Dihydro­nium bis­(2,6-diamino­pyridinium) tris­(pyridine-2,6-dicarboxyl­ato-κ3O,O′,N)dysprosate(III) dihydrate

Rafizadeh, M.; Amani, V.

doi:10.1107/S160053680504064X

Dihydronium bis(2,6-diaminopyridinium) tris(pyridine-2,6-dicarboxylato-κ³O,O′,N)dysprosate(III) dihydrate

The reaction of dysprosium(III) chloride with [H₂pyda]²⁺[pydc]²⁻ (pyda is 2,6-diaminopyridine and H₂pydc is 2,6-pyridinedicarboxylic acid) in an aqueous solution leads to the formation of the title Dy^III complex, (H₅O₂)(C₅H₈N₃)₂[Dy(C₇H₃NO₄)₃]·2H₂O. The Dy ion lies on a twofold rotation axis and is nine-coordinated with a distorted tricapped trigonal–prismatic geometry. The dihydronium cation (H₅O₂)⁺ is located on a twofold axis, the longer O—H bond distance being 1.225 Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680504064X/xu6059sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680504064X/xu6059Isup2.hkl Contains datablock I

CCDC reference: 296730

checkCIF report

Key indicators

Single-crystal X-ray study
T = 145 K
Mean (C-C) = 0.006 Å
R factor = 0.041
wR factor = 0.101
Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT355_ALERT_3_A Long    O-H Bond (0.82A)   O1W    -   H1WC   ...       1.22 Ang.

Author Response: the H1WC is a bridge proton between two oxygen atom.


Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1WC   ..  H1WA    ..       1.80 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1WC   ..  H1WB    ..       1.74 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1WA   ..  H2WA    ..       2.00 Ang.
PLAT420_ALERT_2_B D-H Without Acceptor       O1W    -   H1WC   ...          ?

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.406     0.653
            Tmin(prime) and Tmax expected:      0.519     0.653
            RR(prime) =      0.782
            Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.76
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.41
PLAT128_ALERT_4_C Non-standard setting of Space group P2/c    ....    P2/n
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........        O1W
PLAT420_ALERT_2_C D-H Without Acceptor       N5     -   H5NA   ...          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          9
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C5 H8 N3
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              H5 O2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              H2 O

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

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

Comment top

We have recently become interested in metal complexes with a pyridine-containing ligand system (Rafizadeh et al., 2004). We present here the structure of the title compound, (I), which includes a pyridinedicaboxylate (pydc) anion and a diaminopyridinium (pyda) cation.

The structure of (I) comprises Dy^III complex anions, free pyda cations, dihydronium cations (H₅O₂)⁺ and uncoordinted water molecules (Fig. 1). The Dy ion lies on a twofold rotation axis and the nine coordinated-Dy^III complex assumes a distorted tricapped trigonal-prismatic geometry, formed by three pydc dianions. This is comparable to the situation found in the Yb analogue (Rafizadeh et al., 2004). The Dy—O and Dy—N bond distances (Table 1) agree with those found in previously reported structures (Fernandes et al., 2001).

Atom H1WC atom of the dihydronium cation lies on a twofold axis. The O1W—H1WC bond distance of 1.225 Å and O1W—H1WC—O1Wⁱⁱ bond angle of 170° [symmetry code: (ii) −x − 1/2,y,-z + 1/2] are comparable to the values found in the Yb analogue (1.218 and 1.221 Å and 170°; Rafizadeh et al., 2004) and in the Gd^III analogue [1.216 Å and 164°; Rafizadeh et al., 2005). These also agree with the values deduced from ab initio computations (1.2 Å and 173.5°; Ojamae et al., 1995).

Experimental top

To a solution of [H₂pyda][pydc] (0.5 g, 1.8 mmol) in water (100 ml) was added a solution of DyCl₃·6H₂O (0.226 g, 0.6 mmol) in water (20 ml) and the resulting pale-yellow solution was stirred for 30 min. This solution was left to evaporate slowly at room temperature, affording single crystals of (I) after one week; yield 73.4%, m.p. 536–539 K.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecular structure of (I),with 30% probability displacement ellipsoids [symmetry codes: (i) −x + 1/2, y, −z + 1/2; (ii) −x − 1/2,+y,-z + 1/2].

