catena-Poly[(μ2-3-carb­oxy-5-nitro­benzoato)(μ3-5-nitro­benzene-1,3-dicarboxyl­ato)(1,10-phenanthroline)gadolinium(III)]

Wang, J.; Fang, Z.-L.

doi:10.1107/S1600536810035452

catena-Poly[(μ₂-3-carboxy-5-nitrobenzoato)(μ₃-5-nitrobenzene-1,3-dicarboxylato)(1,10-phenanthroline)gadolinium(III)]

The crystal structure of the title complex, [Gd(C₈H₃NO₆)(C₈H₄NO₆)(C₁₂H₈N₂)]_n, contains polymeric chains made up of Gd^III atoms, 1,10-phenanthroline and fully or half-deprotonated 5-nitrobenzene-1,3-dicarboxylic acid (H₂L) ligands. The Gd^III atom is coordinated in a distorted bicapped trigonal-prismatic fashion by six O atoms from two HL⁻ and three L²⁻ ligands, and by two N atoms from the 1,10-phenanthroline ligand. The L²⁻ ligands bridge the Gd–phenanthroline units, forming chains running parallel to [100]. O—H

O hydrogen bonding as well as π–π stacking interactions with an interplanar distance of 3.599 (2) Å assemble neighboring polymeric chains.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810035452/wm2394sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810035452/wm2394Isup2.hkl Contains datablock I

CCDC reference: 797619

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.012 Å
R factor = 0.045
wR factor = 0.121
Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       4.14 Ratio

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT213_ALERT_2_C Atom O4              has ADP max/min Ratio .....       3.20 prola
PLAT213_ALERT_2_C Atom O6              has ADP max/min Ratio .....       3.10 prola
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.73 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..         12
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.599        155
PLAT234_ALERT_4_C Large Hirshfeld Difference C19    --  C20     ..       0.16 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C20    --  C21     ..       0.15 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C21    --  C22     ..       0.19 Ang.

Alert level G
PLAT153_ALERT_1_G The su's on the Cell Axes   are Equal (x 100000)        300 Ang.
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3
PLAT804_ALERT_5_G ARU-Pack Problem in PLATON Analysis ............          1 Times

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Recently, we became interested in the nature of π–π stacking as it plays an important role in some biological processes (Deisenhofer & Michel, 1989). A series of metal complexes incorporating different aromatic ligands has been prepared and their crystal structures provide useful information about π–π stacking (Wu et al., 2003; Pan & Xu, 2004; Li et al., 2005 Qiu et al., 2009). As part of our ongoing investigations, the title complex, (I), incorporating 1,10-phenanthroline, has been prepared.

As depicted in Fig. 1, the Gd^III atom has a distorted bicapped trigonal-prismatic coordination, defined by six O atoms from two 1-carboxy-5-nitro-3-benzoate (HL^-, where L is 5-nitro-1,3-benzenedicarboxyic acid) and three 5-nitro-1,3-benzenedicarboxylate ligands (L^2-), and two N atoms from the 1,10-phenanthroline ligand. The L^2- ligands link Gd-phenanthroline moieties, forming an infinite polymeric chain running along [100]. The HL^- and L^2- ligands in this complex have two different coordination modes: the first ligand uses one of its carboxylate groups to link one Gd^III ions in a chelating coordination mode, the other carboxylate group links two Gd^III ions in a bis-monodentate coordination mode, whereas the other ligand uses its carboxylate groups to link two Gd^III ions in a bridging coordination mode. In the chain, the closest Gd···Gd separation is 4.333 (3) Å. These chains interact with each other by π–π stacking of adjacent phenanthroline groups (interplanar distance of 3.599 (2) Å). O—H···O hydrogen bonding interactions between carboxyl and carboxylate groups of neighbouring ligands help to consolidate the structure (Table 1; Fig. 2).

