Poly[[tris­(μ2-4,4′-bipyridine N,N′-di­oxide)hexa­nitratodigadolinium(III)] dichloro­methane disolvate]

Dillner, A.J.; Lilly, C.P.; Knaust, J.M.

doi:10.1107/S1600536810033258

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages m1158-m1159

https://doi.org/10.1107/S1600536810033258

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Poly[[tris(μ₂-4,4′-bipyridine N,N′-dioxide)hexanitratodigadolinium(III)] dichloromethane disolvate]

Adam J. Dillner,^a Cassandra P. Lilly ^a and Jacqueline M. Knaust ^a ^*

^aAllegheny College, 520 North Main St., Meadville, PA 16335, USA
^*Correspondence e-mail: jknaust@allegheny.edu

(Received 16 August 2010; accepted 18 August 2010; online 21 August 2010)

The title one-dimensional coordination network, {[Gd₂(NO₃)₆(C₁₀H₈N₂O₂)₃]·2CH₂Cl₂}_n, is isostructural with the previously reported Tb and Tl coordination networks and to its Eu analog. The Gd^III cation is coordinated in a distorted tricapped trigonal-prismatic fashion by nine O atoms from three bridging 4,4′-bipyridine N,N′-dioxide ligands and three chelating nitrate anions. None of the atoms lie on a special position, but there is an inversion center located between the rings of one of the ligands. The network topology is ladder-like, and each ladder interacts with six neighboring ladders through C—H⋯O hydrogen bonds. The packing motif of the ladders allows for the formation of channels that run parallel to the a axis; these channels are filled with CH₂Cl₂ solvent molecules that interact with the ladders through C—H⋯O hydrogen bonds

Related literature

For the isostructural Tb and Tl, coordination networks, see: Long et al. (2002 ); Moitsheki et al. (2006 ). For the isostructural Eu coordination network and detailed background to this study, see: Dillner et al. (2010 ).

Experimental

Crystal data

[Gd₂(NO₃)₆(C₁₀H₈N₂O₂)₃]·2CH₂Cl₂
M_r = 1420.96
Triclinic, $[P \overline 1]$
a = 7.9917 (5) Å
b = 11.5668 (7) Å
c = 13.0347 (8) Å
α = 86.059 (1)°
β = 80.134 (1)°
γ = 78.255 (1)°
V = 1161.52 (12) Å³
Z = 1
Mo Kα radiation
μ = 3.16 mm⁻¹
T = 100 K
0.51 × 0.48 × 0.25 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.529, T_max = 0.746
13791 measured reflections
6990 independent reflections
6776 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.051
S = 1.06
6990 reflections
334 parameters
H-atom parameters constrained
Δρ_max = 1.34 e Å⁻³
Δρ_min = −1.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O7ⁱ	0.95	2.41	3.082 (2)	127
C9—H9⋯O9ⁱⁱ	0.95	2.57	3.287 (2)	132
C12—H12⋯O2ⁱⁱⁱ	0.95	2.43	3.300 (2)	152
C16—H16B⋯O12ⁱⁱ	0.99	2.43	3.246 (3)	139
C16—H16A⋯O8	0.99	2.56	3.302 (3)	132
C16—H16A⋯O9	0.99	2.50	3.084 (3)	117
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+2, -z+2; (iii) -x+2, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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: X-SEED.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810033258/zl2303sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033258/zl2303Isup2.hkl

checkCIF report

Comment top

The description of the structure of the title compound is part of a set of consecutive papers on one-dimensional ladder-like coordination networks of the type [Ln₂(NO₃)₆(C₁₀H₈N₂O₂)₃]_n, with Ln = Eu (Dillner et al., 2010) and Gd (this publication), respectively. Both compounds are also isostructural to the previously reported Tb and Tl, coordination networks (Long et al., 2002 and Moitsheki et al., 2006). The background to this study is given in Dillner et al. (2010).

Related literature top

For the isostructural Tb and Tl, coordination networks, see: Long et al. (2002); Moitsheki et al. (2006). For the isostructural Eu coordination network and detailed background to this study, see: Dillner et al. (2010).