Dihydronium bis(2,6-diaminopyridinium) tris(pyridine-2,6-dicarboxylato-κ³O,O',N)dysprosate(III) dihydrate top

Crystal data top

(H₅O₂)(C₅H₈N₃)₂[Dy(C₇H₃NO₄)₃]·2H₂O	F(000) = 954
M_r = 951.17	D_x = 1.726 Mg m⁻³
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yac	Cell parameters from 1024 reflections
a = 9.654 (2) Å	θ = 3–30°
b = 10.579 (2) Å	µ = 2.13 mm⁻¹
c = 17.972 (4) Å	T = 145 K
β = 94.483 (4)°	Prism, yellow
V = 1830.0 (7) Å³	0.30 × 0.25 × 0.20 mm
Z = 2

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4508 independent reflections
Radiation source: fine-focus sealed tube	3876 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.095
ϕ and ω scans	θ_max = 28.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −12→12
T_min = 0.406, T_max = 0.653	k = −13→13
18268 measured reflections	l = −23→23

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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F²) = 0.101	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.053P)² + 1.585P] where P = (F_o² + 2F_c²)/3
4508 reflections	(Δ/σ)_max < 0.001
259 parameters	Δρ_max = 2.75 e Å⁻³
0 restraints	Δρ_min = −1.14 e Å⁻³