Related literature top

For background to π–π stacking in biological systems, see: Deisenhofer & Michel (1989). For some crystal structures of metal complexes exhibiting π–π stacking, see: Li et al. (2005); Pan & Xu (2004); Wu et al. (2003); Qiu et al. (2009).

Experimental top

A sample of Gd₂O₃ (0.0732 g, 0.20 mmol), 5-nitro-1,3-benzenedicarboxylic acid (0.1015 g, 0.50 mmol), 1,10-phenanthroline (0.0991 g, 0.50 mmol) and distilled water (8 ml) were mixed in a Teflon-lined stainless steel vessel with 15 ml capacity. The mixture was heated under autogenous pressure at 393 K for 48 h and cooled slowly to room temperature.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); 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. Part of the structure of (I), showing the coordination of the Gd atom with the atomic numbering scheme. Non-H atoms are shown with 30% probability displacement ellipsoids, H atoms as spheres of arbitrary radius. [Symmetry codes: (i) 2 - x, -y, 1 - z; (ii) 1 - x, y, 1 - z; (iii) 1 + x, y, z.]
	Fig. 2. View of π–π interactions consolidating the three-dimensional network of (I).

catena-Poly[(µ₂-3-carboxy-5-nitrobenzoato)(µ₃-5-nitrobenzene- 1,3-dicarboxylato)(1,10-phenanthroline)gadolinium(III)] top

Crystal data top

[Gd(C₈H₃NO₆)(C₈H₄NO₆)(C₁₂H₈N₂)]	Z = 2
M_r = 756.69	F(000) = 742
Triclinic, P1	D_x = 1.820 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.300 (3) Å	Cell parameters from 5111 reflections
b = 12.030 (3) Å	θ = 2.6–27.7°
c = 12.150 (3) Å	µ = 2.48 mm⁻¹
α = 70.581 (4)°	T = 298 K
β = 85.925 (4)°	Prism, colorless
γ = 76.512 (2)°	0.28 × 0.26 × 0.22 mm
V = 1380.6 (7) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4860 independent reflections
Radiation source: fine-focus sealed tube	4259 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scan	θ_max = 25.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.544, T_max = 0.612	k = −13→14
6896 measured reflections	l = −14→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0811P)²] where P = (F_o² + 2F_c²)/3
4837 reflections	(Δ/σ)_max < 0.001
407 parameters	Δρ_max = 2.51 e Å⁻³
0 restraints	Δρ_min = −2.59 e Å⁻³

