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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1696–m1697.
Published online 2010 November 30. doi:  10.1107/S1600536810048233
PMCID: PMC3011577

(4-tert-Butyl­pyridine)­chlorido[hydro­tris­(3,5-dimethyl­pyrazol-1-yl)borato]nitro­sylmolybdenum(I) dichloro­methane monosolvate

Abstract

In the title compound, [Mo(C15H22BN6)Cl(NO)(C9H13N)]·CH2Cl2, the MoI atom adopts a distorted MoClN5 octa­hedral geometry with the hydro­tris­(3,5-dimethyl­pyrazol­yl)borate anion in an N,N′,N′′-tridentate tripodal (facial) coordination mode. A 4-tert-butyl­pyrine ligand, chloride anion and a nitrosyl cation complement the coodination of the MoI atom and an intra­molecular C—H(...)Cl hydrogen bond helps to stabilize the configuration of the complex mol­ecule. The packing is stabilized by an inter­molecular C—H(...)Cl hydrogen bond involving the complex mol­ecule and the CH2Cl2 solvent mol­ecule.

Related literature

For bond lengths and angles, see: Kassim & McCleverty (2010 [triangle]). For related compounds, see: Kassim (2003 [triangle]); Kassim et al. (2002 [triangle]); Jones et al. (1997 [triangle]); Amoroso et al. (1994 [triangle]). For background to poly-(pyrazol­yl)borate ligands, see: Trofimenko (1993 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1696-scheme1.jpg

Experimental

Crystal data

  • [Mo(C15H22BN6)Cl(NO)(C9H13N)]·CH2Cl2
  • M r = 678.73
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1696-efi4.jpg
  • a = 13.4525 (18) Å
  • b = 16.345 (2) Å
  • c = 14.818 (2) Å
  • β = 109.376 (2)°
  • V = 3073.7 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.72 mm−1
  • T = 173 K
  • 0.30 × 0.15 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.878, T max = 0.930
  • 19465 measured reflections
  • 7040 independent reflections
  • 5113 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.119
  • S = 1.05
  • 7040 reflections
  • 365 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.54 e Å−3
  • Δρmin = −1.50 e Å−3

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

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810048233/hb5750sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048233/hb5750Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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. One chloride anion; a 4-tert-butylpyridine and a nitrosyl cation, bond via the N-atom, establish the distorted octahedral coordination of the Mo(I) centre (Fig1). In addition, one molecule of CH2Cl2 solvent cystallized together with the complex molecule.

In the complex molecule moeities, [Mo1/Cl1/N11/N12/C13/C14/C15/C16/C17/B1 (A)], [Mo1/N21/N 22/C23/C24/C25/C26/C27/B1 (B)] and [Mo1/O1/N1/N31/N32/C33/C34/C35/C36/C37/B1 (C)] are essentially planar with maximum deviations from the mean plane are 0.040 (4)° for B1, 0.029 (5)° for C27 and 0.043 (1)° for B1 atoms, respectively. The dihedral angles between A/B, A/C and B/C planes are 62.18 (10)°, 56.96 (9)° and 60.87 (10)°, respectively. Whereas the dihedral angles between these moeities and the 4-tert-butylpyridine, [N41/C42/C43/C44/C45/C46/C47/C49 (D)] which is essentially planar with maximum deviation from the mean plane is 0.056 (4)° for C47 atom, are A/D 70.28 (13)°, B/D 18.14 (14)° and C/D 55.67 (13)°, respectively.

The crystal structure is stabilized by an intramolecular hydrogen bonds C(36)—H(36 A)···Cl(1) (Fig2). The crystal packing is stabilized by an intermolecular hydrogen bonds C—H···Cl (Fig3).

Experimental

The title compound was synthesized from a reaction of Mo(NO)Tp*Cl2 (0.5 mmol) with 4- tert-butylpyridine (0.5 mmol) in dichloromethane in the presence of triethylammine at refluxing temperature under N2 atmosphere (Kassim 2003 & Kassim et al. 2002). Green blocks of (I) were obtained from a slow evaporation of dichloromethane solution of the title compound at room temperature. Yeild 87%.

