Bis(3-methyl­phenolato-κO)(nitros­yl-κN)[tris­(3,5-dimethyl­pyrazol-1-yl-κN2)hydridoborato]molybdenum(II)

Nitek, W.; Romańczyk, P.P.; Lubera, T.; Włodarczyk, A.J.

doi:10.1107/S1600536810033763

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages m1239-m1240

doi:10.1107/S1600536810033763

Open

access

Bis(3-methylphenolato-κO)(nitrosyl-κN)[tris(3,5-dimethylpyrazol-1-yl-κN²)hydridoborato]molybdenum(II)

Wojciech Nitek,^a ^* Piotr P. Romańczyk,^b ^* Tomasz Lubera ^b and Andrzej J. Włodarczyk ^b

^aFaculty of Chemistry, Jagiellonian University, ul. R. Ingardena 3, 30-060 Kraków, Poland, and ^bFaculty of Chemical Engineering and Technology, Cracow University of Technology, ul. Warszawska 24, 31-155 Kraków, Poland
^*Correspondence e-mail: nitek@chemia.uj.edu.pl, pr@chemia.pk.edu.pl

(Received 22 June 2010; accepted 20 August 2010; online 11 September 2010)

The title complex, [Mo(C₁₅H₂₂BN₆)(C₇H₇O)₂(NO)], contains an {MoNO}⁴ core stabilized by κ³-hydrotris(3,5-dimethylpyrazol-1-yl)borate, [Tp^Me2]⁻, and two anionic m-cresolate ligands, leading to a distorted octahedral geometry for the Mo atom. The short Mo—O bond lengths [1.935 (2) and 1.971 (2) Å], as well as large Mo—O—Csp² angles [134.2 (2) and 143.54 (19)°], indicate dπ_Mo—pπ_O interactions, which are clearly weaker when compared with {Mo(NO)(Tp^Me2)} alkoxides. The nitrosyl system is virtually linear [179.3 (3)°] with Mo—N and N—O bond lengths of 1.760 (2) and 1.205 (3) Å, respectively. Intra- and intermolecular C—H_{(Ph or CH₃)}⋯π_(Ph) interactions between adjacent phenyl rings are found in the crystal structure (d_H⋯Ph in the range 2.743–2.886 Å). One of the Ph rings shows disorder, i.e. swinging in the ring plane.

Related literature

The importance of this class of Mo complexes comes from the fact that some {MoNO}⁴ alkoxides are efficient catalysts in the cathodic reduction of CHCl₃. For the synthesis, spectroscopic characterization and electrochemical properties of [tris(3,5-dimethylpyrazol-1-yl)borato]nitrosylmolybdenum(II) bis-cresolates, see: Włodarczyk et al. (2008a ). For the spectroscopic characterization of the mono-cresolate analogue of the title compound, see: McCleverty et al. (1983 ). For related structurally characterized {Mo(NO)(Tp^Me2)}-alkoxides, see: Romańczyk et al. (2007 ); Włodarczyk et al. (2008c ). For the electrocatalytic activity of bis-alkoxide Mo nitrosyls in the reduction of CHCl₃, see: Włodarczyk et al. (2008b ).

Experimental

Crystal data

[Mo(C₁₅H₂₂BN₆)(C₇H₇O)₂(NO)]
M_r = 637.40
Triclinic, $[P \overline 1]$
a = 8.041 (5) Å
b = 13.562 (5) Å
c = 14.591 (5) Å
α = 86.103 (5)°
β = 83.533 (5)°
γ = 74.597 (5)°
V = 1523.1 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 295 K
0.22 × 0.15 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997 ) T_min = 0.903, T_max = 0.954
12695 measured reflections
6901 independent reflections
5801 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.105
S = 1.08
6901 reflections
383 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033763/rk2216sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810033763/rk2216Isup2.hkl

checkCIF report

Comment top

The stable 16e complexes containing {MoNO}⁴ core stabilized by tripodal hydrotris(3,5-dimethylpyrazol-1-yl)borate and two anionic co-ligands undergo easily reversible 1e reduction at a potential, E_1/2, which can be tuned in the huge range of 2200 mV by selecting suitable co-ligands (Włodarczyk et al., 2008c). The 17e species based on the {Mo(NO)(Tp^Me2)(O-)₂} moiety very efficiently catalyse the dehalogenation of CHCl₃; their activity is strictly associated with the E_1/2 value (Włodarczyk et al., 2008b). The structural study of title complex is a part of a larger project concerning examination of molecules which may be potentially applied as electrocatalysts.

