Bis[3-dimethyl­amino-1-(pyridin-2-yl)prop-2-en-1-one-κ2N1,O]tris­(nitrato-κ2O,O)gadolinium(III) ethanol disolvate

Liu, X.; Hu, D.

doi:10.1107/S1600536811050458

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1876

https://doi.org/10.1107/S1600536811050458

Open

access

Bis[3-dimethylamino-1-(pyridin-2-yl)prop-2-en-1-one-κ²N¹,O]tris(nitrato-κ²O,O)gadolinium(III) ethanol disolvate

Xia Liu ^a and Dahua Hu ^a ^*

^aDepartment of City Science, Jiangsu City Vocation College, Nanjing, 210003, People's Republic of China
^*Correspondence e-mail: liuxia1107@hotmail.com

(Received 7 November 2011; accepted 24 November 2011; online 30 November 2011)

In the title compound, [Gd(NO₃)₃(C₁₀H₁₂N₂O)₂]·2C₂H₅OH, the Gd^III ion and one nitrate anion are located on a twofold rotation axis. The Gd^III ion is ten-coordinated by two N and two O atoms from two bidentate 3-(N,N-dimethylamino)-1-(2-pyridyl)prop-2-en-1-one) ligands and six O atoms from three nitrate anions in a distorted bicapped square-antiprismatic geometry. In the crystal, the components are linked by O—H⋯O hydrogen bonds. The ethanol solvent molecule is disordered over two positions in a ratio 0.615 (16):0.385 (16).

Related literature

For isotypic structures, see: Hu (2010 ); Shen et al. (2011 ). For compounds containing the 3-(N,N-dimethylamino)-1-(2-pyridyl)prop-2-en-1-one) ligand, see: Bi (2009 ); Hu & Tian (2007 ); Li et al. (2005 ); Shen et al. (2011); Wang et al. (2005 ).

Experimental

Crystal data

[Gd(NO₃)₃(C₁₀H₁₂N₂O)₂]·2C₂H₆O
M_r = 787.85
Monoclinic, C 2/c
a = 21.322 (2) Å
b = 10.9876 (11) Å
c = 16.3844 (16) Å
β = 121.020 (2)°
V = 3289.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.09 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.624, T_max = 0.705
8248 measured reflections
3005 independent reflections
2563 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.087
S = 1.02
3005 reflections
237 parameters
130 restraints
H-atom parameters constrained
Δρ_max = 1.28 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O3	0.82	2.26	3.084 (12)	179
O7B—H7B⋯O3	0.82	2.19	3.00 (2)	168

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811050458/br2183sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050458/br2183Isup2.hkl

checkCIF report

Comment top

The crystal structures of some coordination complexes of the ligand 3-(N,N-dimethylamino)-1-(2-pyridyl)prop-2-en-1-one) with Co, Ni, Zn, Cd, and Pr, have been described ((Bi et al., 2009; Hu & Tian, 2007; Li et al., 2005; Wang et al., 2005 Hu, 2010). Here we report the crystal structure of the title complex with gadolinium(III).

The coordination geometry about Gd(III) center is shown in Fig. 1. Each Gd(III) atom is in a ten coordinate environment comprising two oxygen atoms and two nitrogen atoms from the two bidentate organic ligands L and six oxygen atoms from three tertiary nitrate anions that act as bidentate anionic ligands. Thus the coordination polyhedron of Gd(III) is a distorted bicapped square antiprism. The Gd—O distances lie in two groups; those to the oxygen atoms of organic ligands are 2.348 Å, whereas those to nitrate O atoms are in the range of 2.494 (5)–2.549 (5) Å, which were similar to those in the Pr complex (Hu, 2010; Shen et al., 2011).

Related literature top

For isotypic structures, see: Hu (2010); Shen et al. (2011). For the compounds containing the 3-(N,N-dimethylamino)-1-(2-pyridyl)prop-2-en-1-one) ligand, see: Bi (2009); Hu & Tian (2007); Li et al. (2005); Shen et al. (2011); Wang et al. (2005).

