metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Bis(4-cyano­phenolato)[hydro­tris­­(3,5-di­methyl­pyrazol­yl)borato]nitro­syl­molybdenum(II)–4-hy­droxy­benzo­nitrile–di­chloro­methane (1/1/1)

aSchool of Chemistry, University of Bristol, Cantock Close, BS8 ITS Bristol, England
*Correspondence e-mail: mbkassim@ukm.my

(Received 3 November 2010; accepted 5 November 2010; online 10 November 2010)

In the title compound, [Mo(C15H22BN6)(C7H4NO)2(NO)]·C7H5NO·CH2Cl2, the central MoII atom adopts a distorted cis-MoO2N4 octa­hedral geometry with the hydro­tris­(3,5-dimethyl­pyrazolylborate) anion attached to the metal in an N,N′,N′′-tridentate tripodal coordination mode. Two O-bonded 4-cyano­phenolate anions and a nitrosyl cation complete the coodination of the MoII atom. Two intra­molecular C—H⋯O and one C—H⋯N hydrogen bonds help to establish the configuration of the complex mol­ecule. The crystal structure is stabilized by inter­molecular C—H⋯N and C—H⋯O hydrogen bonds.

Related literature

For related compounds, see: Kassim et al. (2002[Kassim, M. B., Paul, R. L., Jeffery, J. C., McCleverty, J. A. & Ward, M. D. (2002). Inorg. Chim. Acta, 327, 160-168.]); Jones et al. (1997[Jones, P. L., Amoroso, A. J., Jeffery, J. C., McCleverty, J. A., Psillakis, E., Rees, L. H. & Ward, M. D. (1997). Inorg. Chem. 36, 10-18.]); Amoroso et al. (1994[Amoroso, A. J., Cargill Thompson, A. M., Jeffery, J. C., Jones, P. L., McCleverty, J. A. & Ward, M. D. (1994). J. Chem. Soc. Chem. Commun. pp. 2751-2752.]). For background to poly(pyrazol­yl)borate ligands, see: Trofimenko (1993[Trofimenko, S. (1993). Chem. Rev. 93, 943-980.]).

[Scheme 1]

Experimental

Crystal data
  • [Mo(C15H22BN6)(C7H4NO)2(NO)]·C7H5NO·CH2Cl2

  • Mr = 863.42

  • Triclinic, [P \overline 1]

  • a = 11.9792 (19) Å

  • b = 12.630 (2) Å

  • c = 12.891 (2) Å

  • α = 90.120 (3)°

  • β = 92.459 (3)°

  • γ = 94.300 (3)°

  • V = 1943.0 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.53 mm−1

  • T = 173 K

  • 0.18 × 0.10 × 0.05 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.938, Tmax = 0.974

  • 19938 measured reflections

  • 8844 independent reflections

  • 5548 reflections with I > 2σ(I)

  • Rint = 0.066

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.129

  • S = 0.98

  • 8844 reflections

  • 500 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.59 e Å−3

  • Δρmin = −0.69 e Å−3

Table 1
Selected bond lengths (Å)

Mo1—N7 1.762 (4)
Mo1—O1 1.949 (3)
Mo1—O2 1.954 (3)
Mo1—N6 2.179 (3)
Mo1—N4 2.186 (3)
Mo1—N2 2.220 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C5—H5A⋯O2 0.96 2.46 3.189 (5) 133
C10—H10A⋯N7 0.96 2.47 3.228 (6) 136
C15—H15A⋯N7 0.96 2.47 3.288 (6) 143
C4—H4D⋯O4i 0.96 2.52 3.360 (6) 146
C9—H9B⋯O3ii 0.96 2.37 3.219 (6) 147
C37—H37B⋯N9iii 0.96 2.53 3.366 (7) 144
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+2, -z+1; (iii) x-1, y, z+1.

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: PLATON.

