[2-(1-{2-[Aza­nid­yl(ethyl­sulfan­yl)methyl­idene-κN]hydrazin-1-yl­idene-κN1}eth­yl)phenolato-κO](dimethyl sulfoxide-κO)dioxidomolybdenum(VI)

Takjoo, R.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812026566

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages m944-m945

https://doi.org/10.1107/S1600536812026566

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[2-(1-{2-[Azanidyl(ethylsulfanyl)methylidene-κN]hydrazin-1-ylidene-κN¹}ethyl)phenolato-κO](dimethyl sulfoxide-κO)dioxidomolybdenum(VI)

Reza Takjoo,^a ‡ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, School of Sciences, Ferdowsi University of Mashhad, 91775-1436 Mashhad, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department and Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 11 June 2012; accepted 12 June 2012; online 20 June 2012)

The Mo^VI atom in the title complex, [Mo(C₁₁H₁₃N₃OS)O₂(C₂H₆OS)], is N,N′,O-coordinated by the dianionic tridentate ligand, two mutually cis oxide O atoms and a dimethyl sulfoxide O atom, defining a distorted octahedral N₂O₄ donor set. The most prominent feature of the crystal packing is the formation of inversion dimers via pairs of N—H⋯O hydrogen bonds and eight-membered {⋯HNMoO}₂ loops. The Schiff base ligand is disordered over two orientations of equal occupancy.

Related literature

For the coordination chemistry and medicinal applications of thiosemicarbazone derivatives, see: Ahmadi et al. (2012 ); Dilworth & Hueting (2012 ). For related structures, see: Ceylan et al. (2009 ); Takjoo et al. (2012 ).

Experimental

Crystal data

[Mo(C₁₁H₁₃N₃OS)O₂(C₂H₆OS)]
M_r = 441.37
Triclinic, $[P \overline 1]$
a = 8.0411 (3) Å
b = 9.7243 (3) Å
c = 12.0849 (4) Å
α = 73.387 (3)°
β = 84.465 (3)°
γ = 86.077 (3)°
V = 900.47 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.98 mm⁻¹
T = 100 K
0.35 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.691, T_max = 1.000
13626 measured reflections
4149 independent reflections
3811 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.072
S = 1.03
4149 reflections
234 parameters
100 restraints
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.87 e Å⁻³

Table 1
Selected bond lengths (Å)

Mo—O1	2.011 (7)
Mo—O2	2.2747 (16)
Mo—O3	1.7133 (16)
Mo—O4	1.7021 (18)
Mo—N1	2.193 (6)
Mo—N3	1.933 (15)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3n⋯O3ⁱ	0.88	2.23	3.090 (15)	166
N3′—H3n′⋯O3ⁱ	0.88	1.94	2.816 (16)	171
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812026566/hb6848sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812026566/hb6848Isup2.hkl

checkCIF report

Comment top

Schiff bases derived from S-alkyl esters of thiosemicarbazone are capable of complexing both transition and main group metals (Ahmadi et al., 2012) and these may be used as therapeutic and imaging agents (Dilworth & Hueting, 2012). Herein, the crystal and molecular structure of the title complex, (I), is described, which was determined as a part of on-going studies (Takjoo et al., 2012).

The Mo^VI atom in (I), Fig. 1, exists within a distorted octahedral N₂O₄ donor set defined by the N,N,O atoms of the dinegative tridentate ligand, two oxo-O atoms and a DMSO-O atom, Table 1; the oxo-O atoms are cis. The dihedral angle between the five- and six-membered chelate rings is 11.34 (19) Å indicating some bending in the Schiff base ligand (the comparable angle in the second conformation of the disordered ligand is 7.81 (17)°). The molecular structure resembles that of the complex where the Mo atom is coordinated by methanol rather than DMSO (Ceylan et al., 2009).

While whole molecule disorder of the Schiff base ligands precludes a detailed analysis of the crystal packing, a common feature of both orientations is the formation of N—H···O hydrogen bonds between centrosymmetrically related molecules to form a dimeric aggregate via an eight-membered {···HNMoO}₂ synthon, Fig. 2 and Table 2.

Related literature top

For the coordination chemistry and medicinal applications of thiosemicarbazone derivatives, see: Ahmadi et al. (2012); Dilworth & Hueting (2012). For related structures, see: Ceylan et al. (2009); Takjoo et al. (2012).

Experimental top

An ethanolic solution (3 ml) of molybdenyl acetylacetonate (0.33 g, 1 mmol) was added drop-wise to an ethanolic solution (3 ml) of 1-(2-hydroxyphenyl)ethanone S-ethylisothiosemicarbazone hydrobromide (0.32 g, 1 mmol) under stirring. The clear solution was stirred for 1 h and yellow precipitate was appeared. The product was then filtered, washed with cold ethanol and dried in air. The resulting compound was dissolved in DMSO (2 ml) and by slow evaporation of the solvent orange prisms appeared after one week. M.pt. 427 K. Yield: 33%.

