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

Kassim, M.B.; McCleverty, J.A.

doi:10.1107/S160053681004537X

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

In the title compound, [Mo(C₁₅H₂₂BN₆)(C₇H₄NO)₂(NO)]·C₇H₅NO·CH₂Cl₂, the central Mo^II 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 Mo^II 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053681004537X/hb5724sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053681004537X/hb5724Isup2.hkl Contains datablock I

CCDC reference: 802971

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.006 Å
R factor = 0.052
wR factor = 0.129
Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT415_ALERT_2_B Short Inter D-H..H-X       H4A    ..  H4D     ..       1.96 Ang.
PLAT420_ALERT_2_B D-H Without Acceptor       O4     -   H4A    ...          ?

Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H    Uiso(max)/Uso(min) ...       5.67 Ratio
PLAT245_ALERT_2_C U(iso) H1      Smaller than U(eq) B1      by ...       0.01 AngSq
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         22
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         88

Alert level G
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C19    -   C22    ...       1.45 Ang.
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C26    -   C29    ...       1.45 Ang.
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C30    -   C31    ...       1.45 Ang.
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        300 Deg.
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C4
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C5
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C9
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C14
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C15
PLAT794_ALERT_5_G Note: Tentative Bond Valency for Mo1     .......       5.54

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
  11 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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%.

Structure description 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).

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

	Fig. 1. The complex in (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
	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.
	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·CH₂Cl₂	Z = 2
M_r = 863.42	F(000) = 884
Triclinic, P1	D_x = 1.476 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.9792 (19) Å	Cell parameters from 3353 reflections
b = 12.630 (2) Å	θ = 1.6–27.5°
c = 12.891 (2) Å	µ = 0.53 mm⁻¹
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 tube	5548 reflections with I > 2σ(I)
Parallel, Graphite monochromator	R_int = 0.066
ω/2θ scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −15→15
T_min = 0.938, T_max = 0.974	k = −16→16
19938 measured reflections	l = −16→16