Supporting information


Comment top

Poly(pyrazolyl)borate ligands [Trofimenko (1993)] have attracted many researchers for the coordination chemistry of molybdenum complexes [Kassim et al. (2002), Jones et al. (1997) & Amoroso et al. (1994)]. In the title compound, (I), the hydrotris(3,5-dimethyl(pyrazolyl)borate ligand bonds to the central molybdenum atom in a tridentate manner through the N-atom at the 6-position of the pyrazolyl rings. Two 4-hydroxybenzonitrileate and a nitrosyl cation, bond via the O– and N-atom respectively, complete the octahedral coordination of the Mo(II) centre (Fig1). In addition, one molecule of the excess 4-hydroxybenzonitrile ligand and one molecule of CH2Cl2 solvent cystallized in the structure (Fig. 2).

The crystal structure is stabilized by three intramolecular hydrogen bonds C(5)—H(5 A)···O(2), C(10)—H(10 A)···N(7) and C(15)—H(15 A)···N(7). The crystal packing is stabilized by two C—H···O and one C—H···N intermolecular hydrogen bonds (Fig. 3).

Related literature top

For related compounds, see: Kassim et al. (2002); Jones et al. (1997); Amoroso et al. (1994). For background to poly(pyrazolyl)borate ligands, see: Trofimenko (1993).

Experimental top

The title compound was synthesized from a reaction of Mo(NO)Tp*Cl2 (0.1 mmol) with p-cyanophenol (0.25 mmol) in dichloromethane in the presence of triethylammine at refluxing temperature under N2 atmosphere (Kassim et al. 2002). Dark brown plates of (I) were obtained from a slow evaporation of dichloromethane solution of the title compound at room temperature. Yield 80%.

Refinement top

The H atoms attached to the B atom was located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range of 0.93–0.98, and O—H = 0.82 Å) and Uiso(H) (in the range 1.2–1.5 times Ueq of the parent atom), after which the positions were refined with riding constraints.

Structure description top

Poly(pyrazolyl)borate ligands [Trofimenko (1993)] have attracted many researchers for the coordination chemistry of molybdenum complexes [Kassim et al. (2002), Jones et al. (1997) & Amoroso et al. (1994)]. In the title compound, (I), the hydrotris(3,5-dimethyl(pyrazolyl)borate ligand bonds to the central molybdenum atom in a tridentate manner through the N-atom at the 6-position of the pyrazolyl rings. Two 4-hydroxybenzonitrileate and a nitrosyl cation, bond via the O– and N-atom respectively, complete the octahedral coordination of the Mo(II) centre (Fig1). In addition, one molecule of the excess 4-hydroxybenzonitrile ligand and one molecule of CH2Cl2 solvent cystallized in the structure (Fig. 2).

The crystal structure is stabilized by three intramolecular hydrogen bonds C(5)—H(5 A)···O(2), C(10)—H(10 A)···N(7) and C(15)—H(15 A)···N(7). The crystal packing is stabilized by two C—H···O and one C—H···N intermolecular hydrogen bonds (Fig. 3).

For related compounds, see: Kassim et al. (2002); Jones et al. (1997); Amoroso et al. (1994). For background to poly(pyrazolyl)borate ligands, see: Trofimenko (1993).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The complex in (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
[Figure 2] Fig. 2. Molecules in the asymmetric unit with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
[Figure 3] Fig. 3. The packing diagram of the title compound showing the intermolecular H– bonds with dotted line with displacement ellipsoids drawn at the 50% probability level.
Bis(4-hydroxybenzonitrileato)[hydrotris(3,5- dimethylpyrazolyl)borato]nitrosylmolybdenum(II)–4-hydroxybenzonitrile– dichloromethane (1/1/1) top
Crystal data top
[Mo(C15H22BN6)(C7H4NO)2(NO)]·C7H5NO·CH2Cl2Z = 2
Mr = 863.42F(000) = 884
Triclinic, P1Dx = 1.476 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.9792 (19) ÅCell parameters from 3353 reflections
b = 12.630 (2) Åθ = 1.6–27.5°
c = 12.891 (2) ŵ = 0.53 mm1
α = 90.120 (3)°T = 173 K
β = 92.459 (3)°Plate, dark brown
γ = 94.300 (3)°0.18 × 0.10 × 0.05 mm
V = 1943.0 (5) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer
8844 independent reflections
Radiation source: fine-focus sealed tube5548 reflections with I > 2σ(I)
Parallel, Graphite monochromatorRint = 0.066
ω/2θ scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1515
Tmin = 0.938, Tmax = 0.974k = 1616
19938 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 0.98 w = 1/[σ2(Fo2) + (0.0563P)2]
where P = (Fo2 + 2Fc2)/3
8844 reflections(Δ/σ)max = 0.001
500 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = 0.69 e Å3
Crystal data top
[Mo(C15H22BN6)(C7H4NO)2(NO)]·C7H5NO·CH2Cl2γ = 94.300 (3)°
Mr = 863.42V = 1943.0 (5) Å3
Triclinic, P1Z = 2
a = 11.9792 (19) ÅMo Kα radiation
b = 12.630 (2) ŵ = 0.53 mm1
c = 12.891 (2) ÅT = 173 K
α = 90.120 (3)°0.18 × 0.10 × 0.05 mm
β = 92.459 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer
8844 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
5548 reflections with I > 2σ(I)
Tmin = 0.938, Tmax = 0.974Rint = 0.066
19938 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 0.98Δρmax = 0.59 e Å3
8844 reflectionsΔρmin = 0.69 e Å3
500 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat [Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107] with a nominal stability of 0.1 K.