Experimental top

All solvents and chemicals were of analytical grade and were used without further purification. For the synthesis of title compoud, a solution of ligand (0.2 mmol) and Gd(NO₃)₃ (0.1 mmol) in 50 ml e thanol was refluxed for 1 h, and then cooled to room temperature and filtered. Single crystals suitable for X-ray analysis were grown from the ethanol solution by slow evaporation at room temperature in air.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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. Molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering. The solvent molecule is omitted for clarity. symmetry operation i: -x, y, 0.5 - z.

Bis[3-dimethylamino-1-(pyridin-2-yl)prop-2-en-1-one- κ²N¹,O]tris(nitrato-κ²O,O)gadolinium(III) ethanol disolvate top

Crystal data top

[Gd(NO₃)₃(C₁₀H₁₂N₂O)₂]·2C₂H₆O	F(000) = 1588
M_r = 787.85	D_x = 1.591 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1903 reflections
a = 21.322 (2) Å	θ = 2.2–25.3°
b = 10.9876 (11) Å	µ = 2.09 mm⁻¹
c = 16.3844 (16) Å	T = 293 K
β = 121.020 (2)°	Block, colorless
V = 3289.5 (6) Å³	0.25 × 0.22 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3005 independent reflections
Radiation source: fine-focus sealed tube	2563 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
phi and ω scans	θ_max = 25.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −25→23
T_min = 0.624, T_max = 0.705	k = −11→13
8248 measured reflections	l = −13→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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.030P)²] where P = (F_o² + 2F_c²)/3
3005 reflections	(Δ/σ)_max = 0.001
237 parameters	Δρ_max = 1.28 e Å⁻³
130 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

