Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618010586/yf3146sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618010586/yf3146Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618010586/yf3146IIsup3.hkl | |
Chemdraw file https://doi.org/10.1107/S2053229618010586/yf3146Isup4.cdx | |
Chemdraw file https://doi.org/10.1107/S2053229618010586/yf3146IIsup5.cdx | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618010586/yf3146sup6.pdf |
CCDC references: 1857522; 1857521
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).
[ReCl(C17H12FN3O)(CO)3] | Z = 2 |
Mr = 598.98 | F(000) = 572 |
Triclinic, P1 | Dx = 2.039 Mg m−3 |
a = 7.2479 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.1177 (5) Å | Cell parameters from 9612 reflections |
c = 16.9716 (12) Å | θ = 3.0–28.4° |
α = 81.374 (3)° | µ = 6.41 mm−1 |
β = 86.946 (4)° | T = 293 K |
γ = 81.339 (3)° | Block, yellow |
V = 975.51 (11) Å3 | 0.44 × 0.30 × 0.25 mm |
Bruker PHOTON II CPAD diffractometer | 4374 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.091 |
φ and ω scans | θmax = 28.4°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −9→9 |
Tmin = 0.115, Tmax = 0.201 | k = −10→10 |
35815 measured reflections | l = −22→22 |
4881 independent reflections |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-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 parameters | Δρmax = 1.92 e Å−3 |
0 restraints | Δρmin = −2.68 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Re1 | 0.74009 (4) | 0.74654 (4) | 0.18448 (2) | 0.02740 (11) | |
C1 | 0.7287 (13) | 0.8428 (11) | 0.2818 (5) | 0.0370 (19) | |
O1 | 0.7266 (12) | 0.9048 (10) | 0.3380 (5) | 0.057 (2) | |
Cl1 | 0.4334 (3) | 0.8933 (3) | 0.13708 (15) | 0.0426 (5) | |
N1 | 0.7413 (10) | 0.6227 (8) | 0.0783 (4) | 0.0302 (14) | |
F1 | −0.0576 (14) | 1.4218 (11) | 0.4007 (6) | 0.094 (3) | |
N3 | 0.5337 (10) | 0.4421 (8) | 0.2899 (4) | 0.0325 (15) | |
C3 | 0.9750 (12) | 0.6215 (11) | 0.2179 (5) | 0.0340 (17) | |
O3 | 1.1140 (11) | 0.5507 (10) | 0.2366 (5) | 0.0553 (19) | |
N2 | 0.5984 (10) | 0.5236 (8) | 0.2208 (4) | 0.0288 (13) | |
C2 | 0.8696 (13) | 0.9258 (10) | 0.1363 (6) | 0.0358 (18) | |
O2 | 0.9537 (11) | 1.0305 (10) | 0.1093 (6) | 0.064 (2) | |
O4 | 0.4686 (14) | 0.4245 (10) | 0.4221 (4) | 0.062 (2) | |
C4 | 0.7910 (13) | 0.6875 (12) | 0.0038 (5) | 0.0380 (19) | |
H1 | 0.821443 | 0.796120 | −0.005118 | 0.046* | |
C8 | 0.6896 (11) | 0.4669 (10) | 0.0895 (5) | 0.0295 (16) | |
C7 | 0.6954 (12) | 0.3719 (12) | 0.0278 (6) | 0.0372 (19) | |
H4 | 0.661516 | 0.264515 | 0.037214 | 0.045* | |
C6 | 0.7522 (13) | 0.4383 (14) | −0.0478 (6) | 0.045 (2) | |
H3 | 0.759144 | 0.376131 | −0.089964 | 0.054* | |
C5 | 0.7983 (13) | 0.5992 (13) | −0.0592 (5) | 0.042 (2) | |
H2 | 0.834309 | 0.647779 | −0.109737 | 0.050* | |
C9 | 0.6178 (11) | 0.4138 (9) | 0.1692 (5) | 0.0296 (16) | |
C10 | 0.5641 (13) | 0.2612 (10) | 0.2047 (6) | 0.040 (2) | |
H5 | 0.564898 | 0.165006 | 0.181004 | 0.048* | |
C11 | 0.5108 (14) | 0.2814 (11) | 0.2803 (6) | 0.043 (2) | |
H6 | 0.466662 | 0.201438 | 0.318912 | 0.051* | |
C12 | 0.4620 (14) | 0.5187 (13) | 0.3599 (5) | 0.041 (2) | |