Structure description top

For the coordination chemistry and medicinal applications of thiosemicarbazone derivatives, see: Ahmadi et al. (2012); Dilworth & Hueting (2012). For related structures, see: Ceylan et al. (2009); Takjoo et al. (2012).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the centrosymmetric aggregate in (I) mediated by N—H···O hydrogen bonds, shown as blue dashed lines. A similar arragement is found for the second conformation of the Schiff base ligand.

[2-(1-{2-[Azanidyl(ethylsulfanyl)methylidene-κN]hydrazin-1-ylidene- κN¹}ethyl)phenolato-κO](dimethyl sulfoxide-κO)dioxidomolybdenum(VI) top

Crystal data top

[Mo(C₁₁H₁₃N₃OS)O₂(C₂H₆OS)]	Z = 2
M_r = 441.37	F(000) = 448
Triclinic, P1	D_x = 1.628 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0411 (3) Å	Cell parameters from 8498 reflections
b = 9.7243 (3) Å	θ = 2.4–27.5°
c = 12.0849 (4) Å	µ = 0.98 mm⁻¹
α = 73.387 (3)°	T = 100 K
β = 84.465 (3)°	Prism, orange
γ = 86.077 (3)°	0.35 × 0.15 × 0.05 mm
V = 900.47 (5) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4149 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3811 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.037
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.4°
ω scan	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −12→12
T_min = 0.691, T_max = 1.000	l = −15→15
13626 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0278P)² + 1.0887P] where P = (F_o² + 2F_c²)/3
4149 reflections	(Δ/σ)_max = 0.001
234 parameters	Δρ_max = 0.73 e Å⁻³
100 restraints	Δρ_min = −0.87 e Å⁻³