The title complex (Fig. 1) contains a pseudo-mirror plane of symmetry passing through Mo, NO, B and the N31/N32/C33/C34/C35 pyrazolyl ring (approximate C_s symmetry which is reflected in ¹H NMR spectrum). The longer Mo–O distances, i.e. weaker π-donation from O to Mo, in the bis-cresolato complex, than compared with those found for {Mo(NO)(Tp^Me2)}-alkoxides, certainly result from additional electron delocalization to sp²-hybridized carbon (which is precluded in the case of the latter complexes, hence Mo–O_alkoxide av. distance is 1.88Å, see: Romańczyk et al., 2007; Włodarczyk et al., 2008c) and is reflected in hypsochromically shifted ν_NO band in the title complex (McCleverty et al., 1983). The lengthening of the Mo1–N31 bond is attributed to the trans-influence of the NO group. Intermolecular Ph···Ph interactions between adjacent nearly perpendicular rings (C46B···H54ⁱ distance is 2.873Å) and also between rings and methyl groups (C44···H48Bⁱⁱ distance is 2.886Å), stabilize the crystal structure (Fig. 2), symmetry codes: (i) 1+x, y, z; (ii) 1-x, -y, -z. As mentioned above one of the Ph rings (linked with O41) is disordered, i.e. it swings in the ring plane.

Related literature top

The importance of this class of Mo complexes comes from the fact that some {Mo(NO)}⁴ alkoxides are efficient catalysts in the cathodic reduction of CHCl₃. For the synthesis, spectroscopic characterization and electrochemical properties of [tris(3,5-dimethylpyrazol-1-yl)borato]nitrosylmolybdenum(II) bis-cresolates, see: Włodarczyk et al. (2008a). For the spectroscopic characterization of the mono-cresolate analogue of the title compound, see: McCleverty et al. (1983). For related structurally characterized {Mo(NO)(Tp^Me₂)}-alkoxides, see: Romańczyk et al. (2007); Włodarczyk et al. (2008c). For the electrocatalytic activity of bis-alkoxide Mo nitrosyls in the reduction of CHCl₃, see: Włodarczyk et al. (2008b).

Experimental top

The complex was synthesized following the literature from the reaction of [Mo(NO)(Tp^Me)I₂].C₆H₅CH₃ and m-cresol in the presence of Et₃N in boiling dichloromethane and characterized by mass spectrometry, IR, ¹H NMR spectroscopy as well as cyclic voltammetry (Włodarczyk et al., 2008a). A dark brown crystals were grown by slow evaporation of solvent from a dichloromethane/n-hexane solution.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. Intermolecular interactions in the crystal structure of the title compound.

Bis(3-methylphenolato-κO)(nitrosyl-κN)[tris(3,5- dimethylpyrazol-1-yl-κN²)hydridoborato]molybdenum(II) top

Crystal data top

[Mo(C₁₅H₂₂BN₆)(C₇H₇O)₂(NO)]	Z = 2
M_r = 637.40	F(000) = 660
Triclinic, P1	D_x = 1.390 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.041 (5) Å	Cell parameters from 6763 reflections
b = 13.562 (5) Å	θ = 1.0–27.5°
c = 14.591 (5) Å	µ = 0.47 mm⁻¹
α = 86.103 (5)°	T = 295 K
β = 83.533 (5)°	Prism, dark brown
γ = 74.597 (5)°	0.22 × 0.15 × 0.1 mm
V = 1523.1 (12) Å³

Data collection top

Nonius KappaCCD diffractometer	5801 reflections with I > 2σ(I)
ω– and ϕ–scans	R_int = 0.024
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	θ_max = 27.4°, θ_min = 2.9°
T_min = 0.903, T_max = 0.954	h = −10→10
12695 measured reflections	k = −17→17
6901 independent reflections	l = −18→18

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0476P)² + 0.7213P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.041	(Δ/σ)_max = 0.001
wR(F²) = 0.105	Δρ_max = 0.68 e Å⁻³
S = 1.08	Δρ_min = −0.51 e Å⁻³
6901 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
383 parameters	Extinction coefficient: 0.0117 (12)
0 restraints

Crystal data top

[Mo(C₁₅H₂₂BN₆)(C₇H₇O)₂(NO)]	γ = 74.597 (5)°
M_r = 637.40	V = 1523.1 (12) Å³
Triclinic, P1	Z = 2
a = 8.041 (5) Å	Mo Kα radiation
b = 13.562 (5) Å	µ = 0.47 mm⁻¹
c = 14.591 (5) Å	T = 295 K
α = 86.103 (5)°	0.22 × 0.15 × 0.1 mm
β = 83.533 (5)°

