Aqua­[N′-(3-eth­oxy-2-oxidobenzyl-κO)furan-1-carbohydrazidato-κ2N′,O]dioxido­molybdenum(VI)–4,4′-bipyridine (2/1)

Ngan, N.K.; Wong, R.C.S.; Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536811017260

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page m748

doi:10.1107/S1600536811017260

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Aqua[N′-(3-ethoxy-2-oxidobenzyl-κO)furan-1-carbohydrazidato-κ²N′,O]dioxidomolybdenum(VI)–4,4′-bipyridine (2/1)

Ngui Khiong Ngan,^a Richard Chee Seng Wong,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 5 May 2011; accepted 7 May 2011; online 14 May 2011)

The Mo^VI atom in the title co-crystal, [Mo(C₁₄H₁₂N₂O₄)O₂(H₂O)]·0.5C₁₀H₈N₂, is O,N,O′-chelated by the deprotonated Schiff base and coordinated by the oxide and water O atoms in an octahedral geometry. The five-membered chelate ring is planar (r.m.s. deviation = 0.019 Å), but the six-membered chelate ring is puckered (r.m.s. deviation = 0.108 Å). Two mononuclear molecules are linked across a center of inversion by an O—H_water⋯O hydrogen bond; adjacent dinuclear units are linked by an water–4,4′-bipyridine O—H⋯N hydrogen bond, generating a linear chain structure. The 4,4′-bipyridine molecule is disordered over two positions in a 1:1 ratio.

Related literature

For a related Mo^VIO₂–4′,4-bipyridine adduct, see: Dinda et al. (2006 ).

Experimental

Crystal data

[Mo(C₁₄H₁₂N₂O₄)O₂(H₂O)]·0.5C₁₀H₈N₂
M_r = 496.30
Triclinic, $[P \overline 1]$
a = 7.9237 (1) Å
b = 10.1869 (1) Å
c = 13.3215 (2) Å
α = 78.7841 (5)°
β = 78.4605 (5)°
γ = 69.5728 (5)°
V = 978.15 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 100 K
0.2 × 0.2 × 0.2 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.649, T_max = 0.746
9175 measured reflections
4445 independent reflections
4266 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.076
S = 0.98
4445 reflections
275 parameters
24 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯N3	0.83 (1)	1.86 (1)	2.689 (3)	174 (3)
O1w—H12⋯N1ⁱ	0.84 (1)	1.97 (1)	2.794 (2)	167 (3)
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811017260/jh2290sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017260/jh2290Isup2.hkl

checkCIF report

Comment top

The Schiff bases that are synthesized by condensing salicylaldehyde (and its substituted analogs) with aroylhydrazides (and their substituted analogs) function as terdentate O,N,O'-chelates to a wide range of metal ions. A large number of metal derivatives have been reported; in octahedral systems, the ligand generally exists as a doubly-deprotonated species that chelates in a fac manner. A dioxomolybdenum(VI) derivative is known in which 4,4'-bipyridine binds to two metal atoms (Dinda et al., 2006). In the present study, a furan-type of Schiff base leads to a water-coordinated derivative in which 4,4'-bipyridine interacts indirectly, through the water molecule, in an outer-sphere coordination mode. The Mo^VI atom in the co-crystal, MoO₂(H₂O)(C₁₄H₁₂N₂O₄)^.0.5C₁₀H₁₀N₂, is O,N,O'-chelated by the deprotonated Schiff base and coordinated by the oxo and water O atoms in an octahedral geometry (Scheme I, Fig. 1). The five-membed chelate ring is planar [r.m.s. deviation 0.019 Å] but the six-membered chelate ring is puckered [r.m.s. deviation 0.108 Å]. Two mononuclear molecules are linked across a center-of-inversion by an O–H_water···O hydrogen bond; adjacent dinuclear units are linked by an O–H_water···N_{4,4'-bipyridine} hydrogen bond to generate a linear chain structure (Table 1). The 4,4'-bipyridine molecule is disordered over two positions in a 1:1 ratio.

Related literature top

For a related Mo^VIO₂–4',4-bipyridine adduct, see: Dinda et al. (2006).