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0563P)²] where P = (F_o² + 2F_c²)/3
8844 reflections	(Δ/σ)_max = 0.001
500 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[Mo(C₁₅H₂₂BN₆)(C₇H₄NO)₂(NO)]·C₇H₅NO·CH₂Cl₂	γ = 94.300 (3)°
M_r = 863.42	V = 1943.0 (5) Å³
Triclinic, P1	Z = 2
a = 11.9792 (19) Å	Mo Kα radiation
b = 12.630 (2) Å	µ = 0.53 mm⁻¹
c = 12.891 (2) Å	T = 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)
T_min = 0.938, T_max = 0.974	R_int = 0.066
19938 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.59 e Å⁻³
8844 reflections	Δρ_min = −0.69 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Mo1	0.73371 (3)	0.79886 (3)	0.61020 (3)	0.01838 (11)
Cl1	0.10962 (12)	0.73930 (12)	0.85992 (11)	0.0521 (4)
Cl2	0.11742 (12)	0.51320 (11)	0.90460 (11)	0.0526 (4)
O1	0.7960 (2)	0.8548 (2)	0.7431 (2)	0.0219 (6)
O2	0.8338 (2)	0.6892 (2)	0.5782 (2)	0.0244 (7)
O3	0.8373 (3)	0.9671 (3)	0.4762 (2)	0.0372 (8)
O4	0.6205 (3)	0.6806 (2)	1.0784 (2)	0.0334 (8)
H4A	0.5905	0.6522	1.1283	0.050*
N1	0.5443 (3)	0.6553 (3)	0.7131 (2)	0.0190 (7)
N2	0.6586 (3)	0.6735 (3)	0.7118 (2)	0.0187 (8)
N3	0.4812 (3)	0.8253 (3)	0.6395 (2)	0.0192 (7)
N4	0.5838 (3)	0.8832 (3)	0.6333 (2)	0.0195 (8)
N5	0.5173 (3)	0.6799 (3)	0.5197 (2)	0.0203 (8)
N6	0.6173 (3)	0.7294 (3)	0.4898 (2)	0.0204 (8)
N7	0.7943 (3)	0.8988 (3)	0.5306 (3)	0.0250 (8)
N8	1.1473 (3)	1.2538 (3)	0.9349 (3)	0.0345 (10)
N9	1.2037 (4)	0.6758 (4)	0.2015 (3)	0.0447 (11)
N10	0.2755 (3)	1.0246 (3)	0.8680 (3)	0.0385 (10)
C1	0.5158 (4)	0.5900 (3)	0.7920 (3)	0.0224 (9)
C2	0.6143 (4)	0.5627 (3)	0.8408 (3)	0.0265 (10)
H2A	0.6209	0.5175	0.8972	0.032*
C3	0.7015 (4)	0.6152 (3)	0.7898 (3)	0.0229 (9)
C4	0.3968 (4)	0.5638 (4)	0.8183 (4)	0.0340 (11)
H4B	0.3481	0.5955	0.7682	0.051*
H4C	0.3848	0.5910	0.8862	0.051*
H4D	0.3810	0.4882	0.8173	0.051*
C5	0.8241 (4)	0.6155 (4)	0.8143 (3)	0.0307 (11)
H5A	0.8640	0.6592	0.7652	0.046*
H5B	0.8466	0.5443	0.8104	0.046*
H5C	0.8407	0.6432	0.8831	0.046*
C6	0.3999 (3)	0.8931 (3)	0.6482 (3)	0.0213 (9)
C7	0.4492 (4)	0.9948 (3)	0.6481 (3)	0.0246 (10)
H7A	0.4133	1.0572	0.6537	0.029*
C8	0.5630 (4)	0.9862 (3)	0.6380 (3)	0.0225 (9)