Data collection top

Nonius KappaCCD diffractometer	6901 independent reflections
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	5801 reflections with I > 2σ(I)
T_min = 0.903, T_max = 0.954	R_int = 0.024
12695 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.68 e Å⁻³
6901 reflections	Δρ_min = −0.51 e Å⁻³
383 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 > 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
B1	0.0436 (4)	0.5567 (2)	0.2703 (2)	0.0491 (7)
Mo1	0.07282 (3)	0.315037 (17)	0.229233 (15)	0.04338 (10)
N11	0.1515 (3)	0.43407 (18)	0.13985 (15)	0.0483 (5)
N12	0.1411 (3)	0.52830 (17)	0.17426 (15)	0.0478 (5)
C13	0.2049 (4)	0.5870 (2)	0.1076 (2)	0.0584 (7)
C14	0.2583 (4)	0.5300 (3)	0.0305 (2)	0.0667 (9)
H14	0.3091	0.5504	−0.0255	0.08*
C15	0.2223 (4)	0.4361 (3)	0.0517 (2)	0.0579 (7)
C16	0.2551 (5)	0.3471 (3)	−0.0090 (2)	0.0787 (10)
H16A	0.3245	0.2873	0.0206	0.118*
H16B	0.3152	0.3617	−0.0669	0.118*
H16C	0.1466	0.3351	−0.0197	0.118*
C17	0.2090 (6)	0.6948 (3)	0.1220 (3)	0.0778 (10)
H17A	0.0932	0.7386	0.1248	0.117*
H17B	0.2791	0.7176	0.0717	0.117*
H17C	0.2572	0.6972	0.1788	0.117*
N21	−0.1565 (3)	0.44545 (18)	0.25060 (16)	0.0484 (5)
N22	−0.1381 (3)	0.53995 (17)	0.26969 (16)	0.0491 (5)
C23	−0.2964 (4)	0.6069 (2)	0.2796 (2)	0.0596 (8)
C24	−0.4160 (4)	0.5555 (3)	0.2679 (2)	0.0655 (9)
H24	−0.5355	0.5827	0.2715	0.079*
C25	−0.3275 (4)	0.4552 (3)	0.2497 (2)	0.0566 (7)
C26	−0.4001 (4)	0.3693 (3)	0.2310 (3)	0.0755 (10)
H26A	−0.3376	0.3357	0.1769	0.113*
H26B	−0.5202	0.3956	0.2212	0.113*
H26C	−0.3894	0.3213	0.2829	0.113*
C27	−0.3215 (5)	0.7166 (3)	0.2991 (3)	0.0823 (11)
H27A	−0.268	0.7212	0.3536	0.123*
H27B	−0.4432	0.7495	0.3083	0.123*
H27C	−0.2694	0.7498	0.2478	0.123*
N31	0.1762 (3)	0.38254 (16)	0.33866 (15)	0.0427 (5)
N32	0.1396 (3)	0.48717 (16)	0.34540 (15)	0.0439 (5)
C33	0.2048 (4)	0.5086 (2)	0.42083 (19)	0.0503 (6)
C34	0.2859 (4)	0.4179 (2)	0.4624 (2)	0.0550 (7)
H34	0.3435	0.4095	0.5154	0.066*
C35	0.2656 (4)	0.3409 (2)	0.41023 (19)	0.0478 (6)
C36	0.3312 (5)	0.2281 (2)	0.4255 (2)	0.0651 (8)
H36A	0.3851	0.1979	0.3684	0.098*
H36B	0.2362	0.1997	0.4479	0.098*
H36C	0.4144	0.214	0.4701	0.098*
C37	0.1823 (5)	0.6152 (3)	0.4507 (2)	0.0681 (9)
H37A	0.2456	0.6505	0.4062	0.102*
H37B	0.2254	0.6125	0.5098	0.102*
H37C	0.0616	0.6508	0.4551	0.102*
O41	0.3084 (3)	0.23057 (15)	0.21148 (14)	0.0557 (5)
C42	0.3831 (5)	0.1373 (3)	0.1751 (2)	0.0686 (9)
C43	0.3018 (7)	0.0590 (3)	0.1884 (3)	0.0873 (12)
H43	0.1904	0.0701	0.2183	0.105*
C44	0.3901 (10)	−0.0373 (4)	0.1560 (4)	0.123 (2)
H44	0.3371	−0.0908	0.1644	0.148*
C45	0.5542 (10)	−0.0536 (5)	0.1120 (4)	0.136 (3)
H45	0.6119	−0.1184	0.0916	0.164*
C46	0.6349 (7)	0.0241 (5)	0.0976 (3)	0.1104 (19)
C47	0.5484 (5)	0.1210 (3)	0.1283 (3)	0.0871 (13)
H47	0.6008	0.1747	0.1175	0.104*
C48	0.8087 (8)	−0.0018 (6)	0.0543 (5)	0.169 (3)
H48A	0.8837	0.0168	0.0928	0.254*
H48B	0.8129	0.0344	−0.0044	0.254*
H48C	0.846	−0.0742	0.0454	0.254*
O51	−0.0196 (3)	0.24020 (14)	0.33482 (13)	0.0528 (5)
C52	−0.1014 (4)	0.1689 (2)	0.3574 (2)	0.0585 (7)
C53	−0.1504 (5)	0.1115 (3)	0.2944 (3)	0.0760 (10)
H53	−0.1272	0.1236	0.2314	0.091*
C54	−0.2322 (6)	0.0376 (3)	0.3251 (3)	0.0819 (11)
H54	−0.2655	0.0004	0.2825	0.098*
C55	−0.2668 (5)	0.0168 (3)	0.4192 (3)	0.0785 (11)
H55	−0.3208	−0.0347	0.4388	0.094*
C56	−0.2208 (4)	0.0727 (2)	0.4834 (3)	0.0641 (8)
C57	−0.1373 (4)	0.1480 (2)	0.4516 (2)	0.0586 (7)
H57	−0.1045	0.1855	0.4942	0.07*
