Poly[tris­(μ-2-amino­benzene-1,4-dicarboxyl­ato)tetra­kis­(N,N-dimethyl­formamide)­diyttrium(III)]

Kandiah, M.; Wragg, D.S.; Tilset, M.; Lillerud, K.P.

doi:10.1107/S1600536810050555

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Pages m44-m45

https://doi.org/10.1107/S1600536810050555

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Poly[tris(μ-2-aminobenzene-1,4-dicarboxylato)tetrakis(N,N-dimethylformamide)diyttrium(III)]

Mathivathani Kandiah,^a David Stephen Wragg,^a ^* Mats Tilset ^a and Karl Petter Lillerud ^a

^ainGAP Centre for Research Based Innovation, Department of Chemistry, University of Oslo, PO Box 1033 Blindern, 0315 Oslo, Norway
^*Correspondence e-mail: david.wragg@smn.uio.no

(Received 25 October 2010; accepted 2 December 2010; online 8 December 2010)

The asymmetric unit of the title coordination polymer, [Y₂(C₈H₅NO₄)₃(C₃H₇NO)₄]_n, contains one Y³⁺ ion, three half-molecules of the 2-aminobenzene-1,4-dicarboxylate (abz) dianion and two O-bonded N,N-dimethylformamide (DMF) molecules. Each abz half-molecule is completed by crystallographic inversion symmetry and its –NH₂ group is disordered in each case [relative occupancies within the asymmetric unit = 0.462 (18):0.538 (18), 0.93 (2):0.07 (2) and 0.828 (16):0.172 (16)]. The combination of disorder and crystal symmetry means that each of the four C—H atoms of the benzene ring of each of the dianions bears a statistical fraction of an –NH₂ group. The coordination geometry of the yttrium ion is a fairly regular YO₈ square antiprism arising from its coordination by two DMF molecules, four monodentate abz dianions and one O,O-bidentate abz dianion. The polymeric building unit is a dimeric paddle-wheel with two metal ions linked by four bridging abz dianions. Further bridging linkages connect the dimers into a three-dimensional framework containing voids in which highly disordered DMF molecules are presumed to reside.

Related literature

For a related structure containing a similar paddle-wheel motif, see: Braun et al. (2001 ).

Experimental

Crystal data

[Y₂(C₈H₅NO₄)₃(C₃H₇NO)₄]
M_r = 1007.59
Triclinic, $[P \overline 1]$
a = 10.525 (3) Å
b = 11.034 (3) Å
c = 12.855 (3) Å
α = 99.359 (3)°
β = 111.301 (3)°
γ = 101.265 (2)°
V = 1318.8 (6) Å³
Z = 1
Mo Kα radiation
μ = 2.25 mm⁻¹
T = 150 K
0.25 × 0.22 × 0.05 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.575, T_max = 0.894
7363 measured reflections
2345 independent reflections
2111 reflections with I > 2σ(I)
R_int = 0.027
θ_max = 19.7°

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.123
S = 1.11
2345 reflections
298 parameters
46 restraints
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Selected bond lengths (Å)

Y1—O3	2.252 (5)
Y1—O1	2.311 (4)
Y1—O5	2.322 (5)
Y1—O7	2.335 (4)
Y1—O8	2.358 (6)
Y1—O2	2.361 (6)
Y1—O6	2.409 (4)
Y1—O4	2.416 (4)

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Crystal Impact, 2004); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810050555/hb5707sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050555/hb5707Isup2.hkl

checkCIF report

Comment top

The title compound (I) is a metal-organic framework (MOF) which is a weak scatterer of X-rays and data were collected from a very small crystal. These were sufficient for refinement of the framework structure but not the disordered solvent. The asymmetric unit (Fig. 1) of the title compound consists of an yttrium atom coordinated by 8 oxygen atoms, 6 from 2-amino-1,4-benzenedicarboxylic acid (BDC-NH₂) moieties and 2 from coordinated dimethylformamide solvent. The inorganic cornerstone of the MOF is a paddle wheel type unit comprising two yttrium atoms linked by four bridging Y-BDC-NH₂ molecules (Fig. 2). Such units are well known in transition metal MOF structures (Braun, 2001). The paddle wheel carboxylates clearly show one long and one short C—O bond indicating single and double bond character. The single bonded, charge carrying oxygen of the carboxylate group has a shorter Y—O bond distance as would be expected. The axles of the paddle wheel are connected to one BDC-NH₂ and 2 DMF molecules at each end.

The BDC-NH₂ linkers at the ends of the paddle wheel are offset in a trans-type conformation and link the units in chains which, when the structure is viewed along the a-axis (Fig. 3), bisect the angle of the b and c axes. When we view the structure along the axis of the paddle wheel unit (Fig. 4) we see that the bridging BDC-NH₂ molecules also link to further units in chains parallel to the a and b-axes producing a three-dinemsional network. The amino groups are disordered over all four possible positions of the benzene rings of the BDC-NH₂ linker molecules, except in the case of the ring described by C10, C11 and C12, in which the NH₂ was found to be localized on C12. All of the disordered C—N bonds were restrained to have the same bond distance.

