A dinuclear oxomolybdenum(V) compound with picolinate ligands

Okabe, N.; Isomoto, N.; Odoko, M.

doi:10.1107/S160053680102058X

A dinuclear oxomolybdenum(V) compound with picolinate ligands

The title compound, diaquadi-μ₂-oxo-dioxobis(pyridine-2-carboxylato-O,N)molybdenum(V) monohydrate, [Mo₂O₂(C₆H₄NO₂)₂(H₂O)₂]·H₂O, is a dinuclear complex which consists of two Mo^V atoms connected together by a metal–metal single bond and two bridging oxo groups. Each Mo^V atom has a distorted octahedral geometry and is coordinated by three oxo groups, one O atom of the water molecule, and the O and N atoms of one picolinate anion.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680102058X/cf6131sup1.cif Contains datablocks General, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680102058X/cf6131Isup2.hkl Contains datablock I

CCDC reference: 180511

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Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R factor = 0.025
wR factor = 0.108
Data-to-parameter ratio = 14.2

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No syntax errors found

ADDSYM reports no extra symmetry

Comment top

Picolinic acid (pyridine-2-carboxylic acid), (I), is a well known terminal tryptophan metabolite (Mahler & Cordes, 1971). It has biological activity to induce apotosis in leukemia HL-60 cells, which is cell death characterized by DNA fragmentation (Ogata et al., 2000). Molybdenum is a well known biologically essential metal and serves as a component of molybdenum enzymes. It also has antitumor activity for leukemia and lymphomas (Hall et al., 2000). We intended to prepare hybrid complexes of these bioactive substances and determine their structures.

The structure of (I) is a dinuclear complex, as illustrated in Fig. 1. Selected bond lengths and angles are given in Table 1. Each Mo^V atom of the complex has a pseudo-octahedral [MoO₅N] geometry which is defined by three oxo ligands, one O atom of a water ligand, and O and N atoms of picolinate. The Mo^V atoms are bridged by two oxo groups with Mo—O distances of 1.928 (2)–1.956 (3) Å, and two other oxo O atoms are coordinated at short distances [Mo1—O5 1.683 (3) Å and Mo2—O5 1.688 (3) Å]. The Mo atoms are also joined by a Mo—Mo single bond with a short distance [Mo1—Mo2 2.5538 (5) Å]. Similar oxo bridges, short Mo—O distances, and an Mo—Mo single bond are observed in a decanuclear oxomolybdenum(V,VI) cluster with 4-isopropylpyridine (Modec et al., 2001). The geometrical parameters around Mo^V in this 4-isopropylpyridine complex and in the title compound are similar to each other. The coordination of N and O atoms of picolinate to a metal is a common feature for all metal complexes of this ligand: Ni^II and Zn^II (Takenaka et al., 1970), Cu^II (Faure et al., 1973), Mn^II (Okabe & Koizumi, 1998) and Cd^II (Odoko et al. 2001). The crystal structure is stabilized by stacking of picolinate rings and by O—H···O hydrogen bonds (Table 2), in which the coordinated and the hydrate water molecules act as the hydrogen donors, and the O atoms of the bridging oxo groups and carboxylate group of picolinate act as acceptors.

Experimental top

The orange plate crystals were obtained by slow evaporation from a 90% ethanol–water solution of picolinic acid (pyridine-2-carboxylic acid) and molybdenum(V) chloride (4:1 molar ratio).

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation and Rigaku Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation and Rigaku Corporation, 1999); program(s) used to solve structure: SIR97 (Altomare et al., 1999) and DIRDIF94 (Beurskens et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures top

Fig. 1. ORTEPII (Johnson, 1976) drawing of the title compound with the atomic numbering scheme. Ellipsoids for non-H atoms correspond to the 50% probability level.