C58	−0.2607 (6)	0.0553 (3)	0.5851 (3)	0.0866 (12)
H58A	−0.2717	−0.0133	0.5973	0.13*
H58B	−0.3674	0.103	0.606	0.13*
H58C	−0.1686	0.0649	0.6171	0.13*
N61	−0.0075 (3)	0.26435 (19)	0.14084 (17)	0.0542 (6)
O62	−0.0606 (4)	0.2291 (2)	0.07993 (17)	0.0799 (7)
H1	0.035 (4)	0.641 (2)	0.283 (2)	0.053 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0534 (18)	0.0410 (15)	0.0496 (17)	−0.0084 (13)	−0.0011 (13)	−0.0013 (12)
Mo1	0.04415 (14)	0.04337 (14)	0.04167 (14)	−0.00827 (9)	−0.00681 (9)	−0.00342 (9)
N11	0.0433 (12)	0.0542 (13)	0.0430 (12)	−0.0067 (10)	−0.0002 (9)	−0.0021 (10)
N12	0.0471 (12)	0.0482 (12)	0.0464 (12)	−0.0117 (10)	−0.0030 (9)	0.0055 (9)
C13	0.0569 (17)	0.0637 (18)	0.0535 (17)	−0.0177 (14)	−0.0071 (13)	0.0157 (14)
C14	0.0624 (19)	0.087 (2)	0.0480 (16)	−0.0212 (17)	0.0012 (14)	0.0160 (16)
C15	0.0498 (16)	0.077 (2)	0.0420 (14)	−0.0106 (14)	−0.0006 (12)	0.0019 (13)
C16	0.084 (2)	0.096 (3)	0.0488 (18)	−0.013 (2)	0.0071 (16)	−0.0143 (17)
C17	0.094 (3)	0.070 (2)	0.075 (2)	−0.034 (2)	−0.017 (2)	0.0232 (18)
N21	0.0401 (11)	0.0553 (13)	0.0472 (12)	−0.0094 (10)	−0.0024 (9)	0.0010 (10)
N22	0.0443 (12)	0.0478 (12)	0.0483 (12)	−0.0014 (10)	−0.0022 (9)	0.0001 (10)
C23	0.0516 (16)	0.0640 (18)	0.0469 (15)	0.0106 (14)	−0.0009 (12)	0.0037 (13)
C24	0.0375 (14)	0.085 (2)	0.0600 (18)	0.0053 (15)	−0.0010 (13)	0.0065 (16)
C25	0.0395 (14)	0.078 (2)	0.0488 (15)	−0.0120 (14)	−0.0020 (11)	0.0077 (14)
C26	0.0498 (18)	0.094 (3)	0.087 (3)	−0.0272 (18)	−0.0093 (16)	0.010 (2)
C27	0.081 (3)	0.060 (2)	0.086 (3)	0.0149 (18)	−0.003 (2)	−0.0023 (18)
N31	0.0437 (11)	0.0393 (10)	0.0436 (11)	−0.0082 (9)	−0.0043 (9)	−0.0009 (9)
N32	0.0458 (12)	0.0412 (11)	0.0439 (11)	−0.0102 (9)	−0.0023 (9)	−0.0049 (9)
C33	0.0558 (16)	0.0546 (15)	0.0429 (14)	−0.0191 (13)	0.0003 (12)	−0.0080 (12)
C34	0.0639 (18)	0.0622 (17)	0.0422 (14)	−0.0191 (14)	−0.0125 (13)	−0.0028 (12)
C35	0.0481 (14)	0.0521 (15)	0.0432 (14)	−0.0125 (12)	−0.0076 (11)	0.0006 (11)
C36	0.079 (2)	0.0523 (16)	0.0625 (19)	−0.0095 (15)	−0.0258 (16)	0.0074 (14)
C37	0.082 (2)	0.0601 (18)	0.066 (2)	−0.0222 (17)	−0.0030 (17)	−0.0216 (15)
O41	0.0541 (11)	0.0497 (11)	0.0579 (12)	0.0004 (9)	−0.0110 (9)	−0.0110 (9)
C42	0.075 (2)	0.067 (2)	0.0519 (17)	0.0139 (17)	−0.0235 (15)	−0.0163 (15)
C43	0.125 (4)	0.0540 (19)	0.078 (3)	−0.009 (2)	−0.022 (2)	−0.0086 (18)
C44	0.195 (7)	0.059 (2)	0.111 (4)	−0.001 (3)	−0.059 (4)	−0.017 (2)
C45	0.175 (6)	0.094 (4)	0.108 (4)	0.057 (4)	−0.065 (4)	−0.056 (3)
C46	0.098 (3)	0.115 (4)	0.090 (3)	0.045 (3)	−0.036 (3)	−0.051 (3)
C47	0.070 (2)	0.097 (3)	0.078 (2)	0.021 (2)	−0.0231 (19)	−0.039 (2)
C48	0.122 (5)	0.201 (7)	0.151 (6)	0.043 (5)	−0.025 (4)	−0.094 (6)
O51	0.0647 (12)	0.0466 (10)	0.0489 (11)	−0.0155 (9)	−0.0124 (9)	−0.0007 (8)
C52	0.0586 (17)	0.0537 (16)	0.0634 (18)	−0.0119 (14)	−0.0161 (14)	0.0024 (14)
C53	0.100 (3)	0.073 (2)	0.068 (2)	−0.037 (2)	−0.030 (2)	0.0079 (17)
C54	0.105 (3)	0.069 (2)	0.088 (3)	−0.039 (2)	−0.042 (2)	0.0056 (19)
C55	0.081 (2)	0.060 (2)	0.103 (3)	−0.0299 (18)	−0.030 (2)	0.0211 (19)
C56	0.0578 (18)	0.0530 (17)	0.076 (2)	−0.0084 (14)	−0.0079 (15)	0.0113 (15)
C57	0.0628 (18)	0.0496 (16)	0.0618 (18)	−0.0116 (14)	−0.0101 (14)	0.0040 (13)
C58	0.090 (3)	0.073 (2)	0.087 (3)	−0.015 (2)	0.009 (2)	0.013 (2)
N61	0.0602 (15)	0.0551 (14)	0.0491 (13)	−0.0144 (11)	−0.0125 (11)	−0.0046 (11)
O62	0.102 (2)	0.0904 (18)	0.0586 (14)	−0.0349 (15)	−0.0271 (13)	−0.0076 (13)