C13 | 0.3783 (13) | 0.6926 (12) | 0.3462 (5) | 0.0387 (19) | |
H7 | 0.354043 | 0.745165 | 0.294529 | 0.046* | |
C14 | 0.3358 (14) | 0.7781 (12) | 0.4071 (6) | 0.043 (2) | |
H8 | 0.374261 | 0.723952 | 0.456957 | 0.052* | |
C15 | 0.2353 (15) | 0.9477 (12) | 0.4036 (6) | 0.041 (2) | |
C16 | 0.1360 (16) | 1.0284 (13) | 0.3363 (6) | 0.048 (2) | |
H9 | 0.137784 | 0.973945 | 0.291782 | 0.057* | |
C17 | 0.0360 (17) | 1.1871 (15) | 0.3353 (8) | 0.057 (3) | |
H10 | −0.032252 | 1.238874 | 0.291120 | 0.069* | |
C18 | 0.0393 (18) | 1.2673 (15) | 0.4010 (8) | 0.060 (3) | |
C19 | 0.1364 (19) | 1.1946 (15) | 0.4675 (8) | 0.062 (3) | |
H11 | 0.137042 | 1.252146 | 0.510937 | 0.074* | |
C20 | 0.2340 (17) | 1.0330 (14) | 0.4688 (7) | 0.053 (3) | |
H12 | 0.299084 | 0.981389 | 0.513793 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Re1 | 0.03186 (18) | 0.02159 (15) | 0.03008 (17) | −0.00781 (11) | −0.00329 (11) | −0.00328 (11) |
C1 | 0.043 (5) | 0.038 (4) | 0.036 (4) | −0.015 (4) | −0.003 (4) | −0.013 (4) |
O1 | 0.075 (5) | 0.049 (4) | 0.054 (5) | −0.019 (4) | −0.003 (4) | −0.016 (4) |
Cl1 | 0.0403 (12) | 0.0333 (10) | 0.0543 (13) | −0.0007 (8) | −0.0115 (10) | −0.0079 (9) |
N1 | 0.030 (3) | 0.026 (3) | 0.034 (4) | −0.001 (3) | −0.003 (3) | −0.005 (3) |
F1 | 0.102 (7) | 0.063 (5) | 0.110 (7) | 0.012 (5) | 0.021 (5) | −0.020 (5) |
N3 | 0.039 (4) | 0.023 (3) | 0.035 (4) | −0.008 (3) | −0.002 (3) | 0.001 (3) |
C3 | 0.033 (4) | 0.043 (5) | 0.029 (4) | −0.013 (4) | −0.005 (3) | −0.007 (3) |
O3 | 0.053 (5) | 0.056 (5) | 0.057 (5) | −0.006 (4) | −0.011 (4) | −0.008 (4) |
N2 | 0.033 (3) | 0.024 (3) | 0.031 (3) | −0.010 (3) | −0.003 (3) | −0.003 (3) |
C2 | 0.037 (4) | 0.027 (4) | 0.042 (5) | −0.006 (3) | −0.001 (4) | 0.000 (3) |
O2 | 0.052 (5) | 0.046 (4) | 0.091 (6) | −0.021 (4) | 0.007 (4) | 0.008 (4) |
O4 | 0.095 (7) | 0.054 (5) | 0.032 (4) | −0.016 (4) | −0.002 (4) | 0.009 (3) |
C4 | 0.038 (5) | 0.039 (5) | 0.036 (4) | −0.003 (4) | −0.001 (4) | −0.004 (4) |
C8 | 0.023 (4) | 0.030 (4) | 0.036 (4) | 0.000 (3) | −0.004 (3) | −0.009 (3) |
C7 | 0.030 (4) | 0.037 (4) | 0.046 (5) | 0.001 (3) | −0.005 (4) | −0.015 (4) |
C6 | 0.034 (5) | 0.062 (6) | 0.041 (5) | 0.005 (4) | −0.007 (4) | −0.024 (5) |
C5 | 0.041 (5) | 0.056 (6) | 0.029 (4) | −0.004 (4) | 0.002 (4) | −0.010 (4) |
C9 | 0.030 (4) | 0.021 (3) | 0.036 (4) | −0.001 (3) | −0.005 (3) | −0.004 (3) |
C10 | 0.043 (5) | 0.020 (4) | 0.059 (6) | −0.008 (3) | −0.002 (4) | −0.008 (4) |
C11 | 0.047 (5) | 0.028 (4) | 0.052 (6) | −0.011 (4) | −0.002 (4) | −0.001 (4) |
C12 | 0.046 (5) | 0.047 (5) | 0.032 (4) | −0.018 (4) | 0.002 (4) | −0.003 (4) |
C13 | 0.039 (5) | 0.046 (5) | 0.031 (4) | −0.013 (4) | 0.002 (3) | 0.001 (4) |
C14 | 0.051 (6) | 0.038 (5) | 0.040 (5) | −0.014 (4) | 0.004 (4) | 0.001 (4) |
C15 | 0.052 (6) | 0.038 (5) | 0.037 (5) | −0.015 (4) | 0.007 (4) | −0.009 (4) |
C16 | 0.054 (6) | 0.046 (5) | 0.045 (5) | −0.013 (5) | −0.003 (4) | −0.008 (4) |
C17 | 0.054 (7) | 0.056 (7) | 0.061 (7) | −0.010 (5) | −0.005 (5) | −0.004 (5) |
C18 | 0.057 (7) | 0.046 (6) | 0.075 (8) | −0.007 (5) | 0.021 (6) | −0.005 (6) |
C19 | 0.080 (9) | 0.055 (7) | 0.056 (7) | −0.020 (6) | 0.022 (6) | −0.026 (6) |