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
xyzUiso*/Ueq
Mo10.73371 (3)0.79886 (3)0.61020 (3)0.01838 (11)
Cl10.10962 (12)0.73930 (12)0.85992 (11)0.0521 (4)
Cl20.11742 (12)0.51320 (11)0.90460 (11)0.0526 (4)
O10.7960 (2)0.8548 (2)0.7431 (2)0.0219 (6)
O20.8338 (2)0.6892 (2)0.5782 (2)0.0244 (7)
O30.8373 (3)0.9671 (3)0.4762 (2)0.0372 (8)
O40.6205 (3)0.6806 (2)1.0784 (2)0.0334 (8)
H4A0.59050.65221.12830.050*
N10.5443 (3)0.6553 (3)0.7131 (2)0.0190 (7)
N20.6586 (3)0.6735 (3)0.7118 (2)0.0187 (8)
N30.4812 (3)0.8253 (3)0.6395 (2)0.0192 (7)
N40.5838 (3)0.8832 (3)0.6333 (2)0.0195 (8)
N50.5173 (3)0.6799 (3)0.5197 (2)0.0203 (8)
N60.6173 (3)0.7294 (3)0.4898 (2)0.0204 (8)
N70.7943 (3)0.8988 (3)0.5306 (3)0.0250 (8)
N81.1473 (3)1.2538 (3)0.9349 (3)0.0345 (10)
N91.2037 (4)0.6758 (4)0.2015 (3)0.0447 (11)
N100.2755 (3)1.0246 (3)0.8680 (3)0.0385 (10)
C10.5158 (4)0.5900 (3)0.7920 (3)0.0224 (9)
C20.6143 (4)0.5627 (3)0.8408 (3)0.0265 (10)
H2A0.62090.51750.89720.032*
C30.7015 (4)0.6152 (3)0.7898 (3)0.0229 (9)
C40.3968 (4)0.5638 (4)0.8183 (4)0.0340 (11)
H4B0.34810.59550.76820.051*
H4C0.38480.59100.88620.051*
H4D0.38100.48820.81730.051*
C50.8241 (4)0.6155 (4)0.8143 (3)0.0307 (11)
H5A0.86400.65920.76520.046*
H5B0.84660.54430.81040.046*
H5C0.84070.64320.88310.046*
C60.3999 (3)0.8931 (3)0.6482 (3)0.0213 (9)
C70.4492 (4)0.9948 (3)0.6481 (3)0.0246 (10)
H7A0.41331.05720.65370.029*
C80.5630 (4)0.9862 (3)0.6380 (3)0.0225 (9)
C90.2803 (3)0.8542 (4)0.6581 (3)0.0294 (10)
H9A0.27340.77800.65530.044*
H9B0.23570.88180.60220.044*
H9C0.25460.87770.72320.044*
C100.6525 (4)1.0744 (4)0.6366 (3)0.0318 (11)
H10A0.72381.04570.62930.048*
H10B0.65371.11400.70030.048*
H10C0.63791.12040.57920.048*
C110.4625 (4)0.6304 (3)0.4370 (3)0.0224 (9)
C120.5288 (4)0.6482 (3)0.3529 (3)0.0253 (10)
H12A0.51310.62300.28560.030*
C130.6228 (4)0.7104 (3)0.3872 (3)0.0214 (9)
C140.3518 (4)0.5694 (4)0.4444 (3)0.0322 (11)
H14A0.32800.57250.51450.048*
H14B0.35850.49670.42520.048*
H14C0.29780.59960.39850.048*
C150.7181 (4)0.7532 (4)0.3242 (3)0.0288 (11)
H15A0.77200.79400.36820.043*
H15B0.69030.79770.27010.043*
H15C0.75310.69530.29380.043*
C160.8660 (3)0.9372 (3)0.7777 (3)0.0209 (9)
C170.8478 (3)0.9804 (3)0.8746 (3)0.0253 (10)
H17A0.78760.95340.91230.030*
C180.9183 (4)1.0624 (4)0.9145 (3)0.0286 (10)
H18A0.90501.09150.97880.034*
C191.0096 (3)1.1025 (3)0.8595 (3)0.0227 (9)
C201.0283 (4)1.0589 (4)0.7636 (3)0.0291 (11)