Experimental top

Gd(NO₃)₃ (0.051 g 0.15 mmol) was placed in the bottom of a test tube and covered with CH₂Cl₂ (5 ml). 4,4'-bipyridine-N,N'-dioxide^.H₂O (0.0376 g, 0.182 mmol) was dissolved in methanol (8 ml), and this solution was layered over the CH₂Cl₂. The two solutions were allowed to slowly mix. Over a period of several weeks the Gd(NO₃)₃ dissolved, and yellow plate-like crystals of the title compound formed.

Structure description top

For the isostructural Tb and Tl, coordination networks, see: Long et al. (2002); Moitsheki et al. (2006). For the isostructural Eu coordination network and detailed background to this study, see: Dillner et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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: X-SEED (Barbour, 2001).

Figures top

Fig. 1. The coordination environment of the Gd⁺³ cation in the title compound with atom labels and 50% probability displacement ellipsoids. Hydrogen atoms have been omitted for clarity. Color scheme: Gd: green, C: grey, N: blue, O: red, Cl: yellow. Symmetry codes: (i) -x+3, -y+1, -z+1; (ii) x, y, z+1; (iii) x, y, z-1; (vii) -x+2, -y+1, z+2.

Poly[[tris(µ₂-4,4'-bipyridine N,N'-dioxide)hexanitratodigadolinium(III)] dichloromethane disolvate] top

Crystal data top

[Gd₂(NO₃)₆(C₁₀H₈N₂O₂)₃]·2CH₂Cl₂	Z = 1
M_r = 1420.96	F(000) = 692
Triclinic, P1	D_x = 2.031 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9917 (5) Å	Cell parameters from 9995 reflections
b = 11.5668 (7) Å	θ = 2.4–31.4°
c = 13.0347 (8) Å	µ = 3.16 mm⁻¹
α = 86.059 (1)°	T = 100 K
β = 80.134 (1)°	Plate, yellow
γ = 78.255 (1)°	0.51 × 0.48 × 0.25 mm
V = 1161.52 (12) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	6990 independent reflections
Radiation source: fine-focus sealed tube	6776 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 31.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.529, T_max = 0.746	k = −16→16
13791 measured reflections	l = −19→19

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.051	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0269P)² + 0.7108P] where P = (F_o² + 2F_c²)/3
6990 reflections	(Δ/σ)_max = 0.003
334 parameters	Δρ_max = 1.34 e Å⁻³
0 restraints	Δρ_min = −1.26 e Å⁻³

