The structures of two facially coordinated Group VII metal complexes, fac-[ReCl(6,6′-dihydroxy-2,2′-bipyridine)(CO)3]·C4H8O and fac-[MnBr(6,6′-dihydroxy-2,2′-bipyridine)(CO)3]·C4H8O, are reported. These complexes are relevant to catalysis for CO2 reduction.
Supporting information
CCDC references: 1495018; 1495017
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
![[sigma]](https://journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.004 Å
- Mean (C-C) = 0.002 Å
- Disorder in solvent or counterion
- R factor = 0.033
- wR factor = 0.063
- Data-to-parameter ratio = 33.9
checkCIF/PLATON results
No syntax errors found
Datablock: Re_complex
Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.0 Note
PLAT971_ALERT_2_C Check Calcd Residual Density 0.63A From Re1 1.63 eA-3
PLAT971_ALERT_2_C Check Calcd Residual Density 0.69A From Re1 1.55 eA-3
PLAT972_ALERT_2_C Check Calcd Residual Density 0.58A From Re1 -1.69 eA-3
PLAT972_ALERT_2_C Check Calcd Residual Density 0.62A From Re1 -1.59 eA-3
PLAT977_ALERT_2_C Check the Negative Difference Density on H14 -0.34 eA-3
Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 6 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.002 Degree
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records 1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records 1 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for O3 -- C3 .. 6.8 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Re1 -- C1 .. 6.2 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Re1 -- C3 .. 7.4 s.u.
PLAT302_ALERT_4_G Anion/Solvent Disorder ............ Percentage = 20 Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 14 Note
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note
C4 H8 O
PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 62 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min) 1 Note
PLAT933_ALERT_2_G Number of OMIT records in Embedded RES ......... 1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 1 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
14 ALERT level G = General information/check it is not something unexpected
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
12 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
5 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Datablock: Mn_complex
Alert level G
PLAT230_ALERT_2_G Hirshfeld Test Diff for O2 -- C2 .. 6.9 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Mn1 -- C1 .. 11.0 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Mn1 -- C2 .. 13.3 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Mn1 -- C3 .. 11.3 s.u.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 8 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density 12 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
6 ALERT level G = General information/check it is not something unexpected
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
For both compounds, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
(Re_complex)
fac-Tricarbonylchlorido(6,6'-dihydroxy-2,2'-bipyridine)rhenium(I)
tetrahydrofuran monosolvate
top
Crystal data top
| [ReCl(C10H8N2O2)(CO)3]·C4H8O | Z = 2 |
| Mr = 565.97 | F(000) = 544 |
| Triclinic, P1 | Dx = 2.069 Mg m−3 |