Crystal data top

(H₅O₂)(C₅H₈N₃)₂[Dy(C₇H₃NO₄)₃]·2H₂O	V = 1830.0 (7) Å³
M_r = 951.17	Z = 2
Monoclinic, P2/n	Mo Kα radiation
a = 9.654 (2) Å	µ = 2.13 mm⁻¹
b = 10.579 (2) Å	T = 145 K
c = 17.972 (4) Å	0.30 × 0.25 × 0.20 mm
β = 94.483 (4)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4508 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	3876 reflections with I > 2σ(I)
T_min = 0.406, T_max = 0.653	R_int = 0.095
18268 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.03	Δρ_max = 2.75 e Å⁻³
4508 reflections	Δρ_min = −1.14 e Å⁻³
259 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
Dy1	0.2500	0.47398 (2)	0.2500	0.01906 (9)
O1	0.3291 (3)	0.5386 (2)	0.13321 (14)	0.0226 (5)
O2	0.3345 (3)	0.5190 (3)	0.00958 (16)	0.0294 (6)
O3	0.0843 (3)	0.3105 (2)	0.27554 (14)	0.0251 (5)
O4	−0.0561 (3)	0.1502 (3)	0.23905 (15)	0.0280 (6)
O5	0.0330 (3)	0.5742 (3)	0.20749 (15)	0.0248 (5)
O6	−0.0928 (3)	0.7441 (3)	0.17113 (19)	0.0382 (7)
N1	0.1429 (3)	0.3589 (3)	0.13878 (16)	0.0195 (6)
N2	0.2500	0.7096 (4)	0.2500	0.0194 (8)
C1	0.1723 (4)	0.3954 (3)	0.07076 (19)	0.0202 (7)
C2	0.1034 (4)	0.3445 (4)	0.0067 (2)	0.0292 (8)
H2	0.1249	0.3715	−0.0415	0.035*
C3	0.0030 (4)	0.2539 (4)	0.0149 (2)	0.0354 (10)
H3	−0.0468	0.2189	−0.0279	0.042*
C4	−0.0253 (4)	0.2137 (4)	0.0859 (2)	0.0296 (8)
H4	−0.0917	0.1492	0.0925	0.036*
C5	0.0464 (4)	0.2707 (3)	0.1464 (2)	0.0206 (7)
C6	0.2876 (4)	0.4916 (3)	0.0699 (2)	0.0221 (7)
C7	0.0209 (4)	0.2406 (3)	0.2266 (2)	0.0214 (7)
C8	0.1375 (4)	0.7737 (4)	0.2232 (2)	0.0236 (7)
C9	0.1345 (5)	0.9060 (4)	0.2206 (3)	0.0353 (10)
H9	0.0551	0.9496	0.1992	0.042*
C10	0.2500	0.9712 (5)	0.2500	0.0391 (15)
H10	0.2500	1.0610	0.2500	0.047*
C11	0.0139 (4)	0.6938 (4)	0.1978 (2)	0.0249 (7)
N3	−0.1050 (3)	0.0922 (3)	0.38151 (18)	0.0259 (7)
H3N	−0.0765	0.1150	0.3381	0.031*
N4	−0.0386 (4)	0.2897 (3)	0.4235 (2)	0.0339 (8)
H4NA	−0.0061	0.3054	0.3809	0.041*
H4NB	−0.0542	0.3477	0.4497	0.041*
N5	−0.1513 (5)	−0.1036 (4)	0.3290 (2)	0.0430 (10)
H5NA	−0.1245	−0.0767	0.2863	0.052*
H5NB	−0.1999	−0.1766	0.3348	0.052*
C12	−0.0969 (4)	0.1783 (4)	0.4377 (2)	0.0272 (8)
C13	−0.1442 (4)	0.1444 (5)	0.5065 (2)	0.0351 (9)
H13	−0.1404	0.2025	0.5469	0.042*
C14	−0.1965 (5)	0.0243 (4)	0.5140 (2)	0.0347 (9)
H14	−0.2291	0.0002	0.5605	0.042*
C15	−0.2032 (5)	−0.0627 (5)	0.4563 (3)	0.0367 (10)
H15	−0.2402	−0.1448	0.4629	0.044*
C16	−0.1546 (4)	−0.0275 (4)	0.3885 (2)	0.0298 (8)
O1W	−0.2087 (3)	0.4599 (3)	0.18753 (19)	0.0356 (7)
H1WC	−0.2500	0.4502	0.2500	0.043*
H1WA	−0.2568	0.5022	0.1547	0.043*
H1WB	−0.1315	0.5024	0.1890	0.043*
O2W	−0.3942 (3)	−0.3875 (3)	0.11700 (16)	0.0352 (7)
H2WB	−0.4675	−0.3997	0.1254	0.042*
H2WA	−0.3771	−0.4118	0.0747	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Dy1	0.01921 (13)	0.01890 (13)	0.01929 (13)	0.000	0.00300 (8)	0.000
O1	0.0227 (13)	0.0263 (14)	0.0192 (12)	−0.0043 (10)	0.0041 (10)	−0.0005 (10)
O2	0.0356 (16)	0.0329 (15)	0.0206 (13)	−0.0082 (12)	0.0083 (11)	0.0037 (11)
O3	0.0299 (14)	0.0233 (13)	0.0224 (12)	−0.0070 (11)	0.0039 (10)	0.0017 (10)
O4	0.0317 (15)	0.0233 (13)	0.0298 (14)	−0.0066 (11)	0.0077 (11)	0.0024 (11)
O5	0.0207 (13)	0.0216 (12)	0.0318 (14)	0.0008 (11)	−0.0005 (10)	−0.0013 (11)
O6	0.0265 (15)	0.0315 (16)	0.055 (2)	0.0065 (12)	−0.0091 (14)	0.0032 (14)
N1	0.0201 (14)	0.0187 (14)	0.0203 (14)	0.0017 (11)	0.0044 (11)	0.0016 (11)
N2	0.018 (2)	0.022 (2)	0.0184 (19)	0.000	0.0029 (15)	0.000
C1	0.0204 (16)	0.0192 (16)	0.0215 (16)	−0.0003 (13)	0.0036 (13)	−0.0003 (13)
C2	0.030 (2)	0.036 (2)	0.0212 (17)	−0.0026 (17)	0.0023 (15)	−0.0015 (16)
C3	0.037 (2)	0.048 (3)	0.0215 (19)	−0.0096 (19)	−0.0005 (17)	−0.0078 (18)
C4	0.029 (2)	0.031 (2)	0.029 (2)	−0.0073 (16)	0.0025 (16)	−0.0039 (16)
C5	0.0197 (17)	0.0189 (16)	0.0235 (17)	0.0001 (13)	0.0035 (13)	0.0011 (13)
C6	0.0211 (18)	0.0239 (17)	0.0220 (17)	0.0035 (13)	0.0070 (14)	0.0011 (13)
C7	0.0162 (16)	0.0206 (17)	0.0277 (18)	0.0015 (13)	0.0035 (13)	0.0014 (14)
C8	0.0241 (19)	0.0216 (18)	0.0254 (18)	0.0009 (14)	0.0043 (14)	0.0033 (13)
C9	0.033 (2)	0.021 (2)	0.051 (3)	0.0070 (16)	−0.0002 (19)	0.0025 (17)
C10	0.038 (3)	0.014 (2)	0.065 (4)	0.000	0.004 (3)	0.000
C11	0.0246 (18)	0.0250 (18)	0.0250 (18)	0.0038 (15)	0.0019 (14)	0.0003 (14)
N3	0.0252 (16)	0.0242 (16)	0.0289 (16)	−0.0029 (13)	0.0062 (13)	0.0039 (13)
N4	0.039 (2)	0.0279 (17)	0.0366 (19)	−0.0045 (15)	0.0144 (16)	−0.0066 (15)
N5	0.058 (3)	0.031 (2)	0.042 (2)	−0.0177 (18)	0.0138 (18)	−0.0061 (16)
C12	0.0226 (18)	0.031 (2)	0.0288 (19)	0.0012 (15)	0.0053 (15)	0.0034 (16)
C13	0.034 (2)	0.045 (3)	0.026 (2)	0.0009 (19)	0.0044 (17)	−0.0028 (18)
C14	0.030 (2)	0.046 (3)	0.029 (2)	0.0053 (19)	0.0106 (17)	0.0115 (18)
C15	0.035 (2)	0.035 (2)	0.040 (2)	−0.0055 (19)	0.0062 (19)	0.0131 (19)
C16	0.028 (2)	0.026 (2)	0.035 (2)	−0.0051 (16)	0.0047 (16)	0.0033 (16)
O1W	0.0254 (15)	0.0357 (17)	0.0453 (18)	−0.0020 (12)	0.0010 (13)	0.0005 (13)
O2W	0.0303 (15)	0.0443 (18)	0.0311 (15)	−0.0090 (13)	0.0034 (12)	−0.0048 (13)