Crystal data top

[Gd₂(NO₃)₆(C₁₀H₈N₂O₂)₃]·2CH₂Cl₂	γ = 78.255 (1)°
M_r = 1420.96	V = 1161.52 (12) Å³
Triclinic, P1	Z = 1
a = 7.9917 (5) Å	Mo Kα radiation
b = 11.5668 (7) Å	µ = 3.16 mm⁻¹
c = 13.0347 (8) Å	T = 100 K
α = 86.059 (1)°	0.51 × 0.48 × 0.25 mm
β = 80.134 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	6990 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6776 reflections with I > 2σ(I)
T_min = 0.529, T_max = 0.746	R_int = 0.019
13791 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	0 restraints
wR(F²) = 0.051	H-atom parameters constrained
S = 1.06	Δρ_max = 1.34 e Å⁻³
6990 reflections	Δρ_min = −1.26 e Å⁻³
334 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Gd1	0.777386 (9)	0.833312 (7)	0.717678 (6)	0.01052 (3)
O1	1.02444 (16)	0.82720 (11)	0.59321 (10)	0.0154 (2)
O2	0.95666 (17)	0.87415 (12)	0.83066 (9)	0.0156 (2)
O3	0.62864 (17)	0.87372 (12)	0.57713 (9)	0.0165 (2)
O4	0.80192 (19)	0.63739 (12)	0.64108 (12)	0.0228 (3)
O5	0.95223 (19)	0.63785 (12)	0.76314 (11)	0.0215 (3)
O6	0.9729 (2)	0.47510 (14)	0.68376 (16)	0.0329 (4)
O7	0.48223 (18)	0.79088 (13)	0.77573 (10)	0.0200 (3)
O8	0.64333 (17)	0.77345 (13)	0.89476 (11)	0.0200 (3)
O9	0.37413 (18)	0.75493 (13)	0.93691 (11)	0.0224 (3)
O10	0.80809 (18)	1.04012 (12)	0.66218 (10)	0.0186 (3)
O11	0.59902 (18)	1.01912 (12)	0.78729 (11)	0.0191 (3)
O12	0.6429 (3)	1.19502 (15)	0.73675 (17)	0.0438 (5)
N1	1.15539 (19)	0.73739 (13)	0.56764 (11)	0.0133 (3)
N2	0.91991 (19)	0.86889 (13)	0.93448 (11)	0.0126 (3)
N3	0.69504 (19)	0.86834 (13)	0.47630 (11)	0.0132 (3)
N4	0.9111 (2)	0.57955 (14)	0.69595 (14)	0.0191 (3)
N5	0.49582 (19)	0.77173 (13)	0.87144 (12)	0.0149 (3)
N6	0.6826 (2)	1.08859 (15)	0.72846 (13)	0.0201 (3)
C1	1.1729 (3)	0.68680 (17)	0.47533 (15)	0.0200 (4)
H1	1.0924	0.7154	0.4293	0.024*
C2	1.3074 (3)	0.59355 (18)	0.44774 (15)	0.0204 (4)
H2	1.3185	0.5581	0.3827	0.024*
C3	1.4277 (2)	0.55043 (15)	0.51390 (13)	0.0129 (3)
C4	1.4065 (2)	0.60763 (17)	0.60766 (14)	0.0177 (3)
H4	1.4869	0.5823	0.6544	0.021*
C5	1.2700 (2)	0.70055 (17)	0.63297 (14)	0.0179 (3)
H5	1.2569	0.7387	0.6969	0.021*
C6	0.9834 (2)	0.76999 (16)	0.98742 (14)	0.0154 (3)
H6	1.0519	0.7040	0.9506	0.018*
C7	0.9492 (2)	0.76424 (15)	1.09522 (14)	0.0153 (3)
H7	0.9932	0.6941	1.1322	0.018*
C8	0.8502 (2)	0.86129 (15)	1.14956 (13)	0.0126 (3)
C9	0.7879 (2)	0.96209 (15)	1.09168 (13)	0.0147 (3)
H9	0.7208	1.0298	1.1266	0.018*
C10	0.8227 (2)	0.96446 (15)	0.98455 (13)	0.0149 (3)
H10	0.7785	1.0331	0.9458	0.018*
C11	0.7464 (2)	0.96300 (15)	0.42487 (14)	0.0158 (3)
H11	0.7456	1.0312	0.4617	0.019*
C12	0.8003 (2)	0.96117 (16)	0.31859 (13)	0.0158 (3)
H12	0.8341	1.0289	0.2822	0.019*
C13	0.8053 (2)	0.86070 (15)	0.26447 (13)	0.0125 (3)
C14	0.7610 (3)	0.76171 (16)	0.32125 (14)	0.0182 (3)
H14	0.7694	0.6903	0.2871	0.022*
C15	0.7051 (3)	0.76792 (17)	0.42680 (14)	0.0192 (3)
H15	0.6733	0.7008	0.4653	0.023*
C16	0.5603 (3)	0.60138 (19)	1.10231 (18)	0.0274 (4)