| a = 6.9661 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 8.0082 (6) Å | Cell parameters from 5671 reflections |
| c = 16.9007 (13) Å | θ = 2.5–32.4° |
| α = 78.907 (2)° | µ = 6.87 mm−1 |
| β = 79.128 (2)° | T = 100 K |
| γ = 88.886 (2)° | Plate, yellow |
| V = 908.46 (13) Å3 | 0.2 × 0.1 × 0.01 mm |
Data collection top
Bruker APEXII CCD
diffractometer | 8820 independent reflections |
| Radiation source: sealed tube | 7416 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.060 |
| Detector resolution: 8 pixels mm-1 | θmax = 36.3°, θmin = 2.5° |
| ω and φ scans | h = −11→11 |
Absorption correction: multi-scan
(SADABS; Bruker, 2012) | k = −13→13 |
| Tmin = 0.583, Tmax = 0.747 | l = −28→27 |
| 37165 measured reflections | |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.063 | w = 1/[σ2(Fo2) + (0.0215P)2]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.01 | (Δ/σ)max = 0.003 |
| 8820 reflections | Δρmax = 1.71 e Å−3 |
| 260 parameters | Δρmin = −1.88 e Å−3 |
| 62 restraints | |
Special details top
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| | x | y | z | Uiso*/Ueq | Occ. (<1) |
| Re1 | 0.42194 (2) | 0.68445 (2) | 0.77393 (2) | 0.01301 (3) | |
| Cl1 | 0.52023 (8) | 0.69909 (8) | 0.90827 (4) | 0.01477 (11) | |
| O16 | −0.0490 (3) | 0.6754 (3) | 0.84174 (13) | 0.0186 (4) | |
| H16 | −0.170 (5) | 0.680 (5) | 0.865 (2) | 0.028* | |
| O2 | 0.2010 (3) | 1.0152 (3) | 0.78896 (14) | 0.0241 (5) | |
| N1 | 0.2057 (3) | 0.4977 (3) | 0.85218 (14) | 0.0133 (4) | |
| O1S | 1.1132 (3) | 0.3754 (3) | 0.58779 (15) | 0.0292 (5) | |
| O1 | 0.2709 (4) | 0.7047 (3) | 0.61441 (15) | 0.0359 (6) | |
| O26 | 0.8204 (3) | 0.5231 (3) | 0.67795 (14) | 0.0225 (4) | |
| H26 | 0.920 (6) | 0.477 (5) | 0.652 (2) | 0.034* | |
| N2 | 0.5697 (3) | 0.4372 (3) | 0.78476 (14) | 0.0144 (4) | |
| O3 | 0.7668 (3) | 0.9154 (3) | 0.67574 (15) | 0.0294 (5) | |
| C3 | 0.6398 (4) | 0.8253 (4) | 0.71185 (18) | 0.0202 (5) | |
| C1 | 0.3292 (5) | 0.6881 (4) | 0.6741 (2) | 0.0228 (6) | |
| C12 | 0.2792 (4) | 0.3466 (3) | 0.88559 (17) | 0.0144 (5) | |
| C24 | 0.7513 (4) | 0.1272 (4) | 0.82643 (18) | 0.0189 (5) | |
| H24 | 0.8148 | 0.0231 | 0.8415 | 0.023* | |
| C26 | 0.7446 (4) | 0.4026 (3) | 0.74160 (17) | 0.0163 (5) | |
| C23 | 0.5671 (4) | 0.1572 (3) | 0.86943 (18) | 0.0171 (5) | |
| H23 | 0.5019 | 0.0728 | 0.9132 | 0.021* | |
| C16 | 0.0154 (4) | 0.5269 (3) | 0.87765 (16) | 0.0143 (5) | |
| C25 | 0.8405 (4) | 0.2491 (4) | 0.76204 (18) | 0.0184 (5) | |
| H25 | 0.9656 | 0.2298 | 0.7317 | 0.022* | |
| C2 | 0.2812 (4) | 0.8889 (3) | 0.78290 (17) | 0.0157 (5) | |
| C22 | 0.4806 (4) | 0.3117 (3) | 0.84742 (17) | 0.0149 (5) | |
| C13 | 0.1667 (4) | 0.2300 (3) | 0.94723 (18) | 0.0178 (5) | |
| H13 | 0.2222 | 0.1274 | 0.9708 | 0.021* | |
| C15 | −0.1072 (4) | 0.4124 (3) | 0.93829 (17) | 0.0166 (5) | |
| H15 | −0.2416 | 0.4359 | 0.9543 | 0.020* | |
| C14 | −0.0279 (4) | 0.2646 (3) | 0.97415 (18) | 0.0175 (5) | |
| H14 | −0.1061 | 0.1868 | 1.0171 | 0.021* | |
| C1S | 1.3097 (5) | 0.3276 (5) | 0.5990 (2) | 0.0357 (8) | |
| H1SA | 1.3186 | 0.3115 | 0.6577 | 0.043* | |
| H1SB | 1.4051 | 0.4173 | 0.5674 | 0.043* | |
| C2S | 1.3515 (7) | 0.1634 (5) | 0.5683 (3) | 0.0506 (11) | |
| H2SA | 1.4910 | 0.1565 | 0.5431 | 0.061* | 0.748 (11) |
| H2SB | 1.3147 | 0.0633 | 0.6130 | 0.061* | 0.748 (11) |