Refinement

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.

Figures

Fig. 1.
The title compound, (I), with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius.
Fig. 2.
The complex molecule picturing the intramolecular H-bond shown as dotted line. The displacement ellipsoids are drawn at the 50% probability level and H atom is shown as spheres of arbitary radius.
Fig. 3.
The packing diagram of the title compound, (I), view down the crystallographic b-axis showing the intermolecular H-bonds [symmetry code: -x + 1/2, y + 1/2,-z + 1/2]. The displacement ellipsoids are drawn at the 50% probability level and H atoms are shown ...

Crystal data

[Mo(C15H22BN6)Cl(NO)(C9H13N)]·CH2Cl2F(000) = 1396
Mr = 678.73Dx = 1.467 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7070 reflections
a = 13.4525 (18) Åθ = 0.9–0.9°
b = 16.345 (2) ŵ = 0.72 mm1
c = 14.818 (2) ÅT = 173 K
β = 109.376 (2)°Block, green
V = 3073.7 (7) Å30.30 × 0.15 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer7040 independent reflections
Radiation source: fine-focus sealed tube5113 reflections with I > 2σ(I)
graphiteRint = 0.036
ω/2θ scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −17→8
Tmin = 0.878, Tmax = 0.930k = −20→21
19465 measured reflectionsl = −17→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0573P)2 + 2.0808P] where P = (Fo2 + 2Fc2)/3
7040 reflections(Δ/σ)max < 0.001
365 parametersΔρmax = 1.54 e Å3
0 restraintsΔρmin = −1.50 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer 1986) 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)