(I) top

Crystal data top

[Mo₂O₂(C₆H₄NO₂)₂(H₂O)₂]·H₂O	Z = 2
M_r = 554.13	F(000) = 544.0
Triclinic, P1	D_x = 2.126 Mg m⁻³
a = 9.260 (2) Å	Mo Kα radiation, λ = 0.7107 Å
b = 12.145 (2) Å	Cell parameters from 25 reflections
c = 8.261 (1) Å	θ = 14.8–15.0°
α = 98.02 (1)°	µ = 1.51 mm⁻¹
β = 101.89 (1)°	T = 296 K
γ = 103.68 (1)°	Prismatic, orange
V = 865.8 (3) Å³	0.3 × 0.3 × 0.2 mm

Data collection top

Rigaku AFC-5R diffractometer	R_int = 0.011
ω–2θ scans	θ_max = 27.5°
Absorption correction: ψ scan (North et al., 1968)	h = 0→12
T_min = 0.627, T_max = 0.739	k = −15→15
4227 measured reflections	l = −10→10
3977 independent reflections	3 standard reflections every 150 reflections
3473 reflections with I > 2σ(I)	intensity decay: 0.5%

Refinement top

Refinement on F²	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.025	(Δ/σ)_max = −0.001
wR(F²) = 0.108	Δρ_max = 0.81 e Å⁻³
S = 0.92	Δρ_min = −0.52 e Å⁻³
3473 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
245 parameters	Extinction coefficient: 0.0050 (12)
H-atom parameters not refined

Crystal data top

[Mo₂O₂(C₆H₄NO₂)₂(H₂O)₂]·H₂O	γ = 103.68 (1)°
M_r = 554.13	V = 865.8 (3) Å³
Triclinic, P1	Z = 2
a = 9.260 (2) Å	Mo Kα radiation
b = 12.145 (2) Å	µ = 1.51 mm⁻¹
c = 8.261 (1) Å	T = 296 K
α = 98.02 (1)°	0.3 × 0.3 × 0.2 mm
β = 101.89 (1)°

Data collection top

Rigaku AFC-5R diffractometer	3473 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.011
T_min = 0.627, T_max = 0.739	3 standard reflections every 150 reflections
4227 measured reflections	intensity decay: 0.5%
3977 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	245 parameters
wR(F²) = 0.108	H-atom parameters not refined
S = 0.92	Δρ_max = 0.81 e Å⁻³
3473 reflections	Δρ_min = −0.52 e Å⁻³