| H2SC | 1.4472 | 0.1839 | 0.5160 | 0.061* | 0.252 (11) |
| H2SD | 1.4068 | 0.0800 | 0.6090 | 0.061* | 0.252 (11) |
| C4S | 1.0405 (6) | 0.2609 (5) | 0.5432 (2) | 0.0359 (8) | |
| H4SA | 0.9741 | 0.3242 | 0.5000 | 0.043* | 0.748 (11) |
| H4SB | 0.9482 | 0.1754 | 0.5806 | 0.043* | 0.748 (11) |
| H4SC | 1.0571 | 0.3126 | 0.4841 | 0.043* | 0.252 (11) |
| H4SD | 0.9001 | 0.2342 | 0.5649 | 0.043* | 0.252 (11) |
| C3S | 1.2233 (10) | 0.1777 (7) | 0.5060 (4) | 0.0479 (17) | 0.748 (11) |
| H3SA | 1.1924 | 0.0640 | 0.4964 | 0.057* | 0.748 (11) |
| H3SB | 1.2870 | 0.2487 | 0.4533 | 0.057* | 0.748 (11) |
| C3T | 1.164 (2) | 0.0969 (18) | 0.5559 (11) | 0.039 (4) | 0.252 (11) |
| H3TA | 1.1015 | 0.0133 | 0.6046 | 0.047* | 0.252 (11) |
| H3TB | 1.1842 | 0.0430 | 0.5070 | 0.047* | 0.252 (11) |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| Re1 | 0.01156 (4) | 0.01031 (5) | 0.01605 (5) | 0.00098 (3) | −0.00087 (3) | −0.00155 (3) |
| Cl1 | 0.0108 (2) | 0.0149 (3) | 0.0182 (3) | 0.00042 (19) | −0.0026 (2) | −0.0021 (2) |
| O16 | 0.0089 (8) | 0.0184 (10) | 0.0256 (11) | 0.0010 (7) | −0.0010 (7) | 0.0009 (8) |
| O2 | 0.0207 (10) | 0.0160 (10) | 0.0356 (13) | 0.0065 (8) | −0.0050 (9) | −0.0062 (9) |
| N1 | 0.0126 (9) | 0.0123 (10) | 0.0151 (10) | 0.0001 (7) | −0.0021 (8) | −0.0033 (8) |
| O1S | 0.0317 (12) | 0.0209 (11) | 0.0313 (13) | −0.0011 (9) | 0.0069 (10) | −0.0085 (9) |
| O1 | 0.0600 (18) | 0.0264 (13) | 0.0262 (13) | −0.0014 (11) | −0.0207 (12) | −0.0042 (10) |
| O26 | 0.0205 (10) | 0.0160 (10) | 0.0242 (11) | 0.0053 (7) | 0.0071 (8) | 0.0014 (8) |
| N2 | 0.0122 (9) | 0.0123 (10) | 0.0180 (11) | −0.0003 (7) | −0.0007 (8) | −0.0030 (8) |
| O3 | 0.0298 (12) | 0.0213 (11) | 0.0291 (13) | −0.0128 (9) | 0.0121 (10) | −0.0015 (9) |
| C3 | 0.0216 (12) | 0.0176 (13) | 0.0199 (14) | 0.0038 (10) | 0.0010 (10) | −0.0050 (10) |
| C1 | 0.0285 (15) | 0.0139 (13) | 0.0257 (15) | 0.0011 (10) | −0.0056 (12) | −0.0028 (11) |
| C12 | 0.0122 (10) | 0.0122 (11) | 0.0183 (12) | −0.0001 (8) | −0.0033 (9) | −0.0016 (9) |
| C24 | 0.0192 (12) | 0.0142 (12) | 0.0242 (14) | 0.0058 (9) | −0.0063 (11) | −0.0041 (10) |
| C26 | 0.0145 (11) | 0.0140 (12) | 0.0197 (13) | 0.0007 (9) | −0.0010 (9) | −0.0035 (10) |
| C23 | 0.0150 (11) | 0.0118 (11) | 0.0230 (14) | 0.0006 (9) | −0.0016 (10) | −0.0015 (10) |
| C16 | 0.0130 (10) | 0.0158 (12) | 0.0145 (12) | −0.0003 (8) | −0.0029 (9) | −0.0032 (9) |
| C25 | 0.0162 (11) | 0.0160 (12) | 0.0221 (14) | 0.0045 (9) | −0.0006 (10) | −0.0046 (10) |
| C2 | 0.0129 (10) | 0.0158 (12) | 0.0177 (12) | 0.0002 (9) | −0.0021 (9) | −0.0025 (10) |
| C22 | 0.0125 (10) | 0.0105 (11) | 0.0220 (13) | −0.0012 (8) | −0.0035 (9) | −0.0033 (9) |
| C13 | 0.0173 (12) | 0.0116 (11) | 0.0225 (14) | −0.0013 (9) | −0.0013 (10) | −0.0006 (10) |
| C15 | 0.0128 (11) | 0.0173 (12) | 0.0192 (13) | −0.0022 (9) | −0.0025 (9) | −0.0029 (10) |
| C14 | 0.0168 (11) | 0.0144 (12) | 0.0200 (13) | −0.0041 (9) | −0.0020 (10) | −0.0008 (10) |
| C1S | 0.0332 (17) | 0.0256 (17) | 0.043 (2) | 0.0059 (13) | 0.0074 (15) | −0.0073 (15) |
| C2S | 0.067 (3) | 0.033 (2) | 0.050 (3) | 0.021 (2) | −0.004 (2) | −0.0118 (19) |
| C4S | 0.049 (2) | 0.0251 (17) | 0.0300 (18) | −0.0054 (15) | 0.0007 (16) | −0.0050 (14) |