xyzUiso*/Ueq
Mo1−0.01682 (2)0.190933 (16)0.201620 (19)0.02194 (9)
Cl10.09795 (11)0.07454 (9)0.25484 (10)0.0659 (3)
O1−0.1941 (4)0.0915 (3)0.1352 (4)0.0633 (14)
N1−0.1472 (5)0.1227 (3)0.1546 (4)0.0506 (16)
N11−0.1070 (2)0.30427 (15)0.16343 (18)0.0210 (5)
N12−0.0789 (2)0.36951 (15)0.22502 (18)0.0209 (6)
N21−0.0271 (2)0.21357 (17)0.3421 (2)0.0260 (6)
N22−0.0113 (2)0.29123 (17)0.37923 (19)0.0246 (6)
N310.1233 (2)0.27485 (17)0.25025 (19)0.0257 (6)
N320.1155 (2)0.34300 (17)0.30134 (19)0.0244 (6)
N410.0079 (2)0.18807 (16)0.06164 (19)0.0238 (6)
C13−0.1469 (3)0.43159 (19)0.1912 (2)0.0261 (7)
C14−0.2200 (3)0.4062 (2)0.1067 (2)0.0275 (7)
H14−0.27640.43640.06760.033*
C15−0.1933 (3)0.3268 (2)0.0910 (2)0.0239 (7)
C16−0.2479 (3)0.2725 (2)0.0085 (3)0.0361 (9)
H16A−0.19850.2546−0.02150.054*
H16B−0.30410.3021−0.03690.054*
H16C−0.27610.22580.03100.054*
C17−0.1376 (3)0.5122 (2)0.2406 (3)0.0406 (9)
H17A−0.15400.50570.29850.061*
H17B−0.18600.55040.19940.061*
H17C−0.06700.53240.25560.061*
C23−0.0187 (3)0.2914 (2)0.4679 (2)0.0323 (8)
C24−0.0413 (3)0.2125 (3)0.4880 (3)0.0389 (9)
H24−0.05130.19430.54380.047*
C25−0.0460 (3)0.1657 (2)0.4090 (3)0.0334 (8)
C26−0.0657 (4)0.0756 (2)0.3935 (3)0.0450 (10)
H26A−0.11890.06650.33250.068*
H26B−0.08920.05380.44320.068*
H26C−0.00170.04870.39500.068*
C27−0.0024 (4)0.3667 (3)0.5285 (3)0.0457 (10)
H27A0.07100.38100.55060.069*
H27B−0.02500.35640.58250.069*
H27C−0.04270.41090.49140.069*
C330.2073 (3)0.3848 (2)0.3266 (2)0.0295 (8)
C340.2748 (3)0.3431 (2)0.2915 (3)0.0341 (8)
H340.34350.35780.29790.041*
C350.2212 (3)0.2748 (2)0.2446 (3)0.0314 (8)
C360.2608 (3)0.2098 (3)0.1939 (3)0.0440 (10)
H36A0.22540.15920.19590.066*
H36B0.33520.20290.22470.066*
H36C0.24700.22570.12850.066*
C370.2245 (3)0.4632 (2)0.3822 (3)0.0411 (10)
H37A0.16830.50060.35180.062*
H37B0.29040.48690.38410.062*
H37C0.22570.45230.44620.062*
C420.0214 (3)0.1171 (2)0.0216 (3)0.0311 (8)
H420.00790.06860.04830.037*
C430.0542 (3)0.1124 (2)−0.0569 (3)0.0301 (8)
H430.06340.0615−0.08110.036*
C440.0738 (3)0.1834 (2)−0.1005 (2)0.0253 (7)
C450.0539 (3)0.2565 (2)−0.0615 (2)0.0294 (8)
H450.06190.3059−0.08940.035*
C460.0224 (3)0.2567 (2)0.0179 (2)0.0284 (7)
H460.01070.30670.04240.034*
C470.1185 (3)0.1786 (2)−0.1822 (3)0.0323 (8)
C480.2272 (3)0.1384 (3)−0.1414 (3)0.0549 (12)
H48A0.26180.1398−0.18860.082*
H48B0.21920.0827−0.12470.082*
H48C0.26880.1678−0.08550.082*
C490.1299 (5)0.2623 (3)−0.2217 (4)0.0710 (17)
H49A0.15890.2565−0.27250.106*
H49B0.17610.2954−0.17170.106*
H49C0.06200.2880−0.24590.106*
C500.0491 (4)0.1245 (3)−0.2622 (3)0.0522 (12)
H50A−0.02010.1481−0.28730.078*
H50B0.04420.0709−0.23750.078*
H50C0.07930.1206−0.31240.078*
C510.1685 (4)0.5102 (3)0.0856 (4)0.0593 (13)
H51A0.14600.54900.03330.071*
H51B0.22400.53560.13750.071*
Cl520.06149 (10)0.48814 (11)0.12480 (9)0.0811 (5)