H20A1.08921.08510.72650.035*
C210.9575 (4)0.9774 (4)0.7231 (3)0.0309 (11)
H21A0.97060.94870.65860.037*
C221.0870 (4)1.1871 (4)0.9021 (3)0.0283 (10)
C230.9139 (3)0.6850 (3)0.5062 (3)0.0228 (9)
C240.9115 (4)0.5955 (4)0.4432 (3)0.0314 (11)
H24A0.85890.53880.45310.038*
C250.9872 (4)0.5906 (4)0.3657 (3)0.0338 (11)
H25A0.98490.53100.32300.041*
C261.0665 (4)0.6743 (4)0.3515 (3)0.0261 (10)
C271.0730 (4)0.7615 (4)0.4182 (4)0.0342 (11)
H27A1.12770.81690.41050.041*
C280.9978 (4)0.7648 (4)0.4957 (3)0.0323 (11)
H28A1.00360.82180.54180.039*
C291.1427 (4)0.6732 (4)0.2677 (4)0.0317 (11)
C300.3336 (4)0.9645 (4)0.9018 (3)0.0302 (11)
C310.4072 (4)0.8889 (4)0.9451 (3)0.0268 (10)
C320.3746 (4)0.8264 (4)1.0294 (3)0.0317 (11)
H32A0.30440.83171.05620.038*
C330.4462 (4)0.7573 (4)1.0728 (3)0.0304 (11)
H33A0.42410.71591.12900.036*
C340.5512 (4)0.7487 (3)1.0335 (3)0.0257 (10)
C350.5824 (4)0.8075 (3)0.9467 (3)0.0243 (10)
H35A0.65120.79930.91820.029*
C360.5121 (4)0.8775 (3)0.9033 (3)0.0238 (10)
H36A0.53380.91740.84600.029*
C370.1033 (5)0.6406 (4)0.9550 (4)0.0489 (14)
H37A0.03220.64090.98820.059*
H37B0.16250.65701.00760.059*
B10.4723 (4)0.7041 (4)0.6283 (4)0.0223 (11)
H10.386 (3)0.671 (3)0.629 (3)0.009 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mo10.01678 (19)0.0215 (2)0.01643 (18)0.00219 (14)0.00264 (13)0.00082 (13)
Cl10.0532 (9)0.0483 (9)0.0535 (8)0.0093 (7)0.0112 (7)0.0095 (7)
Cl20.0503 (9)0.0440 (9)0.0645 (9)0.0010 (7)0.0197 (7)0.0023 (7)
O10.0210 (16)0.0221 (16)0.0215 (15)0.0056 (13)0.0017 (12)0.0017 (12)
O20.0220 (16)0.0300 (18)0.0217 (15)0.0035 (14)0.0046 (12)0.0013 (13)
O30.035 (2)0.038 (2)0.0381 (19)0.0068 (16)0.0096 (15)0.0151 (16)
O40.0366 (19)0.0328 (19)0.0303 (17)0.0024 (16)0.0029 (14)0.0124 (14)
N10.0199 (19)0.0192 (19)0.0177 (17)0.0026 (15)0.0047 (14)0.0002 (14)
N20.0184 (18)0.022 (2)0.0157 (17)0.0024 (15)0.0015 (14)0.0001 (14)
N30.0163 (18)0.024 (2)0.0171 (17)0.0007 (15)0.0036 (13)0.0012 (14)
N40.0188 (18)0.022 (2)0.0171 (17)0.0017 (15)0.0039 (14)0.0011 (14)
N50.0166 (18)0.025 (2)0.0187 (17)0.0049 (15)0.0003 (14)0.0000 (14)
N60.0188 (19)0.022 (2)0.0196 (17)0.0021 (15)0.0004 (14)0.0010 (14)
N70.021 (2)0.031 (2)0.0217 (19)0.0033 (17)0.0019 (15)0.0013 (16)
N80.025 (2)0.032 (2)0.045 (2)0.0007 (19)0.0017 (18)0.0116 (19)
N90.041 (3)0.053 (3)0.041 (3)0.003 (2)0.018 (2)0.003 (2)
N100.039 (3)0.040 (3)0.039 (2)0.014 (2)0.0002 (19)0.005 (2)