| C3S | 0.083 (4) | 0.027 (3) | 0.031 (3) | 0.016 (3) | −0.001 (3) | −0.010 (2) |
| C3T | 0.054 (7) | 0.018 (6) | 0.038 (9) | 0.002 (5) | 0.015 (6) | −0.009 (6) |
Geometric parameters (Å, º) top
| Re1—Cl1 | 2.5159 (7) | C16—C15 | 1.400 (4) |
| Re1—N1 | 2.198 (2) | C25—H25 | 0.9500 |
| Re1—N2 | 2.206 (2) | C13—H13 | 0.9500 |
| Re1—C3 | 1.920 (3) | C13—C14 | 1.386 (4) |
| Re1—C1 | 1.912 (3) | C15—H15 | 0.9500 |
| Re1—C2 | 1.908 (3) | C15—C14 | 1.378 (4) |
| O16—H16 | 0.86 (4) | C14—H14 | 0.9500 |
| O16—C16 | 1.337 (3) | C1S—H1SA | 0.9900 |
| O2—C2 | 1.158 (3) | C1S—H1SB | 0.9900 |
| N1—C12 | 1.366 (3) | C1S—C2S | 1.507 (5) |
| N1—C16 | 1.344 (3) | C2S—H2SA | 0.9900 |
| O1S—C1S | 1.451 (4) | C2S—H2SB | 0.9900 |
| O1S—C4S | 1.447 (4) | C2S—H2SC | 0.9900 |
| O1—C1 | 1.140 (4) | C2S—H2SD | 0.9900 |
| O26—H26 | 0.87 (4) | C2S—C3S | 1.491 (8) |
| O26—C26 | 1.332 (3) | C2S—C3T | 1.484 (18) |
| N2—C26 | 1.350 (3) | C4S—H4SA | 0.9900 |
| N2—C22 | 1.372 (3) | C4S—H4SB | 0.9900 |
| O3—C3 | 1.152 (4) | C4S—H4SC | 0.9900 |
| C12—C22 | 1.475 (3) | C4S—H4SD | 0.9900 |
| C12—C13 | 1.385 (4) | C4S—C3S | 1.512 (7) |
| C24—H24 | 0.9500 | C4S—C3T | 1.559 (15) |
| C24—C23 | 1.391 (4) | C3S—H3SA | 0.9900 |
| C24—C25 | 1.372 (4) | C3S—H3SB | 0.9900 |
| C26—C25 | 1.403 (4) | C3T—H3TA | 0.9900 |
| C23—H23 | 0.9500 | C3T—H3TB | 0.9900 |
| C23—C22 | 1.383 (4) | | |
| | | |
| N1—Re1—Cl1 | 82.99 (6) | C14—C13—H13 | 120.4 |
| N1—Re1—N2 | 74.09 (8) | C16—C15—H15 | 120.9 |
| N2—Re1—Cl1 | 85.17 (6) | C14—C15—C16 | 118.3 (2) |
| C3—Re1—Cl1 | 92.47 (9) | C14—C15—H15 | 120.9 |
| C3—Re1—N1 | 171.39 (10) | C13—C14—H14 | 120.2 |
| C3—Re1—N2 | 98.30 (10) | C15—C14—C13 | 119.7 (3) |
| C1—Re1—Cl1 | 174.77 (9) | C15—C14—H14 | 120.2 |
| C1—Re1—N1 | 96.46 (11) | O1S—C1S—H1SA | 110.3 |
| C1—Re1—N2 | 99.71 (11) | O1S—C1S—H1SB | 110.3 |
| C1—Re1—C3 | 88.72 (13) | O1S—C1S—C2S | 106.9 (3) |
| C2—Re1—Cl1 | 87.58 (8) | H1SA—C1S—H1SB | 108.6 |
| C2—Re1—N1 | 99.67 (10) | C2S—C1S—H1SA | 110.3 |
| C2—Re1—N2 | 170.95 (10) | C2S—C1S—H1SB | 110.3 |
| C2—Re1—C3 | 87.40 (11) | C1S—C2S—H2SA | 111.5 |
| C2—Re1—C1 | 87.38 (12) | C1S—C2S—H2SB | 111.5 |
| C16—O16—H16 | 106 (2) | C1S—C2S—H2SC | 110.2 |
| C12—N1—Re1 | 115.69 (16) | C1S—C2S—H2SD | 110.2 |
| C16—N1—Re1 | 125.85 (17) | H2SA—C2S—H2SB | 109.3 |
| C16—N1—C12 | 117.9 (2) | H2SC—C2S—H2SD | 108.5 |
| C4S—O1S—C1S | 109.3 (3) | C3S—C2S—C1S | 101.4 (3) |
| C26—O26—H26 | 105 (3) | C3S—C2S—H2SA | 111.5 |
| C26—N2—Re1 | 126.82 (18) | C3S—C2S—H2SB | 111.5 |
| C26—N2—C22 | 117.6 (2) | C3T—C2S—C1S | 107.7 (6) |
| C22—N2—Re1 | 115.29 (16) | C3T—C2S—H2SC | 110.2 |
| O3—C3—Re1 | 177.2 (3) | C3T—C2S—H2SD | 110.2 |
| O1—C1—Re1 | 174.1 (3) | O1S—C4S—H4SA | 111.1 |
| N1—C12—C22 | 115.4 (2) | O1S—C4S—H4SB | 111.1 |
| N1—C12—C13 | 121.9 (2) | O1S—C4S—H4SC | 110.6 |
| C13—C12—C22 | 122.6 (2) | O1S—C4S—H4SD | 110.6 |
| C23—C24—H24 | 120.2 | O1S—C4S—C3S | 103.5 (4) |
| C25—C24—H24 | 120.2 | O1S—C4S—C3T | 105.8 (7) |
| C25—C24—C23 | 119.5 (2) | H4SA—C4S—H4SB | 109.0 |
| O26—C26—N2 | 115.8 (2) | H4SC—C4S—H4SD | 108.7 |
| O26—C26—C25 | 121.9 (2) | C3S—C4S—H4SA | 111.1 |
| N2—C26—C25 | 122.3 (2) | C3S—C4S—H4SB | 111.1 |
| C24—C23—H23 | 120.5 | C3T—C4S—H4SC | 110.6 |
| C22—C23—C24 | 118.9 (3) | C3T—C4S—H4SD | 110.6 |
| C22—C23—H23 | 120.5 | C2S—C3S—C4S | 104.5 (4) |
