The title compound, [MnBr2(C12H12N2)2], has a twofold axis, and the MnII atom is coordinated by four N atoms from two 4,4'-dimethyl-2,2'-bipyridine (dmbpy) ligands and two bromide anions, forming a distorted octahedral environment. The Mn-N and Mn-Br bond distances are 2.261 (2)-2.297 (3) and 2.6193 (5) Å, respectively. The dihedral angle between the pyridine rings of each dmbpy ligand is 16.09 (9)°.
Supporting information
CCDC reference: 238626
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.062
- wR factor = 0.116
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level B
ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.293 0.458
Tmin' and Tmax expected: 0.446 0.458
RR' = 0.657
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.62
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.67 Ratio
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT350_ALERT_3_C Short C-H Bond (0.96A) C2 - H2 ... 0.82 Ang.
PLAT350_ALERT_3_C Short C-H Bond (0.96A) C8 - H8 ... 0.81 Ang.
PLAT733_ALERT_1_C Torsion Calc -49.9(5), Rep -49.9(2) ...... 2.50 su-Rat
N1 -MN1 -N1 -C5 1.555 1.555 4.555 4.555
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.
Crystal data top
[MnBr2(C12H12N2)2] | Dx = 1.612 Mg m−3 |
Mr = 583.23 | Mo Kα radiation, λ = 0.7107 Å |
Orthorhombic, Pbcn | Cell parameters from 29251 reflections |
a = 15.2773 (9) Å | θ = 2.4–30.4° |
b = 10.2049 (5) Å | µ = 3.90 mm−1 |
c = 15.4099 (7) Å | T = 200 K |
V = 2402.5 (2) Å3 | Prism, yellow |
Z = 4 | 0.20 × 0.20 × 0.20 mm |
F(000) = 1164 | |
Data collection top
Rigaku R-AXIS RAPID Imaging Plate diffractometer | 2542 reflections with I > 2σ(I) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.095 |
ω scans | θmax = 30.4°, θmin = 2.4° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −21→21 |
Tmin = 0.293, Tmax = 0.458 | k = −14→14 |
26269 measured reflections | l = −21→18 |
3606 independent reflections | |
Refinement top
Refinement on F2 | Only H-atom displacement parameters refined |
R[F2 > 2σ(F2)] = 0.062 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.116 | (Δ/σ)max = 0.003 |
S = 1.34 | Δρmax = 0.46 e Å−3 |
3606 reflections | Δρmin = −0.49 e Å−3 |
153 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > -10.0 σ(F2). The
weighted R-factor (wR) and goodness of fit (S) are based
