Download citation
Download citation
link to html
The crystal and mol­ecular structures of two ReI tricarbonyl complexes, namely fac-tri­carbonyl­chlorido­[1-(4-fluoro­cinnamo­yl)-3-(pyridin-2-yl-κN)pyrazole-κN2]rhenium(I), [ReCl(C17H12FN3O)(CO)3], (I), and fac-tri­carbonyl­chlorido­[1-(4-nitro­cinnamo­yl)-3-(pyridin-2-yl-κN)pyrazole-κN2]­rhenium(I) acetone monosolvate, [ReCl(C17H12ClN4O3)(CO)3]·C3H6O, (II), are reported. The complexes form centrosymmetric dimers that are linked into one-dimensional columns by C—H...Cl and N—O...H inter­actions in (I) and (II), respectively. C—H...Cl inter­actions in (II) generate two R21(7) loops that merge into a single R21(10) loop. These inter­actions involve the alkene, pyrazole and benzene rings, hence restricting the ligand rotation and giving rise to a planar conformation. Unlike (II), complex (I) exhibits a twisted conformation of the ligand and a pair of molecules forms a centrosymmetric dimer with an R22(10) loop via C—H...O inter­actions. The unique supra­molecular structures of (I) and (II) are determined by their planarity and weak inter­actions. The planar conformation of (II) provides a base for appreciable π–π stacking inter­actions compared to (I). In addition, an N—O...π inter­action stabilizes the supra­molecular structure of (II). We report herein the first n→π* inter­actions of ReI tricarbonyl complexes, which account for 0.33 kJ mol−1. Inter­molecular C—H...Cl and C—H...O inter­actions are present in both complexes, with (II) showing a greater preference for these inter­actions compared to (I), with cumulative contributions of 48.7 and 41.5%, respectively. The influence of inductive (fluoro) and/or resonance (nitro) effects on the π-stacking ability was further supported by LOLIPOP (localized orbital locator-integrated π over plane) analysis. The benzene ring of (II) demonstrated a higher π-stacking ability compared to that of (I), which is supported by the intrinsic planar geometry. The HOMA (harmonic oscillator model of aromaticity) index of (I) revealed more aromaticity with respect to (II), suggesting that NO2 greatly perturbed the aromaticity. The Hirshfeld fingerprint (FP) plots revealed the preference of (II) over (I) for π–π contacts, with contributions of 6.8 and 4.4%, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618010586/yf3146sup1.cif
Contains datablocks I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618010586/yf3146Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618010586/yf3146IIsup3.hkl
Contains datablock II

cdx

Chemdraw file https://doi.org/10.1107/S2053229618010586/yf3146Isup4.cdx
Supplementary material

cdx

Chemdraw file https://doi.org/10.1107/S2053229618010586/yf3146IIsup5.cdx
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618010586/yf3146sup6.pdf
Additional figures

CCDC references: 1857522; 1857521