C9	0.2803 (3)	0.8542 (4)	0.6581 (3)	0.0294 (10)
H9A	0.2734	0.7780	0.6553	0.044*
H9B	0.2357	0.8818	0.6022	0.044*
H9C	0.2546	0.8777	0.7232	0.044*
C10	0.6525 (4)	1.0744 (4)	0.6366 (3)	0.0318 (11)
H10A	0.7238	1.0457	0.6293	0.048*
H10B	0.6537	1.1140	0.7003	0.048*
H10C	0.6379	1.1204	0.5792	0.048*
C11	0.4625 (4)	0.6304 (3)	0.4370 (3)	0.0224 (9)
C12	0.5288 (4)	0.6482 (3)	0.3529 (3)	0.0253 (10)
H12A	0.5131	0.6230	0.2856	0.030*
C13	0.6228 (4)	0.7104 (3)	0.3872 (3)	0.0214 (9)
C14	0.3518 (4)	0.5694 (4)	0.4444 (3)	0.0322 (11)
H14A	0.3280	0.5725	0.5145	0.048*
H14B	0.3585	0.4967	0.4252	0.048*
H14C	0.2978	0.5996	0.3985	0.048*
C15	0.7181 (4)	0.7532 (4)	0.3242 (3)	0.0288 (11)
H15A	0.7720	0.7940	0.3682	0.043*
H15B	0.6903	0.7977	0.2701	0.043*
H15C	0.7531	0.6953	0.2938	0.043*
C16	0.8660 (3)	0.9372 (3)	0.7777 (3)	0.0209 (9)
C17	0.8478 (3)	0.9804 (3)	0.8746 (3)	0.0253 (10)
H17A	0.7876	0.9534	0.9123	0.030*
C18	0.9183 (4)	1.0624 (4)	0.9145 (3)	0.0286 (10)
H18A	0.9050	1.0915	0.9788	0.034*
C19	1.0096 (3)	1.1025 (3)	0.8595 (3)	0.0227 (9)
C20	1.0283 (4)	1.0589 (4)	0.7636 (3)	0.0291 (11)
H20A	1.0892	1.0851	0.7265	0.035*
C21	0.9575 (4)	0.9774 (4)	0.7231 (3)	0.0309 (11)
H21A	0.9706	0.9487	0.6586	0.037*
C22	1.0870 (4)	1.1871 (4)	0.9021 (3)	0.0283 (10)
C23	0.9139 (3)	0.6850 (3)	0.5062 (3)	0.0228 (9)
C24	0.9115 (4)	0.5955 (4)	0.4432 (3)	0.0314 (11)
H24A	0.8589	0.5388	0.4531	0.038*
C25	0.9872 (4)	0.5906 (4)	0.3657 (3)	0.0338 (11)
H25A	0.9849	0.5310	0.3230	0.041*
C26	1.0665 (4)	0.6743 (4)	0.3515 (3)	0.0261 (10)
C27	1.0730 (4)	0.7615 (4)	0.4182 (4)	0.0342 (11)
H27A	1.1277	0.8169	0.4105	0.041*
C28	0.9978 (4)	0.7648 (4)	0.4957 (3)	0.0323 (11)
H28A	1.0036	0.8218	0.5418	0.039*
C29	1.1427 (4)	0.6732 (4)	0.2677 (4)	0.0317 (11)
C30	0.3336 (4)	0.9645 (4)	0.9018 (3)	0.0302 (11)
C31	0.4072 (4)	0.8889 (4)	0.9451 (3)	0.0268 (10)
C32	0.3746 (4)	0.8264 (4)	1.0294 (3)	0.0317 (11)
H32A	0.3044	0.8317	1.0562	0.038*
C33	0.4462 (4)	0.7573 (4)	1.0728 (3)	0.0304 (11)
H33A	0.4241	0.7159	1.1290	0.036*
C34	0.5512 (4)	0.7487 (3)	1.0335 (3)	0.0257 (10)
C35	0.5824 (4)	0.8075 (3)	0.9467 (3)	0.0243 (10)