on F2. R-factor (gt) are based on F. The threshold
expression of F2 > 2.0 σ(F2) is used only for calculating
R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.06226 (2) | 0.26424 (4) | 0.36516 (2) | 0.0517 (1) | |
Mn1 | 0.0000 | 0.10007 (6) | 0.2500 | 0.0356 (2) | |
N1 | −0.1333 (2) | 0.0651 (2) | 0.3094 (2) | 0.0344 (5) | |
N2 | −0.0670 (2) | −0.0666 (3) | 0.1750 (2) | 0.0364 (6) | |
C1 | −0.1677 (2) | 0.1435 (3) | 0.3697 (2) | 0.0423 (7) | |
C2 | −0.2548 (2) | 0.1441 (3) | 0.3898 (2) | 0.0437 (7) | |
C3 | −0.3111 (2) | 0.0605 (3) | 0.3477 (2) | 0.0368 (7) | |
C4 | −0.2754 (2) | −0.0227 (3) | 0.2866 (2) | 0.0354 (6) | |
C5 | −0.1869 (2) | −0.0181 (3) | 0.2690 (2) | 0.0306 (6) | |
C6 | −0.4074 (2) | 0.0629 (4) | 0.3645 (3) | 0.061 (1) | |
C7 | −0.0315 (2) | −0.1340 (4) | 0.1100 (2) | 0.0451 (8) | |
C8 | −0.0722 (2) | −0.2386 (3) | 0.0715 (2) | 0.0441 (8) | |
C9 | −0.1518 (2) | −0.2801 (3) | 0.1008 (2) | 0.0400 (7) | |
C10 | −0.1899 (2) | −0.2080 (3) | 0.1665 (2) | 0.0361 (7) | |
C11 | −0.1468 (2) | −0.1019 (3) | 0.2012 (2) | 0.0312 (6) | |
C12 | −0.1970 (3) | −0.3976 (3) | 0.0633 (2) | 0.0554 (10) | |
H1 | −0.1254 | 0.2001 | 0.4001 | 0.0544 (1)* | |
H2 | −0.2738 | 0.1872 | 0.4302 | 0.0503 (1)* | |
H3 | −0.3115 | −0.0782 | 0.2568 | 0.02933 (10)* | |
H4 | −0.4180 | 0.0940 | 0.4223 | 0.1257 (3)* | |
H5 | −0.4306 | −0.0242 | 0.3586 | 0.1371 (3)* | |
H6 | −0.4353 | 0.1199 | 0.3235 | 0.0876 (2)* | |
H7 | 0.0218 | −0.1153 | 0.0931 | 0.0492 (1)* | |
H8 | −0.0441 | −0.2753 | 0.0345 | 0.0483 (1)* | |
H9 | −0.1716 | −0.4758 | 0.0872 | 0.0651 (1)* | |
H10 | −0.1900 | −0.3978 | 0.0014 | 0.0840 (2)* | |
H11 | −0.2581 | −0.3944 | 0.0774 | 0.0728 (2)* | |
H12 | −0.2413 | −0.2305 | 0.1861 | 0.0359 (1)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0362 (2) | 0.0591 (3) | 0.0599 (3) | −0.0095 (1) | 0.0080 (1) | −0.0158 (2) |
Mn1 | 0.0226 (3) | 0.0451 (4) | 0.0391 (3) | 0.0000 | 0.0044 (3) | 0.0000 |
N1 | 0.030 (1) | 0.040 (1) | 0.033 (1) | −0.004 (1) | 0.0037 (10) | −0.003 (1) |
N2 | 0.028 (1) | 0.045 (1) | 0.036 (1) | 0.004 (1) | 0.0020 (10) | −0.004 (1) |
C1 | 0.035 (2) | 0.050 (2) | 0.042 (2) | −0.006 (1) | 0.004 (1) | −0.011 (2) |
C2 | 0.042 (2) | 0.045 (2) | 0.044 (2) | 0.000 (1) | 0.011 (1) | −0.013 (2) |
C3 | 0.028 (1) | 0.036 (2) | 0.046 (2) | 0.002 (1) | 0.008 (1) | 0.002 (1) |