C20 | 0.062 (7) | 0.049 (6) | 0.049 (6) | −0.007 (5) | 0.004 (5) | −0.015 (5) |
Re1—C2 | 1.908 (9) | C6—C5 | 1.380 (15) |
Re1—C3 | 1.914 (9) | C6—H3 | 0.9300 |
Re1—C1 | 1.923 (8) | C5—H2 | 0.9300 |
Re1—N1 | 2.190 (7) | C9—C10 | 1.395 (11) |
Re1—N2 | 2.207 (6) | C10—C11 | 1.347 (14) |
Re1—Cl1 | 2.472 (2) | C10—H5 | 0.9300 |
C1—O1 | 1.141 (11) | C11—H6 | 0.9300 |
N1—C4 | 1.346 (11) | C12—C13 | 1.440 (14) |
N1—C8 | 1.356 (10) | C13—C14 | 1.326 (14) |
F1—C18 | 1.342 (14) | C13—H7 | 0.9300 |
N3—N2 | 1.355 (10) | C14—C15 | 1.452 (14) |
N3—C11 | 1.374 (11) | C14—H8 | 0.9300 |
N3—C12 | 1.458 (12) | C15—C20 | 1.388 (14) |
C3—O3 | 1.118 (11) | C15—C16 | 1.405 (14) |
N2—C9 | 1.327 (10) | C16—C17 | 1.378 (16) |
C2—O2 | 1.146 (11) | C16—H9 | 0.9300 |
O4—C12 | 1.206 (11) | C17—C18 | 1.377 (18) |
C4—C5 | 1.368 (13) | C17—H10 | 0.9300 |
C4—H1 | 0.9300 | C18—C19 | 1.370 (19) |
C8—C7 | 1.386 (11) | C19—C20 | 1.392 (16) |
C8—C9 | 1.451 (12) | C19—H11 | 0.9300 |
C7—C6 | 1.382 (14) | C20—H12 | 0.9300 |
C7—H4 | 0.9300 | ||
C2—Re1—C3 | 88.6 (4) | C4—C5—C6 | 120.1 (9) |
C2—Re1—C1 | 87.6 (4) | C4—C5—H2 | 120.0 |
C3—Re1—C1 | 87.2 (4) | C6—C5—H2 | 120.0 |
C2—Re1—N1 | 96.6 (3) | N2—C9—C10 | 110.6 (8) |
C3—Re1—N1 | 93.0 (3) | N2—C9—C8 | 117.9 (7) |
C1—Re1—N1 | 175.7 (3) | C10—C9—C8 | 131.5 (8) |
C2—Re1—N2 | 170.4 (3) | C11—C10—C9 | 106.1 (8) |
C3—Re1—N2 | 91.3 (3) | C11—C10—H5 | 127.0 |
C1—Re1—N2 | 102.0 (3) | C9—C10—H5 | 127.0 |
N1—Re1—N2 | 73.8 (3) | C10—C11—N3 | 107.3 (8) |
C2—Re1—Cl1 | 93.4 (3) | C10—C11—H6 | 126.4 |
C3—Re1—Cl1 | 176.4 (3) | N3—C11—H6 | 126.4 |
C1—Re1—Cl1 | 95.8 (3) | O4—C12—C13 | 127.6 (9) |
N1—Re1—Cl1 | 83.81 (18) | O4—C12—N3 | 115.4 (9) |
N2—Re1—Cl1 | 86.30 (19) | C13—C12—N3 | 116.8 (8) |
O1—C1—Re1 | 177.1 (8) | C14—C13—C12 | 120.3 (9) |
C4—N1—C8 | 117.9 (7) | C14—C13—H7 | 119.8 |
C4—N1—Re1 | 125.5 (6) | C12—C13—H7 | 119.8 |
C8—N1—Re1 | 116.6 (5) | C13—C14—C15 | 126.6 (9) |
N2—N3—C11 | 110.1 (7) | C13—C14—H8 | 116.7 |
N2—N3—C12 | 126.1 (7) | C15—C14—H8 | 116.7 |
C11—N3—C12 | 122.8 (8) | C20—C15—C16 | 118.5 (10) |
O3—C3—Re1 | 178.7 (9) | C20—C15—C14 | 119.7 (10) |
C9—N2—N3 | 106.0 (6) | C16—C15—C14 | 121.9 (9) |
C9—N2—Re1 | 115.0 (5) | C17—C16—C15 | 121.0 (10) |
N3—N2—Re1 | 136.6 (5) | C17—C16—H9 | 119.5 |
O2—C2—Re1 | 177.1 (9) | C15—C16—H9 | 119.5 |
N1—C4—C5 | 122.4 (9) | C18—C17—C16 | 118.5 (11) |
N1—C4—H1 | 118.8 | C18—C17—H10 | 120.8 |
C5—C4—H1 | 118.8 | C16—C17—H10 | 120.8 |
N1—C8—C7 | 121.9 (8) | F1—C18—C19 | 118.4 (12) |
N1—C8—C9 | 114.6 (7) | F1—C18—C17 | 119.1 (13) |
C7—C8—C9 | 123.3 (8) | C19—C18—C17 | 122.5 (11) |
C6—C7—C8 | 119.4 (9) | C18—C19—C20 | 118.6 (11) |
C6—C7—H4 | 120.3 | C18—C19—H11 | 120.7 |
C8—C7—H4 | 120.3 | C20—C19—H11 | 120.7 |
C5—C6—C7 | 118.2 (8) | C15—C20—C19 | 120.8 (11) |
C5—C6—H3 | 120.9 | C15—C20—H12 | 119.6 |
C7—C6—H3 | 120.9 | C19—C20—H12 | 119.6 |
C11—N3—N2—C9 | −0.8 (9) | C8—C9—C10—C11 | 179.2 (9) |
C12—N3—N2—C9 | −169.2 (8) | C9—C10—C11—N3 | −0.5 (11) |
C11—N3—N2—Re1 | −161.0 (7) | N2—N3—C11—C10 | 0.8 (11) |
C12—N3—N2—Re1 | 30.6 (13) | C12—N3—C11—C10 | 169.7 (8) |
C8—N1—C4—C5 | −2.8 (13) | N2—N3—C12—O4 | −156.7 (9) |
Re1—N1—C4—C5 | 176.3 (7) | C11—N3—C12—O4 | 36.2 (13) |