Geometric parameters (Å, º) top

Dy1—O1	2.389 (3)	C8—C9	1.400 (5)
Dy1—O1ⁱ	2.389 (3)	C8—C11	1.505 (5)
Dy1—O3	2.424 (3)	C9—C10	1.381 (5)
Dy1—O3ⁱ	2.424 (3)	C9—H9	0.9500
Dy1—O5	2.418 (3)	C10—C9ⁱ	1.381 (5)
Dy1—O5ⁱ	2.418 (3)	C10—H10	0.9500
Dy1—N1	2.495 (3)	N3—C12	1.358 (5)
Dy1—N1ⁱ	2.495 (3)	N3—C16	1.364 (5)
Dy1—N2	2.492 (4)	N3—H3N	0.8800
O1—C6	1.277 (5)	N4—C12	1.339 (5)
O2—C6	1.241 (5)	N4—H4NA	0.8652
O3—C7	1.269 (4)	N4—H4NB	0.7955
O4—C7	1.242 (4)	N5—C16	1.342 (6)
O5—C11	1.289 (5)	N5—H5NA	0.8758
O6—C11	1.223 (5)	N5—H5NB	0.9134
N1—C5	1.333 (4)	C12—C13	1.398 (6)
N1—C1	1.333 (4)	C13—C14	1.378 (7)
N2—C8ⁱ	1.338 (4)	C13—H13	0.9500
N2—C8	1.338 (4)	C14—C15	1.384 (7)
C1—C2	1.393 (5)	C14—H14	0.9500
C1—C6	1.510 (5)	C15—C16	1.390 (6)
C2—C3	1.379 (6)	C15—H15	0.9500
C2—H2	0.9500	O1W—H1WC	1.2246
C3—C4	1.392 (6)	O1W—H1WA	0.8487
C3—H3	0.9500	O1W—H1WB	0.8689
C4—C5	1.382 (5)	O2W—H2WB	0.7462
C4—H4	0.9500	O2W—H2WA	0.8307
C5—C7	1.516 (5)