Crystal data top

[Mo(C₁₁H₁₃N₃OS)O₂(C₂H₆OS)]	γ = 86.077 (3)°
M_r = 441.37	V = 900.47 (5) Å³
Triclinic, P1	Z = 2
a = 8.0411 (3) Å	Mo Kα radiation
b = 9.7243 (3) Å	µ = 0.98 mm⁻¹
c = 12.0849 (4) Å	T = 100 K
α = 73.387 (3)°	0.35 × 0.15 × 0.05 mm
β = 84.465 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4149 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	3811 reflections with I > 2σ(I)
T_min = 0.691, T_max = 1.000	R_int = 0.037
13626 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	100 restraints
wR(F²) = 0.072	H-atom parameters constrained
S = 1.03	Δρ_max = 0.73 e Å⁻³
4149 reflections	Δρ_min = −0.87 e Å⁻³
234 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)
Mo	0.39828 (2)	0.62362 (2)	0.284368 (16)	0.01779 (7)
S2	−0.02453 (7)	0.59823 (6)	0.30257 (5)	0.02079 (13)
O2	0.13555 (19)	0.56941 (17)	0.36645 (13)	0.0208 (3)
O3	0.4236 (2)	0.67549 (16)	0.40557 (15)	0.0217 (3)
O4	0.5828 (2)	0.6597 (2)	0.20227 (15)	0.0370 (5)
C12	−0.1234 (3)	0.4305 (3)	0.3508 (2)	0.0268 (5)
H12A	−0.0630	0.3620	0.3141	0.040*
H12B	−0.2393	0.4441	0.3296	0.040*
H12C	−0.1223	0.3934	0.4351	0.040*
C13	−0.1570 (3)	0.6982 (2)	0.3810 (2)	0.0221 (5)
H13A	−0.1176	0.7959	0.3631	0.033*
H13B	−0.1547	0.6515	0.4643	0.033*
H13C	−0.2717	0.7022	0.3588	0.033*
S1	0.4023 (2)	0.14457 (15)	0.38075 (13)	0.0307 (3)	0.50
O1	0.2528 (12)	0.7850 (6)	0.1938 (4)	0.0162 (9)	0.50
N1	0.3150 (11)	0.5172 (5)	0.1633 (5)	0.0149 (10)	0.50
N2	0.3133 (9)	0.3667 (6)	0.2053 (4)	0.0203 (9)	0.50
N3	0.439 (3)	0.4201 (15)	0.3527 (10)	0.0137 (16)	0.50
H3n	0.4952	0.3893	0.4149	0.016*	0.50
C1	0.2566 (5)	0.8284 (3)	0.07631 (19)	0.0176 (9)	0.50
C2	0.2480 (5)	0.9757 (3)	0.0241 (3)	0.0275 (8)	0.50
H2	0.2412	1.0405	0.0703	0.033*	0.50
C3	0.2494 (5)	1.0281 (3)	−0.0957 (3)	0.0329 (9)	0.50
H3	0.2435	1.1287	−0.1314	0.040*	0.50
C4	0.2593 (5)	0.9332 (4)	−0.16331 (19)	0.0335 (9)	0.50
H4	0.2602	0.9691	−0.2452	0.040*	0.50
C5	0.2679 (5)	0.7860 (3)	−0.1111 (3)	0.0278 (8)	0.50
H5	0.2747	0.7211	−0.1573	0.033*	0.50
C6	0.2666 (4)	0.7335 (2)	0.0087 (3)	0.0183 (8)	0.50
C7	0.2706 (7)	0.5771 (6)	0.0576 (4)	0.0188 (9)	0.50
C8	0.2263 (7)	0.4788 (6)	−0.0121 (4)	0.0277 (8)	0.50
H8A	0.1657	0.3976	0.0391	0.042*	0.50
H8B	0.3291	0.4431	−0.0472	0.042*	0.50
H8C	0.1557	0.5326	−0.0732	0.042*	0.50
C9	0.3817 (12)	0.3257 (6)	0.3040 (5)	0.0185 (11)	0.50
C10	0.3280 (7)	0.0531 (6)	0.2844 (5)	0.0306 (9)	0.50
H10A	0.3694	0.1019	0.2038	0.037*	0.50
H10B	0.3759	−0.0467	0.3039	0.037*	0.50
C11	0.1370 (8)	0.0490 (7)	0.2911 (6)	0.0422 (12)	0.50
H11A	0.1011	0.0621	0.2134	0.063*	0.50
H11B	0.0866	0.1263	0.3222	0.063*	0.50
H11C	0.1013	−0.0439	0.3419	0.063*	0.50
S1'	0.3906 (2)	0.12666 (15)	0.43708 (13)	0.0307 (3)	0.50
O1'	0.2699 (12)	0.7538 (6)	0.1728 (4)	0.0162 (9)	0.50
N1'	0.3129 (11)	0.4692 (6)	0.1856 (5)	0.0149 (10)	0.50
N2'	0.3038 (9)	0.3236 (6)	0.2459 (4)	0.0203 (9)	0.50
N3'	0.434 (3)	0.4047 (15)	0.3800 (10)	0.0137 (16)	0.50
H3n'	0.4895	0.3818	0.4426	0.016*	0.50
C1'	0.2776 (5)	0.7739 (3)	0.05697 (19)	0.0176 (9)	0.50
C2'	0.2822 (5)	0.9143 (3)	−0.0140 (3)	0.0275 (8)	0.50
H2'	0.2816	0.9919	0.0193	0.033*	0.50
C3'	0.2878 (5)	0.9413 (3)	−0.1336 (3)	0.0329 (9)	0.50
H3'	0.2910	1.0372	−0.1821	0.040*	0.50
C4'	0.2888 (5)	0.8278 (4)	−0.18223 (19)	0.0335 (9)	0.50
H4'	0.2926	0.8462	−0.2640	0.040*	0.50
C5'	0.2841 (5)	0.6874 (3)	−0.1113 (3)	0.0278 (8)	0.50
H5'	0.2847	0.6099	−0.1445	0.033*	0.50
C6'	0.2785 (5)	0.6605 (3)	0.0083 (2)	0.0183 (8)	0.50
C7'	0.2681 (7)	0.5090 (6)	0.0789 (5)	0.0188 (9)	0.50