C4—N1—C8—C7 | 3.1 (11) | N2—N3—C12—C13 | 28.2 (13) |
Re1—N1—C8—C7 | −176.1 (6) | C11—N3—C12—C13 | −138.9 (9) |
C4—N1—C8—C9 | −173.3 (7) | O4—C12—C13—C14 | 15.8 (16) |
Re1—N1—C8—C9 | 7.5 (9) | N3—C12—C13—C14 | −169.8 (9) |
N1—C8—C7—C6 | −1.2 (12) | C12—C13—C14—C15 | −173.6 (9) |
C9—C8—C7—C6 | 174.9 (8) | C13—C14—C15—C20 | −167.0 (10) |
C8—C7—C6—C5 | −1.0 (13) | C13—C14—C15—C16 | 13.9 (16) |
N1—C4—C5—C6 | 0.6 (14) | C20—C15—C16—C17 | −1.4 (16) |
C7—C6—C5—C4 | 1.4 (14) | C14—C15—C16—C17 | 177.7 (10) |
N3—N2—C9—C10 | 0.5 (9) | C15—C16—C17—C18 | 1.7 (17) |
Re1—N2—C9—C10 | 165.6 (6) | C16—C17—C18—F1 | −180.0 (11) |
N3—N2—C9—C8 | −178.8 (7) | C16—C17—C18—C19 | −0.7 (19) |
Re1—N2—C9—C8 | −13.7 (9) | F1—C18—C19—C20 | 178.7 (11) |
N1—C8—C9—N2 | 4.3 (10) | C17—C18—C19—C20 | −0.6 (19) |
C7—C8—C9—N2 | −172.1 (8) | C16—C15—C20—C19 | 0.1 (17) |
N1—C8—C9—C10 | −174.9 (9) | C14—C15—C20—C19 | −179.0 (11) |
C7—C8—C9—C10 | 8.8 (14) | C18—C19—C20—C15 | 0.9 (18) |
N2—C9—C10—C11 | 0.0 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H5···Cl1i | 0.93 | 2.74 | 3.624 (9) | 158 |
C13—H7···Cl1 | 0.93 | 2.83 | 3.704 (9) | 158 |
C14—H8···O4ii | 0.93 | 2.46 | 3.380 (13) | 170 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+1. |
[ReCl(C17H12ClN4O3)(CO)3]·C3H6O | Z = 2 |
Mr = 684.06 | F(000) = 664 |
Triclinic, P1 | Dx = 1.788 Mg m−3 |
a = 7.9828 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.0719 (4) Å | Cell parameters from 6351 reflections |
c = 14.4560 (5) Å | θ = 3.0–28.4° |
α = 104.093 (2)° | µ = 4.94 mm−1 |
β = 99.708 (2)° | T = 293 K |
γ = 104.184 (2)° | Plate, orange |
V = 1270.78 (8) Å3 | 0.42 × 0.40 × 0.04 mm |
Bruker PHOTON II CPAD diffractometer | 4505 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.180 |
φ and ω scans | θmax = 28.4°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −10→10 |
Tmin = 0.145, Tmax = 0.821 | k = −16→16 |
59671 measured reflections | l = −19→19 |
6351 independent reflections |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H-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 parameters | Δρmax = 1.29 e Å−3 |
9 restraints | Δρmin = −1.82 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Re1 | 0.42196 (5) | 0.07583 (3) | 0.22200 (3) | 0.03867 (14) | |
Cl1 | 0.1934 (3) | 0.0899 (2) | 0.31813 (17) | 0.0456 (5) | |
O1 | 0.6211 (12) | 0.3421 (7) | 0.3185 (7) | 0.085 (3) | |
O2 | 0.2242 (12) | 0.1563 (9) | 0.0630 (6) | 0.085 (3) | |
O3 | 0.7039 (13) | 0.0564 (9) | 0.1058 (7) | 0.087 (3) | |
O4 | 0.7931 (12) | 0.1937 (7) | 0.4120 (6) | 0.091 (3) | |
O5 | 1.5649 (13) | 0.3057 (11) | 0.9954 (7) | 0.102 (3) | |
O6 | 1.6673 (10) | 0.4749 (8) | 0.9707 (7) | 0.087 (3) | |
N1 | 0.2592 (9) | −0.1125 (6) | 0.1609 (5) | 0.0353 (14) | |
N2 | 0.5200 (8) | −0.0172 (6) | 0.3246 (5) | 0.0334 (14) | |
N3 | 0.6441 (8) | 0.0071 (6) | 0.4121 (5) | 0.0318 (13) | |
N4 | 1.5589 (11) | 0.3749 (10) | 0.9475 (7) | 0.066 (3) | |
C1 | 0.5530 (14) | 0.2415 (9) | 0.2851 (8) | 0.052 (2) | |
C2 | 0.3022 (14) | 0.1269 (8) | 0.1265 (7) | 0.052 (2) | |
C3 | 0.5967 (14) | 0.0619 (8) | 0.1479 (7) | 0.049 (2) | |
C4 | 0.1353 (13) | −0.1589 (8) | 0.0767 (7) | 0.048 (2) | |