Experimental top

3-Ethoxysalicylaldehyde (0.166 g, 1 mmol) and 2-furoylhydrazide (0.120 g, 1 mmol) were condensed in methanol (100 ml). The solution was heated to give a yellow coloration. The cool solution yielded the desired Schiff base as a yellow compound. The ligand (0.270 g, 1 mmol) and di(acetylacetonato)dioxomolybdenum(VI) (0.328 g, 1 mmol) were dissolved in heated in methanol for an hour. To the orange solution was added 4,4'-bipyridine (0.08 g, 0.5 mmol); heating was continued for another hour. The solution was filtered and set aside for the growth of crystals, m.p. 495–497 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of MoO₂(H₂O)(C₁₄H₁₂N₂O₄)^.0.5C₁₀H₁₀N₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the 4,4'-bipyridine molecule is not shown.

Aqua[N'-(3-ethoxy-2-oxidobenzyl-κO)furan-1-carbohydrazidato- κ²N',O]dioxidomolybdenum(VI)–4,4'-bipyridine (2/1) top

Crystal data top

[Mo(C₁₄H₁₂N₂O₄)O₂(H₂O)]·0.5C₁₀H₈N₂	Z = 2
M_r = 496.30	F(000) = 502
Triclinic, P1	D_x = 1.685 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9237 (1) Å	Cell parameters from 8273 reflections
b = 10.1869 (1) Å	θ = 2.5–28.2°
c = 13.3215 (2) Å	µ = 0.72 mm⁻¹
α = 78.7841 (5)°	T = 100 K
β = 78.4605 (5)°	Block, orange
γ = 69.5728 (5)°	0.2 × 0.2 × 0.2 mm
V = 978.15 (2) Å³

Data collection top

Bruker SMART APEX diffractometer	4445 independent reflections
Radiation source: fine-focus sealed tube	4266 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.649, T_max = 0.746	k = −13→13
9175 measured reflections	l = −17→17

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0474P)² + 1.0897P] where P = (F_o² + 2F_c²)/3
4445 reflections	(Δ/σ)_max = 0.001
275 parameters	Δρ_max = 0.73 e Å⁻³
24 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

[Mo(C₁₄H₁₂N₂O₄)O₂(H₂O)]·0.5C₁₀H₈N₂	γ = 69.5728 (5)°
M_r = 496.30	V = 978.15 (2) Å³
Triclinic, P1	Z = 2
a = 7.9237 (1) Å	Mo Kα radiation
b = 10.1869 (1) Å	µ = 0.72 mm⁻¹
c = 13.3215 (2) Å	T = 100 K
α = 78.7841 (5)°	0.2 × 0.2 × 0.2 mm
β = 78.4605 (5)°