O1ⁱ—Dy1—O1	146.77 (12)	C4—C3—H3	120.0
O1ⁱ—Dy1—O5ⁱ	85.73 (9)	C5—C4—C3	117.7 (4)
O1—Dy1—O5ⁱ	79.85 (9)	C5—C4—H4	121.1
O1ⁱ—Dy1—O5	79.85 (9)	C3—C4—H4	121.1
O1—Dy1—O5	85.73 (9)	N1—C5—C4	122.4 (3)
O5ⁱ—Dy1—O5	128.00 (13)	N1—C5—C7	114.3 (3)
O1ⁱ—Dy1—O3	77.10 (9)	C4—C5—C7	123.3 (3)
O1—Dy1—O3	129.16 (9)	O2—C6—O1	125.2 (4)
O5ⁱ—Dy1—O3	145.21 (9)	O2—C6—C1	119.1 (3)
O5—Dy1—O3	78.72 (9)	O1—C6—C1	115.7 (3)
O1ⁱ—Dy1—O3ⁱ	129.16 (9)	O4—C7—O3	125.9 (3)
O1—Dy1—O3ⁱ	77.10 (9)	O4—C7—C5	118.5 (3)
O5ⁱ—Dy1—O3ⁱ	78.72 (9)	O3—C7—C5	115.6 (3)
O5—Dy1—O3ⁱ	145.21 (9)	N2—C8—C9	122.2 (4)
O3—Dy1—O3ⁱ	88.95 (13)	N2—C8—C11	115.2 (3)
O1ⁱ—Dy1—N2	73.38 (6)	C9—C8—C11	122.5 (3)
O1—Dy1—N2	73.38 (6)	C10—C9—C8	118.2 (4)
O5ⁱ—Dy1—N2	64.00 (7)	C10—C9—H9	120.9
O5—Dy1—N2	64.00 (7)	C8—C9—H9	120.9
O3—Dy1—N2	135.53 (7)	C9—C10—C9ⁱ	120.0 (5)
O3ⁱ—Dy1—N2	135.53 (7)	C9—C10—H10	120.0
O1ⁱ—Dy1—N1	134.65 (9)	C9ⁱ—C10—H10	120.0
O1—Dy1—N1	64.94 (9)	O6—C11—O5	126.0 (4)
O5ⁱ—Dy1—N1	139.62 (9)	O6—C11—C8	119.9 (3)
O5—Dy1—N1	70.50 (9)	O5—C11—C8	114.1 (3)
O3—Dy1—N1	64.23 (9)	C12—N3—C16	123.6 (3)
O3ⁱ—Dy1—N1	74.83 (9)	C12—N3—H3N	118.2
N2—Dy1—N1	119.21 (7)	C16—N3—H3N	118.2
O1ⁱ—Dy1—N1ⁱ	64.94 (9)	C12—N4—H4NA	121.6
O1—Dy1—N1ⁱ	134.65 (9)	C12—N4—H4NB	117.6
O5ⁱ—Dy1—N1ⁱ	70.50 (9)	H4NA—N4—H4NB	118.4
O5—Dy1—N1ⁱ	139.62 (9)	C16—N5—H5NA	122.0
O3—Dy1—N1ⁱ	74.83 (9)	C16—N5—H5NB	111.8
O3ⁱ—Dy1—N1ⁱ	64.23 (9)	H5NA—N5—H5NB	124.4
N2—Dy1—N1ⁱ	119.21 (7)	N4—C12—N3	116.6 (3)
N1—Dy1—N1ⁱ	121.57 (13)	N4—C12—C13	124.5 (4)
C6—O1—Dy1	124.9 (2)	N3—C12—C13	118.8 (4)
C7—O3—Dy1	125.0 (2)	C14—C13—C12	118.1 (4)
C11—O5—Dy1	125.8 (2)	C14—C13—H13	120.9
C5—N1—C1	119.8 (3)	C12—C13—H13	120.9
C5—N1—Dy1	120.6 (2)	C13—C14—C15	122.4 (4)
C1—N1—Dy1	119.3 (2)	C13—C14—H14	118.8
C8ⁱ—N2—C8	119.0 (4)	C15—C14—H14	118.8
C8ⁱ—N2—Dy1	120.5 (2)	C14—C15—C16	118.7 (4)
C8—N2—Dy1	120.5 (2)	C14—C15—H15	120.7
N1—C1—C2	121.6 (3)	C16—C15—H15	120.7
N1—C1—C6	114.5 (3)	N5—C16—N3	117.0 (4)
C2—C1—C6	123.9 (3)	N5—C16—C15	124.7 (4)
C3—C2—C1	118.3 (4)	N3—C16—C15	118.4 (4)
C3—C2—H2	120.8	H1WC—O1W—H1WA	118.8
C1—C2—H2	120.9	H1WC—O1W—H1WB	110.8
C2—C3—C4	120.1 (4)	H1WA—O1W—H1WB	99.8
C2—C3—H3	120.0	H2WB—O2W—H2WA	113.0