| O16—C16—N1 | 115.2 (2) | C2S—C3S—H3SA | 110.9 |
| O16—C16—C15 | 121.9 (2) | C2S—C3S—H3SB | 110.9 |
| N1—C16—C15 | 122.9 (2) | C4S—C3S—H3SA | 110.9 |
| C24—C25—C26 | 119.1 (2) | C4S—C3S—H3SB | 110.9 |
| C24—C25—H25 | 120.4 | H3SA—C3S—H3SB | 108.9 |
| C26—C25—H25 | 120.4 | C2S—C3T—C4S | 102.5 (9) |
| O2—C2—Re1 | 177.8 (2) | C2S—C3T—H3TA | 111.3 |
| N2—C22—C12 | 115.6 (2) | C2S—C3T—H3TB | 111.3 |
| N2—C22—C23 | 122.5 (2) | C4S—C3T—H3TA | 111.3 |
| C23—C22—C12 | 121.8 (2) | C4S—C3T—H3TB | 111.3 |
| C12—C13—H13 | 120.4 | H3TA—C3T—H3TB | 109.2 |
| C12—C13—C14 | 119.2 (2) | | |
| | | |
| Re1—N1—C12—C22 | −16.1 (3) | C12—C13—C14—C15 | 1.2 (4) |
| Re1—N1—C12—C13 | 168.2 (2) | C24—C23—C22—N2 | −0.1 (4) |
| Re1—N1—C16—O16 | 10.2 (3) | C24—C23—C22—C12 | 174.8 (3) |
| Re1—N1—C16—C15 | −168.8 (2) | C26—N2—C22—C12 | −172.3 (2) |
| Re1—N2—C26—O26 | −10.9 (4) | C26—N2—C22—C23 | 2.9 (4) |
| Re1—N2—C26—C25 | 169.5 (2) | C23—C24—C25—C26 | 0.8 (4) |
| Re1—N2—C22—C12 | 13.6 (3) | C16—N1—C12—C22 | 172.0 (2) |
| Re1—N2—C22—C23 | −171.2 (2) | C16—N1—C12—C13 | −3.7 (4) |
| O16—C16—C15—C14 | −177.9 (3) | C16—C15—C14—C13 | −2.7 (4) |
| N1—C12—C22—N2 | 1.6 (4) | C25—C24—C23—C22 | −1.7 (4) |
| N1—C12—C22—C23 | −173.7 (3) | C22—N2—C26—O26 | 175.7 (2) |
| N1—C12—C13—C14 | 2.1 (4) | C22—N2—C26—C25 | −3.9 (4) |
| N1—C16—C15—C14 | 1.0 (4) | C22—C12—C13—C14 | −173.4 (3) |
| O1S—C1S—C2S—C3S | 27.5 (5) | C13—C12—C22—N2 | 177.3 (3) |
| O1S—C1S—C2S—C3T | −11.9 (8) | C13—C12—C22—C23 | 2.0 (4) |
| O1S—C4S—C3S—C2S | 34.3 (5) | C1S—O1S—C4S—C3S | −16.8 (4) |
| O1S—C4S—C3T—C2S | −28.0 (10) | C1S—O1S—C4S—C3T | 21.7 (7) |
| O26—C26—C25—C24 | −177.5 (3) | C1S—C2S—C3S—C4S | −37.6 (5) |
| N2—C26—C25—C24 | 2.2 (4) | C1S—C2S—C3T—C4S | 24.0 (11) |
| C12—N1—C16—O16 | −178.8 (2) | C4S—O1S—C1S—C2S | −6.7 (4) |
| C12—N1—C16—C15 | 2.2 (4) | | |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O16—H16···Cl1i | 0.86 (4) | 2.16 (4) | 3.015 (2) | 173 (3) |
| O26—H26···O1S | 0.87 (4) | 1.84 (4) | 2.704 (3) | 173 (4) |
| Symmetry code: (i) x−1, y, z. |
(Mn_complex)
fac-Bromidotricarbonyl(6,6'-dihydroxy-2,2'-bipyridine)manganese(I)
tetrahydrofuran monosolvate
top
Crystal data top
| [MnBr(C10H8N2O2)(CO)3]·C4H8O | F(000) = 960 |
| Mr = 479.17 | Dx = 1.724 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 10.2401 (12) Å | Cell parameters from 9928 reflections |
| b = 13.1783 (15) Å | θ = 2.7–33.9° |
| c = 14.2480 (16) Å | µ = 2.92 mm−1 |
| β = 106.228 (3)° | T = 100 K |
| V = 1846.1 (4) Å3 | Rod, yellow |
| Z = 4 | 0.36 × 0.13 × 0.08 mm |
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer | 7363 independent reflections |
| Radiation source: sealed tube | 5841 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.049 |
| Detector resolution: 8 pixels mm-1 | θmax = 33.7°, θmin = 2.1° |
| ω and φ scans | h = −15→15 |
Absorption correction: multi-scan
(SADABS; Bruker, 2012) | k = −20→20 |
| Tmin = 0.609, Tmax = 0.747 | l = −22→22 |
| 67915 measured reflections | |
Refinement top
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.061 | w = 1/[σ2(Fo2) + (0.0253P)2 + 0.8571P]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.01 | (Δ/σ)max = 0.001 |
| 7363 reflections | Δρmax = 0.62 e Å−3 |
| 252 parameters | Δρmin = −0.45 e Å−3 |
Special details top