H1 | 0.121096 | −0.111281 | 0.036005 | 0.057* | |
C5 | 0.0265 (13) | −0.2764 (8) | 0.0477 (7) | 0.049 (2) | |
H2 | −0.058825 | −0.306426 | −0.011749 | 0.059* | |
C6 | 0.0447 (11) | −0.3476 (8) | 0.1064 (6) | 0.044 (2) | |
H3 | −0.029396 | −0.425927 | 0.088262 | 0.053* | |
C7 | 0.1742 (11) | −0.3017 (7) | 0.1925 (6) | 0.0390 (18) | |
H4 | 0.191391 | −0.349734 | 0.232465 | 0.047* | |
C8 | 0.2800 (10) | −0.1832 (7) | 0.2202 (6) | 0.0338 (16) | |
C9 | 0.4205 (10) | −0.1285 (6) | 0.3098 (5) | 0.0295 (15) | |
C10 | 0.4775 (11) | −0.1781 (7) | 0.3827 (6) | 0.0359 (17) | |
H5 | 0.429040 | −0.254643 | 0.386575 | 0.043* | |
C11 | 0.6185 (10) | −0.0904 (7) | 0.4462 (6) | 0.0349 (17) | |
H6 | 0.686316 | −0.095516 | 0.503099 | 0.042* | |
C12 | 0.7843 (11) | 0.1201 (7) | 0.4546 (7) | 0.0419 (19) | |
C13 | 0.9044 (11) | 0.1331 (8) | 0.5455 (6) | 0.0426 (19) | |
H7 | 0.895068 | 0.069127 | 0.571462 | 0.051* | |
C14 | 1.0269 (12) | 0.2356 (8) | 0.5915 (7) | 0.048 (2) | |
H8 | 1.030418 | 0.295613 | 0.561359 | 0.058* | |
C15 | 1.1572 (11) | 0.2667 (7) | 0.6835 (6) | 0.042 (2) | |
C16 | 1.2790 (13) | 0.3828 (8) | 0.7178 (8) | 0.054 (2) | |
H9 | 1.271234 | 0.436503 | 0.682052 | 0.065* | |
C17 | 1.4098 (13) | 0.4178 (9) | 0.8040 (8) | 0.059 (3) | |
H10 | 1.490533 | 0.494221 | 0.826212 | 0.071* | |
C18 | 1.4183 (11) | 0.3365 (9) | 0.8569 (7) | 0.051 (3) | |
C19 | 1.3015 (11) | 0.2251 (8) | 0.8265 (7) | 0.044 (2) | |
H11 | 1.307963 | 0.172917 | 0.864001 | 0.053* | |
C20 | 1.1721 (11) | 0.1891 (8) | 0.7393 (6) | 0.043 (2) | |
H12 | 1.093993 | 0.111758 | 0.717699 | 0.052* | |
C21A | 1.174 (2) | 0.4473 (11) | 0.3429 (11) | 0.095 (5) | |
O7A | 1.287 (3) | 0.536 (2) | 0.3351 (18) | 0.125 (11)* | 0.57 (4) |
C22A | 1.043 (5) | 0.352 (3) | 0.262 (2) | 0.118 (14)* | 0.57 (4) |
H13A | 0.979557 | 0.385653 | 0.219718 | 0.177* | 0.57 (4) |
H13B | 0.961102 | 0.302379 | 0.287760 | 0.177* | 0.57 (4) |
H13C | 1.103437 | 0.303571 | 0.225087 | 0.177* | 0.57 (4) |
C23A | 1.246 (5) | 0.415 (3) | 0.4296 (18) | 0.111 (11)* | 0.57 (4) |
H14A | 1.183898 | 0.334121 | 0.423154 | 0.167* | 0.57 (4) |
H14B | 1.232415 | 0.467688 | 0.487532 | 0.167* | 0.57 (4) |
H14C | 1.370674 | 0.423664 | 0.434715 | 0.167* | 0.57 (4) |
O7B | 1.189 (5) | 0.5582 (19) | 0.359 (2) | 0.113 (13)* | 0.43 (4) |
C22B | 1.087 (9) | 0.364 (5) | 0.246 (2) | 0.14 (3)* | 0.43 (4) |
H13D | 1.038379 | 0.285624 | 0.250998 | 0.215* | 0.43 (4) |
H13E | 1.172651 | 0.362004 | 0.206246 | 0.215* | 0.43 (4) |
H13F | 0.993175 | 0.389772 | 0.215081 | 0.215* | 0.43 (4) |
C23B | 1.145 (8) | 0.421 (4) | 0.433 (2) | 0.122 (17)* | 0.43 (4) |
H14D | 1.086607 | 0.337580 | 0.418451 | 0.146* | 0.43 (4) |
H14E | 1.072547 | 0.466736 | 0.460118 | 0.146* | 0.43 (4) |
H14F | 1.258007 | 0.443020 | 0.478914 | 0.183* | 0.43 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Re1 | 0.0420 (2) | 0.03484 (19) | 0.0383 (2) | 0.00893 (13) | 0.00485 (14) | 0.01530 (13) |
Cl1 | 0.0494 (12) | 0.0451 (11) | 0.0450 (12) | 0.0179 (10) | 0.0088 (10) | 0.0162 (9) |
O1 | 0.087 (6) | 0.037 (4) | 0.112 (7) | −0.003 (4) | 0.002 (5) | 0.023 (4) |
O2 | 0.096 (6) | 0.104 (7) | 0.077 (6) | 0.053 (6) | 0.002 (5) | 0.056 (5) |