1 molecule of DMF solvent per ASU was located in the void space of the MOF using difference Fourier maps but the resulting model gave a poor refinement. The program Squeeze from the PLATON suite (Spek, 2009 ) was used to remove residual electron density from the solvent accessible voids giving a chemically sensible structure and acceptable refinemnt statistics. The squeeze calculation suggests voids containing 90 electrons or 2.25 DMF molecules in each unit cell. This is in reasonable agreement with the disordered solvent observed in the difference Fourier map.

Related literature top

For a related structure containing a similar paddle-wheel motif, see: Braun et al. (2001).

Experimental top

The Title complex Y-BDC-NH₂ was prepared by dissolving Y(NO₃)₃.6H₂O (0.383 g, 1 mmol) and 2-amino 1,4-benzenedicarboxylic acid (H₂N—H₂BDC) (0.181 g, 1 mmol) in N,N`-dimethylformamide (DMF) (20 ml) at room temperature in a test tube. The mixture thus obtained was placed in a pre-heated oven at 80°C for 24 hrs. Colourless plates of (I) were selected directly from the mother liquor as prepared and mounted on cryoloops.

Structure description top

For a related structure containing a similar paddle-wheel motif, see: Braun et al. (2001).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Crystal Impact, 2004); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP view of the asymmetric unit of (I) with thermal ellipsoids at 50% probability. Hydrogen atoms are omitted for clarity.
	Fig. 2. The paddle wheel unit of the MOF structure of (I).
	Fig. 3. Packing diagram of (I) viewed along the a-axis.
	Fig. 4. Packing diagram of (I) viewed along the axis of the paddle wheel unit.

Poly[tris(µ-2-aminobenzene-1,4-dicarboxylato)tetrakis(N,N- dimethylformamide)diyttrium(III)] top

Crystal data top

[Y₂(C₈H₅NO₄)₃(C₃H₇NO)₄]	Z = 1
M_r = 1007.59	F(000) = 505
Triclinic, P1	D_x = 1.257 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.525 (3) Å	Cell parameters from 3097 reflections
b = 11.034 (3) Å	θ = 2.4–28.2°
c = 12.855 (3) Å	µ = 2.25 mm⁻¹
α = 99.359 (3)°	T = 150 K
β = 111.301 (3)°	Plate, colourless
γ = 101.265 (2)°	0.25 × 0.22 × 0.05 mm
V = 1318.8 (6) Å³

Data collection top

Bruker APEX CCD diffractometer	2345 independent reflections
Radiation source: sealed tube	2111 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
phi and ω scans	θ_max = 19.7°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
T_min = 0.575, T_max = 0.894	k = −10→10
7363 measured reflections	l = −12→12

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0707P)² + 2.6497P] where P = (F_o² + 2F_c²)/3
2345 reflections	(Δ/σ)_max = 0.002
298 parameters	Δρ_max = 0.71 e Å⁻³
46 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Y₂(C₈H₅NO₄)₃(C₃H₇NO)₄]	γ = 101.265 (2)°
M_r = 1007.59	V = 1318.8 (6) Å³
Triclinic, P1	Z = 1
a = 10.525 (3) Å	Mo Kα radiation
b = 11.034 (3) Å	µ = 2.25 mm⁻¹
c = 12.855 (3) Å	T = 150 K
α = 99.359 (3)°	0.25 × 0.22 × 0.05 mm
β = 111.301 (3)°

Data collection top

Bruker APEX CCD diffractometer	2345 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2111 reflections with I > 2σ(I)
T_min = 0.575, T_max = 0.894	R_int = 0.027
7363 measured reflections	θ_max = 19.7°