Crystal data top

[Gd(C₈H₃NO₆)(C₈H₄NO₆)(C₁₂H₈N₂)]	γ = 76.512 (2)°
M_r = 756.69	V = 1380.6 (7) Å³
Triclinic, P1	Z = 2
a = 10.300 (3) Å	Mo Kα radiation
b = 12.030 (3) Å	µ = 2.48 mm⁻¹
c = 12.150 (3) Å	T = 298 K
α = 70.581 (4)°	0.28 × 0.26 × 0.22 mm
β = 85.925 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4860 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4259 reflections with I > 2σ(I)
T_min = 0.544, T_max = 0.612	R_int = 0.030
6896 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.04	Δρ_max = 2.51 e Å⁻³
4837 reflections	Δρ_min = −2.59 e Å⁻³
407 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	1.0366 (7)	0.0929 (6)	0.6625 (5)	0.0330 (14)
C2	1.0511 (6)	0.1117 (6)	0.7766 (5)	0.0308 (13)
C3	1.1673 (7)	0.0513 (6)	0.8416 (6)	0.0407 (16)
H3	1.2371	0.0040	0.8132	0.049*
C4	1.1762 (8)	0.0635 (7)	0.9504 (6)	0.0465 (18)
C5	1.0753 (7)	0.1320 (6)	0.9960 (6)	0.0423 (16)
H5	1.0841	0.1378	1.0694	0.051*
C6	0.9615 (7)	0.1914 (7)	0.9309 (6)	0.0419 (16)
C7	0.9488 (7)	0.1835 (6)	0.8200 (6)	0.0374 (15)
H7	0.8723	0.2261	0.7755	0.045*
C8	0.8451 (9)	0.2616 (8)	0.9788 (7)	0.057 (2)
C9	0.5970 (6)	0.1875 (6)	0.3097 (5)	0.0292 (13)
C10	0.4627 (6)	0.2185 (5)	0.2498 (5)	0.0270 (12)
C11	0.4353 (6)	0.3072 (6)	0.1421 (5)	0.0321 (13)
H11	0.5013	0.3440	0.0995	0.039*
C12	0.3063 (6)	0.3388 (6)	0.1007 (5)	0.0328 (14)
C13	0.2038 (6)	0.2870 (6)	0.1622 (5)	0.0314 (13)
H13	0.1169	0.3128	0.1331	0.038*
C14	0.2355 (6)	0.1959 (5)	0.2679 (5)	0.0256 (12)
C15	0.3643 (6)	0.1606 (5)	0.3105 (5)	0.0279 (12)
H15	0.3858	0.0976	0.3804	0.033*
C17	0.5715 (9)	0.1824 (8)	0.6347 (8)	0.061 (2)
H17	0.5663	0.1088	0.6280	0.073*
C18	0.4954 (10)	0.2208 (11)	0.7209 (9)	0.085 (4)
H18	0.4424	0.1727	0.7704	0.103*
C19	0.4993 (10)	0.3254 (11)	0.7313 (9)	0.081 (3)
H19	0.4484	0.3519	0.7878	0.097*
C20	0.5823 (9)	0.3984 (9)	0.6552 (8)	0.064 (3)
C21	0.5923 (12)	0.5114 (12)	0.6605 (11)	0.091 (4)
H21	0.5419	0.5420	0.7148	0.109*
C22	0.6719 (14)	0.5746 (11)	0.5897 (12)	0.096 (4)
H22	0.6781	0.6476	0.5973	0.115*
C23	0.7507 (11)	0.5337 (9)	0.4998 (10)	0.074 (3)
C24	0.8317 (13)	0.5984 (10)	0.4198 (12)	0.095 (4)
H24	0.8409	0.6722	0.4234	0.114*