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| | x | y | z | Uiso*/Ueq | |
| Br1 | 0.43600 (2) | 0.46594 (2) | 0.34466 (2) | 0.01541 (4) | |
| Mn1 | 0.30177 (2) | 0.52808 (2) | 0.17547 (2) | 0.01092 (4) | |
| O1 | 0.21509 (11) | 0.71004 (8) | 0.26247 (8) | 0.0207 (2) | |
| C1 | 0.25680 (14) | 0.64158 (10) | 0.23009 (10) | 0.0145 (2) | |
| O2 | 0.13075 (11) | 0.60489 (9) | −0.01225 (8) | 0.0236 (2) | |
| C2 | 0.20034 (14) | 0.57322 (10) | 0.05953 (10) | 0.0153 (2) | |
| O3 | 0.05516 (11) | 0.44992 (9) | 0.21988 (8) | 0.0239 (2) | |
| C3 | 0.15176 (14) | 0.47493 (10) | 0.20007 (10) | 0.0161 (2) | |
| O10 | 0.45262 (10) | 0.74298 (7) | 0.18113 (8) | 0.0179 (2) | |
| H10 | 0.487 (2) | 0.8003 (18) | 0.1820 (17) | 0.044 (6)* | |
| N11 | 0.48726 (11) | 0.57633 (8) | 0.15938 (8) | 0.01234 (19) | |
| C12 | 0.54018 (14) | 0.66975 (10) | 0.17494 (9) | 0.0138 (2) | |
| C13 | 0.67743 (14) | 0.69023 (11) | 0.18420 (11) | 0.0174 (3) | |
| H13 | 0.7123 | 0.7572 | 0.1967 | 0.021* | |
| C14 | 0.76061 (15) | 0.61113 (11) | 0.17475 (11) | 0.0197 (3) | |
| H14 | 0.8547 | 0.6225 | 0.1826 | 0.024* | |
| C15 | 0.70589 (14) | 0.51419 (11) | 0.15355 (11) | 0.0176 (3) | |
| H15 | 0.7614 | 0.4590 | 0.1452 | 0.021* | |
| C16 | 0.56946 (14) | 0.49991 (10) | 0.14487 (9) | 0.0132 (2) | |
| O20 | 0.16632 (11) | 0.31944 (8) | 0.08940 (9) | 0.0237 (2) | |
| H20 | 0.128 (2) | 0.2669 (19) | 0.0706 (18) | 0.047 (7)* | |
| N21 | 0.36778 (11) | 0.40010 (8) | 0.11925 (8) | 0.01280 (19) | |
| C22 | 0.29616 (14) | 0.31508 (10) | 0.08977 (10) | 0.0153 (2) | |
| C23 | 0.35367 (15) | 0.22793 (10) | 0.06115 (10) | 0.0173 (3) | |
| H23 | 0.3014 | 0.1678 | 0.0436 | 0.021* | |
| C24 | 0.48671 (15) | 0.23105 (10) | 0.05895 (10) | 0.0175 (3) | |
| H24 | 0.5278 | 0.1730 | 0.0397 | 0.021* | |
| C25 | 0.56093 (15) | 0.32024 (10) | 0.08525 (10) | 0.0161 (2) | |
| H25 | 0.6521 | 0.3246 | 0.0818 | 0.019* | |
| C26 | 0.49997 (13) | 0.40221 (10) | 0.11640 (9) | 0.0128 (2) | |
| O1S | 0.03314 (10) | 0.15416 (8) | 0.02750 (8) | 0.01819 (19) | |
| C1S | −0.07218 (16) | 0.14179 (12) | 0.07676 (12) | 0.0229 (3) | |
| H1SA | −0.0761 | 0.2020 | 0.1174 | 0.027* | |
| H1SB | −0.0539 | 0.0811 | 0.1195 | 0.027* | |
| C2S | −0.20485 (16) | 0.12945 (12) | −0.00295 (13) | 0.0261 (3) | |
| H2SA | −0.2536 | 0.1949 | −0.0179 | 0.031* | |
| H2SB | −0.2648 | 0.0793 | 0.0161 | 0.031* | |
| C3S | −0.15910 (16) | 0.09175 (12) | −0.08984 (12) | 0.0255 (3) | |
| H3SA | −0.1453 | 0.0173 | −0.0871 | 0.031* | |
| H3SB | −0.2257 | 0.1098 | −0.1526 | 0.031* | |
| C4S | −0.02636 (17) | 0.14755 (13) | −0.07673 (11) | 0.0245 (3) | |
| H4SA | 0.0341 | 0.1097 | −0.1077 | 0.029* | |
| H4SB | −0.0426 | 0.2161 | −0.1061 | 0.029* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| Br1 | 0.02180 (7) | 0.01121 (5) | 0.01197 (6) | 0.00286 (5) | 0.00268 (5) | 0.00115 (4) |
| Mn1 | 0.01186 (9) | 0.00999 (8) | 0.01105 (8) | 0.00139 (7) | 0.00341 (7) | 0.00011 (7) |
| O1 | 0.0232 (5) | 0.0170 (5) | 0.0247 (5) | 0.0028 (4) | 0.0110 (4) | −0.0031 (4) |
| C1 | 0.0152 (6) | 0.0146 (5) | 0.0138 (6) | −0.0007 (5) | 0.0044 (5) | 0.0015 (4) |
| O2 | 0.0215 (5) | 0.0314 (6) | 0.0158 (5) | 0.0088 (4) | 0.0020 (4) | 0.0028 (4) |
| C2 | 0.0154 (6) | 0.0152 (6) | 0.0170 (6) | 0.0015 (5) | 0.0075 (5) | −0.0020 (5) |