Refinement top

R[F² > 2σ(F²)] = 0.043	46 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.11	Δρ_max = 0.71 e Å⁻³
2345 reflections	Δρ_min = −0.41 e Å⁻³
298 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)
Y1	0.60986 (6)	0.54621 (5)	0.67714 (5)	0.0325 (3)
O1	0.5003 (5)	0.3303 (4)	0.5952 (4)	0.0458 (12)
O2	0.7957 (6)	0.4535 (6)	0.7557 (5)	0.0777 (17)
O3	0.6664 (4)	0.5086 (4)	0.5242 (4)	0.0489 (12)
O4	0.8360 (5)	0.7070 (5)	0.7643 (5)	0.0628 (15)
O5	0.5711 (5)	0.7170 (4)	0.5974 (4)	0.0429 (11)
O6	0.6807 (5)	0.7297 (4)	0.8365 (4)	0.0512 (13)
O7	0.3832 (5)	0.5508 (4)	0.6623 (5)	0.0497 (12)
O8	0.5809 (6)	0.4663 (5)	0.8289 (5)	0.0664 (16)
C1	0.5309 (7)	0.7437 (6)	0.5023 (7)	0.0425 (18)
C2	0.5175 (7)	0.8788 (6)	0.5026 (6)	0.0450 (18)
C3	0.5023 (8)	0.9231 (7)	0.4060 (6)	0.054 (2)
H3	0.5042	0.8702	0.3407	0.064*	0.70
C4	0.5155 (8)	0.9569 (6)	0.5979 (6)	0.0504 (19)
H4	0.5264	0.9278	0.6654	0.060*	0.80
C5	0.8016 (8)	0.7688 (7)	0.8353 (6)	0.0481 (19)
C6	0.9007 (8)	0.8887 (6)	0.9175 (6)	0.0507 (19)
C7	1.0407 (9)	0.9239 (8)	0.9287 (7)	0.075 (3)
H7	1.0708	0.8716	0.8812	0.090*	0.75
C8	0.8620 (8)	0.9631 (8)	0.9897 (7)	0.071 (2)
H8	0.7680	0.9386	0.9851	0.085*	0.75
C9	0.7040 (8)	0.4813 (6)	0.4410 (8)	0.0452 (18)
C10	0.8564 (7)	0.4903 (6)	0.4706 (6)	0.0426 (18)
C11	0.9565 (8)	0.5420 (7)	0.5837 (6)	0.052 (2)
H11	0.9267	0.5707	0.6424	0.062*
C12	0.9036 (7)	0.4478 (7)	0.3883 (6)	0.052 (2)
H12	0.8372	0.4107	0.3106	0.062*	0.50
C13	0.8097 (13)	0.3559 (13)	0.7616 (12)	0.146 (6)
H13	0.7299	0.2897	0.7062	0.175*
C14	0.8993 (18)	0.1782 (16)	0.8060 (19)	0.234 (10)
H14A	0.9844	0.1670	0.8638	0.351*	0.50
H14B	0.8939	0.1452	0.7286	0.351*	0.50
H14C	0.8149	0.1314	0.8132	0.351*	0.50
H14D	0.8111	0.1288	0.7399	0.351*	0.50
H14E	0.9016	0.1505	0.8752	0.351*	0.50
H14F	0.9806	0.1643	0.7905	0.351*	0.50
C15	1.042 (3)	0.393 (2)	0.903 (2)	0.39 (2)
H15A	1.1003	0.3414	0.9425	0.590*	0.50
H15B	1.0311	0.4561	0.9592	0.590*	0.50
H15C	1.0882	0.4364	0.8598	0.590*	0.50
H15D	1.0461	0.4812	0.8985	0.590*	0.50
H15E	1.1153	0.3666	0.8818	0.590*	0.50
H15F	1.0582	0.3862	0.9812	0.590*	0.50
C16	0.4818 (15)	0.3945 (12)	0.8288 (9)	0.103 (3)
H16	0.3967	0.3770	0.7615	0.124*
C17	0.595 (2)	0.3593 (16)	1.0148 (12)	0.195 (8)
H17A	0.5719	0.3094	1.0652	0.292*	0.50
H17B	0.6263	0.4506	1.0539	0.292*	0.50
H17C	0.6713	0.3351	0.9974	0.292*	0.50
H17D	0.6744	0.4206	1.0125	0.292*	0.50
H17E	0.6200	0.2794	1.0237	0.292*	0.50
H17F	0.5750	0.3949	1.0802	0.292*	0.50
C18	0.354 (2)	0.2376 (18)	0.9021 (16)	0.244 (11)
H18A	0.3789	0.2133	0.9755	0.366*	0.50
H18B	0.3319	0.1625	0.8395	0.366*	0.50
H18C	0.2707	0.2706	0.8872	0.366*	0.50
H18D	0.2754	0.2176	0.8260	0.366*	0.50
H18E	0.3225	0.2684	0.9620	0.366*	0.50
H18F	0.3836	0.1604	0.9143	0.366*	0.50
N1	0.7183 (19)	0.959 (3)	0.972 (4)	0.137 (12)	0.228 (9)
H1A	0.6474	0.9049	0.9113	0.165*	0.228 (9)
H1B	0.7011	1.0097	1.0227	0.165*	0.228 (9)
N1A	1.101 (3)	0.857 (3)	0.862 (3)	0.137 (12)	0.272 (9)