Special details top

Refinement. Refinement using reflections with F² > -10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
Mo1	0.10169 (3)	0.22379 (2)	0.18327 (3)	0.0239 (1)
Mo2	−0.10913 (3)	0.18319 (2)	0.34093 (3)	0.0250 (1)
O1	0.0012 (3)	0.4074 (2)	−0.2042 (3)	0.0432 (6)
O2	−0.0123 (3)	0.2828 (2)	−0.0289 (3)	0.0305 (4)
O3	−0.5394 (3)	0.1857 (2)	0.0543 (3)	0.0373 (5)
O4	−0.2918 (2)	0.2232 (2)	0.1750 (3)	0.0290 (4)
O5	0.2496 (3)	0.2033 (2)	0.3211 (3)	0.0363 (5)
O6	0.1634 (3)	0.1351 (2)	−0.0258 (3)	0.0329 (5)
O7	0.0237 (3)	0.3264 (2)	0.3211 (3)	0.0287 (4)
O8	−0.0747 (3)	0.0912 (2)	0.1457 (3)	0.0296 (5)
O9	−0.0243 (3)	0.1382 (2)	0.5110 (3)	0.0382 (5)
O10	−0.1986 (3)	0.2900 (2)	0.5092 (3)	0.0329 (5)
O11	0.8091 (3)	0.4922 (2)	0.4223 (3)	0.0430 (6)
N1	0.2627 (3)	0.3850 (2)	0.1558 (3)	0.0264 (5)
N2	−0.3246 (3)	0.0434 (2)	0.3144 (3)	0.0265 (5)
C1	0.2079 (3)	0.4397 (3)	0.0370 (4)	0.0274 (6)
C2	0.2876 (4)	0.5472 (3)	0.0195 (4)	0.0358 (7)
C3	0.4324 (4)	0.5987 (3)	0.1261 (4)	0.0385 (7)
C4	0.4888 (4)	0.5419 (3)	0.2480 (5)	0.0403 (8)
C5	0.4031 (4)	0.4352 (3)	0.2594 (4)	0.0342 (7)
C6	0.0530 (4)	0.3722 (3)	−0.0762 (4)	0.0296 (6)
C7	−0.4546 (3)	0.0579 (2)	0.2226 (4)	0.0257 (5)
C8	−0.5963 (4)	−0.0195 (3)	0.2017 (4)	0.0314 (6)
C9	−0.6035 (4)	−0.1143 (3)	0.2783 (4)	0.0366 (7)
C10	−0.4725 (4)	−0.1284 (3)	0.3732 (4)	0.0356 (7)
C11	−0.3319 (4)	−0.0488 (3)	0.3884 (4)	0.0309 (6)
C12	−0.4316 (3)	0.1635 (2)	0.1419 (3)	0.0251 (5)
H2	0.2486	0.5877	−0.0642	0.0341*
H3	0.4921	0.6709	0.1274	0.0411*
H4	0.5893	0.5804	0.3367	0.0409*
H5	0.4487	0.3987	0.3529	0.0362*
H8	−0.6853	−0.0064	0.1435	0.0293*
H9	−0.6981	−0.1681	0.2755	0.0351*
H10	−0.4709	−0.1903	0.4388	0.0364*
H11	−0.2411	−0.0550	0.4589	0.0280*
H12	0.2657	0.1435	−0.0014	0.0437*
H13	0.1077	0.0594	−0.0752	0.0437*
H14	−0.2014	0.3636	0.4926	0.0437*
H15	−0.1334	0.3132	0.6104	0.0437*
H16	0.8703	0.5159	0.3424	0.0455*