H35A	0.6512	0.7993	0.9182	0.029*
C36	0.5121 (4)	0.8775 (3)	0.9033 (3)	0.0238 (10)
H36A	0.5338	0.9174	0.8460	0.029*
C37	0.1033 (5)	0.6406 (4)	0.9550 (4)	0.0489 (14)
H37A	0.0322	0.6409	0.9882	0.059*
H37B	0.1625	0.6570	1.0076	0.059*
B1	0.4723 (4)	0.7041 (4)	0.6283 (4)	0.0223 (11)
H1	0.386 (3)	0.671 (3)	0.629 (3)	0.009 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mo1	0.01678 (19)	0.0215 (2)	0.01643 (18)	−0.00219 (14)	0.00264 (13)	−0.00082 (13)
Cl1	0.0532 (9)	0.0483 (9)	0.0535 (8)	−0.0093 (7)	0.0112 (7)	0.0095 (7)
Cl2	0.0503 (9)	0.0440 (9)	0.0645 (9)	0.0010 (7)	0.0197 (7)	−0.0023 (7)
O1	0.0210 (16)	0.0221 (16)	0.0215 (15)	−0.0056 (13)	0.0017 (12)	−0.0017 (12)
O2	0.0220 (16)	0.0300 (18)	0.0217 (15)	0.0035 (14)	0.0046 (12)	−0.0013 (13)
O3	0.035 (2)	0.038 (2)	0.0381 (19)	−0.0068 (16)	0.0096 (15)	0.0151 (16)
O4	0.0366 (19)	0.0328 (19)	0.0303 (17)	0.0024 (16)	−0.0029 (14)	0.0124 (14)
N1	0.0199 (19)	0.0192 (19)	0.0177 (17)	−0.0026 (15)	0.0047 (14)	0.0002 (14)
N2	0.0184 (18)	0.022 (2)	0.0157 (17)	−0.0024 (15)	0.0015 (14)	0.0001 (14)
N3	0.0163 (18)	0.024 (2)	0.0171 (17)	0.0007 (15)	0.0036 (13)	0.0012 (14)
N4	0.0188 (18)	0.022 (2)	0.0171 (17)	−0.0017 (15)	0.0039 (14)	−0.0011 (14)
N5	0.0166 (18)	0.025 (2)	0.0187 (17)	−0.0049 (15)	0.0003 (14)	0.0000 (14)
N6	0.0188 (19)	0.022 (2)	0.0196 (17)	−0.0021 (15)	0.0004 (14)	−0.0010 (14)
N7	0.021 (2)	0.031 (2)	0.0217 (19)	−0.0033 (17)	0.0019 (15)	0.0013 (16)
N8	0.025 (2)	0.032 (2)	0.045 (2)	−0.0007 (19)	0.0017 (18)	−0.0116 (19)
N9	0.041 (3)	0.053 (3)	0.041 (3)	0.003 (2)	0.018 (2)	0.003 (2)
N10	0.039 (3)	0.040 (3)	0.039 (2)	0.014 (2)	0.0002 (19)	−0.005 (2)
C1	0.029 (2)	0.021 (2)	0.018 (2)	−0.0006 (19)	0.0079 (17)	−0.0010 (17)
C2	0.034 (3)	0.022 (2)	0.024 (2)	0.004 (2)	0.0029 (19)	0.0078 (18)
C3	0.033 (3)	0.017 (2)	0.019 (2)	0.0032 (19)	−0.0033 (18)	−0.0047 (17)
C4	0.029 (3)	0.029 (3)	0.045 (3)	0.003 (2)	0.015 (2)	0.013 (2)
C5	0.026 (3)	0.034 (3)	0.032 (3)	0.005 (2)	−0.0042 (19)	0.004 (2)
C6	0.022 (2)	0.027 (2)	0.015 (2)	0.0038 (19)	0.0023 (16)	0.0015 (17)
C7	0.027 (2)	0.023 (2)	0.024 (2)	0.007 (2)	0.0040 (18)	0.0026 (18)