Computing details top

For both structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SAINT (Bruker, 2016). Program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015) for (I); SHELXL2016/6 (Sheldrick, 2015) for (II). For both structures, molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009), OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

fac-Tricarbonylchlorido[1-(4-fluorocinnamoyl)-3-(pyridin-2-yl-κN)pyrazole-κN2]rhenium(I) (I) top
Crystal data top
[ReCl(C17H12FN3O)(CO)3]Z = 2
Mr = 598.98F(000) = 572
Triclinic, P1Dx = 2.039 Mg m3
a = 7.2479 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.1177 (5) ÅCell parameters from 9612 reflections
c = 16.9716 (12) Åθ = 3.0–28.4°
α = 81.374 (3)°µ = 6.41 mm1
β = 86.946 (4)°T = 293 K
γ = 81.339 (3)°Block, yellow
V = 975.51 (11) Å30.44 × 0.30 × 0.25 mm
Data collection top
Bruker PHOTON II CPAD
diffractometer
4374 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.091
φ and ω scansθmax = 28.4°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 99
Tmin = 0.115, Tmax = 0.201k = 1010
35815 measured reflectionsl = 2222
4881 independent reflections
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0436P)2 + 10.5314P]
where P = (Fo2 + 2Fc2)/3
4881 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 1.92 e Å3
0 restraintsΔρmin = 2.68 e Å3
Special details top

Experimental. The crystal was mounted using perfluoropolyether cryo oil on the tip of a polyimide scoop, which was fastened on a stainless steel mounting pin. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Re10.74009 (4)0.74654 (4)0.18448 (2)0.02740 (11)
C10.7287 (13)0.8428 (11)0.2818 (5)0.0370 (19)
O10.7266 (12)0.9048 (10)0.3380 (5)0.057 (2)
Cl10.4334 (3)0.8933 (3)0.13708 (15)0.0426 (5)
N10.7413 (10)0.6227 (8)0.0783 (4)0.0302 (14)
F10.0576 (14)1.4218 (11)0.4007 (6)0.094 (3)
N30.5337 (10)0.4421 (8)0.2899 (4)0.0325 (15)
C30.9750 (12)0.6215 (11)0.2179 (5)0.0340 (17)
O31.1140 (11)0.5507 (10)0.2366 (5)0.0553 (19)
N20.5984 (10)0.5236 (8)0.2208 (4)0.0288 (13)
C20.8696 (13)0.9258 (10)0.1363 (6)0.0358 (18)
O20.9537 (11)1.0305 (10)0.1093 (6)0.064 (2)
O40.4686 (14)0.4245 (10)0.4221 (4)0.062 (2)
C40.7910 (13)0.6875 (12)0.0038 (5)0.0380 (19)
H10.8214430.7961200.0051180.046*
C80.6896 (11)0.4669 (10)0.0895 (5)0.0295 (16)
C70.6954 (12)0.3719 (12)0.0278 (6)0.0372 (19)
H40.6615160.2645150.0372140.045*
C60.7522 (13)0.4383 (14)0.0478 (6)0.045 (2)
H30.7591440.3761310.0899640.054*
C50.7983 (13)0.5992 (13)0.0592 (5)0.042 (2)
H20.8343090.6477790.1097370.050*
C90.6178 (11)0.4138 (9)0.1692 (5)0.0296 (16)
C100.5641 (13)0.2612 (10)0.2047 (6)0.040 (2)
H50.5648980.1650060.1810040.048*
C110.5108 (14)0.2814 (11)0.2803 (6)0.043 (2)
H60.4666620.2014380.3189120.051*
C120.4620 (14)0.5187 (13)0.3599 (5)0.041 (2)
C130.3783 (13)0.6926 (12)0.3462 (5)0.0387 (19)
H70.3540430.7451650.2945290.046*