C25	0.8966 (12)	0.5558 (9)	0.3378 (11)	0.088 (3)
H25	0.9508	0.5991	0.2843	0.106*
C26	0.8809 (9)	0.4432 (7)	0.3339 (8)	0.057 (2)
H26	0.9240	0.4151	0.2753	0.068*
C27	0.7400 (8)	0.4227 (7)	0.4915 (7)	0.0451 (18)
C28	0.6557 (7)	0.3526 (7)	0.5716 (6)	0.0447 (18)
Gd1	0.82752 (3)	0.14792 (3)	0.44144 (2)	0.02604 (13)
N1	1.2997 (8)	−0.0016 (8)	1.0209 (7)	0.072 (2)
N2	0.2724 (6)	0.4320 (6)	−0.0147 (5)	0.0500 (16)
N3	0.6506 (6)	0.2452 (5)	0.5622 (5)	0.0448 (15)
N4	0.8089 (6)	0.3768 (5)	0.4088 (5)	0.0414 (14)
O1	0.9505 (5)	0.1690 (4)	0.5913 (4)	0.0412 (11)
O2	1.1124 (5)	0.0033 (5)	0.6459 (4)	0.0466 (12)
O3	1.3864 (8)	−0.0642 (9)	0.9807 (8)	0.118 (4)
O4	1.3055 (9)	0.0089 (8)	1.1154 (7)	0.113 (3)
O5	0.8641 (6)	0.2486 (6)	1.0881 (5)	0.0647 (16)
H5A	0.7931	0.2735	1.1164	0.097*
O6	0.7481 (8)	0.3226 (11)	0.9241 (7)	0.140 (5)
O7	0.6825 (4)	0.2498 (4)	0.2637 (4)	0.0335 (10)
O8	0.6158 (4)	0.1067 (4)	0.4063 (4)	0.0413 (11)
O9	0.3605 (6)	0.4789 (5)	−0.0694 (5)	0.0593 (15)
O10	0.1591 (7)	0.4607 (8)	−0.0498 (6)	0.103 (3)
C16	0.1297 (6)	0.1363 (6)	0.3374 (5)	0.0300 (13)
O11	0.0114 (4)	0.1968 (4)	0.3252 (4)	0.0421 (11)
O12	0.1665 (5)	0.0297 (4)	0.4038 (4)	0.0448 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.038 (4)	0.044 (4)	0.022 (3)	−0.013 (3)	−0.002 (3)	−0.014 (3)
C2	0.039 (4)	0.037 (3)	0.020 (3)	−0.010 (3)	−0.004 (3)	−0.012 (3)
C3	0.039 (4)	0.048 (4)	0.032 (4)	−0.001 (3)	−0.007 (3)	−0.013 (3)
C4	0.047 (4)	0.059 (5)	0.030 (4)	−0.007 (3)	−0.014 (3)	−0.010 (3)
C5	0.055 (4)	0.052 (4)	0.023 (3)	−0.011 (3)	−0.004 (3)	−0.016 (3)
C6	0.049 (4)	0.053 (4)	0.025 (4)	−0.010 (3)	0.001 (3)	−0.016 (3)
C7	0.043 (4)	0.052 (4)	0.020 (3)	−0.010 (3)	−0.002 (3)	−0.014 (3)
C8	0.055 (5)	0.080 (6)	0.041 (5)	0.001 (4)	0.000 (4)	−0.038 (4)
C9	0.019 (3)	0.044 (4)	0.024 (3)	−0.006 (2)	−0.001 (2)	−0.012 (3)
C10	0.020 (3)	0.039 (3)	0.021 (3)	−0.005 (2)	0.000 (2)	−0.009 (3)
C11	0.025 (3)	0.045 (4)	0.024 (3)	−0.011 (3)	0.004 (2)	−0.006 (3)
C12	0.038 (4)	0.041 (3)	0.017 (3)	−0.015 (3)	0.000 (3)	−0.002 (3)
C13	0.024 (3)	0.046 (4)	0.024 (3)	−0.007 (3)	−0.001 (2)	−0.011 (3)