C8'	0.2100 (7)	0.3937 (6)	0.0307 (4)	0.0277 (8)	0.50
H8'A	0.1395	0.3280	0.0906	0.042*	0.50
H8'B	0.3076	0.3399	0.0065	0.042*	0.50
H8'C	0.1456	0.4388	−0.0362	0.042*	0.50
C9'	0.3720 (12)	0.3009 (6)	0.3435 (5)	0.0185 (11)	0.50
C10'	0.3169 (7)	0.0189 (5)	0.3535 (5)	0.0306 (9)	0.50
H10C	0.3611	0.0564	0.2717	0.037*	0.50
H10D	0.3621	−0.0809	0.3826	0.037*	0.50
C11'	0.1275 (8)	0.0176 (7)	0.3585 (6)	0.0422 (12)	0.50
H11D	0.0958	−0.0464	0.3151	0.063*	0.50
H11E	0.0821	0.1151	0.3241	0.063*	0.50
H11F	0.0823	−0.0167	0.4394	0.063*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mo	0.01666 (11)	0.01953 (11)	0.01794 (11)	−0.00370 (7)	−0.00961 (7)	−0.00315 (8)
S2	0.0173 (3)	0.0254 (3)	0.0192 (3)	−0.0038 (2)	−0.0098 (2)	−0.0022 (2)
O2	0.0160 (8)	0.0250 (8)	0.0199 (8)	−0.0045 (6)	−0.0099 (6)	−0.0005 (7)
O3	0.0200 (8)	0.0159 (8)	0.0345 (9)	0.0010 (6)	−0.0119 (7)	−0.0130 (7)
O4	0.0225 (9)	0.0648 (14)	0.0226 (9)	−0.0156 (9)	−0.0076 (7)	−0.0053 (9)
C12	0.0229 (12)	0.0233 (12)	0.0397 (14)	−0.0036 (10)	−0.0110 (10)	−0.0141 (11)
C13	0.0203 (11)	0.0164 (11)	0.0312 (12)	−0.0030 (9)	−0.0110 (9)	−0.0056 (9)
S1	0.0580 (6)	0.0097 (4)	0.0242 (6)	0.0007 (4)	−0.0099 (8)	−0.0029 (6)
O1	0.0220 (19)	0.012 (2)	0.0160 (17)	0.0021 (19)	−0.0077 (17)	−0.0041 (12)
N1	0.0204 (11)	0.008 (3)	0.015 (2)	−0.006 (3)	−0.0055 (18)	0.000 (2)
N2	0.0332 (15)	0.012 (3)	0.017 (3)	−0.005 (2)	−0.010 (2)	−0.0030 (19)
N3	0.0215 (15)	0.012 (2)	0.008 (5)	0.000 (2)	−0.009 (5)	−0.002 (3)
C1	0.0167 (15)	0.021 (2)	0.0157 (15)	−0.0021 (17)	−0.0070 (12)	−0.0037 (15)
C2	0.031 (2)	0.021 (2)	0.028 (2)	−0.0037 (16)	−0.0094 (16)	−0.0009 (13)
C3	0.036 (2)	0.028 (2)	0.028 (2)	−0.0096 (17)	−0.0079 (16)	0.0077 (15)
C4	0.029 (2)	0.045 (2)	0.0224 (18)	−0.0022 (18)	−0.0092 (15)	−0.0005 (18)
C5	0.0245 (17)	0.039 (2)	0.0215 (15)	−0.0002 (18)	−0.0089 (13)	−0.0087 (18)
C6	0.0172 (14)	0.017 (2)	0.0203 (14)	−0.0016 (19)	−0.0079 (11)	−0.003 (2)
C7	0.0164 (13)	0.021 (3)	0.025 (2)	−0.003 (2)	−0.0070 (14)	−0.014 (2)
C8	0.037 (2)	0.031 (2)	0.0202 (19)	−0.0053 (19)	−0.0133 (16)	−0.0112 (15)
C9	0.0272 (17)	0.011 (2)	0.018 (4)	−0.0034 (18)	−0.002 (3)	−0.004 (2)
C10	0.046 (2)	0.0160 (18)	0.034 (2)	−0.0063 (15)	0.000 (2)	−0.0140 (19)
C11	0.048 (2)	0.034 (3)	0.052 (3)	−0.0188 (19)	0.012 (3)	−0.026 (3)
S1'	0.0580 (6)	0.0097 (4)	0.0242 (6)	0.0007 (4)	−0.0099 (8)	−0.0029 (6)
O1'	0.0220 (19)	0.012 (2)	0.0160 (17)	0.0021 (19)	−0.0077 (17)	−0.0041 (12)
N1'	0.0204 (11)	0.008 (3)	0.015 (2)	−0.006 (3)	−0.0055 (18)	0.000 (2)
N2'	0.0332 (15)	0.012 (3)	0.017 (3)	−0.005 (2)	−0.010 (2)	−0.0030 (19)
N3'	0.0215 (15)	0.012 (2)	0.008 (5)	0.000 (2)	−0.009 (5)	−0.002 (3)
C1'	0.0167 (15)	0.021 (2)	0.0157 (15)	−0.0021 (17)	−0.0070 (12)	−0.0037 (15)
C2'	0.031 (2)	0.021 (2)	0.028 (2)	−0.0037 (16)	−0.0094 (16)	−0.0009 (13)
C3'	0.036 (2)	0.028 (2)	0.028 (2)	−0.0096 (17)	−0.0079 (16)	0.0077 (15)
C4'	0.029 (2)	0.045 (2)	0.0224 (18)	−0.0022 (18)	−0.0092 (15)	−0.0005 (18)
C5'	0.0245 (17)	0.039 (2)	0.0215 (15)	−0.0002 (18)	−0.0089 (13)	−0.0087 (18)
C6'	0.0172 (14)	0.017 (2)	0.0203 (14)	−0.0016 (19)	−0.0079 (11)	−0.003 (2)
C7'	0.0164 (13)	0.021 (3)	0.025 (2)	−0.003 (2)	−0.0070 (14)	−0.014 (2)
C8'	0.037 (2)	0.031 (2)	0.0202 (19)	−0.0053 (19)	−0.0133 (16)	−0.0112 (15)
C9'	0.0272 (17)	0.011 (2)	0.018 (4)	−0.0034 (18)	−0.002 (3)	−0.004 (2)
C10'	0.046 (2)	0.0160 (18)	0.034 (2)	−0.0063 (15)	0.000 (2)	−0.0140 (19)
C11'	0.048 (2)	0.034 (3)	0.052 (3)	−0.0188 (19)	0.012 (3)	−0.026 (3)