| O3 | 0.0221 (5) | 0.0279 (6) | 0.0248 (5) | −0.0059 (4) | 0.0115 (5) | −0.0049 (4) |
| C3 | 0.0187 (6) | 0.0156 (6) | 0.0143 (6) | 0.0009 (5) | 0.0050 (5) | −0.0025 (5) |
| O10 | 0.0188 (5) | 0.0100 (4) | 0.0261 (5) | 0.0005 (4) | 0.0082 (4) | 0.0000 (4) |
| N11 | 0.0138 (5) | 0.0116 (5) | 0.0121 (5) | 0.0019 (4) | 0.0044 (4) | 0.0015 (4) |
| C12 | 0.0157 (6) | 0.0127 (5) | 0.0127 (5) | 0.0010 (4) | 0.0039 (5) | 0.0012 (4) |
| C13 | 0.0163 (6) | 0.0167 (6) | 0.0190 (6) | −0.0034 (5) | 0.0044 (5) | 0.0001 (5) |
| C14 | 0.0141 (6) | 0.0231 (7) | 0.0222 (7) | −0.0012 (5) | 0.0055 (5) | −0.0003 (5) |
| C15 | 0.0152 (6) | 0.0184 (6) | 0.0201 (6) | 0.0027 (5) | 0.0064 (5) | 0.0003 (5) |
| C16 | 0.0153 (6) | 0.0136 (5) | 0.0108 (5) | 0.0025 (4) | 0.0040 (5) | 0.0012 (4) |
| O20 | 0.0153 (5) | 0.0188 (5) | 0.0360 (6) | −0.0021 (4) | 0.0057 (5) | −0.0110 (5) |
| N21 | 0.0134 (5) | 0.0122 (4) | 0.0120 (5) | 0.0021 (4) | 0.0022 (4) | −0.0006 (4) |
| C22 | 0.0151 (6) | 0.0147 (6) | 0.0149 (6) | 0.0008 (5) | 0.0024 (5) | −0.0024 (5) |
| C23 | 0.0216 (7) | 0.0123 (5) | 0.0172 (6) | 0.0011 (5) | 0.0041 (5) | −0.0028 (5) |
| C24 | 0.0238 (7) | 0.0130 (6) | 0.0172 (6) | 0.0048 (5) | 0.0081 (5) | −0.0006 (5) |
| C25 | 0.0191 (6) | 0.0140 (5) | 0.0171 (6) | 0.0029 (5) | 0.0082 (5) | 0.0006 (5) |
| C26 | 0.0156 (6) | 0.0129 (5) | 0.0100 (5) | 0.0023 (4) | 0.0039 (5) | 0.0008 (4) |
| O1S | 0.0168 (5) | 0.0190 (5) | 0.0194 (5) | −0.0015 (4) | 0.0060 (4) | −0.0021 (4) |
| C1S | 0.0224 (7) | 0.0264 (7) | 0.0229 (7) | 0.0003 (6) | 0.0114 (6) | 0.0015 (6) |
| C2S | 0.0174 (7) | 0.0230 (7) | 0.0388 (9) | 0.0006 (6) | 0.0095 (7) | −0.0029 (6) |
| C3S | 0.0230 (7) | 0.0209 (7) | 0.0285 (8) | −0.0017 (6) | 0.0008 (6) | −0.0052 (6) |
| C4S | 0.0294 (8) | 0.0264 (8) | 0.0185 (7) | −0.0050 (6) | 0.0078 (6) | −0.0020 (6) |
Geometric parameters (Å, º) top
| Br1—Mn1 | 2.5532 (3) | N21—C22 | 1.3407 (17) |
| Mn1—C1 | 1.8043 (14) | N21—C26 | 1.3658 (17) |
| Mn1—C2 | 1.7895 (14) | C22—C23 | 1.4023 (18) |
| Mn1—C3 | 1.8093 (14) | C23—H23 | 0.9500 |
| Mn1—N11 | 2.0757 (11) | C23—C24 | 1.372 (2) |
| Mn1—N21 | 2.0605 (11) | C24—H24 | 0.9500 |
| O1—C1 | 1.1487 (16) | C24—C25 | 1.393 (2) |
| O2—C2 | 1.1492 (17) | C25—H25 | 0.9500 |
| O3—C3 | 1.1503 (17) | C25—C26 | 1.3815 (18) |
| O10—H10 | 0.83 (2) | O1S—C1S | 1.4510 (17) |
| O10—C12 | 1.3368 (16) | O1S—C4S | 1.4416 (18) |
| N11—C12 | 1.3384 (17) | C1S—H1SA | 0.9900 |
| N11—C16 | 1.3648 (16) | C1S—H1SB | 0.9900 |
| C12—C13 | 1.4007 (19) | C1S—C2S | 1.516 (2) |
| C13—H13 | 0.9500 | C2S—H2SA | 0.9900 |
| C13—C14 | 1.376 (2) | C2S—H2SB | 0.9900 |
| C14—H14 | 0.9500 | C2S—C3S | 1.524 (2) |
| C14—C15 | 1.394 (2) | C3S—H3SA | 0.9900 |
| C15—H15 | 0.9500 | C3S—H3SB | 0.9900 |
| C15—C16 | 1.3806 (19) | C3S—C4S | 1.510 (2) |
| C16—C26 | 1.4721 (19) | C4S—H4SA | 0.9900 |
| O20—H20 | 0.80 (2) | C4S—H4SB | 0.9900 |
| O20—C22 | 1.3294 (17) | | |
| | | |
| C1—Mn1—Br1 | 89.64 (4) | O20—C22—N21 | 115.09 (12) |
| C1—Mn1—C3 | 84.52 (6) | O20—C22—C23 | 122.35 (12) |
| C1—Mn1—N11 | 98.36 (5) | N21—C22—C23 | 122.56 (13) |
| C1—Mn1—N21 | 175.75 (5) | C22—C23—H23 | 120.6 |
| C2—Mn1—Br1 | 176.95 (4) | C24—C23—C22 | 118.85 (13) |
| C2—Mn1—C1 | 88.30 (6) | C24—C23—H23 | 120.6 |
| C2—Mn1—C3 | 90.13 (6) | C23—C24—H24 | 120.3 |