H17	0.8662	0.5476	0.5124	0.0455*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mo1	0.0226 (2)	0.0210 (2)	0.0272 (2)	0.0048 (1)	0.0047 (1)	0.0055 (1)
Mo2	0.0248 (2)	0.0215 (2)	0.0271 (2)	0.0035 (1)	0.0059 (1)	0.0053 (1)
O1	0.049 (1)	0.045 (1)	0.032 (1)	0.012 (1)	−0.001 (1)	0.0150 (10)
O2	0.027 (1)	0.031 (1)	0.031 (1)	0.0070 (9)	0.0026 (8)	0.0073 (8)
O3	0.028 (1)	0.041 (1)	0.047 (1)	0.0099 (10)	0.0100 (10)	0.020 (1)
O4	0.028 (1)	0.0251 (10)	0.033 (1)	0.0020 (8)	0.0073 (9)	0.0114 (8)
O5	0.030 (1)	0.037 (1)	0.043 (1)	0.0097 (9)	0.0047 (10)	0.0154 (10)
O6	0.028 (1)	0.027 (1)	0.042 (1)	0.0067 (9)	0.0110 (9)	0.0003 (9)
O7	0.030 (1)	0.0221 (10)	0.032 (1)	0.0020 (8)	0.0102 (9)	0.0026 (8)
O8	0.030 (1)	0.0222 (10)	0.035 (1)	0.0035 (8)	0.0095 (9)	0.0020 (8)
O9	0.039 (1)	0.038 (1)	0.035 (1)	0.008 (1)	0.0035 (10)	0.0123 (10)
O10	0.035 (1)	0.029 (1)	0.030 (1)	0.0033 (9)	0.0096 (9)	0.0010 (8)
O11	0.047 (1)	0.036 (1)	0.039 (1)	0.008 (1)	0.002 (1)	0.0023 (10)
N1	0.026 (1)	0.023 (1)	0.028 (1)	0.0043 (10)	0.0053 (10)	0.0075 (9)
N2	0.030 (1)	0.023 (1)	0.026 (1)	0.0044 (10)	0.0085 (10)	0.0065 (9)
C1	0.031 (1)	0.027 (1)	0.026 (1)	0.010 (1)	0.009 (1)	0.005 (1)
C2	0.048 (2)	0.028 (1)	0.035 (2)	0.011 (1)	0.014 (1)	0.011 (1)
C3	0.042 (2)	0.026 (1)	0.043 (2)	−0.001 (1)	0.015 (1)	0.005 (1)
C4	0.033 (2)	0.038 (2)	0.040 (2)	−0.003 (1)	0.005 (1)	0.002 (1)
C5	0.028 (1)	0.036 (2)	0.034 (2)	0.005 (1)	0.002 (1)	0.010 (1)
C6	0.034 (2)	0.030 (1)	0.028 (1)	0.014 (1)	0.007 (1)	0.006 (1)
C7	0.028 (1)	0.022 (1)	0.029 (1)	0.004 (1)	0.012 (1)	0.007 (1)
C8	0.025 (1)	0.033 (2)	0.033 (1)	0.002 (1)	0.008 (1)	0.009 (1)
C9	0.038 (2)	0.032 (2)	0.035 (2)	−0.004 (1)	0.013 (1)	0.007 (1)
C10	0.048 (2)	0.027 (1)	0.032 (1)	0.006 (1)	0.013 (1)	0.010 (1)
C11	0.037 (2)	0.025 (1)	0.029 (1)	0.005 (1)	0.006 (1)	0.008 (1)
C12	0.027 (1)	0.025 (1)	0.025 (1)	0.006 (1)	0.010 (1)	0.0072 (10)