O3 | 0.096 (7) | 0.107 (7) | 0.086 (6) | 0.040 (6) | 0.056 (6) | 0.046 (5) |
O4 | 0.088 (6) | 0.067 (5) | 0.075 (6) | −0.030 (4) | −0.035 (5) | 0.038 (4) |
O5 | 0.079 (7) | 0.143 (10) | 0.063 (6) | 0.024 (6) | −0.014 (5) | 0.024 (6) |
O6 | 0.039 (4) | 0.081 (6) | 0.090 (6) | 0.005 (4) | −0.015 (4) | −0.033 (5) |
N1 | 0.041 (4) | 0.037 (4) | 0.030 (3) | 0.016 (3) | 0.006 (3) | 0.009 (3) |
N2 | 0.030 (3) | 0.033 (3) | 0.038 (4) | 0.011 (3) | 0.006 (3) | 0.011 (3) |
N3 | 0.028 (3) | 0.032 (3) | 0.031 (3) | 0.007 (3) | 0.001 (3) | 0.009 (3) |
N4 | 0.040 (5) | 0.098 (8) | 0.040 (5) | 0.024 (5) | 0.000 (4) | −0.012 (5) |
C1 | 0.053 (6) | 0.052 (6) | 0.059 (6) | 0.013 (5) | 0.015 (5) | 0.031 (5) |
C2 | 0.062 (6) | 0.043 (5) | 0.053 (6) | 0.013 (5) | 0.021 (5) | 0.017 (4) |
C3 | 0.059 (6) | 0.042 (5) | 0.042 (5) | 0.007 (4) | 0.003 (5) | 0.017 (4) |
C4 | 0.054 (5) | 0.047 (5) | 0.034 (4) | 0.018 (4) | −0.005 (4) | 0.004 (4) |
C5 | 0.047 (5) | 0.050 (5) | 0.038 (5) | 0.013 (4) | −0.006 (4) | 0.004 (4) |
C6 | 0.036 (4) | 0.037 (4) | 0.044 (5) | 0.007 (4) | 0.002 (4) | −0.005 (4) |
C7 | 0.037 (4) | 0.031 (4) | 0.044 (5) | 0.006 (3) | 0.008 (4) | 0.007 (3) |
C8 | 0.034 (4) | 0.035 (4) | 0.032 (4) | 0.010 (3) | 0.009 (3) | 0.009 (3) |
C9 | 0.035 (4) | 0.026 (3) | 0.027 (4) | 0.010 (3) | 0.004 (3) | 0.006 (3) |
C10 | 0.036 (4) | 0.030 (4) | 0.040 (4) | 0.010 (3) | 0.006 (3) | 0.010 (3) |
C11 | 0.036 (4) | 0.039 (4) | 0.033 (4) | 0.015 (3) | 0.007 (3) | 0.015 (3) |
C12 | 0.039 (5) | 0.033 (4) | 0.049 (5) | 0.004 (4) | 0.007 (4) | 0.013 (4) |
C13 | 0.036 (4) | 0.045 (5) | 0.040 (5) | 0.007 (4) | 0.000 (4) | 0.013 (4) |
C14 | 0.041 (5) | 0.043 (5) | 0.054 (6) | 0.004 (4) | 0.001 (4) | 0.017 (4) |
C15 | 0.032 (4) | 0.036 (4) | 0.042 (5) | 0.004 (3) | −0.001 (4) | −0.002 (4) |
C16 | 0.045 (5) | 0.041 (5) | 0.059 (6) | −0.006 (4) | 0.000 (5) | 0.010 (4) |
C17 | 0.047 (5) | 0.045 (5) | 0.056 (6) | −0.009 (4) | −0.002 (5) | −0.004 (5) |
C18 | 0.030 (4) | 0.064 (6) | 0.038 (5) | 0.014 (4) | 0.002 (4) | −0.016 (4) |
C19 | 0.038 (5) | 0.046 (5) | 0.045 (5) | 0.015 (4) | 0.006 (4) | 0.010 (4) |
C20 | 0.030 (4) | 0.043 (5) | 0.044 (5) | 0.004 (4) | 0.004 (4) | 0.001 (4) |
C21A | 0.133 (13) | 0.049 (7) | 0.107 (12) | 0.012 (8) | 0.043 (10) | 0.039 (7) |
Re1—C2 | 1.860 (10) | C13—C14 | 1.310 (12) |
Re1—C3 | 1.912 (11) | C13—H7 | 0.9300 |
Re1—C1 | 1.921 (10) | C14—C15 | 1.445 (12) |
Re1—N1 | 2.197 (7) | C14—H8 | 0.9300 |
Re1—N2 | 2.219 (6) | C15—C20 | 1.390 (13) |
Re1—Cl1 | 2.486 (2) | C15—C16 | 1.409 (12) |
O1—C1 | 1.143 (12) | C16—C17 | 1.382 (14) |
O2—C2 | 1.196 (12) | C16—H9 | 0.9300 |
O3—C3 | 1.135 (13) | C17—C18 | 1.391 (16) |
O4—C12 | 1.194 (11) | C17—H10 | 0.9300 |
O5—N4 | 1.213 (14) | C18—C19 | 1.353 (13) |
O6—N4 | 1.230 (13) | C19—C20 | 1.386 (12) |
N1—C4 | 1.328 (10) | C19—H11 | 0.9300 |
N1—C8 | 1.366 (10) | C20—H12 | 0.9300 |
N2—C9 | 1.328 (10) | C21A—O7A | 1.27 (2) |
N2—N3 | 1.386 (9) | C21A—O7B | 1.27 (2) |
N3—C11 | 1.367 (10) | C21A—C23B | 1.447 (18) |
N3—C12 | 1.450 (10) | C21A—C22B | 1.453 (19) |
N4—C18 | 1.463 (12) | C21A—C22A | 1.460 (18) |
C4—C5 | 1.387 (13) | C21A—C23A | 1.467 (17) |