H1A1	1.0485	0.7865	0.8076	0.165*	0.272 (9)
H1A2	1.1912	0.8867	0.8752	0.165*	0.272 (9)
N2	0.8114 (13)	0.3877 (17)	0.2719 (10)	0.111 (7)	0.50
H2A	0.8456	0.3596	0.2226	0.134*	0.50
H2B	0.7196	0.3783	0.2487	0.134*	0.50
N3	0.5205 (18)	0.9180 (14)	0.7009 (11)	0.079 (6)	0.424 (9)
H3A	0.5124	0.9699	0.7563	0.094*	0.424 (9)
H3B	0.5317	0.8424	0.7082	0.094*	0.424 (9)
N3A	0.499 (10)	0.857 (7)	0.299 (4)	0.079 (6)	0.076 (9)
H3A1	0.5078	0.7784	0.2905	0.094*	0.076 (9)
H3A2	0.4890	0.8945	0.2426	0.094*	0.076 (9)
N4	0.4703 (14)	0.3341 (10)	0.9082 (10)	0.143 (4)
N5	0.9061 (13)	0.3113 (12)	0.8242 (12)	0.157 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Y1	0.0242 (4)	0.0219 (4)	0.0408 (5)	0.0023 (3)	0.0060 (3)	0.0025 (3)
O1	0.057 (3)	0.025 (3)	0.043 (3)	0.004 (2)	0.013 (2)	0.002 (2)
O2	0.064 (4)	0.065 (4)	0.100 (5)	0.033 (3)	0.019 (3)	0.027 (4)
O3	0.036 (3)	0.035 (3)	0.073 (4)	0.003 (2)	0.029 (3)	−0.002 (2)
O4	0.038 (3)	0.047 (3)	0.072 (4)	−0.003 (2)	0.010 (3)	−0.020 (3)
O5	0.049 (3)	0.026 (3)	0.040 (3)	0.004 (2)	0.007 (2)	0.005 (2)
O6	0.053 (4)	0.035 (3)	0.045 (3)	−0.007 (2)	0.012 (3)	−0.001 (2)
O7	0.029 (3)	0.050 (3)	0.058 (4)	0.006 (2)	0.012 (3)	0.003 (3)
O8	0.073 (4)	0.043 (3)	0.069 (4)	−0.006 (3)	0.026 (3)	0.013 (3)
C1	0.036 (4)	0.023 (4)	0.054 (6)	−0.003 (3)	0.011 (4)	0.005 (4)
C2	0.048 (4)	0.025 (4)	0.042 (5)	−0.002 (3)	0.005 (4)	0.001 (4)
C3	0.075 (5)	0.029 (5)	0.042 (5)	0.005 (4)	0.014 (4)	0.005 (4)
C4	0.074 (5)	0.026 (4)	0.037 (5)	0.005 (4)	0.010 (4)	0.011 (4)
C5	0.034 (5)	0.038 (5)	0.043 (5)	−0.007 (4)	−0.006 (4)	0.006 (4)
C6	0.051 (6)	0.033 (4)	0.050 (5)	−0.004 (4)	0.014 (4)	−0.004 (4)
C7	0.059 (6)	0.061 (6)	0.078 (6)	−0.003 (5)	0.022 (5)	−0.014 (5)
C8	0.050 (5)	0.063 (6)	0.071 (6)	−0.008 (5)	0.012 (5)	0.003 (5)
C9	0.038 (5)	0.029 (4)	0.068 (6)	0.008 (3)	0.025 (5)	0.003 (4)
C10	0.028 (4)	0.038 (4)	0.055 (5)	0.003 (3)	0.018 (5)	−0.001 (4)
C11	0.038 (5)	0.058 (5)	0.052 (6)	0.006 (4)	0.025 (4)	−0.011 (4)
C12	0.025 (5)	0.064 (5)	0.047 (5)	0.004 (4)	0.008 (4)	−0.009 (4)
C13	0.087 (9)	0.096 (10)	0.190 (14)	0.024 (8)	−0.015 (9)	0.038 (10)
C14	0.165 (15)	0.162 (15)	0.39 (3)	0.082 (13)	0.069 (17)	0.181 (18)
C15	0.32 (3)	0.23 (2)	0.36 (3)	0.14 (2)	−0.13 (3)	−0.08 (2)
C16	0.146 (11)	0.102 (9)	0.067 (7)	0.034 (8)	0.045 (7)	0.029 (7)
C17	0.26 (2)	0.192 (16)	0.100 (11)	0.050 (15)	0.037 (13)	0.061 (11)
C18	0.23 (2)	0.26 (2)	0.236 (19)	−0.063 (16)	0.147 (17)	0.100 (17)
N1	0.062 (15)	0.114 (19)	0.18 (3)	−0.036 (13)	0.061 (16)	−0.079 (18)
N1A	0.062 (15)	0.114 (19)	0.18 (3)	−0.036 (13)	0.061 (16)	−0.079 (18)
N2	0.031 (8)	0.196 (18)	0.066 (10)	0.025 (9)	0.006 (8)	−0.035 (11)
N3	0.116 (14)	0.044 (9)	0.069 (11)	0.041 (9)	0.020 (10)	0.019 (8)
N3A	0.116 (14)	0.044 (9)	0.069 (11)	0.041 (9)	0.020 (10)	0.019 (8)
N4	0.192 (12)	0.124 (8)	0.099 (8)	0.000 (8)	0.063 (8)	0.040 (7)
N5	0.121 (9)	0.149 (11)	0.199 (12)	0.089 (8)	0.016 (8)	0.096 (10)