C4 | 0.027 (1) | 0.035 (1) | 0.044 (2) | −0.001 (1) | −0.001 (1) | −0.001 (1) |
C5 | 0.026 (1) | 0.036 (1) | 0.030 (1) | 0.000 (1) | 0.000 (1) | 0.003 (1) |
C6 | 0.030 (2) | 0.065 (3) | 0.086 (3) | 0.006 (2) | 0.015 (2) | −0.014 (2) |
C7 | 0.032 (1) | 0.065 (2) | 0.038 (2) | 0.009 (2) | 0.006 (1) | −0.004 (2) |
C8 | 0.045 (2) | 0.053 (2) | 0.034 (2) | 0.021 (2) | −0.002 (1) | −0.012 (2) |
C9 | 0.048 (2) | 0.037 (2) | 0.034 (2) | 0.008 (1) | −0.006 (1) | 0.000 (1) |
C10 | 0.037 (2) | 0.037 (2) | 0.034 (2) | 0.004 (1) | −0.001 (1) | −0.001 (1) |
C11 | 0.029 (1) | 0.033 (1) | 0.032 (1) | 0.006 (1) | 0.000 (1) | 0.003 (1) |
C12 | 0.081 (3) | 0.039 (2) | 0.047 (2) | 0.004 (2) | −0.006 (2) | −0.011 (2) |
Geometric parameters (Å, º) top
Br1—Mn1 | 2.6193 (5) | C4—H3 | 0.915 |
Mn1—N1 | 2.261 (2) | C5—C11 | 1.483 (4) |
Mn1—N1i | 2.261 (2) | C6—H4 | 0.960 |
Mn1—N2 | 2.297 (3) | C6—H5 | 0.961 |
Mn1—N2i | 2.297 (3) | C6—H6 | 0.959 |
N1—C1 | 1.334 (4) | C7—C8 | 1.370 (5) |
N1—C5 | 1.334 (4) | C7—H7 | 0.875 |
N2—C7 | 1.331 (4) | C8—C9 | 1.365 (5) |
N2—C11 | 1.334 (4) | C8—H8 | 0.806 |
C1—C2 | 1.367 (4) | C9—C10 | 1.381 (4) |
C1—H1 | 0.986 | C9—C12 | 1.499 (5) |
C2—C3 | 1.374 (4) | C10—C11 | 1.376 (4) |
C2—H2 | 0.814 | C10—H12 | 0.872 |
C3—C4 | 1.380 (4) | C12—H9 | 0.961 |
C3—C6 | 1.494 (5) | C12—H10 | 0.959 |
C4—C5 | 1.379 (4) | C12—H11 | 0.960 |
| | | |
Br1···Mn1 | 2.6193 (5) | C6···C8iii | 3.378 (5) |
C1···C8ii | 3.571 (4) | | |
| | | |
Br1—Mn1—Br1i | 100.47 (3) | C5—C4—H3 | 120.9 |
Br1—Mn1—N1 | 98.86 (6) | N1—C5—C4 | 122.1 (3) |
Br1—Mn1—N1i | 92.75 (6) | N1—C5—C11 | 116.2 (2) |
Br1—Mn1—N2 | 167.51 (6) | C4—C5—C11 | 121.7 (2) |
Br1—Mn1—N2i | 88.33 (6) | C3—C6—H4 | 109.4 |
Br1i—Mn1—N1 | 92.75 (6) | C3—C6—H5 | 109.4 |
Br1i—Mn1—N1i | 98.86 (6) | C3—C6—H6 | 109.5 |
Br1i—Mn1—N2 | 88.33 (6) | H4—C6—H5 | 109.4 |
Br1i—Mn1—N2i | 167.51 (6) | H4—C6—H6 | 109.6 |
N1—Mn1—N1i | 161.8 (1) | H5—C6—H6 | 109.5 |
N1—Mn1—N2 | 71.66 (8) | N2—C7—C8 | 122.9 (3) |
N1—Mn1—N2i | 94.64 (9) | N2—C7—H7 | 119.3 |
N1i—Mn1—N2 | 94.64 (9) | C8—C7—H7 | 117.6 |
N1i—Mn1—N2i | 71.66 (8) | C7—C8—C9 | 120.2 (3) |
N2—Mn1—N2i | 84.5 (1) | C7—C8—H8 | 115.3 |
Mn1—N1—C1 | 122.8 (2) | C9—C8—H8 | 124.3 |
Mn1—N1—C5 | 117.7 (2) | C8—C9—C10 | 116.9 (3) |
C1—N1—C5 | 117.7 (2) | C8—C9—C12 | 122.1 (3) |