H16A	0.5816	0.6058	1.0252	0.033*
H16B	0.5414	0.6826	1.1273	0.033*
Cl1	0.74334 (7)	0.51440 (4)	1.14775 (4)	0.02581 (10)
Cl2	0.37217 (7)	0.54128 (6)	1.14632 (5)	0.03300 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Gd1	0.01086 (4)	0.01200 (4)	0.00842 (4)	−0.00199 (3)	−0.00084 (3)	−0.00099 (3)
O1	0.0135 (6)	0.0135 (5)	0.0165 (6)	0.0004 (4)	0.0023 (4)	−0.0032 (4)
O2	0.0171 (6)	0.0228 (6)	0.0077 (5)	−0.0069 (5)	−0.0002 (4)	−0.0010 (4)
O3	0.0157 (6)	0.0253 (6)	0.0072 (5)	−0.0025 (5)	−0.0004 (4)	−0.0001 (4)
O4	0.0244 (7)	0.0162 (6)	0.0299 (8)	−0.0021 (5)	−0.0116 (6)	−0.0034 (5)
O5	0.0256 (7)	0.0168 (6)	0.0221 (7)	−0.0001 (5)	−0.0081 (5)	−0.0025 (5)
O6	0.0301 (8)	0.0153 (7)	0.0541 (11)	0.0024 (6)	−0.0136 (8)	−0.0090 (7)
O7	0.0187 (6)	0.0300 (7)	0.0136 (6)	−0.0096 (5)	−0.0040 (5)	0.0010 (5)
O8	0.0145 (6)	0.0303 (7)	0.0169 (6)	−0.0085 (5)	−0.0045 (5)	0.0055 (5)
O9	0.0146 (6)	0.0271 (7)	0.0223 (7)	−0.0042 (5)	0.0027 (5)	0.0063 (5)
O10	0.0202 (6)	0.0169 (6)	0.0166 (6)	−0.0025 (5)	0.0012 (5)	−0.0002 (5)
O11	0.0180 (6)	0.0176 (6)	0.0190 (6)	−0.0021 (5)	0.0025 (5)	−0.0009 (5)
O12	0.0555 (12)	0.0136 (7)	0.0512 (12)	−0.0006 (7)	0.0156 (9)	−0.0018 (7)
N1	0.0120 (6)	0.0130 (6)	0.0139 (6)	−0.0021 (5)	0.0007 (5)	−0.0016 (5)
N2	0.0129 (6)	0.0171 (7)	0.0090 (6)	−0.0055 (5)	−0.0011 (5)	−0.0020 (5)
N3	0.0130 (6)	0.0172 (7)	0.0094 (6)	−0.0027 (5)	−0.0020 (5)	0.0000 (5)
N4	0.0162 (7)	0.0153 (7)	0.0253 (8)	−0.0028 (6)	−0.0022 (6)	−0.0017 (6)
N5	0.0131 (6)	0.0137 (6)	0.0175 (7)	−0.0027 (5)	−0.0018 (5)	0.0012 (5)
N6	0.0220 (8)	0.0162 (7)	0.0195 (8)	−0.0003 (6)	−0.0005 (6)	−0.0008 (6)
C1	0.0214 (9)	0.0221 (9)	0.0145 (8)	0.0037 (7)	−0.0051 (7)	−0.0047 (7)
C2	0.0222 (9)	0.0225 (9)	0.0153 (8)	0.0028 (7)	−0.0057 (7)	−0.0082 (7)
C3	0.0124 (7)	0.0140 (7)	0.0124 (7)	−0.0043 (6)	0.0002 (6)	−0.0025 (6)
C4	0.0143 (8)	0.0231 (9)	0.0152 (8)	0.0008 (6)	−0.0030 (6)	−0.0071 (6)
C5	0.0151 (8)	0.0233 (9)	0.0154 (8)	−0.0016 (6)	−0.0025 (6)	−0.0085 (6)
C6	0.0155 (8)	0.0158 (7)	0.0139 (8)	−0.0013 (6)	−0.0008 (6)	−0.0032 (6)
C7	0.0167 (8)	0.0142 (7)	0.0141 (8)	−0.0004 (6)	−0.0024 (6)	−0.0009 (6)
C8	0.0120 (7)	0.0153 (7)	0.0105 (7)	−0.0027 (6)	−0.0016 (5)	−0.0007 (5)
C9	0.0157 (8)	0.0148 (7)	0.0121 (7)	−0.0007 (6)	−0.0007 (6)	−0.0016 (6)
C10	0.0163 (8)	0.0153 (7)	0.0124 (7)	−0.0021 (6)	−0.0020 (6)	0.0002 (6)
C11	0.0205 (8)	0.0136 (7)	0.0138 (8)	−0.0039 (6)	−0.0028 (6)	−0.0014 (6)
C12	0.0211 (8)	0.0146 (7)	0.0125 (7)	−0.0064 (6)	−0.0017 (6)	0.0001 (6)
C13	0.0118 (7)	0.0146 (7)	0.0105 (7)	−0.0013 (5)	−0.0017 (5)	0.0000 (5)
C14	0.0278 (9)	0.0140 (8)	0.0134 (8)	−0.0051 (7)	−0.0033 (7)	−0.0012 (6)
C15	0.0295 (10)	0.0168 (8)	0.0133 (8)	−0.0095 (7)	−0.0039 (7)	0.0015 (6)
C16	0.0267 (10)	0.0235 (10)	0.0293 (11)	−0.0009 (8)	−0.0048 (8)	0.0068 (8)
Cl1	0.0292 (2)	0.0199 (2)	0.0288 (2)	−0.00077 (18)	−0.01067 (19)	−0.00114 (17)
Cl2	0.0267 (3)	0.0391 (3)	0.0304 (3)	−0.0049 (2)	−0.0016 (2)	0.0060 (2)