Geometric parameters (Å, º) top

Y1—O3	2.252 (5)	C12—N2	1.411 (11)
Y1—O1	2.311 (4)	C12—H12	0.9500
Y1—O5	2.322 (5)	C13—N5	1.284 (14)
Y1—O7	2.335 (4)	C13—H13	0.9500
Y1—O8	2.358 (6)	C14—N5	1.433 (18)
Y1—O2	2.361 (6)	C14—H14A	0.9800
Y1—O6	2.409 (4)	C14—H14B	0.9800
Y1—O4	2.416 (4)	C14—H14C	0.9800
Y1—C5	2.775 (7)	C14—H14D	0.9800
Y1—C9ⁱ	3.021 (7)	C14—H14E	0.9800
O1—C1ⁱ	1.268 (8)	C14—H14F	0.9800
O2—C13	1.126 (13)	C15—N5	1.42 (2)
O3—C9	1.281 (8)	C15—H15A	0.9800
O4—C5	1.251 (9)	C15—H15B	0.9800
O5—C1	1.245 (8)	C15—H15C	0.9800
O6—C5	1.268 (8)	C15—H15D	0.9800
O7—C9ⁱ	1.252 (8)	C15—H15E	0.9800
O8—C16	1.179 (13)	C15—H15F	0.9800
C1—O1ⁱ	1.268 (8)	C16—N4	1.335 (13)
C1—C2	1.524 (9)	C16—H16	0.9500
C2—C3	1.375 (9)	C17—N4	1.451 (17)
C2—C4	1.388 (9)	C17—H17A	0.9800
C3—C4ⁱⁱ	1.379 (9)	C17—H17B	0.9800
C3—N3A	1.432 (13)	C17—H17C	0.9800
C3—H3	0.9500	C17—H17D	0.9800
C4—C3ⁱⁱ	1.379 (9)	C17—H17E	0.9800
C4—N3	1.443 (11)	C17—H17F	0.9800
C4—H4	0.9500	C18—N4	1.427 (16)
C5—C6	1.470 (10)	C18—H18A	0.9800
C6—C8	1.364 (11)	C18—H18B	0.9800
C6—C7	1.395 (11)	C18—H18C	0.9800
C7—C8ⁱⁱⁱ	1.414 (11)	C18—H18D	0.9800
C7—N1A	1.436 (12)	C18—H18E	0.9800
C7—H7	0.9500	C18—H18F	0.9800
C8—C7ⁱⁱⁱ	1.414 (11)	N1—H1A	0.8800
C8—N1	1.436 (13)	N1—H1B	0.8800
C8—H8	0.9500	N1A—H1A1	0.8800
C9—O7ⁱ	1.252 (8)	N1A—H1A2	0.8800
C9—C10	1.487 (10)	N2—H2A	0.8800
C9—Y1ⁱ	3.021 (7)	N2—H2B	0.8800
C10—C12	1.377 (9)	N3—H3A	0.8800
C10—C11	1.390 (9)	N3—H3B	0.8800
C11—C12^iv	1.359 (9)	N3A—H3A1	0.8800
C11—H11	0.9500	N3A—H3A2	0.8800
C12—C11^iv	1.359 (9)