[Gd(NO₃)₃(C₁₀H₁₂N₂O)₂]·2C₂H₆O	V = 3289.5 (6) Å³
M_r = 787.85	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 21.322 (2) Å	µ = 2.09 mm⁻¹
b = 10.9876 (11) Å	T = 293 K
c = 16.3844 (16) Å	0.25 × 0.22 × 0.18 mm
β = 121.020 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3005 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2563 reflections with I > 2σ(I)
T_min = 0.624, T_max = 0.705	R_int = 0.053
8248 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	130 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.02	Δρ_max = 1.28 e Å⁻³
3005 reflections	Δρ_min = −0.64 e Å⁻³
237 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	Occ. (<1)
Gd1	0.5000	0.68895 (3)	0.7500	0.04053 (15)
C1	0.3556 (3)	0.6948 (6)	0.5155 (4)	0.0635 (17)
H1	0.3456	0.7663	0.5369	0.076*
C2	0.3110 (4)	0.6640 (7)	0.4213 (4)	0.072 (2)
H2	0.2723	0.7140	0.3799	0.086*
C3	0.3250 (4)	0.5580 (8)	0.3900 (4)	0.077 (2)
H3	0.2963	0.5349	0.3266	0.093*
C4	0.3821 (3)	0.4859 (6)	0.4536 (4)	0.0626 (18)
H4	0.3916	0.4123	0.4339	0.075*
C5	0.4255 (3)	0.5237 (5)	0.5470 (3)	0.0455 (14)
C6	0.4913 (3)	0.4574 (5)	0.6206 (4)	0.0478 (15)
C7	0.5062 (3)	0.3384 (5)	0.6053 (4)	0.0547 (16)
H7	0.4742	0.2988	0.5486	0.066*
C8	0.5677 (4)	0.2802 (5)	0.6734 (4)	0.0551 (16)
H8	0.5963	0.3232	0.7296	0.066*
C9	0.5512 (4)	0.0952 (6)	0.5869 (5)	0.088 (2)
H9A	0.5037	0.0784	0.5774	0.132*
H9B	0.5772	0.0202	0.5962	0.132*
H9C	0.5459	0.1363	0.5319	0.132*
C10	0.6585 (4)	0.1229 (6)	0.7484 (5)	0.088 (2)
H10A	0.6847	0.1863	0.7937	0.131*
H10B	0.6883	0.0909	0.7252	0.131*
H10C	0.6470	0.0590	0.7785	0.131*
N1	0.4118 (2)	0.6285 (4)	0.5772 (3)	0.0490 (12)
N2	0.5917 (3)	0.1716 (4)	0.6697 (4)	0.0614 (14)
N3	0.6199 (3)	0.7461 (5)	0.7143 (4)	0.0601 (14)
N4	0.5000	0.9580 (8)	0.7500	0.083 (3)
O1	0.5330 (2)	0.5152 (3)	0.6968 (2)	0.0544 (11)
O2	0.5542 (2)	0.7683 (4)	0.6534 (3)	0.0611 (12)
O3	0.6327 (2)	0.7032 (3)	0.7932 (3)	0.0579 (11)
O4	0.6696 (3)	0.7642 (5)	0.6994 (3)	0.0965 (17)
O5	0.5524 (2)	0.8938 (4)	0.8143 (3)	0.0671 (12)
O6	0.5000	1.0655 (6)	0.7500	0.098 (2)
O7	0.7048 (8)	0.4494 (12)	0.8453 (9)	0.156 (6)	0.615 (16)
H7A	0.6849	0.5163	0.8315	0.234*	0.615 (16)
C11	0.7467 (10)	0.443 (2)	0.9319 (11)	0.136 (6)	0.615 (16)
H11A	0.7208	0.3934	0.9538	0.163*	0.615 (16)
H11B	0.7464	0.5250	0.9543	0.163*	0.615 (16)
C12	0.8233 (9)	0.4041 (19)	0.9907 (14)	0.130 (6)	0.615 (16)
H12A	0.8274	0.3454	1.0366	0.195*	0.615 (16)
H12B	0.8535	0.4733	1.0232	0.195*	0.615 (16)
H12C	0.8390	0.3682	0.9508	0.195*	0.615 (16)
O7B	0.7568 (13)	0.525 (2)	0.8763 (16)	0.153 (7)	0.385 (16)
H7B	0.7227	0.5721	0.8609	0.230*	0.385 (16)
C11B	0.773 (2)	0.475 (3)	0.9530 (18)	0.141 (8)	0.385 (16)
H11C	0.7290	0.4706	0.9554	0.169*	0.385 (16)
H11D	0.8060	0.5308	1.0032	0.169*	0.385 (16)
C12B	0.8080 (19)	0.353 (2)	0.979 (3)	0.133 (9)	0.385 (16)
H12D	0.7729	0.2944	0.9740	0.200*	0.385 (16)
H12E	0.8487	0.3549	1.0435	0.200*	0.385 (16)
H12F	0.8249	0.3314	0.9370	0.200*	0.385 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Gd1	0.0412 (3)	0.0372 (2)	0.0343 (2)	0.000	0.01310 (17)	0.000
C1	0.051 (4)	0.072 (4)	0.052 (4)	0.006 (4)	0.016 (3)	0.004 (3)
C2	0.059 (5)	0.090 (6)	0.048 (4)	−0.007 (4)	0.015 (3)	0.008 (4)
C3	0.057 (5)	0.120 (7)	0.038 (4)	−0.027 (5)	0.012 (3)	−0.005 (4)
C4	0.059 (4)	0.074 (5)	0.052 (4)	−0.019 (4)	0.027 (3)	−0.020 (3)
C5	0.042 (4)	0.052 (4)	0.038 (3)	−0.012 (3)	0.017 (3)	−0.003 (3)
C6	0.050 (4)	0.051 (4)	0.046 (3)	−0.008 (3)	0.028 (3)	−0.005 (3)
C7	0.054 (4)	0.049 (4)	0.059 (4)	−0.006 (3)	0.027 (3)	−0.015 (3)
C8	0.064 (4)	0.047 (4)	0.062 (4)	−0.010 (3)	0.037 (3)	−0.012 (3)
C9	0.120 (7)	0.053 (4)	0.095 (5)	−0.001 (4)	0.057 (5)	−0.018 (4)
C10	0.085 (6)	0.073 (5)	0.100 (6)	0.021 (4)	0.044 (5)	0.004 (4)
N1	0.046 (3)	0.046 (3)	0.043 (3)	−0.002 (2)	0.015 (2)	−0.001 (2)
N2	0.068 (4)	0.049 (3)	0.072 (3)	0.002 (3)	0.039 (3)	−0.005 (3)
N3	0.055 (4)	0.067 (3)	0.059 (4)	−0.016 (3)	0.029 (3)	−0.018 (3)
N4	0.112 (9)	0.049 (6)	0.101 (7)	0.000	0.065 (7)	0.000
O1	0.053 (3)	0.047 (2)	0.047 (2)	0.0048 (19)	0.014 (2)	−0.0065 (19)
O2	0.058 (3)	0.067 (3)	0.048 (2)	−0.004 (2)	0.020 (2)	0.003 (2)
O3	0.055 (3)	0.065 (3)	0.045 (2)	−0.002 (2)	0.020 (2)	−0.002 (2)
O4	0.068 (4)	0.153 (5)	0.082 (3)	−0.023 (3)	0.049 (3)	−0.011 (3)
O5	0.074 (3)	0.049 (3)	0.074 (3)	−0.007 (2)	0.036 (3)	−0.009 (2)
O6	0.131 (7)	0.042 (4)	0.150 (7)	0.000	0.093 (6)	0.000
O7	0.147 (8)	0.135 (8)	0.138 (7)	0.024 (6)	0.039 (6)	−0.033 (6)
C11	0.137 (9)	0.136 (9)	0.137 (8)	0.007 (7)	0.072 (7)	−0.005 (7)
C12	0.132 (9)	0.117 (9)	0.127 (8)	0.005 (8)	0.057 (7)	0.001 (8)
O7B	0.146 (10)	0.157 (10)	0.164 (10)	0.004 (8)	0.086 (7)	0.008 (8)
C11B	0.135 (10)	0.140 (10)	0.144 (10)	0.002 (8)	0.071 (7)	−0.011 (8)
C12B	0.129 (11)	0.137 (11)	0.130 (10)	−0.011 (8)	0.064 (8)	0.006 (8)