Geometric parameters (Å, º) top

Mo—O1	2.011 (7)	C8—H8A	0.9800
Mo—O2	2.2747 (16)	C8—H8B	0.9800
Mo—O3	1.7133 (16)	C8—H8C	0.9800
Mo—O4	1.7021 (18)	C10—C11	1.533 (7)
Mo—O1'	1.897 (7)	C10—H10A	0.9900
Mo—N1	2.193 (6)	C10—H10B	0.9900
Mo—N3	1.933 (15)	C11—H11A	0.9800
Mo—N3'	2.127 (15)	C11—H11B	0.9800
Mo—N1'	2.340 (6)	C11—H11C	0.9800
S2—O2	1.5330 (15)	S1'—C9'	1.753 (5)
S2—C13	1.780 (2)	S1'—C10'	1.810 (5)
S2—C12	1.782 (2)	O1'—C1'	1.353 (5)
C12—H12A	0.9800	N1'—C7'	1.315 (6)
C12—H12B	0.9800	N1'—N2'	1.398 (5)
C12—H12C	0.9800	N2'—C9'	1.304 (6)
C13—H13A	0.9800	N3'—C9'	1.353 (6)
C13—H13B	0.9800	N3'—H3n'	0.8800
C13—H13C	0.9800	C1'—C2'	1.3900
S1—C9	1.746 (6)	C1'—C6'	1.3900
S1—C10	1.818 (5)	C2'—C3'	1.3900
O1—C1	1.359 (5)	C2'—H2'	0.9500
N1—C7	1.316 (6)	C3'—C4'	1.3900
N1—N2	1.406 (5)	C3'—H3'	0.9500
N2—C9	1.307 (6)	C4'—C5'	1.3900
N3—C9	1.351 (6)	C4'—H4'	0.9500
N3—H3n	0.8800	C5'—C6'	1.3900
C1—C2	1.3900	C5'—H5'	0.9500
C1—C6	1.3900	C6'—C7'	1.479 (5)
C2—C3	1.3900	C7'—C8'	1.521 (6)
C2—H2	0.9500	C8'—H8'A	0.9800
C3—C4	1.3900	C8'—H8'B	0.9800
C3—H3	0.9500	C8'—H8'C	0.9800
C4—C5	1.3900	C10'—C11'	1.519 (7)
C4—H4	0.9500	C10'—H10C	0.9900
C5—C6	1.3900	C10'—H10D	0.9900
C5—H5	0.9500	C11'—H11D	0.9800
C6—C7	1.465 (6)	C11'—H11E	0.9800
C7—C8	1.522 (6)	C11'—H11F	0.9800