O3—Y1—O1	77.48 (15)	H14C—C14—H14D	56.3
O3—Y1—O5	76.70 (16)	N5—C14—H14E	109.5
O1—Y1—O5	128.81 (15)	H14A—C14—H14E	56.3
O3—Y1—O7	123.79 (17)	H14B—C14—H14E	141.1
O1—Y1—O7	82.81 (16)	H14C—C14—H14E	56.3
O5—Y1—O7	76.18 (16)	H14D—C14—H14E	109.5
O3—Y1—O8	145.22 (18)	N5—C14—H14F	109.5
O1—Y1—O8	75.52 (17)	H14A—C14—H14F	56.3
O5—Y1—O8	137.92 (18)	H14B—C14—H14F	56.3
O7—Y1—O8	73.86 (19)	H14C—C14—H14F	141.1
O3—Y1—O2	81.36 (19)	H14D—C14—H14F	109.5
O1—Y1—O2	77.45 (19)	H14E—C14—H14F	109.5
O5—Y1—O2	139.42 (19)	N5—C15—H15A	109.5
O7—Y1—O2	143.6 (2)	N5—C15—H15B	109.5
O8—Y1—O2	71.7 (2)	H15A—C15—H15B	109.5
O3—Y1—O6	133.34 (16)	N5—C15—H15C	109.5
O1—Y1—O6	148.63 (17)	H15A—C15—H15C	109.5
O5—Y1—O6	73.50 (15)	H15B—C15—H15C	109.5
O7—Y1—O6	82.41 (18)	N5—C15—H15D	109.5
O8—Y1—O6	73.84 (17)	H15A—C15—H15D	141.1
O2—Y1—O6	99.00 (19)	H15B—C15—H15D	56.3
O3—Y1—O4	84.05 (18)	H15C—C15—H15D	56.3
O1—Y1—O4	144.15 (17)	N5—C15—H15E	109.5
O5—Y1—O4	74.57 (17)	H15A—C15—H15E	56.3
O7—Y1—O4	132.62 (17)	H15B—C15—H15E	141.1
O8—Y1—O4	105.82 (19)	H15C—C15—H15E	56.3
O2—Y1—O4	69.5 (2)	H15D—C15—H15E	109.5
O6—Y1—O4	53.92 (17)	N5—C15—H15F	109.5
C1ⁱ—O1—Y1	133.9 (4)	H15A—C15—H15F	56.3
C13—O2—Y1	138.5 (8)	H15B—C15—H15F	56.3
C9—O3—Y1	175.4 (5)	H15C—C15—H15F	141.1
C5—O4—Y1	92.8 (4)	H15D—C15—H15F	109.5
C1—O5—Y1	141.0 (4)	H15E—C15—H15F	109.5
C5—O6—Y1	92.7 (4)	O8—C16—N4	130.2 (12)
C9ⁱ—O7—Y1	111.1 (4)	O8—C16—H16	114.9
C16—O8—Y1	129.7 (7)	N4—C16—H16	114.9
O5—C1—O1ⁱ	126.5 (6)	N4—C17—H17A	109.5
O5—C1—C2	117.0 (7)	N4—C17—H17B	109.5
O1ⁱ—C1—C2	116.5 (7)	H17A—C17—H17B	109.5
C3—C2—C4	119.1 (6)	N4—C17—H17C	109.5
C3—C2—C1	119.9 (7)	H17A—C17—H17C	109.5
C4—C2—C1	120.9 (7)	H17B—C17—H17C	109.5
C2—C3—C4ⁱⁱ	121.2 (7)	N4—C17—H17D	109.5
C2—C3—N3A	127 (3)	H17A—C17—H17D	141.1
C4ⁱⁱ—C3—N3A	111 (3)	H17B—C17—H17D	56.3
C2—C3—H3	119.4	H17C—C17—H17D	56.3
C4ⁱⁱ—C3—H3	119.4	N4—C17—H17E	109.5
C3ⁱⁱ—C4—C2	119.7 (6)	H17A—C17—H17E	56.3
C3ⁱⁱ—C4—N3	115.9 (9)	H17B—C17—H17E	141.1
C2—C4—N3	124.3 (8)	H17C—C17—H17E	56.3
C3ⁱⁱ—C4—H4	120.2	H17D—C17—H17E	109.5
C2—C4—H4	120.2	N4—C17—H17F	109.5
O4—C5—O6	120.5 (6)	H17A—C17—H17F	56.3
O4—C5—C6	120.2 (8)	H17B—C17—H17F	56.3
O6—C5—C6	119.3 (8)	H17C—C17—H17F	141.1
O4—C5—Y1	60.4 (3)	H17D—C17—H17F	109.5
O6—C5—Y1	60.1 (3)	H17E—C17—H17F	109.5
C6—C5—Y1	178.5 (5)	N4—C18—H18A	109.5
C8—C6—C7	118.5 (7)	N4—C18—H18B	109.5
C8—C6—C5	121.4 (8)	H18A—C18—H18B	109.5
C7—C6—C5	120.0 (8)	N4—C18—H18C	109.5
C6—C7—C8ⁱⁱⁱ	120.4 (8)	H18A—C18—H18C	109.5
C6—C7—N1A	126.5 (13)	H18B—C18—H18C	109.5
C8ⁱⁱⁱ—C7—N1A	113.1 (13)	N4—C18—H18D	109.5
C6—C7—H7	119.8	H18A—C18—H18D	141.1
C8ⁱⁱⁱ—C7—H7	119.8	H18B—C18—H18D	56.3
C6—C8—C7ⁱⁱⁱ	121.1 (8)	H18C—C18—H18D	56.3
C6—C8—N1	124.9 (15)	N4—C18—H18E	109.5
C7ⁱⁱⁱ—C8—N1	111.8 (15)	H18A—C18—H18E	56.3
C6—C8—H8	119.4	H18B—C18—H18E	141.1
C7ⁱⁱⁱ—C8—H8	119.4	H18C—C18—H18E	56.3
O7ⁱ—C9—O3	121.8 (6)	H18D—C18—H18E	109.5
O7ⁱ—C9—C10	120.3 (7)	N4—C18—H18F	109.5
O3—C9—C10	117.9 (7)	H18A—C18—H18F	56.3
O7ⁱ—C9—Y1ⁱ	46.1 (3)	H18B—C18—H18F	56.3
O3—C9—Y1ⁱ	75.7 (4)	H18C—C18—H18F	141.1
C10—C9—Y1ⁱ	166.3 (6)	H18D—C18—H18F	109.5
C12—C10—C11	117.7 (6)	H18E—C18—H18F	109.5
C12—C10—C9	121.8 (7)	C8—N1—H1A	120.0
C11—C10—C9	120.5 (7)	C8—N1—H1B	120.0
C12^iv—C11—C10	121.1 (6)	H1A—N1—H1B	120.0
C12^iv—C11—H11	119.5	C7—N1A—H1A1	120.0
C10—C11—H11	119.5	C7—N1A—H1A2	120.0
C11^iv—C12—C10	121.2 (6)	H1A1—N1A—H1A2	120.0
C11^iv—C12—N2	115.9 (8)	C12—N2—H2A	120.0
C10—C12—N2	122.9 (8)	C12—N2—H2B	120.0
C11^iv—C12—H12	119.4	H2A—N2—H2B	120.0
C10—C12—H12	119.4	C4—N3—H3A	120.0
O2—C13—N5	136.2 (13)	C4—N3—H3B	120.0
O2—C13—H13	111.9	H3A—N3—H3B	120.0
N5—C13—H13	111.9	C3—N3A—H3A1	120.0
N5—C14—H14A	109.5	C3—N3A—H3A2	120.0
N5—C14—H14B	109.5	H3A1—N3A—H3A2	120.0
H14A—C14—H14B	109.5	C16—N4—C18	129.6 (14)
N5—C14—H14C	109.5	C16—N4—C17	118.0 (12)
H14A—C14—H14C	109.5	C18—N4—C17	112.3 (12)
H14B—C14—H14C	109.5	C13—N5—C15	121.5 (15)
N5—C14—H14D	109.5	C13—N5—C14	123.9 (14)
H14A—C14—H14D	141.1	C15—N5—C14	113.4 (13)
H14B—C14—H14D	56.3