C10.029 (2)0.021 (2)0.018 (2)0.0006 (19)0.0079 (17)0.0010 (17)
C20.034 (3)0.022 (2)0.024 (2)0.004 (2)0.0029 (19)0.0078 (18)
C30.033 (3)0.017 (2)0.019 (2)0.0032 (19)0.0033 (18)0.0047 (17)
C40.029 (3)0.029 (3)0.045 (3)0.003 (2)0.015 (2)0.013 (2)
C50.026 (3)0.034 (3)0.032 (3)0.005 (2)0.0042 (19)0.004 (2)
C60.022 (2)0.027 (2)0.015 (2)0.0038 (19)0.0023 (16)0.0015 (17)
C70.027 (2)0.023 (2)0.024 (2)0.007 (2)0.0040 (18)0.0026 (18)
C80.030 (2)0.023 (2)0.015 (2)0.002 (2)0.0050 (17)0.0008 (17)
C90.022 (2)0.032 (3)0.035 (3)0.004 (2)0.0073 (19)0.003 (2)
C100.034 (3)0.026 (3)0.035 (3)0.006 (2)0.009 (2)0.000 (2)
C110.028 (2)0.017 (2)0.022 (2)0.0038 (19)0.0070 (18)0.0025 (17)
C120.038 (3)0.024 (2)0.015 (2)0.007 (2)0.0043 (18)0.0023 (17)
C130.030 (2)0.020 (2)0.015 (2)0.0048 (19)0.0010 (17)0.0008 (16)
C140.029 (3)0.032 (3)0.034 (3)0.003 (2)0.007 (2)0.006 (2)
C150.032 (3)0.035 (3)0.019 (2)0.003 (2)0.0080 (18)0.0003 (19)
C160.021 (2)0.021 (2)0.020 (2)0.0004 (18)0.0035 (17)0.0007 (17)
C170.020 (2)0.031 (3)0.024 (2)0.007 (2)0.0060 (17)0.0032 (19)
C180.030 (3)0.029 (3)0.026 (2)0.001 (2)0.0045 (19)0.0070 (19)
C190.019 (2)0.017 (2)0.032 (2)0.0022 (18)0.0036 (18)0.0014 (18)
C200.024 (2)0.037 (3)0.026 (2)0.003 (2)0.0072 (18)0.003 (2)
C210.029 (3)0.036 (3)0.026 (2)0.009 (2)0.0074 (19)0.010 (2)
C220.027 (3)0.028 (3)0.031 (2)0.002 (2)0.0023 (19)0.004 (2)
C230.021 (2)0.028 (3)0.020 (2)0.0064 (19)0.0034 (17)0.0008 (18)
C240.032 (3)0.024 (3)0.038 (3)0.003 (2)0.011 (2)0.001 (2)
C250.041 (3)0.030 (3)0.032 (3)0.005 (2)0.011 (2)0.005 (2)
C260.024 (2)0.032 (3)0.024 (2)0.007 (2)0.0059 (18)0.0026 (19)
C270.021 (2)0.037 (3)0.044 (3)0.005 (2)0.011 (2)0.007 (2)
C280.020 (2)0.039 (3)0.037 (3)0.003 (2)0.0048 (19)0.018 (2)
C290.032 (3)0.027 (3)0.037 (3)0.004 (2)0.010 (2)0.004 (2)
C300.030 (3)0.037 (3)0.024 (2)0.003 (2)0.005 (2)0.004 (2)
C310.031 (3)0.024 (3)0.025 (2)0.001 (2)0.0023 (19)0.0020 (19)
C320.027 (3)0.040 (3)0.028 (2)0.003 (2)0.0056 (19)0.000 (2)
C330.030 (3)0.035 (3)0.026 (2)0.001 (2)0.0057 (19)0.010 (2)
C340.028 (2)0.026 (3)0.023 (2)0.001 (2)0.0053 (18)0.0008 (18)
C350.024 (2)0.025 (2)0.024 (2)0.000 (2)0.0036 (18)0.0016 (18)
C360.028 (2)0.024 (2)0.018 (2)0.002 (2)0.0011 (18)0.0032 (17)
C370.067 (4)0.043 (3)0.036 (3)0.004 (3)0.010 (3)0.000 (2)
B10.022 (3)0.022 (3)0.022 (2)0.000 (2)0.003 (2)0.002 (2)
Geometric parameters (Å, º) top
Mo1—N71.762 (4)C10—H10C0.9600
Mo1—O11.949 (3)C11—C121.380 (6)