Geometric parameters (Å, º) top

Mo1—Mo2	2.5538 (5)	N1—C1	1.341 (4)
Mo1—O2	2.155 (2)	N1—C5	1.348 (4)
Mo1—O5	1.683 (3)	N2—C7	1.348 (4)
Mo1—O6	2.156 (3)	N2—C11	1.343 (4)
Mo1—O7	1.934 (3)	C1—C2	1.383 (4)
Mo1—O8	1.941 (2)	C1—C6	1.510 (4)
Mo1—N1	2.234 (3)	C2—C3	1.388 (4)
Mo2—O4	2.144 (2)	C2—H2	0.962
Mo2—O7	1.928 (2)	C3—C4	1.382 (5)
Mo2—O8	1.956 (3)	C3—H3	0.917
Mo2—O9	1.688 (3)	C4—C5	1.377 (5)
Mo2—O10	2.187 (3)	C4—H4	1.020
Mo2—N2	2.242 (2)	C5—H5	1.010
O1—C6	1.243 (4)	C7—C8	1.383 (4)
O2—C6	1.267 (4)	C7—C12	1.517 (4)
O3—C12	1.215 (4)	C8—C9	1.384 (5)
O4—C12	1.278 (3)	C8—H8	0.925
O6—H12	0.905	C9—C10	1.363 (5)
O6—H13	0.929	C9—H9	0.955
O10—H14	0.928	C10—C11	1.396 (4)
O10—H15	0.888	C10—H10	0.986
O11—H16	0.985	C11—H11	0.944
O11—H17	0.903

Mo1···Mo2	2.5538 (5)	O6···O8^viii	2.654 (3)
O1···O10ⁱ	2.658 (3)	O7···O11^ix	2.733 (3)
O1···O11ⁱⁱ	2.953 (4)	O7···O11^iv	3.289 (4)
O1···C1ⁱⁱⁱ	3.346 (5)	O8···C8^v	3.567 (4)
O1···C2ⁱⁱⁱ	3.455 (5)	O9···O9^vi	3.477 (5)
O1···C6ⁱⁱⁱ	3.488 (4)	O10···O11^iv	2.643 (4)
O1···O7ⁱⁱⁱ	3.546 (4)	O10···C9^x	3.393 (4)
O3···O6^iv	2.594 (3)	O10···C6^xi	3.580 (3)
O3···C3ⁱⁱⁱ	3.245 (4)	O11···O11^xii	3.454 (6)
O3···O5^iv	3.250 (4)	O11···C2ⁱⁱ	3.509 (4)
O3···C8^v	3.351 (4)	N2···C9^x	3.591 (4)
O3···C9^v	3.381 (5)	C2···C4ⁱⁱ	3.552 (6)
O3···C7^v	3.460 (4)	C3···C10^xiii	3.452 (4)
O3···C5^iv	3.469 (4)	C3···C3ⁱⁱ	3.572 (8)
O3···N1^iv	3.476 (4)	C7···C12^v	3.536 (4)
O3···C10^v	3.533 (4)	C7···C10^x	3.569 (5)
O4···C2ⁱⁱⁱ	3.404 (4)	C7···C7^v	3.596 (6)
O4···O11^iv	3.411 (3)	C8···C12^v	3.211 (4)
O4···C8^v	3.491 (3)	C8···C10^x	3.569 (4)
O5···C10^vi	3.293 (4)	C9···C11^x	3.404 (5)
O5···C11^vi	3.323 (4)	C9···C12^v	3.535 (5)
O5···C8^vii	3.464 (4)