O3—Y1—O1—C1ⁱ	−15.5 (6)	Y1—O5—C1—O1ⁱ	−3.7 (11)
O5—Y1—O1—C1ⁱ	45.7 (6)	Y1—O5—C1—C2	176.1 (4)
O7—Y1—O1—C1ⁱ	111.5 (6)	O5—C1—C2—C3	166.7 (6)
O8—Y1—O1—C1ⁱ	−173.4 (6)	O1ⁱ—C1—C2—C3	−13.4 (9)
O2—Y1—O1—C1ⁱ	−99.3 (6)	O5—C1—C2—C4	−15.5 (9)
O6—Y1—O1—C1ⁱ	173.9 (5)	O1ⁱ—C1—C2—C4	164.4 (6)
O4—Y1—O1—C1ⁱ	−76.3 (6)	C4—C2—C3—C4ⁱⁱ	−0.4 (12)
C5—Y1—O1—C1ⁱ	−125.7 (8)	C1—C2—C3—C4ⁱⁱ	177.5 (6)
C9ⁱ—Y1—O1—C1ⁱ	90.3 (6)	C4—C2—C3—N3A	−179 (5)
O3—Y1—O2—C13	−90.5 (14)	C1—C2—C3—N3A	−1 (5)
O1—Y1—O2—C13	−11.4 (14)	C3—C2—C4—C3ⁱⁱ	0.3 (12)
O5—Y1—O2—C13	−148.1 (14)	C1—C2—C4—C3ⁱⁱ	−177.5 (6)
O7—Y1—O2—C13	47.4 (15)	C3—C2—C4—N3	175.5 (10)
O8—Y1—O2—C13	67.2 (14)	C1—C2—C4—N3	−2.3 (13)
O6—Y1—O2—C13	136.8 (14)	Y1—O4—C5—O6	0.9 (7)
O4—Y1—O2—C13	−177.3 (15)	Y1—O4—C5—C6	−178.3 (6)
C5—Y1—O2—C13	159.4 (14)	Y1—O6—C5—O4	−0.9 (7)
C9ⁱ—Y1—O2—C13	6.9 (16)	Y1—O6—C5—C6	178.3 (6)
O3—Y1—O4—C5	157.9 (4)	O3—Y1—C5—O4	−23.3 (5)
O1—Y1—O4—C5	−143.2 (4)	O1—Y1—C5—O4	81.3 (8)
O5—Y1—O4—C5	80.1 (4)	O5—Y1—C5—O4	−91.7 (4)
O7—Y1—O4—C5	26.3 (5)	O7—Y1—C5—O4	−160.0 (4)
O8—Y1—O4—C5	−56.1 (4)	O8—Y1—C5—O4	127.0 (4)
O2—Y1—O4—C5	−119.1 (5)	O2—Y1—C5—O4	55.4 (4)
O6—Y1—O4—C5	−0.5 (4)	O6—Y1—C5—O4	179.1 (7)
C9ⁱ—Y1—O4—C5	57.5 (6)	C9ⁱ—Y1—C5—O4	−140.8 (4)
O3—Y1—O5—C1	33.5 (7)	O3—Y1—C5—O6	157.6 (4)
O1—Y1—O5—C1	−28.1 (7)	O1—Y1—C5—O6	−97.8 (7)
O7—Y1—O5—C1	−96.8 (7)	O5—Y1—C5—O6	89.2 (4)
O8—Y1—O5—C1	−142.4 (6)	O7—Y1—C5—O6	20.9 (4)
O2—Y1—O5—C1	92.6 (7)	O8—Y1—C5—O6	−52.1 (4)
O6—Y1—O5—C1	177.2 (7)	O2—Y1—C5—O6	−123.7 (4)
O4—Y1—O5—C1	120.9 (7)	O4—Y1—C5—O6	−179.1 (7)
C5—Y1—O5—C1	148.7 (7)	C9ⁱ—Y1—C5—O6	40.1 (5)
C9ⁱ—Y1—O5—C1	−74.1 (7)	C8—C6—C7—C8ⁱⁱⁱ	−2.4 (14)
O3—Y1—O6—C5	−29.7 (5)	C5—C6—C7—C8ⁱⁱⁱ	−177.8 (7)
O1—Y1—O6—C5	137.5 (4)	C8—C6—C7—N1A	179 (2)
O5—Y1—O6—C5	−82.2 (4)	C5—C6—C7—N1A	4 (3)
O7—Y1—O6—C5	−159.9 (4)	C7—C6—C8—C7ⁱⁱⁱ	2.4 (14)
O8—Y1—O6—C5	124.7 (4)	C5—C6—C8—C7ⁱⁱⁱ	177.8 (7)
O2—Y1—O6—C5	56.9 (4)	C7—C6—C8—N1	164 (2)
O4—Y1—O6—C5	0.5 (4)	C5—C6—C8—N1	−20 (3)
C9ⁱ—Y1—O6—C5	−146.5 (4)	O7ⁱ—C9—C10—C12	−8.9 (10)
O3—Y1—O7—C9ⁱ	5.9 (5)	O3—C9—C10—C12	171.8 (6)
O1—Y1—O7—C9ⁱ	−63.8 (4)	Y1ⁱ—C9—C10—C12	−16 (2)
O5—Y1—O7—C9ⁱ	69.1 (4)	O7ⁱ—C9—C10—C11	171.4 (6)
O8—Y1—O7—C9ⁱ	−140.8 (5)	O3—C9—C10—C11	−8.0 (9)
O2—Y1—O7—C9ⁱ	−121.2 (5)	Y1ⁱ—C9—C10—C11	163.8 (15)
O6—Y1—O7—C9ⁱ	143.9 (4)	C12—C10—C11—C12^iv	1.1 (12)
O4—Y1—O7—C9ⁱ	122.4 (4)	C9—C10—C11—C12^iv	−179.2 (7)
C5—Y1—O7—C9ⁱ	134.4 (4)	C11—C10—C12—C11^iv	−1.1 (12)
O3—Y1—O8—C16	−84.4 (9)	C9—C10—C12—C11^iv	179.2 (7)
O1—Y1—O8—C16	−44.2 (8)	C11—C10—C12—N2	176.7 (11)
O5—Y1—O8—C16	88.6 (9)	C9—C10—C12—N2	−3.1 (14)
O7—Y1—O8—C16	42.4 (9)	Y1—O2—C13—N5	−162.0 (14)
O2—Y1—O8—C16	−125.5 (9)	Y1—O8—C16—N4	168.8 (9)
O6—Y1—O8—C16	129.0 (9)	O8—C16—N4—C18	−172.8 (16)
O4—Y1—O8—C16	173.0 (8)	O8—C16—N4—C17	2 (2)
C5—Y1—O8—C16	151.0 (9)	O2—C13—N5—C15	−8 (3)
C9ⁱ—Y1—O8—C16	28.2 (9)	O2—C13—N5—C14	−175.0 (19)