| C2—Mn1—N11 | 96.27 (5) | C23—C24—C25 | 119.32 (12) |
| C2—Mn1—N21 | 94.71 (5) | C25—C24—H24 | 120.3 |
| C3—Mn1—Br1 | 87.43 (5) | C24—C25—H25 | 120.5 |
| C3—Mn1—N11 | 173.04 (5) | C26—C25—C24 | 118.99 (13) |
| C3—Mn1—N21 | 98.45 (5) | C26—C25—H25 | 120.5 |
| N11—Mn1—Br1 | 86.26 (3) | N21—C26—C16 | 114.61 (11) |
| N21—Mn1—Br1 | 87.48 (3) | N21—C26—C25 | 122.29 (12) |
| N21—Mn1—N11 | 78.35 (4) | C25—C26—C16 | 123.05 (12) |
| O1—C1—Mn1 | 173.11 (12) | C4S—O1S—C1S | 109.52 (11) |
| O2—C2—Mn1 | 176.22 (12) | O1S—C1S—H1SA | 110.5 |
| O3—C3—Mn1 | 173.41 (12) | O1S—C1S—H1SB | 110.5 |
| C12—O10—H10 | 111.3 (16) | O1S—C1S—C2S | 106.33 (12) |
| C12—N11—Mn1 | 127.17 (9) | H1SA—C1S—H1SB | 108.7 |
| C12—N11—C16 | 117.75 (11) | C2S—C1S—H1SA | 110.5 |
| C16—N11—Mn1 | 114.38 (9) | C2S—C1S—H1SB | 110.5 |
| O10—C12—N11 | 115.28 (12) | C1S—C2S—H2SA | 111.1 |
| O10—C12—C13 | 121.90 (12) | C1S—C2S—H2SB | 111.1 |
| N11—C12—C13 | 122.82 (12) | C1S—C2S—C3S | 103.23 (12) |
| C12—C13—H13 | 120.8 | H2SA—C2S—H2SB | 109.1 |
| C14—C13—C12 | 118.49 (13) | C3S—C2S—H2SA | 111.1 |
| C14—C13—H13 | 120.8 | C3S—C2S—H2SB | 111.1 |
| C13—C14—H14 | 120.2 | C2S—C3S—H3SA | 111.3 |
| C13—C14—C15 | 119.54 (13) | C2S—C3S—H3SB | 111.3 |
| C15—C14—H14 | 120.2 | H3SA—C3S—H3SB | 109.2 |
| C14—C15—H15 | 120.7 | C4S—C3S—C2S | 102.18 (12) |
| C16—C15—C14 | 118.67 (13) | C4S—C3S—H3SA | 111.3 |
| C16—C15—H15 | 120.7 | C4S—C3S—H3SB | 111.3 |
| N11—C16—C15 | 122.50 (12) | O1S—C4S—C3S | 105.28 (12) |
| N11—C16—C26 | 114.58 (11) | O1S—C4S—H4SA | 110.7 |
| C15—C16—C26 | 122.89 (12) | O1S—C4S—H4SB | 110.7 |
| C22—O20—H20 | 111.0 (17) | C3S—C4S—H4SA | 110.7 |
| C22—N21—Mn1 | 126.56 (9) | C3S—C4S—H4SB | 110.7 |
| C22—N21—C26 | 117.88 (11) | H4SA—C4S—H4SB | 108.8 |
| C26—N21—Mn1 | 115.50 (8) | | |
| | | |
| Mn1—N11—C12—O10 | −15.18 (17) | C15—C16—C26—C25 | −7.6 (2) |
| Mn1—N11—C12—C13 | 164.82 (10) | C16—N11—C12—O10 | 175.02 (11) |
| Mn1—N11—C16—C15 | −165.73 (11) | C16—N11—C12—C13 | −4.98 (19) |
| Mn1—N11—C16—C26 | 16.04 (14) | O20—C22—C23—C24 | 176.82 (14) |
| Mn1—N21—C22—O20 | 6.44 (18) | N21—C22—C23—C24 | −3.0 (2) |
| Mn1—N21—C22—C23 | −173.72 (10) | C22—N21—C26—C16 | 176.89 (11) |
| Mn1—N21—C26—C16 | −5.87 (14) | C22—N21—C26—C25 | −0.53 (19) |
| Mn1—N21—C26—C25 | 176.72 (10) | C22—C23—C24—C25 | 0.1 (2) |
| O10—C12—C13—C14 | −178.55 (13) | C23—C24—C25—C26 | 2.4 (2) |
| N11—C12—C13—C14 | 1.4 (2) | C24—C25—C26—C16 | −179.43 (12) |
| N11—C16—C26—N21 | −6.80 (16) | C24—C25—C26—N21 | −2.2 (2) |
| N11—C16—C26—C25 | 170.60 (12) | C26—N21—C22—O20 | −176.65 (12) |
| C12—N11—C16—C15 | 5.36 (19) | C26—N21—C22—C23 | 3.18 (19) |
| C12—N11—C16—C26 | −172.87 (11) | O1S—C1S—C2S—C3S | 23.09 (16) |
| C12—C13—C14—C15 | 1.9 (2) | C1S—O1S—C4S—C3S | −21.18 (16) |
| C13—C14—C15—C16 | −1.5 (2) | C1S—C2S—C3S—C4S | −34.94 (16) |
| C14—C15—C16—N11 | −2.2 (2) | C2S—C3S—C4S—O1S | 34.76 (16) |
| C14—C15—C16—C26 | 175.91 (13) | C4S—O1S—C1S—C2S | −1.46 (16) |
| C15—C16—C26—N21 | 174.98 (12) | | |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O10—H10···Br1i | 0.83 (2) | 2.39 (2) | 3.2098 (10) | 170 (2) |
| O20—H20···O1S | 0.80 (2) | 1.79 (2) | 2.5903 (15) | 176 (2) |
| Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
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