Geometric parameters (Å, º) top

Gd1—O3	2.3216 (13)	C1—H1	0.9500
Gd1—O1	2.3230 (13)	C2—C3	1.395 (2)
Gd1—O2	2.3534 (13)	C2—H2	0.9500
Gd1—O11	2.4601 (13)	C3—C4	1.398 (2)
Gd1—O8	2.4879 (14)	C3—C3ⁱ	1.481 (3)
Gd1—O7	2.4872 (14)	C4—C5	1.379 (2)
Gd1—O5	2.4958 (14)	C4—H4	0.9500
Gd1—O4	2.4967 (14)	C5—H5	0.9500
Gd1—O10	2.4992 (14)	C6—C7	1.384 (2)
Gd1—N6	2.9021 (17)	C6—H6	0.9500
Gd1—N5	2.9152 (15)	C7—C8	1.394 (2)
Gd1—N4	2.9277 (16)	C7—H7	0.9500
O1—N1	1.3308 (18)	C8—C9	1.396 (2)
O2—N2	1.3346 (18)	C8—C13ⁱⁱ	1.479 (2)
O3—N3	1.3310 (18)	C9—C10	1.376 (2)
O4—N4	1.277 (2)	C9—H9	0.9500
O5—N4	1.265 (2)	C10—H10	0.9500
O6—N4	1.219 (2)	C11—C12	1.379 (2)
O7—N5	1.271 (2)	C11—H11	0.9500
O8—N5	1.271 (2)	C12—C13	1.391 (2)
O9—N5	1.217 (2)	C12—H12	0.9500
O10—N6	1.268 (2)	C13—C14	1.394 (2)
O11—N6	1.280 (2)	C13—C8ⁱⁱⁱ	1.479 (2)
O12—N6	1.215 (2)	C14—C15	1.374 (3)
N1—C5	1.343 (2)	C14—H14	0.9500
N1—C1	1.347 (2)	C15—H15	0.9500
N2—C6	1.348 (2)	C16—Cl1	1.766 (2)
N2—C10	1.352 (2)	C16—Cl2	1.774 (2)
N3—C11	1.343 (2)	C16—H16A	0.9900
N3—C15	1.349 (2)	C16—H16B	0.9900
C1—C2	1.378 (3)