O4—Mo—O3	104.39 (8)	C6—C5—H5	120.0
O4—Mo—O1'	94.2 (3)	C4—C5—H5	120.0
O3—Mo—O1'	115.50 (14)	C5—C6—C1	120.0
O4—Mo—N3	98.5 (7)	C5—C6—C7	116.8 (3)
O3—Mo—N3	96.7 (3)	C1—C6—C7	123.2 (3)
O1'—Mo—N3	141.2 (5)	N1—C7—C6	120.7 (4)
O4—Mo—O1	99.5 (3)	N1—C7—C8	117.9 (5)
O3—Mo—O1	102.65 (14)	C6—C7—C8	121.4 (4)
O1'—Mo—O1	12.9 (2)	N2—C9—N3	122.3 (8)
N3—Mo—O1	149.3 (6)	N2—C9—S1	121.5 (5)
O4—Mo—N3'	103.0 (6)	N3—C9—S1	116.2 (8)
O3—Mo—N3'	90.1 (3)	C11—C10—S1	113.6 (4)
O1'—Mo—N3'	144.7 (5)	C11—C10—H10A	108.9
N3—Mo—N3'	7.2 (8)	S1—C10—H10A	108.9
O1—Mo—N3'	150.4 (6)	C11—C10—H10B	108.9
O4—Mo—N1	90.4 (2)	S1—C10—H10B	108.9
O3—Mo—N1	163.71 (19)	H10A—C10—H10B	107.7
O1'—Mo—N1	69.3 (2)	C10—C11—H11A	109.5
N3—Mo—N1	74.0 (3)	C10—C11—H11B	109.5
O1—Mo—N1	81.2 (2)	H11A—C11—H11B	109.5
N3'—Mo—N1	79.8 (3)	C10—C11—H11C	109.5
O4—Mo—O2	170.16 (7)	H11A—C11—H11C	109.5
O3—Mo—O2	85.28 (7)	H11B—C11—H11C	109.5
O1'—Mo—O2	79.7 (3)	C9'—S1'—C10'	102.2 (3)
N3—Mo—O2	82.0 (7)	C1'—O1'—Mo	128.9 (4)
O1—Mo—O2	76.2 (3)	C7'—N1'—N2'	117.3 (5)
N3'—Mo—O2	78.5 (6)	C7'—N1'—Mo	125.2 (4)
N1—Mo—O2	80.3 (2)	N2'—N1'—Mo	117.5 (4)
O4—Mo—N1'	94.7 (2)	C9'—N2'—N1'	108.8 (5)
O3—Mo—N1'	154.27 (16)	C9'—N3'—Mo	119.4 (9)
O1'—Mo—N1'	79.4 (2)	C9'—N3'—H3n'	120.3
N3—Mo—N1'	63.1 (3)	Mo—N3'—H3n'	120.3
O1—Mo—N1'	90.7 (2)	O1'—C1'—C2'	117.6 (3)
N3'—Mo—N1'	68.7 (3)	O1'—C1'—C6'	122.4 (3)
N1—Mo—N1'	11.27 (17)	C2'—C1'—C6'	120.0
O2—Mo—N1'	76.6 (2)	C1'—C2'—C3'	120.0
O2—S2—C13	103.33 (10)	C1'—C2'—H2'	120.0
O2—S2—C12	103.52 (10)	C3'—C2'—H2'	120.0
C13—S2—C12	99.67 (12)	C4'—C3'—C2'	120.0
S2—O2—Mo	125.84 (9)	C4'—C3'—H3'	120.0
S2—C12—H12A	109.5	C2'—C3'—H3'	120.0
S2—C12—H12B	109.5	C3'—C4'—C5'	120.0
H12A—C12—H12B	109.5	C3'—C4'—H4'	120.0
S2—C12—H12C	109.5	C5'—C4'—H4'	120.0
H12A—C12—H12C	109.5	C6'—C5'—C4'	120.0
H12B—C12—H12C	109.5	C6'—C5'—H5'	120.0
S2—C13—H13A	109.5	C4'—C5'—H5'	120.0
S2—C13—H13B	109.5	C5'—C6'—C1'	120.0
H13A—C13—H13B	109.5	C5'—C6'—C7'	117.2 (3)
S2—C13—H13C	109.5	C1'—C6'—C7'	122.7 (3)
H13A—C13—H13C	109.5	N1'—C7'—C6'	120.5 (4)
H13B—C13—H13C	109.5	N1'—C7'—C8'	117.6 (5)
C9—S1—C10	103.3 (3)	C6'—C7'—C8'	121.8 (4)
C1—O1—Mo	124.2 (4)	C7'—C8'—H8'A	109.5
C7—N1—N2	117.6 (5)	C7'—C8'—H8'B	109.5
C7—N1—Mo	127.8 (4)	H8'A—C8'—H8'B	109.5
N2—N1—Mo	114.5 (4)	C7'—C8'—H8'C	109.5
C9—N2—N1	108.9 (5)	H8'A—C8'—H8'C	109.5
C9—N3—Mo	119.3 (10)	H8'B—C8'—H8'C	109.5
C9—N3—H3n	120.3	N2'—C9'—N3'	124.3 (8)
Mo—N3—H3n	120.3	N2'—C9'—S1'	120.4 (5)
O1—C1—C2	116.7 (3)	N3'—C9'—S1'	115.2 (7)
O1—C1—C6	123.3 (3)	C11'—C10'—S1'	113.5 (4)
C2—C1—C6	120.0	C11'—C10'—H10C	108.9
C3—C2—C1	120.0	S1'—C10'—H10C	108.9
C3—C2—H2	120.0	C11'—C10'—H10D	108.9
C1—C2—H2	120.0	S1'—C10'—H10D	108.9
C4—C3—C2	120.0	H10C—C10'—H10D	107.7
C4—C3—H3	120.0	C10'—C11'—H11D	109.5
C2—C3—H3	120.0	C10'—C11'—H11E	109.5
C3—C4—C5	120.0	H11D—C11'—H11E	109.5
C3—C4—H4	120.0	C10'—C11'—H11F	109.5
C5—C4—H4	120.0	H11D—C11'—H11F	109.5
C6—C5—C4	120.0	H11E—C11'—H11F	109.5