Geometric parameters (Å, º) top

B1—N32	1.533 (4)	C33—C37	1.497 (4)
B1—N22	1.539 (4)	C34—C35	1.387 (4)
B1—N12	1.546 (4)	C34—H34	0.93
B1—H1	1.15 (3)	C35—C36	1.490 (4)
Mo1—N11	2.186 (2)	C36—H36A	0.96
Mo1—N21	2.200 (2)	C36—H36B	0.96
Mo1—N31	2.232 (2)	C36—H36C	0.96
Mo1—O41	1.935 (2)	C37—H37A	0.96
Mo1—O51	1.971 (2)	C37—H37B	0.96
Mo1—N61	1.760 (2)	C37—H37C	0.96
N11—C15	1.349 (4)	O41—C42	1.362 (4)
N11—N12	1.383 (3)	C42—C43	1.380 (6)
N12—C13	1.357 (4)	C42—C47	1.395 (6)
C13—C14	1.373 (5)	C43—C44	1.395 (6)
C13—C17	1.501 (5)	C43—H43	0.93
C14—C15	1.386 (5)	C44—C45	1.370 (10)
C14—H14	0.93	C44—H44	0.93
C15—C16	1.495 (5)	C45—C46	1.370 (9)
C16—H16A	0.96	C45—H45	0.93
C16—H16B	0.96	C46—C47	1.391 (6)
C16—H16C	0.96	C46—C48	1.430 (8)
C17—H17A	0.96	C47—H47	0.93
C17—H17B	0.96	C48—H48A	0.96
C17—H17C	0.96	C48—H48B	0.96
N21—C25	1.347 (4)	C48—H48C	0.96
N21—N22	1.379 (3)	O51—C52	1.311 (4)
N22—C23	1.352 (4)	C52—C53	1.396 (5)
C23—C24	1.360 (5)	C52—C57	1.397 (5)
C23—C27	1.490 (5)	C53—C54	1.364 (5)
C24—C25	1.385 (5)	C53—H53	0.93
C24—H24	0.93	C54—C55	1.394 (6)
C25—C26	1.488 (5)	C54—H54	0.93
C26—H26A	0.96	C55—C56	1.383 (5)
C26—H26B	0.96	C55—H55	0.93
C26—H26C	0.96	C56—C57	1.393 (4)
C27—H27A	0.96	C56—C58	1.499 (5)
C27—H27B	0.96	C57—H57	0.93
C27—H27C	0.96	C58—H58A	0.96
N31—C35	1.342 (3)	C58—H58B	0.96
N31—N32	1.378 (3)	C58—H58C	0.96
N32—C33	1.351 (3)	N61—O62	1.205 (3)
C33—C34	1.367 (4)