Geometric parameters (Å, º) top

Gd1—O1	2.352 (4)	C9—H9A	0.9600
Gd1—O1ⁱ	2.352 (4)	C9—H9B	0.9600
Gd1—O5	2.492 (4)	C9—H9C	0.9600
Gd1—O5ⁱ	2.492 (4)	C10—N2	1.444 (7)
Gd1—O3	2.543 (4)	C10—H10A	0.9600
Gd1—O3ⁱ	2.543 (4)	C10—H10B	0.9600
Gd1—O2	2.547 (4)	C10—H10C	0.9600
Gd1—O2ⁱ	2.547 (4)	N3—O4	1.220 (6)
Gd1—N1	2.551 (4)	N3—O2	1.254 (6)
Gd1—N1ⁱ	2.551 (4)	N3—O3	1.267 (6)
Gd1—N3ⁱ	2.968 (6)	N4—O6	1.181 (9)
C1—N1	1.319 (7)	N4—O5ⁱ	1.281 (5)
C1—C2	1.374 (8)	N4—O5	1.281 (5)
C1—H1	0.9300	O7—C11	1.228 (9)
C2—C3	1.366 (9)	O7—H7A	0.8200
C2—H2	0.9300	C11—C12	1.469 (9)
C3—C4	1.374 (8)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C5	1.382 (7)	C12—H12A	0.9600
C4—H4	0.9300	C12—H12B	0.9600
C5—N1	1.344 (7)	C12—H12C	0.9600
C5—C6	1.487 (7)	O7B—C11B	1.242 (10)
C6—O1	1.268 (6)	O7B—H7B	0.8200
C6—C7	1.399 (7)	C11B—C12B	1.485 (10)
C7—C8	1.365 (8)	C11B—H11C	0.9700
C7—H7	0.9300	C11B—H11D	0.9700
C8—N2	1.311 (7)	C12B—H12D	0.9600
C8—H8	0.9300	C12B—H12E	0.9600
C9—N2	1.444 (7)	C12B—H12F	0.9600