Mo1—O21.954 (3)C11—C141.489 (6)
Mo1—N62.179 (3)C12—C131.380 (6)
Mo1—N42.186 (3)C12—H12A0.9300
Mo1—N22.220 (3)C13—C151.498 (6)
Cl1—C371.750 (5)C14—H14A0.9600
Cl2—C371.757 (5)C14—H14B0.9600
O1—C161.348 (5)C14—H14C0.9600
O2—C231.366 (5)C15—H15A0.9600
O3—N71.211 (4)C15—H15B0.9600
O4—C341.353 (5)C15—H15C0.9600
O4—H4A0.8200C16—C211.392 (6)
N1—C11.350 (5)C16—C171.395 (5)
N1—N21.372 (4)C17—C181.372 (6)
N1—B11.523 (6)C17—H17A0.9300
N2—C31.354 (5)C18—C191.394 (6)
N3—C61.352 (5)C18—H18A0.9300
N3—N41.387 (4)C19—C201.386 (6)
N3—B11.532 (6)C19—C221.452 (6)
N4—C81.345 (5)C20—C211.372 (6)
N5—C111.355 (5)C20—H20A0.9300
N5—N61.379 (4)C21—H21A0.9300
N5—B11.560 (5)C23—C281.380 (6)
N6—C131.349 (5)C23—C241.389 (6)
N8—C221.136 (5)C24—C251.382 (6)
N9—C291.146 (5)C24—H24A0.9300
N10—C301.143 (6)C25—C261.385 (6)
C1—C21.379 (6)C25—H25A0.9300
C1—C41.493 (6)C26—C271.391 (6)
C2—C31.386 (6)C26—C291.445 (6)
C2—H2A0.9300C27—C281.377 (6)
C3—C51.489 (6)C27—H27A0.9300
C4—H4B0.9600C28—H28A0.9300
C4—H4C0.9600C30—C311.444 (7)
C4—H4D0.9600C31—C321.397 (6)
C5—H5A0.9600C31—C361.405 (6)
C5—H5B0.9600C32—C331.372 (6)
C5—H5C0.9600C32—H32A0.9300
C6—C71.373 (6)C33—C341.388 (6)
C6—C91.491 (6)C33—H33A0.9300
C7—C81.388 (6)C34—C351.393 (6)
C7—H7A0.9300C35—C361.370 (6)
C8—C101.488 (6)C35—H35A0.9300
C9—H9A0.9600C36—H36A0.9300
C9—H9B0.9600C37—H37A0.9700
C9—H9C0.9600C37—H37B0.9700
C10—H10A0.9600B1—H11.09 (4)
C10—H10B0.9600
N7—Mo1—O197.65 (13)N6—C13—C12109.4 (4)
N7—Mo1—O297.14 (14)N6—C13—C15123.2 (4)
O1—Mo1—O2102.85 (11)C12—C13—C15127.5 (4)
N7—Mo1—N695.33 (14)C11—C14—H14A109.5
O1—Mo1—N6162.05 (11)C11—C14—H14B109.5
O2—Mo1—N687.73 (12)H14A—C14—H14B109.5
N7—Mo1—N493.57 (14)C11—C14—H14C109.5
O1—Mo1—N488.99 (12)H14A—C14—H14C109.5
O2—Mo1—N4162.77 (12)H14B—C14—H14C109.5
N6—Mo1—N477.84 (12)C13—C15—H15A109.5
N7—Mo1—N2179.42 (15)C13—C15—H15B109.5
O1—Mo1—N281.80 (11)H15A—C15—H15B109.5
O2—Mo1—N282.84 (12)C13—C15—H15C109.5
N6—Mo1—N285.25 (12)H15A—C15—H15C109.5
N4—Mo1—N286.58 (12)H15B—C15—H15C109.5
C16—O1—Mo1137.6 (2)O1—C16—C21122.9 (4)
C23—O2—Mo1131.6 (3)O1—C16—C17117.9 (4)
C34—O4—H4A109.5C21—C16—C17119.1 (4)
C1—N1—N2110.3 (3)C18—C17—C16120.2 (4)
C1—N1—B1130.9 (4)C18—C17—H17A119.9
N2—N1—B1118.8 (3)C16—C17—H17A119.9
C3—N2—N1106.4 (3)C17—C18—C19120.5 (4)
C3—N2—Mo1133.0 (3)C17—C18—H18A119.8
N1—N2—Mo1119.9 (2)C19—C18—H18A119.8
C6—N3—N4109.1 (3)C20—C19—C18119.3 (4)
C6—N3—B1130.0 (3)C20—C19—C22119.6 (4)
N4—N3—B1120.6 (3)C18—C19—C22121.1 (4)