Data collection top

Bruker SMART APEX diffractometer	4445 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4266 reflections with I > 2σ(I)
T_min = 0.649, T_max = 0.746	R_int = 0.019
9175 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	24 restraints
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.73 e Å⁻³
4445 reflections	Δρ_min = −0.72 e Å⁻³
275 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Mo1	0.74598 (2)	0.304217 (17)	0.170071 (12)	0.01695 (7)
O1	1.1355 (2)	0.30269 (16)	−0.20486 (13)	0.0246 (3)
O2	0.9252 (2)	0.21432 (15)	0.05147 (12)	0.0195 (3)
O3	0.6036 (2)	0.46573 (17)	0.23935 (12)	0.0218 (3)
O4	0.3337 (2)	0.5786 (2)	0.37565 (13)	0.0304 (4)
O5	0.8232 (2)	0.17630 (17)	0.26946 (12)	0.0224 (3)
O6	0.5697 (2)	0.26804 (17)	0.13977 (12)	0.0223 (3)
O1W	0.9855 (2)	0.36664 (17)	0.18299 (12)	0.0210 (3)
H11	1.047 (3)	0.327 (3)	0.2310 (16)	0.028 (8)*
H12	1.017 (4)	0.435 (2)	0.150 (2)	0.043 (9)*
N1	0.8802 (2)	0.43227 (18)	−0.05053 (13)	0.0173 (3)
N2	0.7547 (2)	0.47579 (18)	0.03625 (13)	0.0163 (3)
N3	1.1836 (3)	0.2227 (2)	0.33511 (17)	0.0305 (5)
C1	1.2652 (3)	0.2079 (3)	−0.26360 (19)	0.0270 (5)
H1	1.3224	0.2325	−0.3310	0.032*
C2	1.3007 (3)	0.0757 (3)	−0.2131 (2)	0.0275 (5)
H2	1.3847	−0.0080	−0.2377	0.033*
C3	1.1882 (3)	0.0854 (2)	−0.11569 (18)	0.0229 (4)
H3	1.1818	0.0099	−0.0622	0.027*
C4	1.0916 (3)	0.2245 (2)	−0.11444 (16)	0.0193 (4)
C5	0.9575 (3)	0.2954 (2)	−0.03452 (16)	0.0176 (4)
C6	0.6621 (3)	0.6087 (2)	0.02969 (16)	0.0179 (4)
H6	0.6873	0.6688	−0.0314	0.022*
C7	0.5219 (3)	0.6710 (2)	0.11060 (16)	0.0197 (4)
C8	0.4088 (3)	0.8115 (2)	0.08794 (18)	0.0240 (4)
H8	0.4312	0.8640	0.0224	0.029*
C9	0.2662 (3)	0.8737 (3)	0.1600 (2)	0.0297 (5)
H9	0.1900	0.9680	0.1436	0.036*
C10	0.2339 (3)	0.7978 (3)	0.25712 (19)	0.0304 (5)
H10	0.1334	0.8398	0.3059	0.036*
C11	0.3482 (3)	0.6612 (3)	0.28256 (18)	0.0252 (5)
C12	0.4943 (3)	0.5964 (2)	0.20924 (16)	0.0207 (4)
C13	0.1903 (3)	0.6364 (3)	0.45495 (19)	0.0340 (6)
H13A	0.0704	0.6616	0.4318	0.041*
H13B	0.2028	0.7225	0.4722	0.041*
C14	0.2070 (4)	0.5235 (4)	0.5478 (2)	0.0386 (6)
H14A	0.1101	0.5580	0.6041	0.058*
H14B	0.3257	0.5005	0.5703	0.058*
H14C	0.1960	0.4385	0.5293	0.058*
C15	1.2028 (5)	0.0903 (4)	0.3618 (3)	0.0214 (8)*	0.50
H15	1.1241	0.0543	0.3384	0.026*	0.50
C16	1.3288 (5)	−0.0028 (4)	0.4216 (3)	0.0206 (8)*	0.50
H16	1.3433	−0.1009	0.4325	0.025*	0.50
C15'	1.1327 (6)	0.1138 (4)	0.4102 (3)	0.0199 (8)*	0.50
H15'	1.0185	0.1015	0.4124	0.024*	0.50
C16'	1.2513 (5)	0.0266 (4)	0.4794 (3)	0.0208 (8)*	0.50