C14	0.023 (3)	0.035 (3)	0.019 (3)	−0.008 (2)	0.001 (2)	−0.008 (2)
C15	0.027 (3)	0.036 (3)	0.019 (3)	−0.006 (2)	−0.002 (2)	−0.006 (3)
C17	0.054 (5)	0.060 (5)	0.057 (6)	−0.004 (4)	0.025 (4)	−0.014 (4)
C18	0.073 (7)	0.093 (8)	0.062 (7)	0.011 (6)	0.037 (5)	−0.014 (6)
C19	0.070 (7)	0.101 (8)	0.052 (6)	0.010 (6)	0.029 (5)	−0.024 (6)
C20	0.065 (6)	0.072 (6)	0.053 (5)	0.019 (4)	−0.007 (4)	−0.039 (5)
C21	0.084 (8)	0.117 (10)	0.088 (9)	−0.001 (7)	0.008 (7)	−0.071 (8)
C22	0.113 (10)	0.080 (7)	0.116 (10)	0.008 (7)	−0.021 (8)	−0.075 (8)
C23	0.089 (7)	0.057 (5)	0.079 (7)	−0.002 (5)	−0.022 (6)	−0.033 (5)
C24	0.114 (10)	0.056 (6)	0.128 (11)	−0.026 (6)	−0.008 (8)	−0.039 (7)
C25	0.106 (9)	0.049 (5)	0.099 (9)	−0.029 (5)	0.006 (7)	−0.004 (6)
C26	0.072 (6)	0.041 (4)	0.050 (5)	−0.014 (4)	0.002 (4)	−0.006 (4)
C27	0.047 (4)	0.041 (4)	0.047 (5)	0.002 (3)	−0.015 (4)	−0.019 (3)
C28	0.038 (4)	0.054 (5)	0.036 (4)	0.004 (3)	−0.005 (3)	−0.017 (4)
Gd1	0.02026 (18)	0.0381 (2)	0.01841 (18)	−0.00571 (12)	0.00062 (11)	−0.00808 (13)
N1	0.068 (5)	0.094 (6)	0.053 (5)	0.011 (4)	−0.035 (4)	−0.034 (4)
N2	0.049 (4)	0.065 (4)	0.023 (3)	−0.016 (3)	−0.006 (3)	0.006 (3)
N3	0.041 (3)	0.051 (4)	0.036 (3)	0.003 (3)	0.011 (3)	−0.017 (3)
N4	0.046 (3)	0.042 (3)	0.030 (3)	−0.004 (3)	−0.002 (3)	−0.007 (3)
O1	0.052 (3)	0.048 (3)	0.026 (2)	−0.009 (2)	−0.013 (2)	−0.014 (2)
O2	0.043 (3)	0.059 (3)	0.046 (3)	−0.004 (2)	−0.002 (2)	−0.031 (3)
O3	0.082 (5)	0.163 (8)	0.098 (6)	0.055 (6)	−0.056 (5)	−0.072 (6)
O4	0.113 (6)	0.153 (8)	0.066 (5)	0.039 (6)	−0.060 (5)	−0.058 (5)
O5	0.060 (4)	0.104 (5)	0.033 (3)	−0.009 (3)	0.009 (3)	−0.035 (3)
O6	0.092 (6)	0.236 (11)	0.086 (6)	0.077 (7)	−0.041 (5)	−0.112 (7)
O7	0.027 (2)	0.044 (2)	0.024 (2)	−0.0110 (18)	−0.0016 (18)	−0.0002 (19)
O8	0.026 (2)	0.056 (3)	0.030 (3)	−0.014 (2)	−0.0062 (19)	0.006 (2)
O9	0.060 (4)	0.069 (4)	0.031 (3)	−0.023 (3)	0.008 (3)	0.012 (3)
O10	0.065 (5)	0.137 (7)	0.063 (5)	−0.040 (4)	−0.032 (4)	0.044 (4)
C16	0.032 (3)	0.045 (4)	0.014 (3)	−0.013 (3)	0.001 (2)	−0.009 (3)
O11	0.026 (2)	0.056 (3)	0.040 (3)	−0.012 (2)	0.008 (2)	−0.010 (2)
O12	0.040 (3)	0.054 (3)	0.032 (3)	−0.021 (2)	−0.005 (2)	0.004 (2)