C8—N4—N3106.5 (3)C21—C20—C19120.4 (4)
C8—N4—Mo1134.3 (3)C21—C20—H20A119.8
N3—N4—Mo1119.1 (2)C19—C20—H20A119.8
C11—N5—N6109.8 (3)C20—C21—C16120.5 (4)
C11—N5—B1128.8 (4)C20—C21—H21A119.7
N6—N5—B1120.1 (3)C16—C21—H21A119.7
C13—N6—N5106.5 (3)N8—C22—C19179.4 (5)
C13—N6—Mo1134.9 (3)O2—C23—C28122.6 (4)
N5—N6—Mo1118.1 (2)O2—C23—C24118.2 (4)
O3—N7—Mo1179.1 (3)C28—C23—C24119.2 (4)
N1—C1—C2107.0 (4)C25—C24—C23120.0 (4)
N1—C1—C4122.2 (4)C25—C24—H24A120.0
C2—C1—C4130.6 (4)C23—C24—H24A120.0
C1—C2—C3107.1 (4)C24—C25—C26120.1 (4)
C1—C2—H2A126.5C24—C25—H25A119.9
C3—C2—H2A126.5C26—C25—H25A119.9
N2—C3—C2109.1 (4)C25—C26—C27119.9 (4)
N2—C3—C5122.4 (4)C25—C26—C29121.1 (4)
C2—C3—C5128.5 (4)C27—C26—C29119.0 (4)
C1—C4—H4B109.5C28—C27—C26119.3 (4)
C1—C4—H4C109.5C28—C27—H27A120.4
H4B—C4—H4C109.5C26—C27—H27A120.4
C1—C4—H4D109.5C27—C28—C23121.2 (4)
H4B—C4—H4D109.5C27—C28—H28A119.4
H4C—C4—H4D109.5C23—C28—H28A119.4
C3—C5—H5A109.5N9—C29—C26177.8 (5)
C3—C5—H5B109.5N10—C30—C31179.6 (5)
H5A—C5—H5B109.5C32—C31—C36119.3 (4)
C3—C5—H5C109.5C32—C31—C30120.1 (4)
H5A—C5—H5C109.5C36—C31—C30120.6 (4)
H5B—C5—H5C109.5C33—C32—C31120.0 (4)
N3—C6—C7108.1 (4)C33—C32—H32A120.0
N3—C6—C9121.6 (4)C31—C32—H32A120.0
C7—C6—C9130.2 (4)C32—C33—C34120.5 (4)
C6—C7—C8106.5 (4)C32—C33—H33A119.7
C6—C7—H7A126.7C34—C33—H33A119.7
C8—C7—H7A126.7O4—C34—C33119.3 (4)
N4—C8—C7109.7 (4)O4—C34—C35121.0 (4)
N4—C8—C10123.2 (4)C33—C34—C35119.7 (4)
C7—C8—C10127.1 (4)C36—C35—C34120.3 (4)
C6—C9—H9A109.5C36—C35—H35A119.9
C6—C9—H9B109.5C34—C35—H35A119.9
H9A—C9—H9B109.5C35—C36—C31120.1 (4)
C6—C9—H9C109.5C35—C36—H36A120.0
H9A—C9—H9C109.5C31—C36—H36A120.0
H9B—C9—H9C109.5Cl1—C37—Cl2112.9 (3)
C8—C10—H10A109.5Cl1—C37—H37A109.0
C8—C10—H10B109.5Cl2—C37—H37A109.0
H10A—C10—H10B109.5Cl1—C37—H37B109.0
C8—C10—H10C109.5Cl2—C37—H37B109.0
H10A—C10—H10C109.5H37A—C37—H37B107.8
H10B—C10—H10C109.5N1—B1—N3110.1 (3)
N5—C11—C12107.0 (4)N1—B1—N5109.8 (3)
N5—C11—C14122.7 (4)N3—B1—N5106.2 (3)
C12—C11—C14130.3 (4)N1—B1—H1111.3 (19)
C13—C12—C11107.3 (4)N3—B1—H1111.6 (19)
C13—C12—H12A126.4N5—B1—H1107.7 (18)
C11—C12—H12A126.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O20.962.463.189 (5)133
C10—H10A···N70.962.473.228 (6)136
C15—H15A···N70.962.473.288 (6)143
C4—H4D···O4i0.962.523.360 (6)146
C9—H9B···O3ii0.962.373.219 (6)147
C37—H37B···N9iii0.962.533.366 (7)144
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y+2, z+1; (iii) x1, y, z+1.

