C5—H5	119.7	C29—C30—H30	120.1
C4—C5—H5	119.7	C25—C30—H30	120.1
C5—C6—C1	120.4 (3)	C32—C31—C35	115.2 (3)
C5—C6—H6	119.8	C32—C31—C27	121.8 (3)
C1—C6—H6	119.8	C35—C31—C27	123.0 (3)
C8—C7—C11	116.9 (3)	C33—C32—C31	120.9 (4)
C8—C7—C3	121.2 (3)	C33—C32—H32	119.5
C11—C7—C3	121.8 (3)	C31—C32—H32	119.5
C9—C8—C7	119.7 (4)	N3—C33—C32	124.0 (4)
C9—C8—H8	120.1	N3—C33—H33	118.0
C7—C8—H8	120.1	C32—C33—H33	118.0
N1—C9—C8	124.1 (4)	N3—C34—C35	124.7 (4)
N1—C9—H9	118.0	N3—C34—H34	117.7
C8—C9—H9	118.0	C35—C34—H34	117.7
N1—C10—C11	124.5 (4)	C34—C35—C31	119.7 (4)
N1—C10—H10	117.7	C34—C35—H35	120.1
C11—C10—H10	117.7	C31—C35—H35	120.1
C10—C11—C7	118.8 (4)	O6—C36—O5	123.6 (3)
C10—C11—H11	120.6	O6—C36—C25	118.6 (3)
C7—C11—H11	120.6	O5—C36—C25	117.8 (3)
O1—C12—O2	120.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O1i	0.71 (3)	2.12 (3)	2.826 (3)	173 (4)
O7—H7B···N1iii	0.89 (4)	1.89 (4)	2.772 (4)	173 (3)
O8—H8B···O2ii	0.75 (3)	2.05 (3)	2.793 (3)	173 (4)
O8—H8A···N3iv	0.84 (4)	1.95 (4)	2.789 (4)	175 (3)

Table 1

Selected bond lengths (Å)

Gd1—O5i	2.290 (2)
Gd1—O4ii	2.295 (2)
Gd1—O3	2.395 (2)
Gd1—O6	2.405 (2)
Gd1—O8	2.443 (2)
Gd1—O7	2.447 (2)
Gd1—O2	2.468 (2)
Gd1—O1	2.532 (2)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O1i	0.71 (3)	2.12 (3)	2.826 (3)	173 (4)
O7—H7B⋯N1iii	0.89 (4)	1.89 (4)	2.772 (4)	173 (3)
O8—H8B⋯O2ii	0.75 (3)	2.05 (3)	2.793 (3)	173 (4)
O8—H8A⋯N3iv	0.84 (4)	1.95 (4)	2.789 (4)	175 (3)

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