C140.3358 (14)0.7781 (12)0.4071 (6)0.043 (2)
H80.3742610.7239520.4569570.052*
C150.2353 (15)0.9477 (12)0.4036 (6)0.041 (2)
C160.1360 (16)1.0284 (13)0.3363 (6)0.048 (2)
H90.1377840.9739450.2917820.057*
C170.0360 (17)1.1871 (15)0.3353 (8)0.057 (3)
H100.0322521.2388740.2911200.069*
C180.0393 (18)1.2673 (15)0.4010 (8)0.060 (3)
C190.1364 (19)1.1946 (15)0.4675 (8)0.062 (3)
H110.1370421.2521460.5109370.074*
C200.2340 (17)1.0330 (14)0.4688 (7)0.053 (3)
H120.2990840.9813890.5137930.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Re10.03186 (18)0.02159 (15)0.03008 (17)0.00781 (11)0.00329 (11)0.00328 (11)
C10.043 (5)0.038 (4)0.036 (4)0.015 (4)0.003 (4)0.013 (4)
O10.075 (5)0.049 (4)0.054 (5)0.019 (4)0.003 (4)0.016 (4)
Cl10.0403 (12)0.0333 (10)0.0543 (13)0.0007 (8)0.0115 (10)0.0079 (9)
N10.030 (3)0.026 (3)0.034 (4)0.001 (3)0.003 (3)0.005 (3)
F10.102 (7)0.063 (5)0.110 (7)0.012 (5)0.021 (5)0.020 (5)
N30.039 (4)0.023 (3)0.035 (4)0.008 (3)0.002 (3)0.001 (3)
C30.033 (4)0.043 (5)0.029 (4)0.013 (4)0.005 (3)0.007 (3)
O30.053 (5)0.056 (5)0.057 (5)0.006 (4)0.011 (4)0.008 (4)
N20.033 (3)0.024 (3)0.031 (3)0.010 (3)0.003 (3)0.003 (3)
C20.037 (4)0.027 (4)0.042 (5)0.006 (3)0.001 (4)0.000 (3)
O20.052 (5)0.046 (4)0.091 (6)0.021 (4)0.007 (4)0.008 (4)
O40.095 (7)0.054 (5)0.032 (4)0.016 (4)0.002 (4)0.009 (3)
C40.038 (5)0.039 (5)0.036 (4)0.003 (4)0.001 (4)0.004 (4)
C80.023 (4)0.030 (4)0.036 (4)0.000 (3)0.004 (3)0.009 (3)
C70.030 (4)0.037 (4)0.046 (5)0.001 (3)0.005 (4)0.015 (4)
C60.034 (5)0.062 (6)0.041 (5)0.005 (4)0.007 (4)0.024 (5)
C50.041 (5)0.056 (6)0.029 (4)0.004 (4)0.002 (4)0.010 (4)
C90.030 (4)0.021 (3)0.036 (4)0.001 (3)0.005 (3)0.004 (3)
C100.043 (5)0.020 (4)0.059 (6)0.008 (3)0.002 (4)0.008 (4)
C110.047 (5)0.028 (4)0.052 (6)0.011 (4)0.002 (4)0.001 (4)
C120.046 (5)0.047 (5)0.032 (4)0.018 (4)0.002 (4)0.003 (4)
C130.039 (5)0.046 (5)0.031 (4)0.013 (4)0.002 (3)0.001 (4)
C140.051 (6)0.038 (5)0.040 (5)0.014 (4)0.004 (4)0.001 (4)
C150.052 (6)0.038 (5)0.037 (5)0.015 (4)0.007 (4)0.009 (4)
C160.054 (6)0.046 (5)0.045 (5)0.013 (5)0.003 (4)0.008 (4)
C170.054 (7)0.056 (7)0.061 (7)0.010 (5)0.005 (5)0.004 (5)
C180.057 (7)0.046 (6)0.075 (8)0.007 (5)0.021 (6)0.005 (6)
C190.080 (9)0.055 (7)0.056 (7)0.020 (6)0.022 (6)0.026 (6)
C200.062 (7)0.049 (6)0.049 (6)0.007 (5)0.004 (5)0.015 (5)
Geometric parameters (Å, º) top
Re1—C21.908 (9)C6—C51.380 (15)
Re1—C31.914 (9)C6—H30.9300
Re1—C11.923 (8)C5—H20.9300
Re1—N12.190 (7)C9—C101.395 (11)
Re1—N22.207 (6)C10—C111.347 (14)
Re1—Cl12.472 (2)C10—H50.9300
C1—O11.141 (11)C11—H60.9300
N1—C41.346 (11)C12—C131.440 (14)
N1—C81.356 (10)C13—C141.326 (14)
F1—C181.342 (14)C13—H70.9300
N3—N21.355 (10)C14—C151.452 (14)
N3—C111.374 (11)C14—H80.9300
N3—C121.458 (12)C15—C201.388 (14)
C3—O31.118 (11)C15—C161.405 (14)
N2—C91.327 (10)C16—C171.378 (16)
C2—O21.146 (11)C16—H90.9300
O4—C121.206 (11)C17—C181.377 (18)
C4—C51.368 (13)C17—H100.9300