C13—S2—O2—Mo	−125.78 (12)	Mo—N3—C9—S1	−172.6 (9)
C12—S2—O2—Mo	130.66 (13)	C10—S1—C9—N2	4.7 (8)
O3—Mo—O2—S2	139.32 (13)	C10—S1—C9—N3	−175.7 (12)
O1'—Mo—O2—S2	22.32 (18)	C9—S1—C10—C11	−81.4 (5)
N3—Mo—O2—S2	−123.3 (3)	O4—Mo—O1'—C1'	44.6 (7)
O1—Mo—O2—S2	35.04 (18)	O3—Mo—O1'—C1'	152.7 (6)
N3'—Mo—O2—S2	−129.7 (3)	N3—Mo—O1'—C1'	−64.4 (14)
N1—Mo—O2—S2	−48.22 (18)	O1—Mo—O1'—C1'	160 (3)
N1'—Mo—O2—S2	−59.11 (17)	N3'—Mo—O1'—C1'	−74.9 (13)
O4—Mo—O1—C1	42.4 (7)	N1—Mo—O1'—C1'	−44.2 (7)
O3—Mo—O1—C1	149.6 (6)	O2—Mo—O1'—C1'	−127.6 (8)
O1'—Mo—O1—C1	−23.9 (18)	N1'—Mo—O1'—C1'	−49.4 (7)
N3—Mo—O1—C1	−82.8 (13)	O4—Mo—N1'—C7'	−69.8 (7)
N3'—Mo—O1—C1	−97.0 (11)	O3—Mo—N1'—C7'	151.9 (4)
N1—Mo—O1—C1	−46.5 (7)	O1'—Mo—N1'—C7'	23.5 (7)
O2—Mo—O1—C1	−128.6 (7)	N3—Mo—N1'—C7'	−166.9 (11)
N1'—Mo—O1—C1	−52.6 (7)	O1—Mo—N1'—C7'	29.8 (8)
O4—Mo—N1—C7	−71.6 (8)	N3'—Mo—N1'—C7'	−171.9 (11)
O3—Mo—N1—C7	133.1 (5)	N1—Mo—N1'—C7'	−2.3 (17)
O1'—Mo—N1—C7	22.7 (7)	O2—Mo—N1'—C7'	105.4 (7)
N3—Mo—N1—C7	−170.3 (11)	O4—Mo—N1'—N2'	112.3 (6)
O1—Mo—N1—C7	28.0 (8)	O3—Mo—N1'—N2'	−26.0 (10)
N3'—Mo—N1—C7	−174.7 (10)	O1'—Mo—N1'—N2'	−154.4 (7)
O2—Mo—N1—C7	105.3 (8)	N3—Mo—N1'—N2'	15.2 (9)
N1'—Mo—N1—C7	175 (3)	O1—Mo—N1'—N2'	−148.1 (7)
O4—Mo—N1—N2	107.1 (6)	N3'—Mo—N1'—N2'	10.2 (9)
O3—Mo—N1—N2	−48.2 (12)	N1—Mo—N1'—N2'	180 (3)
O1'—Mo—N1—N2	−158.6 (7)	O2—Mo—N1'—N2'	−72.5 (6)
N3—Mo—N1—N2	8.4 (9)	C7'—N1'—N2'—C9'	172.1 (8)
O1—Mo—N1—N2	−153.3 (7)	Mo—N1'—N2'—C9'	−9.8 (9)
N3'—Mo—N1—N2	4.0 (9)	O4—Mo—N3'—C9'	−98.7 (15)
O2—Mo—N1—N2	−76.0 (6)	O3—Mo—N3'—C9'	156.5 (15)
N1'—Mo—N1—N2	−5.9 (18)	O1'—Mo—N3'—C9'	18 (2)
C7—N1—N2—C9	171.6 (8)	N3—Mo—N3'—C9'	−47 (8)
Mo—N1—N2—C9	−7.2 (9)	O1—Mo—N3'—C9'	40 (2)
O4—Mo—N3—C9	−95.9 (15)	N1—Mo—N3'—C9'	−10.7 (14)
O3—Mo—N3—C9	158.4 (14)	O2—Mo—N3'—C9'	71.4 (15)
O1'—Mo—N3—C9	12 (2)	N1'—Mo—N3'—C9'	−8.6 (13)
O1—Mo—N3—C9	30 (2)	Mo—O1'—C1'—C2'	−132.5 (5)
N3'—Mo—N3—C9	135 (10)	Mo—O1'—C1'—C6'	48.3 (9)
N1—Mo—N3—C9	−7.9 (13)	O1'—C1'—C2'—C3'	−179.1 (6)
O2—Mo—N3—C9	74.2 (15)	C6'—C1'—C2'—C3'	0.0
N1'—Mo—N3—C9	−4.8 (12)	C1'—C2'—C3'—C4'	0.0
Mo—O1—C1—C2	−138.2 (4)	C2'—C3'—C4'—C5'	0.0
Mo—O1—C1—C6	42.6 (9)	C3'—C4'—C5'—C6'	0.0
O1—C1—C2—C3	−179.3 (6)	C4'—C5'—C6'—C1'	0.0
C6—C1—C2—C3	0.0	C4'—C5'—C6'—C7'	178.0 (4)
C1—C2—C3—C4	0.0	O1'—C1'—C6'—C5'	179.1 (6)
C2—C3—C4—C5	0.0	C2'—C1'—C6'—C5'	0.0
C3—C4—C5—C6	0.0	O1'—C1'—C6'—C7'	1.2 (6)
C4—C5—C6—C1	0.0	C2'—C1'—C6'—C7'	−177.9 (4)
C4—C5—C6—C7	178.1 (4)	N2'—N1'—C7'—C6'	−178.4 (6)
O1—C1—C6—C5	179.2 (6)	Mo—N1'—C7'—C6'	3.7 (10)
C2—C1—C6—C5	0.0	N2'—N1'—C7'—C8'	0.1 (11)
O1—C1—C6—C7	1.3 (6)	Mo—N1'—C7'—C8'	−177.8 (5)
C2—C1—C6—C7	−178.0 (4)	C5'—C6'—C7'—N1'	159.1 (6)
N2—N1—C7—C6	179.0 (6)	C1'—C6'—C7'—N1'	−23.0 (8)
Mo—N1—C7—C6	−2.4 (11)	C5'—C6'—C7'—C8'	−19.4 (6)
N2—N1—C7—C8	−2.0 (11)	C1'—C6'—C7'—C8'	158.6 (4)
Mo—N1—C7—C8	176.7 (5)	N1'—N2'—C9'—N3'	2.3 (17)
C5—C6—C7—N1	161.3 (6)	N1'—N2'—C9'—S1'	−176.8 (6)
C1—C6—C7—N1	−20.6 (8)	Mo—N3'—C9'—N2'	7 (2)
C5—C6—C7—C8	−17.7 (6)	Mo—N3'—C9'—S1'	−173.7 (8)
C1—C6—C7—C8	160.3 (4)	C10'—S1'—C9'—N2'	5.2 (8)
N1—N2—C9—N3	0.9 (16)	C10'—S1'—C9'—N3'	−174.0 (12)
N1—N2—C9—S1	−179.5 (6)	C9'—S1'—C10'—C11'	−80.7 (5)
Mo—N3—C9—N2	7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3n···O3ⁱ	0.88	2.23	3.090 (15)	166
N3′—H3n′···O3ⁱ	0.88	1.94	2.816 (16)	171