Cl530.21867 (12)0.42286 (8)0.04752 (10)0.0710 (4)
B10.0133 (3)0.3618 (2)0.3211 (3)0.0258 (8)
H10.021 (2)0.4210 (19)0.360 (2)0.016 (8)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mo10.02209 (15)0.02111 (14)0.02357 (15)−0.00110 (12)0.00883 (11)0.00138 (11)
Cl10.0607 (8)0.0723 (8)0.0686 (8)−0.0042 (6)0.0267 (7)0.0112 (6)
O10.073 (3)0.081 (4)0.044 (3)0.029 (2)0.030 (2)0.024 (2)
N10.106 (5)0.029 (2)0.029 (2)0.036 (2)0.039 (3)0.0152 (18)
N110.0200 (13)0.0219 (13)0.0212 (13)−0.0019 (11)0.0071 (11)−0.0018 (10)
N120.0203 (14)0.0220 (13)0.0224 (13)−0.0034 (11)0.0097 (11)−0.0033 (10)
N210.0244 (15)0.0284 (15)0.0253 (14)−0.0024 (11)0.0087 (12)0.0045 (11)
N220.0220 (15)0.0313 (15)0.0195 (13)−0.0025 (11)0.0055 (11)−0.0001 (11)
N310.0199 (15)0.0320 (15)0.0261 (15)−0.0033 (12)0.0087 (12)0.0007 (12)
N320.0233 (15)0.0271 (14)0.0226 (14)−0.0034 (12)0.0075 (12)−0.0007 (11)
N410.0241 (14)0.0217 (13)0.0272 (14)0.0014 (11)0.0105 (12)0.0019 (11)
C130.0289 (18)0.0224 (16)0.0329 (18)0.0021 (14)0.0181 (15)0.0013 (13)
C140.0249 (18)0.0273 (17)0.0310 (18)0.0056 (14)0.0103 (15)0.0040 (14)
C150.0208 (16)0.0293 (18)0.0238 (16)0.0003 (13)0.0105 (13)0.0016 (12)
C160.028 (2)0.042 (2)0.0318 (19)0.0042 (16)0.0010 (16)−0.0053 (16)
C170.041 (2)0.0288 (19)0.052 (2)0.0030 (17)0.0155 (19)−0.0067 (17)
C230.0283 (19)0.049 (2)0.0201 (17)−0.0032 (16)0.0088 (15)0.0009 (14)
C240.038 (2)0.058 (3)0.0223 (18)−0.0022 (18)0.0116 (16)0.0103 (16)
C250.029 (2)0.039 (2)0.0291 (19)−0.0049 (16)0.0062 (15)0.0095 (15)
C260.053 (3)0.042 (2)0.042 (2)−0.014 (2)0.018 (2)0.0110 (18)
C270.052 (3)0.059 (3)0.028 (2)−0.008 (2)0.0166 (19)−0.0121 (18)
C330.0238 (18)0.038 (2)0.0221 (17)−0.0094 (15)0.0012 (14)0.0051 (14)
C340.0181 (18)0.048 (2)0.035 (2)−0.0075 (16)0.0071 (15)0.0048 (16)
C350.0209 (18)0.042 (2)0.0311 (19)0.0007 (15)0.0085 (15)0.0064 (15)
C360.025 (2)0.057 (3)0.054 (3)0.0037 (18)0.0183 (19)−0.004 (2)
C370.039 (2)0.043 (2)0.038 (2)−0.0185 (18)0.0083 (18)−0.0068 (17)
C420.039 (2)0.0226 (18)0.0367 (19)−0.0040 (15)0.0187 (17)−0.0005 (14)
C430.035 (2)0.0227 (17)0.037 (2)−0.0006 (15)0.0183 (16)−0.0036 (14)
C440.0223 (16)0.0277 (17)0.0278 (17)0.0002 (14)0.0108 (14)−0.0001 (13)
C450.037 (2)0.0235 (17)0.0324 (19)0.0017 (15)0.0181 (16)0.0053 (14)
C460.034 (2)0.0216 (16)0.0327 (18)0.0025 (14)0.0146 (16)0.0006 (13)
C470.038 (2)0.0307 (19)0.037 (2)−0.0018 (15)0.0238 (17)0.0000 (14)
C480.038 (3)0.076 (3)0.060 (3)0.007 (2)0.028 (2)−0.006 (2)
C490.124 (5)0.041 (3)0.084 (4)−0.003 (3)0.083 (4)0.007 (2)
C500.057 (3)0.073 (3)0.034 (2)−0.012 (2)0.025 (2)−0.007 (2)
C510.046 (3)0.076 (3)0.056 (3)−0.023 (2)0.016 (2)−0.001 (2)
Cl520.0496 (8)0.1453 (14)0.0461 (7)−0.0186 (8)0.0129 (6)0.0341 (8)
Cl530.0898 (10)0.0600 (8)0.0600 (8)−0.0163 (7)0.0207 (7)0.0117 (6)
B10.027 (2)0.0265 (19)0.0240 (19)−0.0045 (15)0.0088 (16)−0.0033 (14)