O3—Gd1—O1	85.06 (5)	C5—N1—C1	121.14 (15)
O3—Gd1—O2	154.22 (5)	O2—N2—C6	119.65 (14)
O1—Gd1—O2	83.54 (5)	O2—N2—C10	119.01 (14)
O3—Gd1—O11	85.96 (5)	C6—N2—C10	121.33 (15)
O1—Gd1—O11	122.79 (4)	O3—N3—C11	120.02 (15)
O2—Gd1—O11	80.97 (5)	O3—N3—C15	118.90 (15)
O3—Gd1—O8	123.47 (4)	C11—N3—C15	121.06 (15)
O1—Gd1—O8	148.53 (5)	O6—N4—O5	122.12 (18)
O2—Gd1—O8	74.82 (4)	O6—N4—O4	122.15 (18)
O11—Gd1—O8	76.46 (5)	O5—N4—O4	115.72 (15)
O3—Gd1—O7	72.31 (4)	O6—N4—Gd1	177.12 (15)
O1—Gd1—O7	150.94 (5)	O5—N4—Gd1	57.84 (9)
O2—Gd1—O7	124.33 (4)	O4—N4—Gd1	57.95 (9)
O11—Gd1—O7	74.51 (5)	O9—N5—O8	122.12 (16)
O8—Gd1—O7	51.32 (4)	O9—N5—O7	122.00 (16)
O3—Gd1—O5	125.67 (5)	O8—N5—O7	115.87 (15)
O1—Gd1—O5	79.17 (5)	O9—N5—Gd1	175.14 (13)
O2—Gd1—O5	74.49 (5)	O8—N5—Gd1	58.03 (9)
O11—Gd1—O5	144.96 (5)	O7—N5—Gd1	58.00 (8)
O8—Gd1—O5	73.25 (5)	O12—N6—O10	122.46 (18)
O7—Gd1—O5	99.15 (5)	O12—N6—O11	121.17 (17)
O3—Gd1—O4	75.01 (5)	O10—N6—O11	116.37 (15)
O1—Gd1—O4	78.88 (5)	O12—N6—Gd1	177.69 (16)
O2—Gd1—O4	124.87 (5)	O10—N6—Gd1	59.06 (9)
O11—Gd1—O4	150.14 (5)	O11—N6—Gd1	57.34 (8)
O8—Gd1—O4	94.89 (5)	N1—C1—C2	120.02 (17)
O7—Gd1—O4	77.84 (5)	N1—C1—H1	120.0
O5—Gd1—O4	51.08 (5)	C2—C1—H1	120.0
O3—Gd1—O10	76.63 (5)	C1—C2—C3	120.99 (16)
O1—Gd1—O10	71.20 (4)	C1—C2—H2	119.5
O2—Gd1—O10	77.83 (5)	C3—C2—H2	119.5
O11—Gd1—O10	51.76 (4)	C2—C3—C4	116.88 (16)
O8—Gd1—O10	124.27 (5)	C2—C3—C3ⁱ	121.81 (19)
O7—Gd1—O10	118.86 (5)	C4—C3—C3ⁱ	121.3 (2)
O5—Gd1—O10	141.26 (5)	C5—C4—C3	120.61 (17)
O4—Gd1—O10	140.09 (5)	C5—C4—H4	119.7
O3—Gd1—N6	80.79 (5)	C3—C4—H4	119.7
O1—Gd1—N6	96.87 (5)	N1—C5—C4	120.33 (16)
O2—Gd1—N6	77.73 (5)	N1—C5—H5	119.8
O11—Gd1—N6	25.98 (4)	C4—C5—H5	119.8
O8—Gd1—N6	100.45 (5)	N2—C6—C7	120.24 (16)
O7—Gd1—N6	97.21 (5)	N2—C6—H6	119.9
O5—Gd1—N6	152.20 (5)	C7—C6—H6	119.9
O4—Gd1—N6	155.69 (5)	C6—C7—C8	120.07 (16)
O10—Gd1—N6	25.79 (4)	C6—C7—H7	120.0
O3—Gd1—N5	97.81 (4)	C8—C7—H7	120.0
O1—Gd1—N5	164.46 (4)	C7—C8—C9	117.78 (15)
O2—Gd1—N5	99.36 (4)	C7—C8—C13ⁱⁱ	123.06 (15)
O11—Gd1—N5	72.72 (4)	C9—C8—C13ⁱⁱ	119.14 (15)
O8—Gd1—N5	25.68 (4)	C10—C9—C8	120.69 (16)
O7—Gd1—N5	25.68 (4)	C10—C9—H9	119.7
O5—Gd1—N5	86.86 (5)	C8—C9—H9	119.7
O4—Gd1—N5	87.08 (5)	N2—C10—C9	119.89 (16)
O10—Gd1—N5	124.33 (4)	N2—C10—H10	120.1
N6—Gd1—N5	98.67 (5)	C9—C10—H10	120.1
O3—Gd1—N4	100.41 (5)	N3—C11—C12	120.02 (16)
O1—Gd1—N4	77.11 (5)	N3—C11—H11	120.0
O2—Gd1—N4	99.46 (5)	C12—C11—H11	120.0
O11—Gd1—N4	159.79 (5)	C11—C12—C13	120.29 (16)
O8—Gd1—N4	84.12 (5)	C11—C12—H12	119.9
O7—Gd1—N4	89.07 (5)	C13—C12—H12	119.9
O5—Gd1—N4	25.41 (5)	C12—C13—C14	118.11 (15)
O4—Gd1—N4	25.69 (5)	C12—C13—C8ⁱⁱⁱ	120.50 (15)
O10—Gd1—N4	148.30 (5)	C14—C13—C8ⁱⁱⁱ	121.35 (15)
N6—Gd1—N4	173.67 (5)	C15—C14—C13	119.68 (16)
N5—Gd1—N4	87.36 (4)	C15—C14—H14	120.2
N1—O1—Gd1	129.39 (10)	C13—C14—H14	120.2
N2—O2—Gd1	124.82 (10)	N3—C15—C14	120.67 (17)
N3—O3—Gd1	127.48 (10)	N3—C15—H15	119.7
N4—O4—Gd1	96.36 (10)	C14—C15—H15	119.7
N4—O5—Gd1	96.75 (11)	Cl1—C16—Cl2	111.26 (12)
N5—O7—Gd1	96.32 (10)	Cl1—C16—H16A	109.4
N5—O8—Gd1	96.29 (10)	Cl2—C16—H16A	109.4
N6—O10—Gd1	95.16 (11)	Cl1—C16—H16B	109.4
N6—O11—Gd1	96.67 (10)	Cl2—C16—H16B	109.4
O1—N1—C5	119.58 (14)	H16A—C16—H16B	108.0
O1—N1—C1	119.26 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O7^iv	0.95	2.41	3.082 (2)	127
C9—H9···O9^v	0.95	2.57	3.287 (2)	132
C12—H12···O2^vi	0.95	2.43	3.300 (2)	152
C16—H16B···O12^v	0.99	2.43	3.246 (3)	139
C16—H16A···O8	0.99	2.56	3.302 (3)	132
C16—H16A···O9	0.99	2.50	3.084 (3)	117