H16'	1.2182	−0.0413	0.5320	0.025*	0.50
C17	1.4335 (4)	0.0471 (2)	0.4655 (2)	0.0340 (6)
C18	1.4347 (8)	0.1850 (6)	0.4256 (5)	0.0223 (19)*	0.50
H18	1.5229	0.2190	0.4409	0.027*	0.50
C19	1.3061 (8)	0.2709 (7)	0.3637 (4)	0.0284 (19)*	0.50
H19	1.3025	0.3660	0.3403	0.034*	0.50
C18'	1.4505 (8)	0.1689 (6)	0.4113 (5)	0.0148 (14)*	0.50
H18'	1.5499	0.1977	0.4166	0.018*	0.50
C19'	1.3228 (6)	0.2528 (5)	0.3477 (4)	0.0116 (11)*	0.50
H19'	1.3389	0.3383	0.3109	0.014*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mo1	0.01730 (11)	0.01891 (11)	0.01575 (11)	−0.00872 (7)	−0.00505 (7)	0.00321 (7)
O1	0.0285 (8)	0.0188 (7)	0.0251 (8)	−0.0096 (6)	0.0024 (6)	−0.0023 (6)
O2	0.0230 (7)	0.0158 (7)	0.0197 (7)	−0.0081 (6)	−0.0036 (6)	0.0017 (5)
O3	0.0227 (7)	0.0251 (8)	0.0170 (7)	−0.0075 (6)	−0.0037 (6)	−0.0008 (6)
O4	0.0255 (8)	0.0428 (10)	0.0201 (8)	−0.0114 (8)	0.0031 (6)	−0.0039 (7)
O5	0.0226 (7)	0.0246 (8)	0.0220 (7)	−0.0124 (6)	−0.0085 (6)	0.0068 (6)
O6	0.0212 (7)	0.0279 (8)	0.0204 (7)	−0.0117 (6)	−0.0057 (6)	0.0007 (6)
O1W	0.0224 (8)	0.0227 (8)	0.0212 (7)	−0.0133 (6)	−0.0097 (6)	0.0074 (6)
N1	0.0178 (8)	0.0179 (8)	0.0163 (8)	−0.0066 (7)	−0.0023 (6)	−0.0013 (6)
N2	0.0162 (8)	0.0193 (8)	0.0140 (8)	−0.0062 (7)	−0.0041 (6)	−0.0011 (6)
N3	0.0383 (12)	0.0186 (9)	0.0381 (12)	−0.0039 (8)	−0.0241 (9)	−0.0027 (8)
C1	0.0269 (11)	0.0288 (11)	0.0255 (11)	−0.0111 (9)	0.0035 (9)	−0.0081 (9)
C2	0.0260 (11)	0.0220 (11)	0.0355 (13)	−0.0066 (9)	−0.0012 (9)	−0.0116 (9)
C3	0.0216 (10)	0.0179 (10)	0.0285 (11)	−0.0063 (8)	−0.0049 (8)	−0.0006 (8)
C4	0.0196 (9)	0.0186 (10)	0.0217 (10)	−0.0087 (8)	−0.0045 (8)	−0.0010 (8)
C5	0.0177 (9)	0.0182 (9)	0.0192 (9)	−0.0082 (8)	−0.0062 (7)	0.0002 (7)
C6	0.0191 (9)	0.0193 (9)	0.0165 (9)	−0.0071 (8)	−0.0065 (7)	0.0006 (7)
C7	0.0183 (9)	0.0222 (10)	0.0198 (10)	−0.0054 (8)	−0.0063 (8)	−0.0046 (8)
C8	0.0235 (11)	0.0244 (11)	0.0223 (10)	−0.0030 (9)	−0.0078 (8)	−0.0036 (8)
C9	0.0230 (11)	0.0308 (12)	0.0308 (12)	0.0022 (9)	−0.0088 (9)	−0.0091 (10)
C10	0.0195 (10)	0.0425 (14)	0.0272 (12)	−0.0035 (10)	−0.0025 (9)	−0.0133 (10)
C11	0.0204 (10)	0.0371 (13)	0.0209 (10)	−0.0115 (9)	−0.0031 (8)	−0.0061 (9)
C12	0.0185 (10)	0.0252 (10)	0.0203 (10)	−0.0077 (8)	−0.0053 (8)	−0.0039 (8)
C13	0.0256 (12)	0.0534 (16)	0.0240 (11)	−0.0151 (11)	0.0054 (9)	−0.0122 (11)
C14	0.0331 (14)	0.0623 (19)	0.0219 (12)	−0.0197 (13)	0.0026 (10)	−0.0080 (12)
C17	0.0435 (15)	0.0168 (10)	0.0499 (16)	−0.0094 (10)	−0.0341 (13)	0.0040 (10)