C4—H10.9300C18—C191.370 (19)
C8—C71.386 (11)C19—C201.392 (16)
C8—C91.451 (12)C19—H110.9300
C7—C61.382 (14)C20—H120.9300
C7—H40.9300
C2—Re1—C388.6 (4)C4—C5—C6120.1 (9)
C2—Re1—C187.6 (4)C4—C5—H2120.0
C3—Re1—C187.2 (4)C6—C5—H2120.0
C2—Re1—N196.6 (3)N2—C9—C10110.6 (8)
C3—Re1—N193.0 (3)N2—C9—C8117.9 (7)
C1—Re1—N1175.7 (3)C10—C9—C8131.5 (8)
C2—Re1—N2170.4 (3)C11—C10—C9106.1 (8)
C3—Re1—N291.3 (3)C11—C10—H5127.0
C1—Re1—N2102.0 (3)C9—C10—H5127.0
N1—Re1—N273.8 (3)C10—C11—N3107.3 (8)
C2—Re1—Cl193.4 (3)C10—C11—H6126.4
C3—Re1—Cl1176.4 (3)N3—C11—H6126.4
C1—Re1—Cl195.8 (3)O4—C12—C13127.6 (9)
N1—Re1—Cl183.81 (18)O4—C12—N3115.4 (9)
N2—Re1—Cl186.30 (19)C13—C12—N3116.8 (8)
O1—C1—Re1177.1 (8)C14—C13—C12120.3 (9)
C4—N1—C8117.9 (7)C14—C13—H7119.8
C4—N1—Re1125.5 (6)C12—C13—H7119.8
C8—N1—Re1116.6 (5)C13—C14—C15126.6 (9)
N2—N3—C11110.1 (7)C13—C14—H8116.7
N2—N3—C12126.1 (7)C15—C14—H8116.7
C11—N3—C12122.8 (8)C20—C15—C16118.5 (10)
O3—C3—Re1178.7 (9)C20—C15—C14119.7 (10)
C9—N2—N3106.0 (6)C16—C15—C14121.9 (9)
C9—N2—Re1115.0 (5)C17—C16—C15121.0 (10)
N3—N2—Re1136.6 (5)C17—C16—H9119.5
O2—C2—Re1177.1 (9)C15—C16—H9119.5
N1—C4—C5122.4 (9)C18—C17—C16118.5 (11)
N1—C4—H1118.8C18—C17—H10120.8
C5—C4—H1118.8C16—C17—H10120.8
N1—C8—C7121.9 (8)F1—C18—C19118.4 (12)
N1—C8—C9114.6 (7)F1—C18—C17119.1 (13)
C7—C8—C9123.3 (8)C19—C18—C17122.5 (11)
C6—C7—C8119.4 (9)C18—C19—C20118.6 (11)
C6—C7—H4120.3C18—C19—H11120.7
C8—C7—H4120.3C20—C19—H11120.7
C5—C6—C7118.2 (8)C15—C20—C19120.8 (11)
C5—C6—H3120.9C15—C20—H12119.6
C7—C6—H3120.9C19—C20—H12119.6
C11—N3—N2—C90.8 (9)C8—C9—C10—C11179.2 (9)
C12—N3—N2—C9169.2 (8)C9—C10—C11—N30.5 (11)
C11—N3—N2—Re1161.0 (7)N2—N3—C11—C100.8 (11)
C12—N3—N2—Re130.6 (13)C12—N3—C11—C10169.7 (8)
C8—N1—C4—C52.8 (13)N2—N3—C12—O4156.7 (9)
Re1—N1—C4—C5176.3 (7)C11—N3—C12—O436.2 (13)
C4—N1—C8—C73.1 (11)N2—N3—C12—C1328.2 (13)
Re1—N1—C8—C7176.1 (6)C11—N3—C12—C13138.9 (9)
C4—N1—C8—C9173.3 (7)O4—C12—C13—C1415.8 (16)
Re1—N1—C8—C97.5 (9)N3—C12—C13—C14169.8 (9)
N1—C8—C7—C61.2 (12)C12—C13—C14—C15173.6 (9)
C9—C8—C7—C6174.9 (8)C13—C14—C15—C20167.0 (10)
C8—C7—C6—C51.0 (13)C13—C14—C15—C1613.9 (16)
N1—C4—C5—C60.6 (14)C20—C15—C16—C171.4 (16)
C7—C6—C5—C41.4 (14)C14—C15—C16—C17177.7 (10)
N3—N2—C9—C100.5 (9)C15—C16—C17—C181.7 (17)
Re1—N2—C9—C10165.6 (6)C16—C17—C18—F1180.0 (11)
N3—N2—C9—C8178.8 (7)C16—C17—C18—C190.7 (19)
Re1—N2—C9—C813.7 (9)F1—C18—C19—C20178.7 (11)
N1—C8—C9—N24.3 (10)C17—C18—C19—C200.6 (19)
C7—C8—C9—N2172.1 (8)C16—C15—C20—C190.1 (17)
N1—C8—C9—C10174.9 (9)C14—C15—C20—C19179.0 (11)
C7—C8—C9—C108.8 (14)C18—C19—C20—C150.9 (18)
N2—C9—C10—C110.0 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H5···Cl1i0.932.743.624 (9)158
C13—H7···Cl10.932.833.704 (9)158
C14—H8···O4ii0.932.463.380 (13)170
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1.
fac-Tricarbonylchlorido[1-(4-nitrocinnamoyl)-3-(pyridin-2-yl-κN)pyrazole-κN2]rhenium(I) acetone monosolvate (II) top