N32—B1—N22	109.8 (2)	N32—N31—Mo1	120.68 (15)
N32—B1—N12	109.9 (2)	C33—N32—N31	109.4 (2)
N22—B1—N12	106.9 (2)	C33—N32—B1	131.7 (2)
N32—B1—H1	109.4 (15)	N31—N32—B1	118.9 (2)
N22—B1—H1	111.0 (15)	N32—C33—C34	107.9 (2)
N12—B1—H1	109.7 (15)	N32—C33—C37	123.3 (3)
N11—Mo1—N21	78.50 (9)	C34—C33—C37	128.7 (3)
N11—Mo1—N31	83.91 (8)	C33—C34—C35	106.6 (2)
N11—Mo1—O41	88.87 (9)	C33—C34—H34	126.7
N11—Mo1—O51	163.39 (8)	C35—C34—H34	126.7
N21—Mo1—N31	84.92 (9)	N31—C35—C34	109.6 (2)
N21—Mo1—O51	89.71 (9)	N31—C35—C36	122.3 (2)
N21—Mo1—O41	163.62 (9)	C34—C35—C36	128.1 (3)
N31—Mo1—N61	178.48 (10)	C35—C36—H36A	109.5
O41—Mo1—O51	100.29 (9)	C35—C36—H36B	109.5
N61—Mo1—O41	96.67 (11)	H36A—C36—H36B	109.5
N61—Mo1—O51	98.05 (10)	C35—C36—H36C	109.5
N61—Mo1—N11	94.57 (10)	H36A—C36—H36C	109.5
N61—Mo1—N21	94.71 (11)	H36B—C36—H36C	109.5
O41—Mo1—N31	83.40 (9)	C33—C37—H37A	109.5
O51—Mo1—N31	83.43 (8)	C33—C37—H37B	109.5
C15—N11—N12	106.6 (2)	H37A—C37—H37B	109.5
C15—N11—Mo1	133.1 (2)	C33—C37—H37C	109.5
N12—N11—Mo1	120.27 (16)	H37A—C37—H37C	109.5
C13—N12—N11	109.4 (2)	H37B—C37—H37C	109.5
C13—N12—B1	130.2 (3)	Mo1—O41—C42	134.2 (2)
N11—N12—B1	119.9 (2)	O41—C42—C43	121.2 (4)
N12—C13—C14	107.6 (3)	O41—C42—C47	118.3 (4)
N12—C13—C17	122.9 (3)	C43—C42—C47	120.5 (4)
C14—C13—C17	129.5 (3)	C42—C43—C44	118.7 (5)
C13—C14—C15	107.1 (3)	C42—C43—H43	120.6
C13—C14—H14	126.5	C44—C43—H43	120.6
C15—C14—H14	126.5	C45—C44—C43	120.6 (6)
N11—C15—C14	109.4 (3)	C45—C44—H44	119.7
N11—C15—C16	122.5 (3)	C43—C44—H44	119.7
C14—C15—C16	128.1 (3)	C44—C45—C46	121.1 (5)
C15—C16—H16A	109.5	C44—C45—H45	119.5
C15—C16—H16B	109.5	C46—C45—H45	119.5
H16A—C16—H16B	109.5	C45—C46—C47	119.4 (5)
C15—C16—H16C	109.5	C45—C46—C48	116.7 (6)
H16A—C16—H16C	109.5	C47—C46—C48	123.9 (7)
H16B—C16—H16C	109.5	C46—C47—C42	119.8 (5)
C13—C17—H17A	109.5	C46—C47—H47	120.1
C13—C17—H17B	109.5	C42—C47—H47	120.1
H17A—C17—H17B	109.5	C46—C48—H48A	109.5
C13—C17—H17C	109.5	C46—C48—H48B	109.5
H17A—C17—H17C	109.5	H48A—C48—H48B	109.5
H17B—C17—H17C	109.5	C46—C48—H48C	109.5
C25—N21—N22	107.0 (2)	H48A—C48—H48C	109.5
C25—N21—Mo1	132.7 (2)	H48B—C48—H48C	109.5
N22—N21—Mo1	120.31 (16)	Mo1—O51—C52	143.54 (19)
C23—N22—N21	109.1 (2)	O51—C52—C53	124.7 (3)
C23—N22—B1	130.5 (3)	O51—C52—C57	117.0 (3)
N21—N22—B1	120.2 (2)	C53—C52—C57	118.3 (3)
N22—C23—C24	107.8 (3)	C54—C53—C52	120.2 (4)
N22—C23—C27	122.6 (3)	C54—C53—H53	119.9
C24—C23—C27	129.6 (3)	C52—C53—H53	119.9
C23—C24—C25	107.5 (3)	C53—C54—C55	121.2 (3)
C23—C24—H24	126.2	C53—C54—H54	119.4
C25—C24—H24	126.2	C55—C54—H54	119.4
N21—C25—C24	108.6 (3)	C56—C55—C54	120.1 (3)
N21—C25—C26	123.3 (3)	C56—C55—H55	120
C24—C25—C26	128.1 (3)	C54—C55—H55	120
C25—C26—H26A	109.5	C55—C56—C57	118.4 (3)
C25—C26—H26B	109.5	C55—C56—C58	121.8 (3)
H26A—C26—H26B	109.5	C57—C56—C58	119.7 (3)
C25—C26—H26C	109.5	C56—C57—C52	121.8 (3)
H26A—C26—H26C	109.5	C56—C57—H57	119.1
H26B—C26—H26C	109.5	C52—C57—H57	119.1
C23—C27—H27A	109.5	C56—C58—H58A	109.5
C23—C27—H27B	109.5	C56—C58—H58B	109.5
H27A—C27—H27B	109.5	H58A—C58—H58B	109.5
C23—C27—H27C	109.5	C56—C58—H58C	109.5
H27A—C27—H27C	109.5	H58A—C58—H58C	109.5
H27B—C27—H27C	109.5	H58B—C58—H58C	109.5
C35—N31—N32	106.5 (2)	Mo1—N61—O62	179.3 (3)
C35—N31—Mo1	132.66 (18)