Geometric parameters (Å, º) top

Mo1—O6	1.7007 (15)	C7—C8	1.410 (3)
Mo1—O5	1.7093 (15)	C8—C9	1.379 (3)
Mo1—O3	1.9262 (16)	C8—H8	0.9500
Mo1—O2	2.0270 (15)	C9—C10	1.398 (4)
Mo1—O1W	2.2479 (15)	C9—H9	0.9500
Mo1—N2	2.2495 (17)	C10—C11	1.389 (4)
O1—C4	1.364 (3)	C10—H10	0.9500
O1—C1	1.371 (3)	C11—C12	1.413 (3)
O2—C5	1.313 (2)	C13—C14	1.509 (4)
O3—C12	1.345 (3)	C13—H13A	0.9900
O4—C11	1.365 (3)	C13—H13B	0.9900
O4—C13	1.431 (3)	C14—H14A	0.9800
O1W—H11	0.833 (10)	C14—H14B	0.9800
O1W—H12	0.837 (11)	C14—H14C	0.9800
N1—C5	1.305 (3)	C15—C16	1.377 (5)
N1—N2	1.398 (2)	C15—H15	0.9500
N2—C6	1.291 (3)	C16—C17	1.376 (4)
N3—C15	1.288 (4)	C16—H16	0.9500
N3—C19'	1.291 (5)	C15'—C16'	1.403 (5)
N3—C19	1.371 (6)	C15'—H15'	0.9500
N3—C15'	1.454 (4)	C16'—C17	1.500 (5)
C1—C2	1.344 (4)	C16'—H16'	0.9500
C1—H1	0.9500	C17—C18'	1.345 (5)
C2—C3	1.419 (3)	C17—C18	1.405 (6)
C2—H2	0.9500	C17—C17ⁱ	1.487 (4)
C3—C4	1.356 (3)	C18—C19	1.386 (7)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.448 (3)	C19—H19	0.9500
C6—C7	1.447 (3)	C18'—C19'	1.389 (6)
C6—H6	0.9500	C18'—H18'	0.9500
C7—C12	1.402 (3)	C19'—H19'	0.9500

O6—Mo1—O5	105.24 (7)	C8—C9—H9	120.0
O6—Mo1—O3	97.40 (7)	C10—C9—H9	120.0
O5—Mo1—O3	103.06 (7)	C11—C10—C9	120.2 (2)
O6—Mo1—O2	93.86 (7)	C11—C10—H10	119.9
O5—Mo1—O2	98.70 (7)	C9—C10—H10	119.9
O3—Mo1—O2	151.84 (6)	O4—C11—C10	125.6 (2)
O6—Mo1—O1W	170.71 (7)	O4—C11—C12	114.2 (2)
O5—Mo1—O1W	82.87 (6)	C10—C11—C12	120.2 (2)
O3—Mo1—O1W	84.91 (6)	O3—C12—C7	123.18 (19)
O2—Mo1—O1W	80.25 (6)	O3—C12—C11	117.5 (2)
O6—Mo1—N2	95.98 (7)	C7—C12—C11	119.3 (2)
O5—Mo1—N2	157.48 (7)	O4—C13—C14	106.5 (2)
O3—Mo1—N2	81.20 (6)	O4—C13—H13A	110.4