Mo2—Mo1—O2	100.88 (7)	Mo1—O8—Mo2	81.88 (8)
Mo2—Mo1—O5	100.84 (9)	Mo2—O10—H14	119.8
Mo2—Mo1—O6	137.13 (6)	Mo2—O10—H15	109.9
Mo2—Mo1—O7	48.50 (7)	H14—O10—H15	95.7
Mo2—Mo1—O8	49.32 (8)	H16—O11—H17	96.9
Mo2—Mo1—N1	133.91 (7)	Mo1—N1—C1	116.5 (2)
O2—Mo1—O5	157.3 (1)	Mo1—N1—C5	124.5 (2)
O2—Mo1—O6	77.23 (9)	C1—N1—C5	118.8 (3)
O2—Mo1—O7	86.28 (9)	Mo2—N2—C7	116.1 (2)
O2—Mo1—O8	90.43 (9)	Mo2—N2—C11	124.5 (2)
O2—Mo1—N1	72.44 (8)	C7—N2—C11	119.4 (3)
O5—Mo1—O6	91.1 (1)	N1—C1—C2	122.7 (3)
O5—Mo1—O7	103.5 (1)	N1—C1—C6	113.7 (3)
O5—Mo1—O8	108.7 (1)	C2—C1—C6	123.6 (3)
O5—Mo1—N1	87.8 (1)	C1—C2—C3	118.4 (3)
O6—Mo1—O7	163.30 (10)	C1—C2—H2	123.3
O6—Mo1—O8	87.83 (9)	C3—C2—H2	118.3
O6—Mo1—N1	87.07 (9)	C2—C3—C4	118.7 (3)
O7—Mo1—O8	95.01 (10)	C2—C3—H3	124.8
O7—Mo1—N1	85.42 (10)	C4—C3—H3	116.3
O8—Mo1—N1	162.81 (10)	C3—C4—C5	120.0 (3)
Mo1—Mo2—O4	100.79 (7)	C3—C4—H4	121.1
Mo1—Mo2—O7	48.70 (8)	C5—C4—H4	118.7
Mo1—Mo2—O8	48.79 (6)	N1—C5—C4	121.4 (3)
Mo1—Mo2—O9	102.81 (10)	N1—C5—H5	122.0
Mo1—Mo2—O10	134.76 (6)	C4—C5—H5	116.6
Mo1—Mo2—N2	136.76 (7)	O1—C6—O2	126.0 (3)
O4—Mo2—O7	87.56 (9)	O1—C6—C1	119.0 (3)
O4—Mo2—O8	89.06 (9)	O2—C6—C1	115.0 (3)
O4—Mo2—O9	156.4 (1)	N2—C7—C8	122.0 (3)
O4—Mo2—O10	75.87 (9)	N2—C7—C12	114.6 (2)
O4—Mo2—N2	72.43 (9)	C8—C7—C12	123.4 (3)
O7—Mo2—O8	94.70 (10)	C7—C8—C9	118.4 (3)
O7—Mo2—O9	109.0 (1)	C7—C8—H8	121.1
O7—Mo2—O10	86.13 (10)	C9—C8—H8	120.3
O7—Mo2—N2	159.8 (1)	C8—C9—C10	119.7 (3)
O8—Mo2—O9	105.7 (1)	C8—C9—H9	122.7
O8—Mo2—O10	164.87 (9)	C10—C9—H9	117.4
O8—Mo2—N2	88.02 (9)	C9—C10—C11	119.7 (3)
O9—Mo2—O10	88.2 (1)	C9—C10—H10	123.6
O9—Mo2—N2	89.4 (1)	C11—C10—H10	116.6
O10—Mo2—N2	86.16 (9)	N2—C11—C10	120.8 (3)
Mo1—O2—C6	121.6 (2)	N2—C11—H11	118.4
Mo2—O4—C12	123.0 (2)	C10—C11—H11	120.6
Mo1—O6—H12	110.4	O3—C12—O4	125.1 (3)
Mo1—O6—H13	119.1	O3—C12—C7	121.2 (3)
H12—O6—H13	111.9	O4—C12—C7	113.7 (3)
Mo1—O7—Mo2	82.81 (8)