Mn1—N2—C7 | 125.5 (2) | C10—C9—C12 | 121.0 (3) |
Mn1—N2—C11 | 117.1 (2) | C9—C10—C11 | 120.2 (3) |
C7—N2—C11 | 117.4 (3) | C9—C10—H12 | 119.6 |
N1—C1—C2 | 123.0 (3) | C11—C10—H12 | 120.3 |
N1—C1—H1 | 115.1 | N2—C11—C5 | 115.8 (2) |
C2—C1—H1 | 121.8 | N2—C11—C10 | 122.2 (3) |
C1—C2—C3 | 119.9 (3) | C5—C11—C10 | 121.9 (2) |
C1—C2—H2 | 121.5 | C9—C12—H9 | 109.4 |
C3—C2—H2 | 118.2 | C9—C12—H10 | 109.5 |
C2—C3—C4 | 117.2 (3) | C9—C12—H11 | 109.5 |
C2—C3—C6 | 121.6 (3) | H9—C12—H10 | 109.5 |
C4—C3—C6 | 121.1 (3) | H9—C12—H11 | 109.4 |
C3—C4—C5 | 120.1 (3) | H10—C12—H11 | 109.6 |
C3—C4—H3 | 119.0 | | |
| | | |
Br1—Mn1—N1—C1 | 16.5 (2) | N1—C5—C11—C10 | 167.4 (3) |
Br1—Mn1—N1—C5 | −179.0 (2) | N2—Mn1—N1—C1 | −171.8 (2) |
Br1—Mn1—N1i—C1i | −84.5 (2) | N2—Mn1—N1—C5 | −7.3 (2) |
Br1—Mn1—N1i—C5i | 80.0 (2) | N2—Mn1—N1i—C1i | 105.6 (2) |
Br1—Mn1—N2—C7 | −135.9 (3) | N2—Mn1—N1i—C5i | −89.9 (2) |
Br1—Mn1—N2—C11 | 41.3 (4) | N2—Mn1—N2i—C7i | −80.8 (2) |
Br1—Mn1—N2i—C7i | 89.0 (3) | N2—Mn1—N2i—C11i | 96.4 (2) |
Br1—Mn1—N2i—C11i | −93.8 (2) | N2—C7—C8—C9 | −1.5 (5) |
Mn1—N1—C1—C2 | 162.8 (2) | N2—C11—C5—C4 | 163.7 (3) |
Mn1—N1—C5—C4 | −163.9 (2) | N2—C11—C10—C9 | −1.7 (5) |
Mn1—N1—C5—C11 | 13.6 (3) | C1—N1—C5—C4 | 1.4 (4) |
Mn1—N1i—C1i—C2i | 162.8 (2) | C1—N1—C5—C11 | 178.8 (3) |
Mn1—N1i—C5i—C4i | −163.9 (2) | C1—C2—C3—C4 | 0.8 (5) |
Mn1—N1i—C5i—C11i | 13.6 (3) | C1—C2—C3—C6 | −176.8 (3) |
Mn1—N2—C7—C8 | 175.3 (2) | C2—C1—N1—C5 | −1.7 (5) |
Mn1—N2—C11—C5 | 7.2 (3) | C2—C3—C4—C5 | −1.1 (4) |
Mn1—N2—C11—C10 | −173.9 (2) | C3—C4—C5—C11 | −177.3 (3) |
Mn1—N2i—C7i—C8i | 175.3 (2) | C4—C5—C11—C10 | −15.2 (4) |
Mn1—N2i—C11i—C5i | 7.2 (3) | C5—C4—C3—C6 | 176.5 (3) |
Mn1—N2i—C11i—C10i | −173.9 (2) | C5—C11—N2—C7 | −175.4 (3) |
N1—Mn1—N1i—C1i | 145.6 (2) | C5—C11—C10—C9 | 177.1 (3) |
N1—Mn1—N1i—C5i | −49.9 (2) | C7—N2—C11—C10 | 3.5 (4) |
N1—Mn1—N2—C7 | −177.6 (3) | C7—C8—C9—C10 | 3.2 (5) |
N1—Mn1—N2—C11 | −0.4 (2) | C7—C8—C9—C12 | −177.3 (3) |
N1—Mn1—N2i—C7i | −9.8 (3) | C8—C7—N2—C11 | −1.9 (5) |
N1—Mn1—N2i—C11i | 167.4 (2) | C8—C9—C10—C11 | −1.7 (5) |
N1—C1—C2—C3 | 0.6 (5) | C11—C10—C9—C12 | 178.8 (3) |
N1—C5—C4—C3 | 0.0 (4) | C11—C10—C9—C12 | 178.8 (3) |
N1—C5—C11—N2 | −13.7 (4) | | |
Symmetry codes: (i) −x, y, −z+1/2; (ii) x, −y, z+1/2; (iii) x−1/2, y+1/2, −z+1/2. |