O2—Mo1—N2	71.99 (6)	C14—C13—H13A	110.4
O1W—Mo1—N2	75.43 (6)	O4—C13—H13B	110.4
C4—O1—C1	105.58 (18)	C14—C13—H13B	110.4
C5—O2—Mo1	118.96 (13)	H13A—C13—H13B	108.6
C12—O3—Mo1	134.52 (14)	C13—C14—H14A	109.5
C11—O4—C13	118.0 (2)	C13—C14—H14B	109.5
Mo1—O1W—H11	120.4 (18)	H14A—C14—H14B	109.5
Mo1—O1W—H12	128.8 (19)	C13—C14—H14C	109.5
H11—O1W—H12	110.1 (17)	H14A—C14—H14C	109.5
C5—N1—N2	109.13 (17)	H14B—C14—H14C	109.5
C6—N2—N1	115.97 (17)	N3—C15—C16	124.9 (4)
C6—N2—Mo1	128.78 (14)	N3—C15—H15	117.5
N1—N2—Mo1	115.24 (12)	C16—C15—H15	117.5
C15—N3—C19	116.8 (4)	C17—C16—C15	119.5 (4)
C19'—N3—C15'	117.2 (3)	C17—C16—H16	120.2
C2—C1—O1	110.9 (2)	C15—C16—H16	120.2
C2—C1—H1	124.5	C16'—C15'—N3	120.4 (4)
O1—C1—H1	124.5	C16'—C15'—H15'	119.8
C1—C2—C3	106.6 (2)	N3—C15'—H15'	119.8
C1—C2—H2	126.7	C15'—C16'—C17	116.0 (3)
C3—C2—H2	126.7	C15'—C16'—H16'	122.0
C4—C3—C2	106.1 (2)	C17—C16'—H16'	122.0
C4—C3—H3	126.9	C16—C17—C18	115.8 (3)
C2—C3—H3	126.9	C18'—C17—C17ⁱ	122.4 (3)
C3—C4—O1	110.83 (19)	C16—C17—C17ⁱ	122.2 (3)
C3—C4—C5	130.1 (2)	C18—C17—C17ⁱ	120.9 (3)
O1—C4—C5	119.02 (18)	C18'—C17—C16'	117.6 (3)
N1—C5—O2	124.54 (19)	C17ⁱ—C17—C16'	117.9 (3)
N1—C5—C4	119.62 (19)	C19—C18—C17	119.3 (5)
O2—C5—C4	115.83 (18)	C19—C18—H18	120.4
N2—C6—C7	123.35 (19)	C17—C18—H18	120.4
N2—C6—H6	118.3	N3—C19—C18	121.9 (6)
C7—C6—H6	118.3	N3—C19—H19	119.1
C12—C7—C8	119.5 (2)	C18—C19—H19	119.1
C12—C7—C6	122.4 (2)	C17—C18'—C19'	120.1 (4)
C8—C7—C6	118.11 (19)	C17—C18'—H18'	119.9
C9—C8—C7	120.7 (2)	C19'—C18'—H18'	119.9
C9—C8—H8	119.7	N3—C19'—C18'	124.6 (4)
C7—C8—H8	119.7	N3—C19'—H19'	117.7
C8—C9—C10	120.0 (2)	C18'—C19'—H19'	117.7