C4—H1 | 0.9300 | C22A—H13A | 0.9600 |
C5—C6 | 1.361 (13) | C22A—H13B | 0.9600 |
C5—H2 | 0.9300 | C22A—H13C | 0.9600 |
C6—C7 | 1.369 (12) | C23A—H14A | 0.9600 |
C6—H3 | 0.9300 | C23A—H14B | 0.9600 |
C7—C8 | 1.391 (11) | C23A—H14C | 0.9600 |
C7—H4 | 0.9300 | C22B—H13D | 0.9600 |
C8—C9 | 1.450 (10) | C22B—H13E | 0.9600 |
C9—C10 | 1.398 (10) | C22B—H13F | 0.9600 |
C10—C11 | 1.350 (11) | C23B—H14D | 0.9600 |
C10—H5 | 0.9300 | C23B—H14E | 0.9600 |
C11—H6 | 0.9300 | C23B—H14F | 0.9600 |
C12—C13 | 1.440 (12) | ||
C2—Re1—C3 | 89.2 (4) | C13—C12—N3 | 116.3 (7) |
C2—Re1—C1 | 86.6 (4) | C14—C13—C12 | 119.6 (9) |
C3—Re1—C1 | 89.4 (4) | C14—C13—H7 | 120.2 |
C2—Re1—N1 | 95.0 (3) | C12—C13—H7 | 120.2 |
C3—Re1—N1 | 95.7 (3) | C13—C14—C15 | 127.9 (9) |
C1—Re1—N1 | 174.7 (3) | C13—C14—H8 | 116.0 |
C2—Re1—N2 | 168.8 (3) | C15—C14—H8 | 116.0 |
C3—Re1—N2 | 94.5 (3) | C20—C15—C16 | 117.9 (8) |
C1—Re1—N2 | 103.9 (3) | C20—C15—C14 | 124.3 (8) |
N1—Re1—N2 | 74.2 (2) | C16—C15—C14 | 117.7 (9) |
C2—Re1—Cl1 | 91.3 (3) | C17—C16—C15 | 120.9 (10) |
C3—Re1—Cl1 | 178.9 (3) | C17—C16—H9 | 119.6 |
C1—Re1—Cl1 | 91.5 (3) | C15—C16—H9 | 119.6 |
N1—Re1—Cl1 | 83.35 (18) | C16—C17—C18 | 118.7 (9) |
N2—Re1—Cl1 | 84.81 (17) | C16—C17—H10 | 120.6 |
C4—N1—C8 | 118.7 (7) | C18—C17—H10 | 120.6 |
C4—N1—Re1 | 125.5 (6) | C19—C18—C17 | 121.7 (9) |
C8—N1—Re1 | 115.5 (5) | C19—C18—N4 | 120.4 (11) |
C9—N2—N3 | 103.7 (6) | C17—C18—N4 | 117.8 (10) |
C9—N2—Re1 | 115.4 (5) | C18—C19—C20 | 119.6 (9) |
N3—N2—Re1 | 140.2 (5) | C18—C19—H11 | 120.2 |
C11—N3—N2 | 110.5 (6) | C20—C19—H11 | 120.2 |
C11—N3—C12 | 127.2 (7) | C19—C20—C15 | 121.1 (8) |
N2—N3—C12 | 122.1 (6) | C19—C20—H12 | 119.5 |
O5—N4—O6 | 123.0 (10) | C15—C20—H12 | 119.5 |
O5—N4—C18 | 118.3 (11) | O7B—C21A—C23B | 105 (3) |
O6—N4—C18 | 118.7 (12) | O7B—C21A—C22B | 120 (3) |
O1—C1—Re1 | 174.9 (9) | C23B—C21A—C22B | 123 (3) |
O2—C2—Re1 | 177.9 (9) | O7A—C21A—C22A | 126 (3) |
O3—C3—Re1 | 178.1 (10) | O7A—C21A—C23A | 109 (2) |
N1—C4—C5 | 122.0 (9) | C22A—C21A—C23A | 117 (2) |
N1—C4—H1 | 119.0 | C21A—C22A—H13A | 109.5 |
C5—C4—H1 | 119.0 | C21A—C22A—H13B | 109.5 |
C6—C5—C4 | 120.0 (8) | H13A—C22A—H13B | 109.5 |
C6—C5—H2 | 120.0 | C21A—C22A—H13C | 109.5 |
C4—C5—H2 | 120.0 | H13A—C22A—H13C | 109.5 |
C5—C6—C7 | 118.7 (8) | H13B—C22A—H13C | 109.5 |
C5—C6—H3 | 120.7 | C21A—C23A—H14A | 109.5 |
C7—C6—H3 | 120.7 | C21A—C23A—H14B | 109.5 |
C6—C7—C8 | 120.0 (8) | H14A—C23A—H14B | 109.5 |
C6—C7—H4 | 120.0 | C21A—C23A—H14C | 109.5 |
C8—C7—H4 | 120.0 | H14A—C23A—H14C | 109.5 |
N1—C8—C7 | 120.6 (7) | H14B—C23A—H14C | 109.5 |
N1—C8—C9 | 116.1 (7) | C21A—C22B—H13D | 109.5 |
C7—C8—C9 | 123.2 (7) | C21A—C22B—H13E | 109.5 |
N2—C9—C10 | 112.9 (7) | H13D—C22B—H13E | 109.5 |
N2—C9—C8 | 117.4 (7) | C21A—C22B—H13F | 109.5 |
C10—C9—C8 | 129.6 (7) | H13D—C22B—H13F | 109.5 |
C11—C10—C9 | 104.9 (7) | H13E—C22B—H13F | 109.5 |
C11—C10—H5 | 127.6 | C21A—C23B—H14D | 109.5 |
C9—C10—H5 | 127.6 | C21A—C23B—H14E | 109.5 |
C10—C11—N3 | 108.0 (7) | H14D—C23B—H14E | 109.5 |
C10—C11—H6 | 126.0 | C21A—C23B—H14F | 109.5 |
N3—C11—H6 | 126.0 | H14D—C23B—H14F | 109.5 |
O4—C12—C13 | 125.2 (8) | H14E—C23B—H14F | 109.5 |