N61—Mo1—N11—C15	−38.0 (3)	O51—Mo1—N31—C35	49.1 (2)
O41—Mo1—N11—C15	58.6 (3)	N11—Mo1—N31—C35	−141.7 (2)
O51—Mo1—N11—C15	−177.5 (3)	N21—Mo1—N31—C35	139.4 (2)
N21—Mo1—N11—C15	−131.9 (3)	O41—Mo1—N31—N32	133.34 (19)
N31—Mo1—N11—C15	142.0 (3)	O51—Mo1—N31—N32	−125.45 (19)
N61—Mo1—N11—N12	146.0 (2)	N11—Mo1—N31—N32	43.78 (18)
O41—Mo1—N11—N12	−117.38 (19)	N21—Mo1—N31—N32	−35.16 (18)
O51—Mo1—N11—N12	6.6 (4)	C35—N31—N32—C33	−0.6 (3)
N21—Mo1—N11—N12	52.13 (19)	Mo1—N31—N32—C33	175.22 (17)
N31—Mo1—N11—N12	−33.90 (19)	C35—N31—N32—B1	177.5 (2)
C15—N11—N12—C13	0.0 (3)	Mo1—N31—N32—B1	−6.7 (3)
Mo1—N11—N12—C13	176.92 (18)	N22—B1—N32—C33	−119.4 (3)
C15—N11—N12—B1	172.1 (2)	N12—B1—N32—C33	123.3 (3)
Mo1—N11—N12—B1	−11.0 (3)	N22—B1—N32—N31	63.0 (3)
N32—B1—N12—C13	−123.7 (3)	N12—B1—N32—N31	−54.3 (3)
N22—B1—N12—C13	117.2 (3)	N31—N32—C33—C34	0.8 (3)
N32—B1—N12—N11	66.1 (3)	B1—N32—C33—C34	−177.0 (3)
N22—B1—N12—N11	−53.0 (3)	N31—N32—C33—C37	−177.6 (3)
N11—N12—C13—C14	−0.7 (3)	B1—N32—C33—C37	4.6 (5)
B1—N12—C13—C14	−171.7 (3)	N32—C33—C34—C35	−0.7 (3)
N11—N12—C13—C17	178.7 (3)	C37—C33—C34—C35	177.6 (3)
B1—N12—C13—C17	7.7 (5)	N32—N31—C35—C34	0.1 (3)
N12—C13—C14—C15	1.0 (4)	Mo1—N31—C35—C34	−174.97 (19)
C17—C13—C14—C15	−178.3 (3)	N32—N31—C35—C36	−179.0 (3)
N12—N11—C15—C14	0.6 (3)	Mo1—N31—C35—C36	5.9 (4)
Mo1—N11—C15—C14	−175.7 (2)	C33—C34—C35—N31	0.4 (3)
N12—N11—C15—C16	179.9 (3)	C33—C34—C35—C36	179.4 (3)
Mo1—N11—C15—C16	3.6 (5)	N61—Mo1—O41—C42	−24.6 (3)
C13—C14—C15—N11	−1.0 (4)	O51—Mo1—O41—C42	74.9 (3)
C13—C14—C15—C16	179.8 (3)	N11—Mo1—O41—C42	−119.1 (3)
N61—Mo1—N21—C25	38.2 (3)	N21—Mo1—O41—C42	−158.3 (3)
O41—Mo1—N21—C25	172.2 (3)	N31—Mo1—O41—C42	156.9 (3)
O51—Mo1—N21—C25	−59.8 (3)	Mo1—O41—C42—C43	−37.3 (5)
N11—Mo1—N21—C25	132.0 (3)	Mo1—O41—C42—C47	146.1 (3)
N31—Mo1—N21—C25	−143.2 (3)	O41—C42—C43—C44	−174.9 (4)
N61—Mo1—N21—N22	−142.2 (2)	C47—C42—C43—C44	1.6 (6)
O41—Mo1—N21—N22	−8.3 (4)	C42—C43—C44—C45	0.0 (7)
O51—Mo1—N21—N22	119.75 (19)	C43—C44—C45—C46	−0.8 (8)
N11—Mo1—N21—N22	−48.47 (19)	C44—C45—C46—C47	0.0 (8)
N31—Mo1—N21—N22	36.33 (19)	C44—C45—C46—C48	177.6 (5)
C25—N21—N22—C23	−0.5 (3)	C45—C46—C47—C42	1.6 (6)
Mo1—N21—N22—C23	179.83 (18)	C48—C46—C47—C42	−175.8 (5)
C25—N21—N22—B1	−176.5 (2)	O41—C42—C47—C46	174.2 (3)
Mo1—N21—N22—B1	3.8 (3)	C43—C42—C47—C46	−2.4 (6)
N32—B1—N22—C23	122.9 (3)	N61—Mo1—O51—C52	5.9 (3)
N12—B1—N22—C23	−117.9 (3)	O41—Mo1—O51—C52	−92.5 (3)
N32—B1—N22—N21	−62.1 (3)	N11—Mo1—O51—C52	145.0 (3)
N12—B1—N22—N21	57.1 (3)	N21—Mo1—O51—C52	100.6 (3)
N21—N22—C23—C24	0.6 (3)	N31—Mo1—O51—C52	−174.5 (3)
B1—N22—C23—C24	176.1 (3)	Mo1—O51—C52—C53	2.9 (6)
N21—N22—C23—C27	−178.9 (3)	Mo1—O51—C52—C57	−178.7 (2)
B1—N22—C23—C27	−3.4 (5)	O51—C52—C53—C54	178.7 (4)
N22—C23—C24—C25	−0.5 (4)	C57—C52—C53—C54	0.4 (6)
C27—C23—C24—C25	179.0 (3)	C52—C53—C54—C55	−0.8 (6)
N22—N21—C25—C24	0.2 (3)	C53—C54—C55—C56	1.2 (6)
Mo1—N21—C25—C24	179.8 (2)	C54—C55—C56—C57	−1.2 (5)
N22—N21—C25—C26	179.7 (3)	C54—C55—C56—C58	178.0 (4)
Mo1—N21—C25—C26	−0.7 (4)	C55—C56—C57—C52	0.8 (5)
C23—C24—C25—N21	0.2 (4)	C58—C56—C57—C52	−178.3 (3)
C23—C24—C25—C26	−179.3 (3)	O51—C52—C57—C56	−178.9 (3)
O41—Mo1—N31—C35	−52.1 (2)	C53—C52—C57—C56	−0.4 (5)