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

Experimental details

Crystal data
Chemical formula	[Y₂(C₈H₅NO₄)₃(C₃H₇NO)₄]
M_r	1007.59
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	10.525 (3), 11.034 (3), 12.855 (3)
α, β, γ (°)	99.359 (3), 111.301 (3), 101.265 (2)
V (Å³)	1318.8 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	2.25
Crystal size (mm)	0.25 × 0.22 × 0.05

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.575, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	7363, 2345, 2111
R_int	0.027
θ_max (°)	19.7
(sin θ/λ)_max (Å⁻¹)	0.474

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.123, 1.11
No. of reflections	2345
No. of parameters	298
No. of restraints	46
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.41

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Crystal Impact, 2004), PLATON (Spek, 2009).

Selected bond lengths (Å) top

Y1—O3	2.252 (5)	Y1—O8	2.358 (6)
Y1—O1	2.311 (4)	Y1—O2	2.361 (6)
Y1—O5	2.322 (5)	Y1—O6	2.409 (4)
Y1—O7	2.335 (4)	Y1—O4	2.416 (4)

Acknowledgements

The authors thank the Research Council of Norway and inGAP for funding.

References

Braun, M. E., Steffek, C. D., Kim, J., Rasmussen, P. G. & Yaghi, O. M. (2001). Chem. Commun. pp. 2532–2533. Web of Science CSD CrossRef Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Crystal Impact (2004). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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