Geometric parameters (Å, º) top

C1—O2	1.242 (8)	C19—H19	0.9300
C1—O1	1.256 (8)	C20—C28	1.405 (10)
C1—C2	1.500 (8)	C20—C21	1.411 (16)
C2—C3	1.390 (9)	C21—C22	1.322 (18)
C2—C7	1.391 (9)	C21—H21	0.9300
C3—C4	1.390 (10)	C22—C23	1.463 (16)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.374 (10)	C23—C24	1.391 (16)
C4—N1	1.487 (10)	C23—C27	1.402 (12)
C5—C6	1.370 (10)	C24—C25	1.338 (16)
C5—H5	0.9300	C24—H24	0.9300
C6—C7	1.399 (9)	C25—C26	1.417 (13)
C6—C8	1.498 (10)	C25—H25	0.9300
C7—H7	0.9300	C26—N4	1.309 (10)
C8—O6	1.187 (10)	C26—H26	0.9300
C8—O5	1.308 (9)	C27—N4	1.380 (9)
C9—O8	1.243 (8)	C27—C28	1.445 (11)
C9—O7	1.268 (7)	C28—N3	1.348 (9)
C9—C10	1.519 (8)	Gd1—O12ⁱ	2.322 (5)
C10—C11	1.383 (9)	Gd1—O2ⁱⁱ	2.342 (4)
C10—C15	1.392 (8)	Gd1—O11ⁱⁱⁱ	2.349 (4)
C11—C12	1.376 (9)	Gd1—O1	2.403 (4)
C11—H11	0.9300	Gd1—O8	2.442 (4)
C12—C13	1.396 (9)	Gd1—O7	2.499 (4)
C12—N2	1.479 (8)	Gd1—N3	2.571 (5)
C13—C14	1.383 (9)	Gd1—N4	2.611 (6)
C13—H13	0.9300	N1—O4	1.204 (9)
C14—C15	1.378 (8)	N1—O3	1.214 (10)
C14—C16	1.498 (8)	N2—O10	1.204 (9)
C15—H15	0.9300	N2—O9	1.220 (8)
C17—N3	1.324 (11)	O2—Gd1ⁱⁱ	2.342 (4)
C17—C18	1.401 (12)	O5—H5A	0.8200
C17—H17	0.9300	C16—O12	1.252 (8)
C18—C19	1.316 (16)	C16—O11	1.257 (7)
C18—H18	0.9300	O11—Gd1^iv	2.349 (4)
C19—C20	1.434 (15)	O12—Gd1ⁱ	2.322 (5)