O1—Gd1—O1ⁱ	71.45 (19)	C3—C4—C5	119.4 (6)
O1—Gd1—O5	137.36 (14)	C3—C4—H4	120.3
O1ⁱ—Gd1—O5	136.97 (13)	C5—C4—H4	120.3
O1—Gd1—O5ⁱ	136.97 (13)	N1—C5—C4	121.2 (5)
O1ⁱ—Gd1—O5ⁱ	137.36 (14)	N1—C5—C6	114.4 (4)
O5—Gd1—O5ⁱ	50.8 (2)	C4—C5—C6	124.4 (6)
O1—Gd1—O3	69.56 (13)	O1—C6—C7	122.4 (5)
O1ⁱ—Gd1—O3	116.68 (13)	O1—C6—C5	116.4 (5)
O5—Gd1—O3	68.60 (14)	C7—C6—C5	121.3 (5)
O5ⁱ—Gd1—O3	104.71 (14)	C8—C7—C6	120.2 (5)
O1—Gd1—O3ⁱ	116.68 (13)	C8—C7—H7	119.9
O1ⁱ—Gd1—O3ⁱ	69.56 (13)	C6—C7—H7	119.9
O5—Gd1—O3ⁱ	104.71 (14)	N2—C8—C7	128.4 (6)
O5ⁱ—Gd1—O3ⁱ	68.60 (14)	N2—C8—H8	115.8
O3—Gd1—O3ⁱ	172.95 (18)	C7—C8—H8	115.8
O1—Gd1—O2	74.31 (13)	N2—C9—H9A	109.5
O1ⁱ—Gd1—O2	145.72 (14)	N2—C9—H9B	109.5
O5—Gd1—O2	72.87 (13)	H9A—C9—H9B	109.5
O5ⁱ—Gd1—O2	71.10 (14)	N2—C9—H9C	109.5
O3—Gd1—O2	49.88 (13)	H9A—C9—H9C	109.5
O3ⁱ—Gd1—O2	127.03 (13)	H9B—C9—H9C	109.5
O1—Gd1—O2ⁱ	145.72 (14)	N2—C10—H10A	109.5
O1ⁱ—Gd1—O2ⁱ	74.31 (13)	N2—C10—H10B	109.5
O5—Gd1—O2ⁱ	71.10 (14)	H10A—C10—H10B	109.5
O5ⁱ—Gd1—O2ⁱ	72.87 (13)	N2—C10—H10C	109.5
O3—Gd1—O2ⁱ	127.03 (13)	H10A—C10—H10C	109.5
O3ⁱ—Gd1—O2ⁱ	49.88 (13)	H10B—C10—H10C	109.5
O2—Gd1—O2ⁱ	139.96 (19)	C1—N1—C5	118.3 (5)
O1—Gd1—N1	64.37 (14)	C1—N1—Gd1	124.5 (4)
O1ⁱ—Gd1—N1	90.57 (13)	C5—N1—Gd1	117.2 (3)
O5—Gd1—N1	128.14 (14)	C8—N2—C9	120.9 (6)
O5ⁱ—Gd1—N1	81.52 (14)	C8—N2—C10	121.7 (5)
O3—Gd1—N1	113.76 (14)	C9—N2—C10	117.4 (5)
O3ⁱ—Gd1—N1	68.23 (14)	O4—N3—O2	122.5 (6)
O2—Gd1—N1	73.16 (14)	O4—N3—O3	120.8 (6)
O2ⁱ—Gd1—N1	117.89 (15)	O2—N3—O3	116.7 (5)
O1—Gd1—N1ⁱ	90.57 (13)	O6—N4—O5ⁱ	123.4 (4)
O1ⁱ—Gd1—N1ⁱ	64.37 (14)	O6—N4—O5	123.4 (4)
O5—Gd1—N1ⁱ	81.52 (14)	O5ⁱ—N4—O5	113.2 (8)
O5ⁱ—Gd1—N1ⁱ	128.14 (14)	C6—O1—Gd1	125.4 (4)
O3—Gd1—N1ⁱ	68.23 (14)	N3—O2—Gd1	96.7 (3)
O3ⁱ—Gd1—N1ⁱ	113.76 (14)	N3—O3—Gd1	96.6 (3)
O2—Gd1—N1ⁱ	117.89 (15)	N4—O5—Gd1	98.0 (4)
O2ⁱ—Gd1—N1ⁱ	73.16 (14)	C11—O7—H7A	109.5
N1—Gd1—N1ⁱ	149.8 (2)	O7—C11—C12	132.5 (19)
O1—Gd1—N3ⁱ	134.19 (15)	O7—C11—H11A	104.1
O1ⁱ—Gd1—N3ⁱ	69.29 (14)	C12—C11—H11A	104.1
O5—Gd1—N3ⁱ	88.23 (15)	O7—C11—H11B	104.1
O5ⁱ—Gd1—N3ⁱ	69.43 (14)	C12—C11—H11B	104.1
O3—Gd1—N3ⁱ	151.60 (13)	H11A—C11—H11B	105.5
O3ⁱ—Gd1—N3ⁱ	25.09 (12)	C11B—O7B—H7B	109.5
O2—Gd1—N3ⁱ	139.72 (13)	O7B—C11B—C12B	122 (3)
O2ⁱ—Gd1—N3ⁱ	24.81 (12)	O7B—C11B—H11C	106.8
N1—Gd1—N3ⁱ	93.27 (16)	C12B—C11B—H11C	106.8
N1ⁱ—Gd1—N3ⁱ	93.04 (15)	O7B—C11B—H11D	106.8
N1—C1—C2	123.7 (6)	C12B—C11B—H11D	106.8
N1—C1—H1	118.2	H11C—C11B—H11D	106.7
C2—C1—H1	118.2	C11B—C12B—H12D	109.5
C3—C2—C1	118.2 (7)	C11B—C12B—H12E	109.5
C3—C2—H2	120.9	H12D—C12B—H12E	109.5
C1—C2—H2	120.9	C11B—C12B—H12F	109.5
C2—C3—C4	119.2 (6)	H12D—C12B—H12F	109.5
C2—C3—H3	120.4	H12E—C12B—H12F	109.5
C4—C3—H3	120.4