Experimental details

Crystal data
Chemical formula	[Mo(C₁₅H₂₂BN₆)(C₇H₇O)₂(NO)]
M_r	637.40
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.041 (5), 13.562 (5), 14.591 (5)
α, β, γ (°)	86.103 (5), 83.533 (5), 74.597 (5)
V (Å³)	1523.1 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.22 × 0.15 × 0.1

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)
T_min, T_max	0.903, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	12695, 6901, 5801
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.105, 1.08
No. of reflections	6901
No. of parameters	383
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.51

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
McCleverty, J. A., Denti, G., Reynolds, S. J., Drane, A. S., El Murr, N., Rae, A. E., Bailey, N. A., Adams, H. & Smith, J. M. A. (1983). J. Chem. Soc. Dalton Trans. pp. 81–89. CSD CrossRef Web of Science Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Romańczyk, P. P., Guzik, M. N. & Włodarczyk, A. J. (2007). Polyhedron, 26, 1182–1190. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Włodarczyk, A. J., Romańczyk, P. P., Kurek, S. S., Nitek, W. & McCleverty, J. A. (2008c). Polyhedron, 27, 783–796. Google Scholar
Włodarczyk, A. J., Romańczyk, P. P. & Lubera, T. (2008a). Czasop. Techn. Polit. Krak. 1-Ch, pp. 165–170. Google Scholar
Włodarczyk, A. J., Romańczyk, P. P., Lubera, T. & Kurek, S. S. (2008b). Electrochem. Commun. 10, 1856–1859. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.