O1ⁱ—Dy1—O1—C6	−134.7 (3)	O3ⁱ—Dy1—N2—C8	139.8 (2)
O5ⁱ—Dy1—O1—C6	159.6 (3)	N1—Dy1—N2—C8	41.6 (2)
O5—Dy1—O1—C6	−70.5 (3)	N1ⁱ—Dy1—N2—C8	−138.4 (2)
O3—Dy1—O1—C6	1.2 (3)	C5—N1—C1—C2	0.7 (5)
O3ⁱ—Dy1—O1—C6	79.0 (3)	Dy1—N1—C1—C2	−172.4 (3)
N2—Dy1—O1—C6	−134.7 (3)	C5—N1—C1—C6	−177.5 (3)
N1—Dy1—O1—C6	−0.1 (3)	Dy1—N1—C1—C6	9.4 (4)
N1ⁱ—Dy1—O1—C6	110.4 (3)	N1—C1—C2—C3	−0.3 (6)
O1ⁱ—Dy1—O3—C7	156.8 (3)	C6—C1—C2—C3	177.8 (4)
O1—Dy1—O3—C7	−0.1 (3)	C1—C2—C3—C4	−1.2 (6)
O5ⁱ—Dy1—O3—C7	−140.8 (3)	C2—C3—C4—C5	2.3 (6)
O5—Dy1—O3—C7	74.8 (3)	C1—N1—C5—C4	0.4 (5)
O3ⁱ—Dy1—O3—C7	−72.5 (3)	Dy1—N1—C5—C4	173.4 (3)
N2—Dy1—O3—C7	107.5 (3)	C1—N1—C5—C7	−178.5 (3)
N1—Dy1—O3—C7	1.1 (3)	Dy1—N1—C5—C7	−5.5 (4)
N1ⁱ—Dy1—O3—C7	−136.0 (3)	C3—C4—C5—N1	−1.9 (6)
O1ⁱ—Dy1—O5—C11	82.0 (3)	C3—C4—C5—C7	176.9 (4)
O1—Dy1—O5—C11	−67.9 (3)	Dy1—O1—C6—O2	−175.1 (3)
O5ⁱ—Dy1—O5—C11	5.7 (3)	Dy1—O1—C6—C1	4.7 (4)
O3—Dy1—O5—C11	160.7 (3)	N1—C1—C6—O2	170.7 (3)
O3ⁱ—Dy1—O5—C11	−127.9 (3)	C2—C1—C6—O2	−7.5 (6)
N2—Dy1—O5—C11	5.7 (3)	N1—C1—C6—O1	−9.1 (5)
N1—Dy1—O5—C11	−132.8 (3)	C2—C1—C6—O1	172.6 (4)
N1ⁱ—Dy1—O5—C11	111.0 (3)	Dy1—O3—C7—O4	174.1 (3)
O1ⁱ—Dy1—N1—C5	−31.7 (3)	Dy1—O3—C7—C5	−4.2 (4)
O1—Dy1—N1—C5	−178.4 (3)	N1—C5—C7—O4	−172.3 (3)
O5ⁱ—Dy1—N1—C5	149.8 (2)	C4—C5—C7—O4	8.8 (5)
O5—Dy1—N1—C5	−83.9 (3)	N1—C5—C7—O3	6.2 (5)
O3—Dy1—N1—C5	2.7 (2)	C4—C5—C7—O3	−172.7 (4)
O3ⁱ—Dy1—N1—C5	99.0 (3)	C8ⁱ—N2—C8—C9	1.5 (3)
N2—Dy1—N1—C5	−126.9 (2)	Dy1—N2—C8—C9	−178.5 (3)
N1ⁱ—Dy1—N1—C5	53.1 (2)	C8ⁱ—N2—C8—C11	−177.1 (4)
O1ⁱ—Dy1—N1—C1	141.4 (2)	Dy1—N2—C8—C11	2.9 (4)
O1—Dy1—N1—C1	−5.3 (2)	N2—C8—C9—C10	−3.0 (6)
O5ⁱ—Dy1—N1—C1	−37.1 (3)	C11—C8—C9—C10	175.6 (3)
O5—Dy1—N1—C1	89.2 (3)	C8—C9—C10—C9ⁱ	1.4 (3)
O3—Dy1—N1—C1	175.7 (3)	Dy1—O5—C11—O6	174.3 (3)
O3ⁱ—Dy1—N1—C1	−88.0 (3)	Dy1—O5—C11—C8	−6.2 (4)
N2—Dy1—N1—C1	46.1 (3)	N2—C8—C11—O6	−178.6 (3)
N1ⁱ—Dy1—N1—C1	−133.9 (3)	C9—C8—C11—O6	2.7 (6)
O1ⁱ—Dy1—N2—C8ⁱ	89.30 (19)	N2—C8—C11—O5	1.9 (5)
O1—Dy1—N2—C8ⁱ	−90.70 (19)	C9—C8—C11—O5	−176.8 (4)
O5ⁱ—Dy1—N2—C8ⁱ	−4.09 (19)	C16—N3—C12—N4	176.4 (4)
O5—Dy1—N2—C8ⁱ	175.91 (19)	C16—N3—C12—C13	−1.2 (6)
O3—Dy1—N2—C8ⁱ	139.8 (2)	N4—C12—C13—C14	−177.2 (4)
O3ⁱ—Dy1—N2—C8ⁱ	−40.2 (2)	N3—C12—C13—C14	0.3 (6)
N1—Dy1—N2—C8ⁱ	−138.4 (2)	C12—C13—C14—C15	0.1 (7)
N1ⁱ—Dy1—N2—C8ⁱ	41.6 (2)	C13—C14—C15—C16	0.4 (7)
O1ⁱ—Dy1—N2—C8	−90.70 (19)	C12—N3—C16—N5	−177.5 (4)
O1—Dy1—N2—C8	89.30 (19)	C12—N3—C16—C15	1.7 (6)
O5ⁱ—Dy1—N2—C8	175.91 (19)	C14—C15—C16—N5	177.9 (4)
O5—Dy1—N2—C8	−4.09 (19)	C14—C15—C16—N3	−1.2 (7)
O3—Dy1—N2—C8	−40.2 (2)