C8	0.030 (2)	0.023 (2)	0.015 (2)	0.002 (2)	0.0050 (17)	0.0008 (17)
C9	0.022 (2)	0.032 (3)	0.035 (3)	0.004 (2)	0.0073 (19)	0.003 (2)
C10	0.034 (3)	0.026 (3)	0.035 (3)	−0.006 (2)	0.009 (2)	0.000 (2)
C11	0.028 (2)	0.017 (2)	0.022 (2)	0.0038 (19)	−0.0070 (18)	−0.0025 (17)
C12	0.038 (3)	0.024 (2)	0.015 (2)	0.007 (2)	−0.0043 (18)	−0.0023 (17)
C13	0.030 (2)	0.020 (2)	0.015 (2)	0.0048 (19)	0.0010 (17)	0.0008 (16)
C14	0.029 (3)	0.032 (3)	0.034 (3)	−0.003 (2)	−0.007 (2)	−0.006 (2)
C15	0.032 (3)	0.035 (3)	0.019 (2)	0.003 (2)	0.0080 (18)	−0.0003 (19)
C16	0.021 (2)	0.021 (2)	0.020 (2)	−0.0004 (18)	−0.0035 (17)	0.0007 (17)
C17	0.020 (2)	0.031 (3)	0.024 (2)	−0.007 (2)	0.0060 (17)	−0.0032 (19)
C18	0.030 (3)	0.029 (3)	0.026 (2)	−0.001 (2)	0.0045 (19)	−0.0070 (19)
C19	0.019 (2)	0.017 (2)	0.032 (2)	0.0022 (18)	−0.0036 (18)	−0.0014 (18)
C20	0.024 (2)	0.037 (3)	0.026 (2)	−0.003 (2)	0.0072 (18)	−0.003 (2)
C21	0.029 (3)	0.036 (3)	0.026 (2)	−0.009 (2)	0.0074 (19)	−0.010 (2)
C22	0.027 (3)	0.028 (3)	0.031 (2)	0.002 (2)	0.0023 (19)	−0.004 (2)
C23	0.021 (2)	0.028 (3)	0.020 (2)	0.0064 (19)	0.0034 (17)	−0.0008 (18)
C24	0.032 (3)	0.024 (3)	0.038 (3)	−0.003 (2)	0.011 (2)	0.001 (2)
C25	0.041 (3)	0.030 (3)	0.032 (3)	0.005 (2)	0.011 (2)	−0.005 (2)
C26	0.024 (2)	0.032 (3)	0.024 (2)	0.007 (2)	0.0059 (18)	0.0026 (19)
C27	0.021 (2)	0.037 (3)	0.044 (3)	−0.005 (2)	0.011 (2)	−0.007 (2)
C28	0.020 (2)	0.039 (3)	0.037 (3)	−0.003 (2)	0.0048 (19)	−0.018 (2)
C29	0.032 (3)	0.027 (3)	0.037 (3)	0.004 (2)	0.010 (2)	0.004 (2)
C30	0.030 (3)	0.037 (3)	0.024 (2)	0.003 (2)	0.005 (2)	−0.004 (2)
C31	0.031 (3)	0.024 (3)	0.025 (2)	0.001 (2)	−0.0023 (19)	−0.0020 (19)
C32	0.027 (3)	0.040 (3)	0.028 (2)	−0.003 (2)	0.0056 (19)	0.000 (2)
C33	0.030 (3)	0.035 (3)	0.026 (2)	−0.001 (2)	0.0057 (19)	0.010 (2)
C34	0.028 (2)	0.026 (3)	0.023 (2)	−0.001 (2)	−0.0053 (18)	0.0008 (18)
C35	0.024 (2)	0.025 (2)	0.024 (2)	0.000 (2)	0.0036 (18)	−0.0016 (18)
C36	0.028 (2)	0.024 (2)	0.018 (2)	−0.002 (2)	−0.0011 (18)	−0.0032 (17)
C37	0.067 (4)	0.043 (3)	0.036 (3)	−0.004 (3)	0.010 (3)	0.000 (2)
B1	0.022 (3)	0.022 (3)	0.022 (2)	0.000 (2)	0.003 (2)	−0.002 (2)