Crystal data top
[ReCl(C17H12ClN4O3)(CO)3]·C3H6OZ = 2
Mr = 684.06F(000) = 664
Triclinic, P1Dx = 1.788 Mg m3
a = 7.9828 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.0719 (4) ÅCell parameters from 6351 reflections
c = 14.4560 (5) Åθ = 3.0–28.4°
α = 104.093 (2)°µ = 4.94 mm1
β = 99.708 (2)°T = 293 K
γ = 104.184 (2)°Plate, orange
V = 1270.78 (8) Å30.42 × 0.40 × 0.04 mm
Data collection top
Bruker PHOTON II CPAD
diffractometer
4505 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.180
φ and ω scansθmax = 28.4°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 1010
Tmin = 0.145, Tmax = 0.821k = 1616
59671 measured reflectionsl = 1919
6351 independent reflections
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0784P)2 + 2.9606P]
where P = (Fo2 + 2Fc2)/3
6351 reflections(Δ/σ)max < 0.001
327 parametersΔρmax = 1.29 e Å3
9 restraintsΔρmin = 1.82 e Å3
Special details top

Experimental. The crystal was mounted using perfluoropolyether cryo oil on the tip of a polyimide scoop, which was fastened on a stainless steel mounting pin. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Re10.42196 (5)0.07583 (3)0.22200 (3)0.03867 (14)
Cl10.1934 (3)0.0899 (2)0.31813 (17)0.0456 (5)
O10.6211 (12)0.3421 (7)0.3185 (7)0.085 (3)
O20.2242 (12)0.1563 (9)0.0630 (6)0.085 (3)
O30.7039 (13)0.0564 (9)0.1058 (7)0.087 (3)
O40.7931 (12)0.1937 (7)0.4120 (6)0.091 (3)
O51.5649 (13)0.3057 (11)0.9954 (7)0.102 (3)
O61.6673 (10)0.4749 (8)0.9707 (7)0.087 (3)
N10.2592 (9)0.1125 (6)0.1609 (5)0.0353 (14)
N20.5200 (8)0.0172 (6)0.3246 (5)0.0334 (14)
N30.6441 (8)0.0071 (6)0.4121 (5)0.0318 (13)
N41.5589 (11)0.3749 (10)0.9475 (7)0.066 (3)
C10.5530 (14)0.2415 (9)0.2851 (8)0.052 (2)
C20.3022 (14)0.1269 (8)0.1265 (7)0.052 (2)
C30.5967 (14)0.0619 (8)0.1479 (7)0.049 (2)
C40.1353 (13)0.1589 (8)0.0767 (7)0.048 (2)
H10.1210960.1112810.0360050.057*
C50.0265 (13)0.2764 (8)0.0477 (7)0.049 (2)
H20.0588250.3064260.0117490.059*
C60.0447 (11)0.3476 (8)0.1064 (6)0.044 (2)
H30.0293960.4259270.0882620.053*
C70.1742 (11)0.3017 (7)0.1925 (6)0.0390 (18)
H40.1913910.3497340.2324650.047*
C80.2800 (10)0.1832 (7)0.2202 (6)0.0338 (16)
C90.4205 (10)0.1285 (6)0.3098 (5)0.0295 (15)
C100.4775 (11)0.1781 (7)0.3827 (6)0.0359 (17)
H50.4290400.2546430.3865750.043*
C110.6185 (10)0.0904 (7)0.4462 (6)0.0349 (17)
H60.6863160.0955160.5030990.042*
C120.7843 (11)0.1201 (7)0.4546 (7)0.0419 (19)
C130.9044 (11)0.1331 (8)0.5455 (6)0.0426 (19)
H70.8950680.0691270.5714620.051*
C141.0269 (12)0.2356 (8)0.5915 (7)0.048 (2)
H81.0304180.2956130.5613590.058*
C151.1572 (11)0.2667 (7)0.6835 (6)0.042 (2)
C161.2790 (13)0.3828 (8)0.7178 (8)0.054 (2)
H91.2712340.4365030.6820520.065*
C171.4098 (13)0.4178 (9)0.8040 (8)0.059 (3)
H101.4905330.4942210.8262120.071*
C181.4183 (11)0.3365 (9)0.8569 (7)0.051 (3)
C191.3015 (11)0.2251 (8)0.8265 (7)0.044 (2)
H111.3079630.1729170.8640010.053*