Symmetry code: (i) −x+1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	(H₅O₂)(C₅H₈N₃)₂[Dy(C₇H₃NO₄)₃]·2H₂O
M_r	951.17
Crystal system, space group	Monoclinic, P2/n
Temperature (K)	145
a, b, c (Å)	9.654 (2), 10.579 (2), 17.972 (4)
β (°)	94.483 (4)
V (Å³)	1830.0 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.13
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.406, 0.653
No. of measured, independent and observed [I > 2σ(I)] reflections	18268, 4508, 3876
R_int	0.095
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.101, 1.03
No. of reflections	4508
No. of parameters	259
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.75, −1.14

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1998), SHELXTL.

Selected bond lengths (Å) top

Dy1—O1	2.389 (3)	Dy1—N1	2.495 (3)
Dy1—O3	2.424 (3)	Dy1—N2	2.492 (4)
Dy1—O5	2.418 (3)

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Dihydro­nium bis­(2,6-diamino­pyridinium) tris­(pyridine-2,6-dicarboxyl­ato-κ3O,O′,N)dysprosate(III) dihydrate

Supporting information

Key indicators

checkCIF/PLATON results

Dihydronium bis(2,6-diaminopyridinium) tris(pyridine-2,6-dicarboxylato-κ³O,O′,N)dysprosate(III) dihydrate