Geometric parameters (Å, º) top

Mo1—N7	1.762 (4)	C10—H10C	0.9600
Mo1—O1	1.949 (3)	C11—C12	1.380 (6)
Mo1—O2	1.954 (3)	C11—C14	1.489 (6)
Mo1—N6	2.179 (3)	C12—C13	1.380 (6)
Mo1—N4	2.186 (3)	C12—H12A	0.9300
Mo1—N2	2.220 (3)	C13—C15	1.498 (6)
Cl1—C37	1.750 (5)	C14—H14A	0.9600
Cl2—C37	1.757 (5)	C14—H14B	0.9600
O1—C16	1.348 (5)	C14—H14C	0.9600
O2—C23	1.366 (5)	C15—H15A	0.9600
O3—N7	1.211 (4)	C15—H15B	0.9600
O4—C34	1.353 (5)	C15—H15C	0.9600
O4—H4A	0.8200	C16—C21	1.392 (6)
N1—C1	1.350 (5)	C16—C17	1.395 (5)
N1—N2	1.372 (4)	C17—C18	1.372 (6)
N1—B1	1.523 (6)	C17—H17A	0.9300
N2—C3	1.354 (5)	C18—C19	1.394 (6)
N3—C6	1.352 (5)	C18—H18A	0.9300
N3—N4	1.387 (4)	C19—C20	1.386 (6)
N3—B1	1.532 (6)	C19—C22	1.452 (6)
N4—C8	1.345 (5)	C20—C21	1.372 (6)
N5—C11	1.355 (5)	C20—H20A	0.9300
N5—N6	1.379 (4)	C21—H21A	0.9300
N5—B1	1.560 (5)	C23—C28	1.380 (6)
N6—C13	1.349 (5)	C23—C24	1.389 (6)
N8—C22	1.136 (5)	C24—C25	1.382 (6)
N9—C29	1.146 (5)	C24—H24A	0.9300
N10—C30	1.143 (6)	C25—C26	1.385 (6)
C1—C2	1.379 (6)	C25—H25A	0.9300
C1—C4	1.493 (6)	C26—C27	1.391 (6)
C2—C3	1.386 (6)	C26—C29	1.445 (6)
C2—H2A	0.9300	C27—C28	1.377 (6)
C3—C5	1.489 (6)	C27—H27A	0.9300
C4—H4B	0.9600	C28—H28A	0.9300
C4—H4C	0.9600	C30—C31	1.444 (7)
C4—H4D	0.9600	C31—C32	1.397 (6)
C5—H5A	0.9600	C31—C36	1.405 (6)
C5—H5B	0.9600	C32—C33	1.372 (6)
C5—H5C	0.9600	C32—H32A	0.9300
C6—C7	1.373 (6)	C33—C34	1.388 (6)
C6—C9	1.491 (6)	C33—H33A	0.9300
C7—C8	1.388 (6)	C34—C35	1.393 (6)
C7—H7A	0.9300	C35—C36	1.370 (6)
C8—C10	1.488 (6)	C35—H35A	0.9300
C9—H9A	0.9600	C36—H36A	0.9300
C9—H9B	0.9600	C37—H37A	0.9700
C9—H9C	0.9600	C37—H37B	0.9700
C10—H10A	0.9600	B1—H1	1.09 (4)
C10—H10B	0.9600

N7—Mo1—O1	97.65 (13)	N6—C13—C12	109.4 (4)
N7—Mo1—O2	97.14 (14)	N6—C13—C15	123.2 (4)
O1—Mo1—O2	102.85 (11)	C12—C13—C15	127.5 (4)
N7—Mo1—N6	95.33 (14)	C11—C14—H14A	109.5
O1—Mo1—N6	162.05 (11)	C11—C14—H14B	109.5
O2—Mo1—N6	87.73 (12)	H14A—C14—H14B	109.5
N7—Mo1—N4	93.57 (14)	C11—C14—H14C	109.5
O1—Mo1—N4	88.99 (12)	H14A—C14—H14C	109.5
O2—Mo1—N4	162.77 (12)	H14B—C14—H14C	109.5
N6—Mo1—N4	77.84 (12)	C13—C15—H15A	109.5
N7—Mo1—N2	179.42 (15)	C13—C15—H15B	109.5
O1—Mo1—N2	81.80 (11)	H15A—C15—H15B	109.5
O2—Mo1—N2	82.84 (12)	C13—C15—H15C	109.5
N6—Mo1—N2	85.25 (12)	H15A—C15—H15C	109.5
N4—Mo1—N2	86.58 (12)	H15B—C15—H15C	109.5
C16—O1—Mo1	137.6 (2)	O1—C16—C21	122.9 (4)
C23—O2—Mo1	131.6 (3)	O1—C16—C17	117.9 (4)
C34—O4—H4A	109.5	C21—C16—C17	119.1 (4)
C1—N1—N2	110.3 (3)	C18—C17—C16	120.2 (4)
C1—N1—B1	130.9 (4)	C18—C17—H17A	119.9
N2—N1—B1	118.8 (3)	C16—C17—H17A	119.9
C3—N2—N1	106.4 (3)	C17—C18—C19	120.5 (4)
C3—N2—Mo1	133.0 (3)	C17—C18—H18A	119.8
N1—N2—Mo1	119.9 (2)	C19—C18—H18A	119.8
C6—N3—N4	109.1 (3)	C20—C19—C18	119.3 (4)
C6—N3—B1	130.0 (3)	C20—C19—C22	119.6 (4)
N4—N3—B1	120.6 (3)	C18—C19—C22	121.1 (4)
C8—N4—N3	106.5 (3)	C21—C20—C19	120.4 (4)
C8—N4—Mo1	134.3 (3)	C21—C20—H20A	119.8
N3—N4—Mo1	119.1 (2)	C19—C20—H20A	119.8
C11—N5—N6	109.8 (3)	C20—C21—C16	120.5 (4)
C11—N5—B1	128.8 (4)	C20—C21—H21A	119.7
N6—N5—B1	120.1 (3)	C16—C21—H21A	119.7
C13—N6—N5	106.5 (3)	N8—C22—C19	179.4 (5)
C13—N6—Mo1	134.9 (3)	O2—C23—C28	122.6 (4)
N5—N6—Mo1	118.1 (2)	O2—C23—C24	118.2 (4)
O3—N7—Mo1	179.1 (3)	C28—C23—C24	119.2 (4)
N1—C1—C2	107.0 (4)	C25—C24—C23	120.0 (4)
N1—C1—C4	122.2 (4)	C25—C24—H24A	120.0
C2—C1—C4	130.6 (4)	C23—C24—H24A	120.0
C1—C2—C3	107.1 (4)	C24—C25—C26	120.1 (4)
C1—C2—H2A	126.5	C24—C25—H25A	119.9
C3—C2—H2A	126.5	C26—C25—H25A	119.9
N2—C3—C2	109.1 (4)	C25—C26—C27	119.9 (4)
N2—C3—C5	122.4 (4)	C25—C26—C29	121.1 (4)
C2—C3—C5	128.5 (4)	C27—C26—C29	119.0 (4)
C1—C4—H4B	109.5	C28—C27—C26	119.3 (4)
C1—C4—H4C	109.5	C28—C27—H27A	120.4
H4B—C4—H4C	109.5	C26—C27—H27A	120.4
C1—C4—H4D	109.5	C27—C28—C23	121.2 (4)
H4B—C4—H4D	109.5	C27—C28—H28A	119.4
H4C—C4—H4D	109.5	C23—C28—H28A	119.4
C3—C5—H5A	109.5	N9—C29—C26	177.8 (5)
C3—C5—H5B	109.5	N10—C30—C31	179.6 (5)
H5A—C5—H5B	109.5	C32—C31—C36	119.3 (4)
C3—C5—H5C	109.5	C32—C31—C30	120.1 (4)
H5A—C5—H5C	109.5	C36—C31—C30	120.6 (4)
H5B—C5—H5C	109.5	C33—C32—C31	120.0 (4)
N3—C6—C7	108.1 (4)	C33—C32—H32A	120.0
N3—C6—C9	121.6 (4)	C31—C32—H32A	120.0
C7—C6—C9	130.2 (4)	C32—C33—C34	120.5 (4)
C6—C7—C8	106.5 (4)	C32—C33—H33A	119.7
C6—C7—H7A	126.7	C34—C33—H33A	119.7
C8—C7—H7A	126.7	O4—C34—C33	119.3 (4)
N4—C8—C7	109.7 (4)	O4—C34—C35	121.0 (4)
N4—C8—C10	123.2 (4)	C33—C34—C35	119.7 (4)
C7—C8—C10	127.1 (4)	C36—C35—C34	120.3 (4)
C6—C9—H9A	109.5	C36—C35—H35A	119.9
C6—C9—H9B	109.5	C34—C35—H35A	119.9
H9A—C9—H9B	109.5	C35—C36—C31	120.1 (4)
C6—C9—H9C	109.5	C35—C36—H36A	120.0
H9A—C9—H9C	109.5	C31—C36—H36A	120.0
H9B—C9—H9C	109.5	Cl1—C37—Cl2	112.9 (3)
C8—C10—H10A	109.5	Cl1—C37—H37A	109.0
C8—C10—H10B	109.5	Cl2—C37—H37A	109.0
H10A—C10—H10B	109.5	Cl1—C37—H37B	109.0
C8—C10—H10C	109.5	Cl2—C37—H37B	109.0
H10A—C10—H10C	109.5	H37A—C37—H37B	107.8
H10B—C10—H10C	109.5	N1—B1—N3	110.1 (3)
N5—C11—C12	107.0 (4)	N1—B1—N5	109.8 (3)
N5—C11—C14	122.7 (4)	N3—B1—N5	106.2 (3)
C12—C11—C14	130.3 (4)	N1—B1—H1	111.3 (19)
C13—C12—C11	107.3 (4)	N3—B1—H1	111.6 (19)
C13—C12—H12A	126.4	N5—B1—H1	107.7 (18)
C11—C12—H12A	126.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Experimental details

Crystal data
Chemical formula	[Mo(C₁₅H₂₂BN₆)(C₇H₄NO)₂(NO)]·C₇H₅NO·CH₂Cl₂
M_r	863.42
Crystal system, space group	Triclinic, 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)
V (Å³)	1943.0 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.53
Crystal size (mm)	0.18 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.938, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	19938, 8844, 5548
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.129, 0.98
No. of reflections	8844
No. of parameters	500
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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—N7	1.762 (4)	Mo1—N6	2.179 (3)
Mo1—O1	1.949 (3)	Mo1—N4	2.186 (3)
Mo1—O2	1.954 (3)	Mo1—N2	2.220 (3)