O6—Mo1—O2—C5	97.28 (15)	C13—O4—C11—C12	179.4 (2)
O5—Mo1—O2—C5	−156.65 (15)	C9—C10—C11—O4	177.9 (2)
O3—Mo1—O2—C5	−16.3 (2)	C9—C10—C11—C12	−2.1 (4)
O1W—Mo1—O2—C5	−75.49 (14)	Mo1—O3—C12—C7	−32.0 (3)
N2—Mo1—O2—C5	2.25 (14)	Mo1—O3—C12—C11	149.69 (17)
O6—Mo1—O3—C12	−66.0 (2)	C8—C7—C12—O3	−175.3 (2)
O5—Mo1—O3—C12	−173.64 (19)	C6—C7—C12—O3	5.3 (3)
O2—Mo1—O3—C12	46.7 (3)	C8—C7—C12—C11	3.0 (3)
O1W—Mo1—O3—C12	104.91 (19)	C6—C7—C12—C11	−176.4 (2)
N2—Mo1—O3—C12	28.90 (19)	O4—C11—C12—O3	−2.0 (3)
C5—N1—N2—C6	−177.34 (18)	C10—C11—C12—O3	178.0 (2)
C5—N1—N2—Mo1	3.9 (2)	O4—C11—C12—C7	179.61 (19)
O6—Mo1—N2—C6	85.90 (18)	C10—C11—C12—C7	−0.3 (3)
O5—Mo1—N2—C6	−113.6 (2)	C11—O4—C13—C14	180.0 (2)
O3—Mo1—N2—C6	−10.70 (18)	C19'—N3—C15—C16	16.4 (3)
O2—Mo1—N2—C6	178.02 (19)	C19—N3—C15—C16	4.2 (3)
O1W—Mo1—N2—C6	−97.69 (18)	C15'—N3—C15—C16	−89.7 (5)
O6—Mo1—N2—N1	−95.50 (14)	N3—C15—C16—C17	6.3 (3)
O5—Mo1—N2—N1	65.0 (2)	C15—N3—C15'—C16'	76.3 (5)
O3—Mo1—N2—N1	167.90 (14)	C19'—N3—C15'—C16'	−12.7 (5)
O2—Mo1—N2—N1	−3.38 (12)	C19—N3—C15'—C16'	−25.7 (5)
O1W—Mo1—N2—N1	80.91 (13)	N3—C15'—C16'—C17	−4.0 (5)
C4—O1—C1—C2	0.5 (3)	C15—C16—C17—C18'	−25.2 (4)
O1—C1—C2—C3	−0.4 (3)	C15—C16—C17—C18	−14.9 (4)
C1—C2—C3—C4	0.1 (3)	C15—C16—C17—C17ⁱ	177.4 (3)
C2—C3—C4—O1	0.2 (3)	C15—C16—C17—C16'	82.9 (4)
C2—C3—C4—C5	−179.5 (2)	C15'—C16'—C17—C18'	18.8 (6)
C1—O1—C4—C3	−0.4 (2)	C15'—C16'—C17—C16	−70.2 (4)
C1—O1—C4—C5	179.28 (19)	C15'—C16'—C17—C18	30.1 (5)
N2—N1—C5—O2	−2.2 (3)	C15'—C16'—C17—C17ⁱ	−177.6 (3)
N2—N1—C5—C4	179.02 (17)	C18'—C17—C18—C19	80 (2)
Mo1—O2—C5—N1	−0.9 (3)	C16—C17—C18—C19	13.7 (6)
Mo1—O2—C5—C4	177.96 (13)	C17ⁱ—C17—C18—C19	−178.5 (5)
C3—C4—C5—N1	−179.8 (2)	C16'—C17—C18—C19	−27.0 (6)
O1—C4—C5—N1	0.6 (3)	C15—N3—C19—C18	−5.3 (6)
C3—C4—C5—O2	1.3 (3)	C19'—N3—C19—C18	−76 (2)
O1—C4—C5—O2	−178.33 (18)	C15'—N3—C19—C18	30.5 (6)
N1—N2—C6—C7	177.65 (18)	C17—C18—C19—N3	−3.8 (7)
Mo1—N2—C6—C7	−3.8 (3)	C16—C17—C18'—C19'	22.4 (7)
N2—C6—C7—C12	10.2 (3)	C18—C17—C18'—C19'	−95 (2)
N2—C6—C7—C8	−169.2 (2)	C17ⁱ—C17—C18'—C19'	179.8 (5)
C12—C7—C8—C9	−3.2 (3)	C16'—C17—C18'—C19'	−17.4 (7)
C6—C7—C8—C9	176.2 (2)	C15—N3—C19'—C18'	−19.5 (7)
C7—C8—C9—C10	0.8 (4)	C19—N3—C19'—C18'	95 (2)
C8—C9—C10—C11	1.9 (4)	C15'—N3—C19'—C18'	15.7 (7)
C13—O4—C11—C10	−0.6 (3)	C17—C18'—C19'—N3	−0.3 (9)

Symmetry code: (i) −x+3, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···N3	0.83 (1)	1.86 (1)	2.689 (3)	174 (3)
O1w—H12···N1ⁱⁱ	0.84 (1)	1.97 (1)	2.794 (2)	167 (3)

Symmetry code: (ii) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Mo(C₁₄H₁₂N₂O₄)O₂(H₂O)]·0.5C₁₀H₈N₂
M_r	496.30
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.9237 (1), 10.1869 (1), 13.3215 (2)
α, β, γ (°)	78.7841 (5), 78.4605 (5), 69.5728 (5)
V (Å³)	978.15 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.2 × 0.2 × 0.2

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.649, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	9175, 4445, 4266
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.076, 0.98
No. of reflections	4445
No. of parameters	275
No. of restraints	24
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.72

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···N3	0.83 (1)	1.86 (1)	2.689 (3)	174 (3)
O1w—H12···N1ⁱ	0.84 (1)	1.97 (1)	2.794 (2)	167 (3)

Symmetry code: (i) −x+2, −y+1, −z.

Acknowledgements

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dinda, R., Ghosh, S., Falvello, L. R., Tomas, M. & Mak, T. C. W. (2006). Polyhedron, 25, 2375–2382. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). 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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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