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Mo(C₁₁H₁₃N₃OS)O₂(C₂H₆OS)]
M_r	441.37
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.0411 (3), 9.7243 (3), 12.0849 (4)
α, β, γ (°)	73.387 (3), 84.465 (3), 86.077 (3)
V (Å³)	900.47 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.98
Crystal size (mm)	0.35 × 0.15 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.691, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13626, 4149, 3811
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.072, 1.03
No. of reflections	4149
No. of parameters	234
No. of restraints	100
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.87

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Mo—O1	2.011 (7)	Mo—O4	1.7021 (18)
Mo—O2	2.2747 (16)	Mo—N1	2.193 (6)
Mo—O3	1.7133 (16)	Mo—N3	1.933 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3n···O3ⁱ	0.88	2.23	3.090 (15)	166
N3'—H3n'···O3ⁱ	0.88	1.94	2.816 (16)	171

Symmetry code: (i) −x+1, −y+1, −z+1.

Footnotes

‡Additional correspondence author, e-mail: r.takjoo@um.ac.ir.

Acknowledgements

The authors are grateful to the Ferdowsi University of Mashhad for financial support, and thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/3).

References

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Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Ceylan, B. I., Kurt, Y. D. & Ulkuseven, B. (2009). Rev. Inorg. Chem. 29, 49–67. CAS Google Scholar
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