Mo1—Mo2—O4—C12	140.1 (2)	O5—Mo1—Mo2—O10	94.7 (1)
Mo1—Mo2—N2—C7	−91.3 (2)	O5—Mo1—Mo2—N2	−108.8 (1)
Mo1—Mo2—N2—C11	91.4 (3)	O5—Mo1—O2—C6	−29.2 (4)
Mo1—O2—C6—O1	173.9 (3)	O5—Mo1—N1—C1	173.4 (2)
Mo1—O2—C6—C1	−5.9 (4)	O5—Mo1—N1—C5	−13.0 (3)
Mo1—O7—Mo2—O4	−106.67 (8)	O6—Mo1—Mo2—O7	−157.9 (1)
Mo1—O7—Mo2—O8	−17.81 (9)	O6—Mo1—Mo2—O8	−1.8 (1)
Mo1—O7—Mo2—O9	90.5 (1)	O6—Mo1—Mo2—O9	97.9 (1)
Mo1—O7—Mo2—O10	177.34 (9)	O6—Mo1—Mo2—O10	−161.7 (1)
Mo1—O7—Mo2—N2	−114.8 (3)	O6—Mo1—Mo2—N2	−5.2 (1)
Mo1—O8—Mo2—O4	105.26 (9)	O6—Mo1—O2—C6	−89.9 (3)
Mo1—O8—Mo2—O7	17.79 (10)	O6—Mo1—N1—C1	82.2 (2)
Mo1—O8—Mo2—O9	−93.5 (1)	O6—Mo1—N1—C5	−104.3 (3)
Mo1—O8—Mo2—O10	110.3 (3)	O7—Mo1—Mo2—O8	156.1 (1)
Mo1—O8—Mo2—N2	177.70 (10)	O7—Mo1—Mo2—O9	−104.2 (1)
Mo1—N1—C1—C2	172.0 (3)	O7—Mo1—Mo2—O10	−3.7 (1)
Mo1—N1—C1—C6	−8.8 (4)	O7—Mo1—Mo2—N2	152.7 (1)
Mo1—N1—C5—C4	−171.9 (3)	O7—Mo1—O2—C6	87.5 (3)
Mo2—Mo1—O2—C6	133.9 (2)	O7—Mo1—N1—C1	−82.9 (2)
Mo2—Mo1—N1—C1	−83.7 (2)	O7—Mo1—N1—C5	90.6 (3)
Mo2—Mo1—N1—C5	89.9 (3)	O7—Mo2—Mo1—O8	−156.1 (1)
Mo2—O4—C12—O3	176.8 (2)	O7—Mo2—Mo1—N1	1.0 (1)
Mo2—O4—C12—C7	−3.5 (3)	O7—Mo2—O4—C12	−172.8 (2)
Mo2—O7—Mo1—O2	108.07 (8)	O7—Mo2—N2—C7	4.4 (4)
Mo2—O7—Mo1—O5	−92.7 (1)	O7—Mo2—N2—C11	−172.9 (3)
Mo2—O7—Mo1—O6	117.2 (3)	O8—Mo1—Mo2—O9	99.7 (1)
Mo2—O7—Mo1—O8	17.97 (10)	O8—Mo1—Mo2—O10	−159.8 (1)
Mo2—O7—Mo1—N1	−179.27 (9)	O8—Mo1—Mo2—N2	−3.4 (1)
Mo2—O8—Mo1—O2	−104.04 (9)	O8—Mo1—O2—C6	−177.5 (3)
Mo2—O8—Mo1—O5	88.3 (1)	O8—Mo1—N1—C1	9.3 (5)
Mo2—O8—Mo1—O6	178.75 (9)	O8—Mo1—N1—C5	−177.2 (3)
Mo2—O8—Mo1—O7	−17.74 (10)	O8—Mo2—Mo1—N1	157.1 (1)
Mo2—O8—Mo1—N1	−108.4 (3)	O8—Mo2—O4—C12	92.5 (2)
Mo2—N2—C7—C8	−177.5 (2)	O8—Mo2—N2—C7	−93.8 (2)
Mo2—N2—C7—C12	4.0 (3)	O8—Mo2—N2—C11	88.9 (3)
Mo2—N2—C11—C10	176.2 (2)	O9—Mo2—Mo1—N1	−103.2 (1)
O1—C6—C1—N1	−170.2 (3)	O9—Mo2—O4—C12	−37.1 (4)
O1—C6—C1—C2	9.0 (5)	O9—Mo2—N2—C7	160.5 (2)
O2—Mo1—Mo2—O4	1.96 (8)	O9—Mo2—N2—C11	−16.8 (3)
O2—Mo1—Mo2—O7	−75.0 (1)	O10—Mo2—Mo1—N1	−2.7 (1)
O2—Mo1—Mo2—O8	81.1 (1)	O10—Mo2—O4—C12	−86.2 (2)
O2—Mo1—Mo2—O9	−179.21 (10)	O10—Mo2—N2—C7	72.2 (2)
O2—Mo1—Mo2—O10	−78.8 (1)	O10—Mo2—N2—C11	−105.1 (3)
O2—Mo1—Mo2—N2	77.7 (1)	N1—Mo1—Mo2—N2	153.7 (1)
O2—Mo1—N1—C1	4.6 (2)	N1—Mo1—O2—C6	1.1 (2)
O2—Mo1—N1—C5	178.2 (3)	N1—C1—C2—C3	2.0 (6)
O2—C6—C1—N1	9.6 (4)	N1—C5—C4—C3	−1.3 (6)
O2—C6—C1—C2	−171.2 (3)	N2—Mo2—O4—C12	4.2 (2)
O3—C12—C7—N2	179.1 (3)	N2—C7—C8—C9	0.2 (5)
O3—C12—C7—C8	0.6 (5)	N2—C11—C10—C9	1.9 (5)
O4—Mo2—Mo1—O5	175.44 (10)	C1—N1—C5—C4	1.5 (5)
O4—Mo2—Mo1—O6	−80.9 (1)	C1—C2—C3—C4	−1.7 (6)
O4—Mo2—Mo1—O7	77.0 (1)	C2—C1—N1—C5	−1.9 (5)
O4—Mo2—Mo1—O8	−79.1 (1)	C2—C3—C4—C5	1.4 (6)
O4—Mo2—Mo1—N1	78.0 (1)	C3—C2—C1—C6	−177.1 (3)
O4—Mo2—N2—C7	−4.2 (2)	C5—N1—C1—C6	177.3 (3)
O4—Mo2—N2—C11	178.6 (3)	C7—N2—C11—C10	−1.0 (5)
O4—C12—C7—N2	−0.6 (4)	C7—C8—C9—C10	0.8 (5)
O4—C12—C7—C8	−179.1 (3)	C8—C7—N2—C11	−0.1 (5)
O5—Mo1—Mo2—O7	98.5 (1)	C8—C9—C10—C11	−1.8 (5)
O5—Mo1—Mo2—O8	−105.5 (1)	C9—C8—C7—C12	178.6 (3)
O5—Mo1—Mo2—O9	−5.7 (1)	C11—N2—C7—C12	−178.6 (3)

Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z; (iii) −x, −y+1, −z; (iv) x−1, y, z; (v) −x−1, −y, −z; (vi) −x, −y, −z+1; (vii) x+1, y, z; (viii) −x, −y, −z; (ix) −x+1, −y+1, −z+1; (x) −x−1, −y, −z+1; (xi) x, y, z+1; (xii) −x+2, −y+1, −z+1; (xiii) x+1, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H12···O3^vii	0.905	1.699	2.594 (3)	169
O6—H13···O8^viii	0.929	1.772	2.654 (3)	158
O10—H14···O11^iv	0.928	1.730	2.643 (3)	167
O10—H15···O1^xi	0.888	1.805	2.658 (2)	160
O11—H16···O1ⁱⁱ	0.985	1.980	2.953 (4)	169
O11—H17···O7^ix	0.903	1.835	2.733 (3)	173

Symmetry codes: (ii) −x+1, −y+1, −z; (iv) x−1, y, z; (vii) x+1, y, z; (viii) −x, −y, −z; (ix) −x+1, −y+1, −z+1; (xi) x, y, z+1.

Experimental details

Crystal data
Chemical formula	[Mo₂O₂(C₆H₄NO₂)₂(H₂O)₂]·H₂O
M_r	554.13
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.260 (2), 12.145 (2), 8.261 (1)
α, β, γ (°)	98.02 (1), 101.89 (1), 103.68 (1)
V (Å³)	865.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.51
Crystal size (mm)	0.3 × 0.3 × 0.2

Data collection
Diffractometer	Rigaku AFC-5R diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.627, 0.739
No. of measured, independent and observed [I > 2σ(I)] reflections	4227, 3977, 3473
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.108, 0.92
No. of reflections	3473
No. of parameters	245
No. of restraints	?
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.52

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation and Rigaku Corporation, 1999), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation and Rigaku Corporation, 1999), SIR97 (Altomare et al., 1999) and DIRDIF94 (Beurskens et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), TEXSAN.

Selected geometric parameters (Å, º) top

Mo1—Mo2	2.5538 (5)	Mo2—O8	1.956 (3)
Mo1—O2	2.155 (2)	Mo2—O9	1.688 (3)
Mo1—O5	1.683 (3)	Mo2—O10	2.187 (3)
Mo1—O6	2.156 (3)	Mo2—N2	2.242 (2)
Mo1—O7	1.934 (3)	O1—C6	1.243 (4)
Mo1—O8	1.941 (2)	O2—C6	1.267 (4)
Mo1—N1	2.234 (3)	O3—C12	1.215 (4)
Mo2—O4	2.144 (2)	O4—C12	1.278 (3)
Mo2—O7	1.928 (2)

O2—Mo1—O5	157.3 (1)	O4—Mo2—N2	72.43 (9)
O2—Mo1—O6	77.23 (9)	O7—Mo2—O8	94.70 (10)
O2—Mo1—O7	86.28 (9)	O7—Mo2—O9	109.0 (1)
O2—Mo1—O8	90.43 (9)	O7—Mo2—O10	86.13 (10)
O2—Mo1—N1	72.44 (8)	O7—Mo2—N2	159.8 (1)
O5—Mo1—O6	91.1 (1)	O8—Mo2—O9	105.7 (1)
O5—Mo1—O7	103.5 (1)	O8—Mo2—O10	164.87 (9)
O5—Mo1—O8	108.7 (1)	O8—Mo2—N2	88.02 (9)
O5—Mo1—N1	87.8 (1)	O9—Mo2—O10	88.2 (1)
O6—Mo1—O7	163.30 (10)	O9—Mo2—N2	89.4 (1)
O6—Mo1—O8	87.83 (9)	O10—Mo2—N2	86.16 (9)
O6—Mo1—N1	87.07 (9)	Mo1—O2—C6	121.6 (2)
O7—Mo1—O8	95.01 (10)	Mo2—O4—C12	123.0 (2)
O7—Mo1—N1	85.42 (10)	Mo1—O7—Mo2	82.81 (8)
O8—Mo1—N1	162.81 (10)	Mo1—O8—Mo2	81.88 (8)
O4—Mo2—O7	87.56 (9)	Mo1—N1—C1	116.5 (2)
O4—Mo2—O8	89.06 (9)	Mo1—N1—C5	124.5 (2)
O4—Mo2—O9	156.4 (1)	Mo2—N2—C7	116.1 (2)
O4—Mo2—O10	75.87 (9)	Mo2—N2—C11	124.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H12···O3ⁱ	0.905	1.699	2.594 (3)	169
O6—H13···O8ⁱⁱ	0.929	1.772	2.654 (3)	158
O10—H14···O11ⁱⁱⁱ	0.928	1.730	2.643 (3)	167
O10—H15···O1^iv	0.888	1.805	2.658 (2)	160
O11—H16···O1^v	0.985	1.980	2.953 (4)	169
O11—H17···O7^vi	0.903	1.835	2.733 (3)	173

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

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