C201.1721 (11)0.1891 (8)0.7393 (6)0.043 (2)
H121.0939930.1117580.7176990.052*
C21A1.174 (2)0.4473 (11)0.3429 (11)0.095 (5)
O7A1.287 (3)0.536 (2)0.3351 (18)0.125 (11)*0.57 (4)
C22A1.043 (5)0.352 (3)0.262 (2)0.118 (14)*0.57 (4)
H13A0.9795570.3856530.2197180.177*0.57 (4)
H13B0.9611020.3023790.2877600.177*0.57 (4)
H13C1.1034370.3035710.2250870.177*0.57 (4)
C23A1.246 (5)0.415 (3)0.4296 (18)0.111 (11)*0.57 (4)
H14A1.1838980.3341210.4231540.167*0.57 (4)
H14B1.2324150.4676880.4875320.167*0.57 (4)
H14C1.3706740.4236640.4347150.167*0.57 (4)
O7B1.189 (5)0.5582 (19)0.359 (2)0.113 (13)*0.43 (4)
C22B1.087 (9)0.364 (5)0.246 (2)0.14 (3)*0.43 (4)
H13D1.0383790.2856240.2509980.215*0.43 (4)
H13E1.1726510.3620040.2062460.215*0.43 (4)
H13F0.9931750.3897720.2150810.215*0.43 (4)
C23B1.145 (8)0.421 (4)0.433 (2)0.122 (17)*0.43 (4)
H14D1.0866070.3375800.4184510.146*0.43 (4)
H14E1.0725470.4667360.4601180.146*0.43 (4)
H14F1.2580070.4430200.4789140.183*0.43 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Re10.0420 (2)0.03484 (19)0.0383 (2)0.00893 (13)0.00485 (14)0.01530 (13)
Cl10.0494 (12)0.0451 (11)0.0450 (12)0.0179 (10)0.0088 (10)0.0162 (9)
O10.087 (6)0.037 (4)0.112 (7)0.003 (4)0.002 (5)0.023 (4)
O20.096 (6)0.104 (7)0.077 (6)0.053 (6)0.002 (5)0.056 (5)
O30.096 (7)0.107 (7)0.086 (6)0.040 (6)0.056 (6)0.046 (5)
O40.088 (6)0.067 (5)0.075 (6)0.030 (4)0.035 (5)0.038 (4)
O50.079 (7)0.143 (10)0.063 (6)0.024 (6)0.014 (5)0.024 (6)
O60.039 (4)0.081 (6)0.090 (6)0.005 (4)0.015 (4)0.033 (5)
N10.041 (4)0.037 (4)0.030 (3)0.016 (3)0.006 (3)0.009 (3)
N20.030 (3)0.033 (3)0.038 (4)0.011 (3)0.006 (3)0.011 (3)
N30.028 (3)0.032 (3)0.031 (3)0.007 (3)0.001 (3)0.009 (3)
N40.040 (5)0.098 (8)0.040 (5)0.024 (5)0.000 (4)0.012 (5)
C10.053 (6)0.052 (6)0.059 (6)0.013 (5)0.015 (5)0.031 (5)
C20.062 (6)0.043 (5)0.053 (6)0.013 (5)0.021 (5)0.017 (4)
C30.059 (6)0.042 (5)0.042 (5)0.007 (4)0.003 (5)0.017 (4)
C40.054 (5)0.047 (5)0.034 (4)0.018 (4)0.005 (4)0.004 (4)
C50.047 (5)0.050 (5)0.038 (5)0.013 (4)0.006 (4)0.004 (4)
C60.036 (4)0.037 (4)0.044 (5)0.007 (4)0.002 (4)0.005 (4)
C70.037 (4)0.031 (4)0.044 (5)0.006 (3)0.008 (4)0.007 (3)
C80.034 (4)0.035 (4)0.032 (4)0.010 (3)0.009 (3)0.009 (3)
C90.035 (4)0.026 (3)0.027 (4)0.010 (3)0.004 (3)0.006 (3)
C100.036 (4)0.030 (4)0.040 (4)0.010 (3)0.006 (3)0.010 (3)
C110.036 (4)0.039 (4)0.033 (4)0.015 (3)0.007 (3)0.015 (3)
C120.039 (5)0.033 (4)0.049 (5)0.004 (4)0.007 (4)0.013 (4)
C130.036 (4)0.045 (5)0.040 (5)0.007 (4)0.000 (4)0.013 (4)
C140.041 (5)0.043 (5)0.054 (6)0.004 (4)0.001 (4)0.017 (4)
C150.032 (4)0.036 (4)0.042 (5)0.004 (3)0.001 (4)0.002 (4)
C160.045 (5)0.041 (5)0.059 (6)0.006 (4)0.000 (5)0.010 (4)
C170.047 (5)0.045 (5)0.056 (6)0.009 (4)0.002 (5)0.004 (5)
C180.030 (4)0.064 (6)0.038 (5)0.014 (4)0.002 (4)0.016 (4)
C190.038 (5)0.046 (5)0.045 (5)0.015 (4)0.006 (4)0.010 (4)
C200.030 (4)0.043 (5)0.044 (5)0.004 (4)0.004 (4)0.001 (4)