O2—C1—O1	125.4 (6)	C25—C24—C23	120.8 (10)
O2—C1—C2	116.8 (6)	C25—C24—H24	119.6
O1—C1—C2	117.8 (6)	C23—C24—H24	119.6
C3—C2—C7	120.1 (6)	C24—C25—C26	118.6 (10)
C3—C2—C1	118.6 (6)	C24—C25—H25	120.7
C7—C2—C1	121.3 (6)	C26—C25—H25	120.7
C4—C3—C2	118.1 (6)	N4—C26—C25	123.3 (9)
C4—C3—H3	121.0	N4—C26—H26	118.3
C2—C3—H3	121.0	C25—C26—H26	118.3
C5—C4—C3	122.9 (7)	N4—C27—C23	121.9 (9)
C5—C4—N1	118.7 (6)	N4—C27—C28	118.2 (6)
C3—C4—N1	118.4 (7)	C23—C27—C28	119.9 (8)
C6—C5—C4	118.5 (6)	N3—C28—C20	122.7 (8)
C6—C5—H5	120.8	N3—C28—C27	118.0 (6)
C4—C5—H5	120.8	C20—C28—C27	119.4 (8)
C5—C6—C7	120.7 (7)	O12ⁱ—Gd1—O2ⁱⁱ	76.27 (19)
C5—C6—C8	120.9 (6)	O12ⁱ—Gd1—O11ⁱⁱⁱ	124.82 (17)
C7—C6—C8	118.3 (7)	O2ⁱⁱ—Gd1—O11ⁱⁱⁱ	76.07 (18)
C2—C7—C6	119.7 (6)	O12ⁱ—Gd1—O1	75.73 (17)
C2—C7—H7	120.1	O2ⁱⁱ—Gd1—O1	126.15 (17)
C6—C7—H7	120.1	O11ⁱⁱⁱ—Gd1—O1	83.73 (17)
O6—C8—O5	124.0 (7)	O12ⁱ—Gd1—O8	80.85 (15)
O6—C8—C6	124.2 (7)	O2ⁱⁱ—Gd1—O8	75.42 (17)
O5—C8—C6	111.8 (7)	O11ⁱⁱⁱ—Gd1—O8	134.60 (16)
O8—C9—O7	122.3 (5)	O1—Gd1—O8	141.63 (17)
O8—C9—C10	118.4 (5)	O12ⁱ—Gd1—O7	132.49 (15)
O7—C9—C10	119.1 (5)	O2ⁱⁱ—Gd1—O7	81.73 (16)
C11—C10—C15	120.8 (5)	O11ⁱⁱⁱ—Gd1—O7	88.64 (15)
C11—C10—C9	121.4 (5)	O1—Gd1—O7	147.63 (16)
C15—C10—C9	117.6 (5)	O8—Gd1—O7	52.84 (14)
C12—C11—C10	117.3 (6)	O12ⁱ—Gd1—N3	84.99 (19)
C12—C11—H11	121.4	O2ⁱⁱ—Gd1—N3	145.6 (2)
C10—C11—H11	121.4	O11ⁱⁱⁱ—Gd1—N3	137.47 (19)
C11—C12—C13	123.4 (6)	O1—Gd1—N3	74.72 (18)
C11—C12—N2	119.3 (6)	O8—Gd1—N3	73.32 (19)
C13—C12—N2	117.3 (6)	O7—Gd1—N3	90.53 (17)
C14—C13—C12	117.9 (6)	O12ⁱ—Gd1—N4	138.41 (18)
C14—C13—H13	121.1	O2ⁱⁱ—Gd1—N4	144.26 (19)
C12—C13—H13	121.1	O11ⁱⁱⁱ—Gd1—N4	74.83 (18)
C15—C14—C13	120.1 (5)	O1—Gd1—N4	70.35 (17)
C15—C14—C16	119.7 (5)	O8—Gd1—N4	112.27 (17)
C13—C14—C16	120.2 (5)	O7—Gd1—N4	77.29 (16)
C14—C15—C10	120.5 (6)	N3—Gd1—N4	63.6 (2)
C14—C15—H15	119.8	O4—N1—O3	124.4 (8)
C10—C15—H15	119.8	O4—N1—C4	117.7 (8)
N3—C17—C18	123.5 (10)	O3—N1—C4	117.9 (7)
N3—C17—H17	118.2	O10—N2—O9	122.6 (6)
C18—C17—H17	118.2	O10—N2—C12	119.1 (6)
C19—C18—C17	119.6 (10)	O9—N2—C12	118.3 (6)
C19—C18—H18	120.2	C17—N3—C28	117.6 (6)
C17—C18—H18	120.2	C17—N3—Gd1	121.2 (5)
C18—C19—C20	119.8 (8)	C28—N3—Gd1	119.7 (5)
C18—C19—H19	120.1	C26—N4—C27	117.6 (7)
C20—C19—H19	120.1	C26—N4—Gd1	124.1 (5)
C28—C20—C21	119.8 (10)	C27—N4—Gd1	116.9 (5)
C28—C20—C19	116.8 (9)	C1—O1—Gd1	130.5 (4)
C21—C20—C19	123.4 (9)	C1—O2—Gd1ⁱⁱ	153.7 (4)
C22—C21—C20	121.3 (10)	C8—O5—H5A	109.5
C22—C21—H21	119.4	C9—O7—Gd1	90.7 (3)
C20—C21—H21	119.4	C9—O8—Gd1	94.0 (4)
C21—C22—C23	122.2 (10)	O12—C16—O11	124.9 (6)
C21—C22—H22	118.9	O12—C16—C14	117.3 (5)
C23—C22—H22	118.9	O11—C16—C14	117.8 (6)
C24—C23—C27	117.7 (10)	C16—O11—Gd1^iv	127.2 (4)
C24—C23—C22	124.9 (10)	C16—O12—Gd1ⁱ	161.3 (4)
C27—C23—C22	117.4 (11)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O7^v	0.82	2.03	2.737 (7)	145

Symmetry code: (v) x, y, z+1.

Experimental details

Crystal data
Chemical formula	[Gd(C₈H₃NO₆)(C₈H₄NO₆)(C₁₂H₈N₂)]
M_r	756.69
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.300 (3), 12.030 (3), 12.150 (3)
α, β, γ (°)	70.581 (4), 85.925 (4), 76.512 (2)
V (Å³)	1380.6 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.48
Crystal size (mm)	0.28 × 0.26 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.544, 0.612
No. of measured, independent and observed [I > 2σ(I)] reflections	6896, 4860, 4259
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.121, 1.04
No. of reflections	4837
No. of parameters	407
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.51, −2.59

Computer programs: SMART (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).