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

Experimental details

Crystal data
Chemical formula	[Gd₂(NO₃)₆(C₁₀H₈N₂O₂)₃]·2CH₂Cl₂
M_r	1420.96
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.9917 (5), 11.5668 (7), 13.0347 (8)
α, β, γ (°)	86.059 (1), 80.134 (1), 78.255 (1)
V (Å³)	1161.52 (12)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	3.16
Crystal size (mm)	0.51 × 0.48 × 0.25

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.529, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	13791, 6990, 6776
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.736

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.051, 1.06
No. of reflections	6990
No. of parameters	334
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.34, −1.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O7ⁱ	0.95	2.41	3.082 (2)	127.3
C9—H9···O9ⁱⁱ	0.95	2.57	3.287 (2)	132.0
C12—H12···O2ⁱⁱⁱ	0.95	2.43	3.300 (2)	151.9
C16—H16B···O12ⁱⁱ	0.99	2.43	3.246 (3)	139.2
C16—H16A···O8	0.99	2.56	3.302 (3)	131.9
C16—H16A···O9	0.99	2.50	3.084 (3)	117.2

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

Acknowledgements

The authors are thankful to Allegheny College for providing funding in support of this research. The diffractometer was funded by the NSF (grant No. 0087210), the Ohio Board of Regents (grant No. CAP-491) and by Youngstown State University. The authors would like to acknowledge Youngstown State University and the STaRBURSTT CyberInstrumentation Consortium for assistance with the crystallography.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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