C21A0.133 (13)0.049 (7)0.107 (12)0.012 (8)0.043 (10)0.039 (7)
Geometric parameters (Å, º) top
Re1—C21.860 (10)C13—C141.310 (12)
Re1—C31.912 (11)C13—H70.9300
Re1—C11.921 (10)C14—C151.445 (12)
Re1—N12.197 (7)C14—H80.9300
Re1—N22.219 (6)C15—C201.390 (13)
Re1—Cl12.486 (2)C15—C161.409 (12)
O1—C11.143 (12)C16—C171.382 (14)
O2—C21.196 (12)C16—H90.9300
O3—C31.135 (13)C17—C181.391 (16)
O4—C121.194 (11)C17—H100.9300
O5—N41.213 (14)C18—C191.353 (13)
O6—N41.230 (13)C19—C201.386 (12)
N1—C41.328 (10)C19—H110.9300
N1—C81.366 (10)C20—H120.9300
N2—C91.328 (10)C21A—O7A1.27 (2)
N2—N31.386 (9)C21A—O7B1.27 (2)
N3—C111.367 (10)C21A—C23B1.447 (18)
N3—C121.450 (10)C21A—C22B1.453 (19)
N4—C181.463 (12)C21A—C22A1.460 (18)
C4—C51.387 (13)C21A—C23A1.467 (17)
C4—H10.9300C22A—H13A0.9600
C5—C61.361 (13)C22A—H13B0.9600
C5—H20.9300C22A—H13C0.9600
C6—C71.369 (12)C23A—H14A0.9600
C6—H30.9300C23A—H14B0.9600
C7—C81.391 (11)C23A—H14C0.9600
C7—H40.9300C22B—H13D0.9600
C8—C91.450 (10)C22B—H13E0.9600
C9—C101.398 (10)C22B—H13F0.9600
C10—C111.350 (11)C23B—H14D0.9600
C10—H50.9300C23B—H14E0.9600
C11—H60.9300C23B—H14F0.9600
C12—C131.440 (12)
C2—Re1—C389.2 (4)C13—C12—N3116.3 (7)
C2—Re1—C186.6 (4)C14—C13—C12119.6 (9)
C3—Re1—C189.4 (4)C14—C13—H7120.2
C2—Re1—N195.0 (3)C12—C13—H7120.2
C3—Re1—N195.7 (3)C13—C14—C15127.9 (9)
C1—Re1—N1174.7 (3)C13—C14—H8116.0
C2—Re1—N2168.8 (3)C15—C14—H8116.0
C3—Re1—N294.5 (3)C20—C15—C16117.9 (8)
C1—Re1—N2103.9 (3)C20—C15—C14124.3 (8)
N1—Re1—N274.2 (2)C16—C15—C14117.7 (9)
C2—Re1—Cl191.3 (3)C17—C16—C15120.9 (10)
C3—Re1—Cl1178.9 (3)C17—C16—H9119.6
C1—Re1—Cl191.5 (3)C15—C16—H9119.6
N1—Re1—Cl183.35 (18)C16—C17—C18118.7 (9)
N2—Re1—Cl184.81 (17)C16—C17—H10120.6
C4—N1—C8118.7 (7)C18—C17—H10120.6
C4—N1—Re1125.5 (6)C19—C18—C17121.7 (9)
C8—N1—Re1115.5 (5)C19—C18—N4120.4 (11)
C9—N2—N3103.7 (6)C17—C18—N4117.8 (10)
C9—N2—Re1115.4 (5)C18—C19—C20119.6 (9)
N3—N2—Re1140.2 (5)C18—C19—H11120.2
C11—N3—N2110.5 (6)C20—C19—H11120.2
C11—N3—C12127.2 (7)C19—C20—C15121.1 (8)
N2—N3—C12122.1 (6)C19—C20—H12119.5
O5—N4—O6123.0 (10)C15—C20—H12119.5
O5—N4—C18118.3 (11)O7B—C21A—C23B105 (3)
O6—N4—C18118.7 (12)O7B—C21A—C22B120 (3)
O1—C1—Re1174.9 (9)C23B—C21A—C22B123 (3)
O2—C2—Re1177.9 (9)O7A—C21A—C22A126 (3)
O3—C3—Re1178.1 (10)O7A—C21A—C23A109 (2)
N1—C4—C5122.0 (9)C22A—C21A—C23A117 (2)
N1—C4—H1119.0C21A—C22A—H13A109.5
C5—C4—H1119.0C21A—C22A—H13B109.5
C6—C5—C4120.0 (8)H13A—C22A—H13B109.5
C6—C5—H2120.0C21A—C22A—H13C109.5
C4—C5—H2120.0H13A—C22A—H13C109.5
C5—C6—C7118.7 (8)H13B—C22A—H13C109.5
C5—C6—H3120.7C21A—C23A—H14A109.5
C7—C6—H3120.7C21A—C23A—H14B109.5
C6—C7—C8120.0 (8)H14A—C23A—H14B109.5
C6—C7—H4120.0C21A—C23A—H14C109.5
C8—C7—H4120.0H14A—C23A—H14C109.5
N1—C8—C7120.6 (7)H14B—C23A—H14C109.5
N1—C8—C9116.1 (7)C21A—C22B—H13D109.5
C7—C8—C9123.2 (7)C21A—C22B—H13E109.5
N2—C9—C10112.9 (7)H13D—C22B—H13E109.5
N2—C9—C8117.4 (7)C21A—C22B—H13F109.5
C10—C9—C8129.6 (7)H13D—C22B—H13F109.5