Geometric parameters (Å, °)

Mo1—N11.999 (6)C27—H27A0.9600
Mo1—N212.164 (3)C27—H27B0.9600
Mo1—N112.184 (3)C27—H27C0.9600
Mo1—N412.207 (3)C33—C341.368 (5)
Mo1—N312.248 (3)C33—C371.499 (5)
Mo1—Cl12.4119 (14)C34—C351.385 (5)
O1—N10.787 (6)C34—H340.9300
N11—C151.345 (4)C35—C361.496 (5)
N11—N121.373 (3)C36—H36A0.9600
N12—C131.347 (4)C36—H36B0.9600
N12—B11.552 (5)C36—H36C0.9600
N21—C251.352 (4)C37—H37A0.9600
N21—N221.371 (4)C37—H37B0.9600
N22—C231.350 (4)C37—H37C0.9600
N22—B11.540 (5)C42—C431.376 (5)
N31—C351.347 (4)C42—H420.9300
N31—N321.371 (4)C43—C441.395 (5)
N32—C331.351 (4)C43—H430.9300
N32—B11.529 (5)C44—C451.390 (5)
N41—C461.341 (4)C44—C471.522 (5)
N41—C421.342 (4)C45—C461.376 (5)
C13—C141.375 (5)C45—H450.9300
C13—C171.492 (5)C46—H460.9300
C14—C151.385 (5)C47—C491.517 (5)
C14—H140.9300C47—C501.525 (5)
C15—C161.493 (5)C47—C481.532 (6)
C16—H16A0.9600C48—H48A0.9600
C16—H16B0.9600C48—H48B0.9600
C16—H16C0.9600C48—H48C0.9600
C17—H17A0.9600C49—H49A0.9600
C17—H17B0.9600C49—H49B0.9600
C17—H17C0.9600C49—H49C0.9600
C23—C241.380 (5)C50—H50A0.9600
C23—C271.496 (5)C50—H50B0.9600
C24—C251.382 (5)C50—H50C0.9600
C24—H240.9300C51—Cl531.751 (5)
C25—C261.501 (5)C51—Cl521.758 (5)
C26—H26A0.9600C51—H51A0.9700
C26—H26B0.9600C51—H51B0.9700
C26—H26C0.9600B1—H11.12 (3)
N1—Mo1—N2195.86 (16)C23—C27—H27C109.5
N1—Mo1—N1192.03 (16)H27A—C27—H27C109.5
N21—Mo1—N1184.08 (10)H27B—C27—H27C109.5
N1—Mo1—N4192.79 (16)N32—C33—C34107.7 (3)
N21—Mo1—N41170.21 (10)N32—C33—C37123.0 (3)
N11—Mo1—N4191.05 (9)C34—C33—C37129.4 (3)
N1—Mo1—N31176.27 (16)C33—C34—C35107.0 (3)
N21—Mo1—N3184.37 (10)C33—C34—H34126.5
N11—Mo1—N3184.28 (10)C35—C34—H34126.5
N41—Mo1—N3186.70 (10)N31—C35—C34108.9 (3)
N1—Mo1—Cl193.79 (15)N31—C35—C36123.4 (3)
N21—Mo1—Cl193.37 (8)C34—C35—C36127.7 (3)
N11—Mo1—Cl1173.86 (8)C35—C36—H36A109.5
N41—Mo1—Cl190.63 (8)C35—C36—H36B109.5
N31—Mo1—Cl189.92 (8)H36A—C36—H36B109.5
O1—N1—Mo1173.1 (9)C35—C36—H36C109.5
C15—N11—N12107.0 (2)H36A—C36—H36C109.5
C15—N11—Mo1134.3 (2)H36B—C36—H36C109.5
N12—N11—Mo1118.68 (19)C33—C37—H37A109.5
C13—N12—N11109.5 (3)C33—C37—H37B109.5
C13—N12—B1129.8 (3)H37A—C37—H37B109.5
N11—N12—B1120.5 (3)C33—C37—H37C109.5
C25—N21—N22106.5 (3)H37A—C37—H37C109.5
C25—N21—Mo1134.0 (3)H37B—C37—H37C109.5