O4—C12—N3 | 118.5 (8) | ||
C9—N2—N3—C11 | 1.3 (8) | N2—N3—C11—C10 | −0.8 (9) |
Re1—N2—N3—C11 | 170.1 (6) | C12—N3—C11—C10 | −177.4 (7) |
C9—N2—N3—C12 | 178.2 (7) | C11—N3—C12—O4 | 175.7 (10) |
Re1—N2—N3—C12 | −13.0 (12) | N2—N3—C12—O4 | −0.6 (13) |
C8—N1—C4—C5 | 0.3 (13) | C11—N3—C12—C13 | −3.5 (12) |
Re1—N1—C4—C5 | −173.8 (7) | N2—N3—C12—C13 | −179.8 (7) |
N1—C4—C5—C6 | 0.2 (15) | O4—C12—C13—C14 | 5.5 (16) |
C4—C5—C6—C7 | −1.4 (14) | N3—C12—C13—C14 | −175.4 (8) |
C5—C6—C7—C8 | 2.2 (13) | C12—C13—C14—C15 | 179.1 (9) |
C4—N1—C8—C7 | 0.5 (12) | C13—C14—C15—C20 | −0.2 (16) |
Re1—N1—C8—C7 | 175.1 (6) | C13—C14—C15—C16 | 178.7 (10) |
C4—N1—C8—C9 | 178.4 (7) | C20—C15—C16—C17 | 0.5 (15) |
Re1—N1—C8—C9 | −7.0 (9) | C14—C15—C16—C17 | −178.5 (10) |
C6—C7—C8—N1 | −1.7 (12) | C15—C16—C17—C18 | −0.5 (16) |
C6—C7—C8—C9 | −179.5 (8) | C16—C17—C18—C19 | −0.5 (15) |
N3—N2—C9—C10 | −1.4 (8) | C16—C17—C18—N4 | 179.4 (9) |
Re1—N2—C9—C10 | −173.5 (5) | O5—N4—C18—C19 | −1.8 (14) |
N3—N2—C9—C8 | −177.5 (6) | O6—N4—C18—C19 | 176.9 (9) |
Re1—N2—C9—C8 | 10.4 (9) | O5—N4—C18—C17 | 178.3 (10) |
N1—C8—C9—N2 | −2.4 (10) | O6—N4—C18—C17 | −2.9 (13) |
C7—C8—C9—N2 | 175.5 (7) | C17—C18—C19—C20 | 1.6 (14) |
N1—C8—C9—C10 | −177.7 (8) | N4—C18—C19—C20 | −178.3 (8) |
C7—C8—C9—C10 | 0.2 (13) | C18—C19—C20—C15 | −1.7 (13) |
N2—C9—C10—C11 | 1.0 (9) | C16—C15—C20—C19 | 0.6 (13) |
C8—C9—C10—C11 | 176.5 (8) | C14—C15—C20—C19 | 179.6 (9) |
C9—C10—C11—N3 | −0.1 (9) |
The hydrogen bond geometry for the disordered solvent molecule was being omitted for clarity purpose |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H3···O6i | 0.93 | 2.53 | 3.211 (13) | 131 |
C7—H4···O7Aii | 0.93 | 2.41 | 3.33 (3) | 170 |
C10—H5···O7Aii | 0.93 | 2.37 | 3.26 (3) | 160 |
C11—H6···Cl1iii | 0.93 | 2.58 | 3.482 (9) | 164 |
C13—H7···Cl1iii | 0.93 | 2.82 | 3.717 (10) | 163 |
C14—H8···O4 | 0.93 | 2.44 | 2.782 (13) | 102 |
C20—H12···Cl1iii | 0.93 | 2.78 | 3.681 (10) | 165 |
Symmetry codes: (i) x−2, y−1, z−1; (ii) x−1, y−1, z; (iii) −x+1, −y, −z+1. |
(I) | (II) | (I) | (II) | ||
Re1—C1 | 1.923 (8) | 1.921 (10) | N1–Re1–N2 | 73.8 (3) | 74.2 (2) |
Re1—C2 | 1.908 (9) | 1.860 (10) | N1–Re1–C2 | 96.6 (3) | 95.0 (3) |
Re1—C3 | 1.914 (9) | 1.912 (11) | C1–Re1–N2 | 102.0 (3) | 103.9 (3) |
Re1—N1 | 2.190 (7) | 2.197 (7) | C1–Re1–C2 | 87.6 (4) | 86.6 (4) |
Re1—N2 | 2.207 (6) | 2.219 (6) | N1–Re1–C3 | 93.0 (3) | 95.7 (3) |
Re1—Cl1 | 2.472 (2) | 2.486 (2) | N2–Re1–C3 | 91.3 (3) | 94.5 (3) |
C1—O1 | 1.141 (11) | 1.143 (12) | C2–Re1–C3 | 88.6 (4) | 89.2 (4) |
C2—O2 | 1.146 (11) | 1.196 (12) | C1–Re1–C3 | 87.2 (4) | 89.4 (4) |
C3—O3 | 1.118 (11) | 1.135 (13) | N1–Re1–Cl1 | 83.8 (18) | 83.4 (18) |
C12—C13 | 1.440 (14) | 1.440 (12) | N2–Re1–Cl1 | 86.3 (19) | 84.8 (17) |
C14—C15 | 1.452 (14) | 1.445 (12) | C2–Re1–Cl1 | 93.4 (3) | 91.3 (3) |
C1—Re1—Cl1 | 95.8 (3) | 91.5 (3) | |||
C3—Re1—Cl1 | 176.4 (3) | 178.9 (3) |
(I) | (II) | |||||
Cg2 | Cg3 | Cg4 | Cg2 | Cg3 | Cg4 | |
LOLIPOP | 0.137 | 0.059 | 0.321 | 0.0283 | 0.0576 | 0.298 |
HOMA | 0.825 | 0.968 | 0.963 | 0.745 | 0.942 | 0.935 |
Cg2, Cg3 and Cg4 represent the pyrazole, pyridine and benzene rings, respectively. |