Experimental details

Crystal data
Chemical formula[Mo(C15H22BN6)(C7H4NO)2(NO)]·C7H5NO·CH2Cl2
Mr863.42
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)11.9792 (19), 12.630 (2), 12.891 (2)
α, β, γ (°)90.120 (3), 92.459 (3), 94.300 (3)
V3)1943.0 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.53
Crystal size (mm)0.18 × 0.10 × 0.05
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.938, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections
19938, 8844, 5548
Rint0.066
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.129, 0.98
No. of reflections8844
No. of parameters500
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.59, 0.69

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Selected bond lengths (Å) top
Mo1—N71.762 (4)Mo1—N62.179 (3)
Mo1—O11.949 (3)Mo1—N42.186 (3)
Mo1—O21.954 (3)Mo1—N22.220 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O20.962.463.189 (5)133
C10—H10A···N70.962.473.228 (6)136
C15—H15A···N70.962.473.288 (6)143
C4—H4D···O4i0.962.523.360 (6)146
C9—H9B···O3ii0.962.373.219 (6)147
C37—H37B···N9iii0.962.533.366 (7)144
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y+2, z+1; (iii) x1, y, z+1.
 

Footnotes

Present address: School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi Selangor, Malaysia.

Acknowledgements

The authors thank the University of Bristol for providing the facilities and Universiti Kebangsaan Malaysia/World Bank for MBK's PhD scholarship and grant UKM-OUP-TK-16–73/2010.

References

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First citationBruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationJones, P. L., Amoroso, A. J., Jeffery, J. C., McCleverty, J. A., Psillakis, E., Rees, L. H. & Ward, M. D. (1997). Inorg. Chem. 36, 10–18.  CSD CrossRef CAS Web of Science Google Scholar
First citationKassim, M. B., Paul, R. L., Jeffery, J. C., McCleverty, J. A. & Ward, M. D. (2002). Inorg. Chim. Acta, 327, 160–168.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTrofimenko, S. (1993). Chem. Rev. 93, 943–980.  CrossRef CAS Web of Science Google Scholar

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