N22—N21—Mo1119.55 (19)N41—C42—C43123.4 (3)
C23—N22—N21109.9 (3)N41—C42—H42118.3
C23—N22—B1129.9 (3)C43—C42—H42118.3
N21—N22—B1120.2 (3)C42—C43—C44120.5 (3)
C35—N31—N32106.9 (3)C42—C43—H43119.8
C35—N31—Mo1135.5 (2)C44—C43—H43119.8
N32—N31—Mo1117.6 (2)C45—C44—C43115.5 (3)
C33—N32—N31109.4 (3)C45—C44—C47123.9 (3)
C33—N32—B1130.0 (3)C43—C44—C47120.6 (3)
N31—N32—B1120.5 (3)C46—C45—C44120.9 (3)
C46—N41—C42116.5 (3)C46—C45—H45119.5
C46—N41—Mo1121.9 (2)C44—C45—H45119.5
C42—N41—Mo1121.2 (2)N41—C46—C45123.1 (3)
N12—C13—C14107.7 (3)N41—C46—H46118.4
N12—C13—C17123.1 (3)C45—C46—H46118.4
C14—C13—C17129.2 (3)C49—C47—C44112.1 (3)
C13—C14—C15106.8 (3)C49—C47—C50109.7 (4)
C13—C14—H14126.6C44—C47—C50110.3 (3)
C15—C14—H14126.6C49—C47—C48109.4 (4)
N11—C15—C14109.0 (3)C44—C47—C48106.7 (3)
N11—C15—C16123.4 (3)C50—C47—C48108.5 (3)
C14—C15—C16127.6 (3)C47—C48—H48A109.5
C15—C16—H16A109.5C47—C48—H48B109.5
C15—C16—H16B109.5H48A—C48—H48B109.5
H16A—C16—H16B109.5C47—C48—H48C109.5
C15—C16—H16C109.5H48A—C48—H48C109.5
H16A—C16—H16C109.5H48B—C48—H48C109.5
H16B—C16—H16C109.5C47—C49—H49A109.5
C13—C17—H17A109.5C47—C49—H49B109.5
C13—C17—H17B109.5H49A—C49—H49B109.5
H17A—C17—H17B109.5C47—C49—H49C109.5
C13—C17—H17C109.5H49A—C49—H49C109.5
H17A—C17—H17C109.5H49B—C49—H49C109.5
H17B—C17—H17C109.5C47—C50—H50A109.5
N22—C23—C24107.5 (3)C47—C50—H50B109.5
N22—C23—C27122.9 (3)H50A—C50—H50B109.5
C24—C23—C27129.7 (3)C47—C50—H50C109.5
C23—C24—C25106.6 (3)H50A—C50—H50C109.5
C23—C24—H24126.7H50B—C50—H50C109.5
C25—C24—H24126.7Cl53—C51—Cl52112.7 (3)
N21—C25—C24109.5 (3)Cl53—C51—H51A109.1
N21—C25—C26121.5 (3)Cl52—C51—H51A109.1
C24—C25—C26129.0 (3)Cl53—C51—H51B109.1
C25—C26—H26A109.5Cl52—C51—H51B109.1
C25—C26—H26B109.5H51A—C51—H51B107.8
H26A—C26—H26B109.5N32—B1—N22109.3 (3)
C25—C26—H26C109.5N32—B1—N12109.7 (3)
H26A—C26—H26C109.5N22—B1—N12108.6 (3)
H26B—C26—H26C109.5N32—B1—H1109.8 (16)
C23—C27—H27A109.5N22—B1—H1110.9 (16)
C23—C27—H27B109.5N12—B1—H1108.5 (16)
H27A—C27—H27B109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C36—H36A···Cl10.962.573.437 (5)150
C51—H51B···Cl1i0.972.483.412 (6)161

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5750).

References

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