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O3	0.82	2.26	3.084 (12)	179
O7B—H7B···O3	0.82	2.19	3.00 (2)	168

Experimental details

Crystal data
Chemical formula	[Gd(NO₃)₃(C₁₀H₁₂N₂O)₂]·2C₂H₆O
M_r	787.85
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	21.322 (2), 10.9876 (11), 16.3844 (16)
β (°)	121.020 (2)
V (Å³)	3289.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.09
Crystal size (mm)	0.25 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.624, 0.705
No. of measured, independent and observed [I > 2σ(I)] reflections	8248, 3005, 2563
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.087, 1.02
No. of reflections	3005
No. of parameters	237
No. of restraints	130
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.28, −0.64

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O3	0.82	2.26	3.084 (12)	178.5
O7B—H7B···O3	0.82	2.19	3.00 (2)	168.2

Acknowledgements

The authors are indebted to the Qinglan project for financial support.

References

Bi, J.-H. (2009). Acta Cryst. E65, m633. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc.,Madison, Wisconsin, USA. Google Scholar
Hu, D.-H. (2010). Acta Cryst. E66, m709. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hu, T.-L. & Tian, J.-L. (2007). Acta Cryst. E63, m1092–m1093. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, G.-X., Li, J.-Q. & Kang, X.-Z. (2005). Acta Cryst. E61, m410–m411. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shen, J.-B., Liu, J.-L. & Zhao, G.-L. (2011). Acta Cryst. E67, m1357. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, P., Xu, X.-N., Zheng, L.-F. & Bao, Y.-Q. (2005). Acta Cryst. E61, m1462–m1463. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.