C11—C10—C9104.9 (7)H13E—C22B—H13F109.5
C11—C10—H5127.6C21A—C23B—H14D109.5
C9—C10—H5127.6C21A—C23B—H14E109.5
C10—C11—N3108.0 (7)H14D—C23B—H14E109.5
C10—C11—H6126.0C21A—C23B—H14F109.5
N3—C11—H6126.0H14D—C23B—H14F109.5
O4—C12—C13125.2 (8)H14E—C23B—H14F109.5
O4—C12—N3118.5 (8)
C9—N2—N3—C111.3 (8)N2—N3—C11—C100.8 (9)
Re1—N2—N3—C11170.1 (6)C12—N3—C11—C10177.4 (7)
C9—N2—N3—C12178.2 (7)C11—N3—C12—O4175.7 (10)
Re1—N2—N3—C1213.0 (12)N2—N3—C12—O40.6 (13)
C8—N1—C4—C50.3 (13)C11—N3—C12—C133.5 (12)
Re1—N1—C4—C5173.8 (7)N2—N3—C12—C13179.8 (7)
N1—C4—C5—C60.2 (15)O4—C12—C13—C145.5 (16)
C4—C5—C6—C71.4 (14)N3—C12—C13—C14175.4 (8)
C5—C6—C7—C82.2 (13)C12—C13—C14—C15179.1 (9)
C4—N1—C8—C70.5 (12)C13—C14—C15—C200.2 (16)
Re1—N1—C8—C7175.1 (6)C13—C14—C15—C16178.7 (10)
C4—N1—C8—C9178.4 (7)C20—C15—C16—C170.5 (15)
Re1—N1—C8—C97.0 (9)C14—C15—C16—C17178.5 (10)
C6—C7—C8—N11.7 (12)C15—C16—C17—C180.5 (16)
C6—C7—C8—C9179.5 (8)C16—C17—C18—C190.5 (15)
N3—N2—C9—C101.4 (8)C16—C17—C18—N4179.4 (9)
Re1—N2—C9—C10173.5 (5)O5—N4—C18—C191.8 (14)
N3—N2—C9—C8177.5 (6)O6—N4—C18—C19176.9 (9)
Re1—N2—C9—C810.4 (9)O5—N4—C18—C17178.3 (10)
N1—C8—C9—N22.4 (10)O6—N4—C18—C172.9 (13)
C7—C8—C9—N2175.5 (7)C17—C18—C19—C201.6 (14)
N1—C8—C9—C10177.7 (8)N4—C18—C19—C20178.3 (8)
C7—C8—C9—C100.2 (13)C18—C19—C20—C151.7 (13)
N2—C9—C10—C111.0 (9)C16—C15—C20—C190.6 (13)
C8—C9—C10—C11176.5 (8)C14—C15—C20—C19179.6 (9)
C9—C10—C11—N30.1 (9)
Hydrogen-bond geometry (Å, º) top
The hydrogen bond geometry for the disordered solvent molecule was being omitted for clarity purpose
D—H···AD—HH···AD···AD—H···A
C6—H3···O6i0.932.533.211 (13)131
C7—H4···O7Aii0.932.413.33 (3)170
C10—H5···O7Aii0.932.373.26 (3)160
C11—H6···Cl1iii0.932.583.482 (9)164
C13—H7···Cl1iii0.932.823.717 (10)163
C14—H8···O40.932.442.782 (13)102
C20—H12···Cl1iii0.932.783.681 (10)165
Symmetry codes: (i) x2, y1, z1; (ii) x1, y1, z; (iii) x+1, y, z+1.
Selected geometric parameters (Å, °) for (I) and (II) top
(I)(II)(I)(II)
Re1—C11.923 (8)1.921 (10)N1–Re1–N273.8 (3)74.2 (2)
Re1—C21.908 (9)1.860 (10)N1–Re1–C296.6 (3)95.0 (3)
Re1—C31.914 (9)1.912 (11)C1–Re1–N2102.0 (3)103.9 (3)
Re1—N12.190 (7)2.197 (7)C1–Re1–C287.6 (4)86.6 (4)
Re1—N22.207 (6)2.219 (6)N1–Re1–C393.0 (3)95.7 (3)
Re1—Cl12.472 (2)2.486 (2)N2–Re1–C391.3 (3)94.5 (3)
C1—O11.141 (11)1.143 (12)C2–Re1–C388.6 (4)89.2 (4)
C2—O21.146 (11)1.196 (12)C1–Re1–C387.2 (4)89.4 (4)
C3—O31.118 (11)1.135 (13)N1–Re1–Cl183.8 (18)83.4 (18)
C12—C131.440 (14)1.440 (12)N2–Re1–Cl186.3 (19)84.8 (17)
C14—C151.452 (14)1.445 (12)C2–Re1–Cl193.4 (3)91.3 (3)
C1—Re1—Cl195.8 (3)91.5 (3)
C3—Re1—Cl1176.4 (3)178.9 (3)
LOLIPOP and HOMA index for (I) and (II) top
(I)(II)
Cg2Cg3Cg4Cg2Cg3Cg4
LOLIPOP0.1370.0590.3210.02830.05760.298
HOMA0.8250.9680.9630.7450.9420.935
Cg2, Cg3 and Cg4 represent the pyrazole, pyridine and benzene rings, respectively.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds