Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055262/bt2572sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055262/bt2572Isup2.hkl |
CCDC reference: 672672
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.047
- wR factor = 0.125
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 6.03 su PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C20
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn1 (2) 2.00
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
All reagents and solvents were used as obtained without further purification. The CHN elemental analyses were performed on a Perkin–Elmer elemental analyzer.
To an methanol solution of manganese chloride tetrahydrate (40 mg, 0.2 mmol) was added L (34.8 mg, 0.2 mmol) in 10 ml of methanol. The solution was stirred for a few minutes, then the solution was filtered. After standing the solution at room temperature for several days, colorless block crystals were isolated. Yield: 32.2 mg, 60%. Anal. Calcd. for C22H30Cl2MnN6O2: C, 49.22; H, 5.59; N, 15.66. Found: C, 49.17; H, 5.50; N, 15.62.
All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with O—H = 0.82 Å, N—H = 0.90 Å and C—H = 0.96 Å and U(H) set to 1.2Ueq(C,N,O).
Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).
[MnCl2(C10H11N3)2]·2CH3OH | Z = 2 |
Mr = 536.36 | F(000) = 558 |
Triclinic, P1 | Dx = 1.354 Mg m−3 |
a = 9.637 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.649 (3) Å | Cell parameters from 1874 reflections |
c = 14.442 (4) Å | θ = 2.4–23.2° |
α = 79.178 (4)° | µ = 0.73 mm−1 |
β = 78.343 (4)° | T = 298 K |
γ = 65.894 (4)° | Block, colourless |
V = 1315.7 (7) Å3 | 0.41 × 0.22 × 0.17 mm |
Siemens SMART CCD area-detector diffractometer | 4597 independent reflections |
Radiation source: fine-focus sealed tube | 2867 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→11 |
Tmin = 0.753, Tmax = 0.885 | k = −12→11 |
6933 measured reflections | l = −17→16 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0535P)2 + 0.4067P] where P = (Fo2 + 2Fc2)/3 |
4597 reflections | (Δ/σ)max < 0.001 |
298 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
[MnCl2(C10H11N3)2]·2CH3OH | γ = 65.894 (4)° |
Mr = 536.36 | V = 1315.7 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.637 (3) Å | Mo Kα radiation |
b = 10.649 (3) Å | µ = 0.73 mm−1 |
c = 14.442 (4) Å | T = 298 K |
α = 79.178 (4)° | 0.41 × 0.22 × 0.17 mm |
β = 78.343 (4)° |
Siemens SMART CCD area-detector diffractometer | 4597 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2867 reflections with I > 2σ(I) |
Tmin = 0.753, Tmax = 0.885 | Rint = 0.020 |
6933 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.31 e Å−3 |
4597 reflections | Δρmin = −0.24 e Å−3 |
298 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Mn1 | 0.03600 (6) | 0.77674 (5) | 0.25965 (4) | 0.04575 (19) | |
Cl1 | 0.05456 (13) | 0.98490 (10) | 0.29881 (7) | 0.0636 (3) | |
Cl2 | −0.24018 (12) | 0.85917 (13) | 0.27296 (7) | 0.0760 (4) | |
N1 | 0.2973 (3) | 0.7055 (3) | 0.1725 (2) | 0.0449 (7) | |
N2 | 0.0861 (3) | 0.7875 (3) | 0.10128 (19) | 0.0449 (7) | |
N3 | −0.1387 (4) | 0.8679 (4) | 0.0390 (2) | 0.0736 (10) | |
H3A | −0.1879 | 0.8741 | 0.0958 | 0.088* | |
H3B | −0.1880 | 0.8911 | −0.0090 | 0.088* | |
N4 | 0.0720 (3) | 0.5423 (3) | 0.29246 (19) | 0.0434 (7) | |
N5 | 0.1309 (3) | 0.6444 (3) | 0.39243 (19) | 0.0440 (7) | |
N6 | 0.1863 (4) | 0.7605 (3) | 0.4883 (2) | 0.0711 (10) | |
H6A | 0.1532 | 0.8348 | 0.4497 | 0.085* | |
H6B | 0.2206 | 0.7620 | 0.5385 | 0.085* | |
O1 | 0.2760 (4) | 0.7735 (3) | 0.6695 (2) | 0.0863 (10) | |
H1 | 0.2054 | 0.8466 | 0.6822 | 0.130* | |
O2 | 0.7131 (4) | 0.9445 (4) | 0.8698 (2) | 0.0924 (10) | |
H2 | 0.7655 | 0.9740 | 0.8266 | 0.139* | |
C1 | 0.2407 (4) | 0.7379 (3) | 0.0889 (2) | 0.0436 (8) | |
C2 | 0.0140 (5) | 0.8224 (4) | 0.0253 (3) | 0.0544 (10) | |
C3 | 0.0983 (5) | 0.8106 (4) | −0.0680 (3) | 0.0621 (11) | |
H3 | 0.0470 | 0.8367 | −0.1209 | 0.075* | |
C4 | 0.2517 (5) | 0.7617 (4) | −0.0791 (3) | 0.0625 (11) | |
H4 | 0.3063 | 0.7539 | −0.1401 | 0.075* | |
C5 | 0.3329 (5) | 0.7213 (4) | 0.0003 (2) | 0.0497 (9) | |
C6 | 0.4929 (5) | 0.6667 (4) | −0.0013 (3) | 0.0596 (11) | |
C7 | 0.5471 (5) | 0.6343 (4) | 0.0835 (3) | 0.0644 (11) | |
H7 | 0.6526 | 0.5981 | 0.0843 | 0.077* | |
C8 | 0.4486 (5) | 0.6537 (4) | 0.1696 (3) | 0.0554 (10) | |
C9 | 0.6011 (5) | 0.6424 (5) | −0.0936 (3) | 0.0815 (14) | |
H9A | 0.6051 | 0.7289 | −0.1251 | 0.122* | |
H9B | 0.5650 | 0.6034 | −0.1339 | 0.122* | |
H9C | 0.7018 | 0.5796 | −0.0806 | 0.122* | |
C10 | 0.5090 (5) | 0.6191 (5) | 0.2626 (3) | 0.0782 (13) | |
H10A | 0.4275 | 0.6625 | 0.3111 | 0.117* | |
H10B | 0.5896 | 0.6522 | 0.2572 | 0.117* | |
H10C | 0.5485 | 0.5205 | 0.2794 | 0.117* | |
C11 | 0.1292 (4) | 0.5249 (3) | 0.3733 (2) | 0.0414 (8) | |
C12 | 0.1846 (4) | 0.6429 (4) | 0.4704 (3) | 0.0502 (9) | |
C13 | 0.2383 (4) | 0.5185 (4) | 0.5337 (3) | 0.0564 (10) | |
H13 | 0.2750 | 0.5189 | 0.5884 | 0.068* | |
C14 | 0.2361 (4) | 0.4015 (4) | 0.5147 (3) | 0.0568 (10) | |
H14 | 0.2713 | 0.3211 | 0.5565 | 0.068* | |
C15 | 0.1809 (4) | 0.3981 (4) | 0.4314 (2) | 0.0485 (9) | |
C16 | 0.1720 (5) | 0.2840 (4) | 0.4025 (3) | 0.0572 (10) | |
C17 | 0.1094 (5) | 0.3053 (4) | 0.3206 (3) | 0.0591 (11) | |
H17 | 0.1008 | 0.2313 | 0.3002 | 0.071* | |
C18 | 0.0586 (4) | 0.4350 (4) | 0.2675 (3) | 0.0517 (9) | |
C19 | 0.2261 (6) | 0.1429 (4) | 0.4589 (3) | 0.0798 (14) | |
H19A | 0.3153 | 0.1289 | 0.4859 | 0.120* | |
H19B | 0.2515 | 0.0732 | 0.4178 | 0.120* | |
H19C | 0.1461 | 0.1367 | 0.5091 | 0.120* | |
C20 | −0.0165 (5) | 0.4602 (5) | 0.1806 (3) | 0.0722 (12) | |
H20A | −0.1079 | 0.4408 | 0.1979 | 0.108* | |
H20B | 0.0532 | 0.4008 | 0.1346 | 0.108* | |
H20C | −0.0428 | 0.5552 | 0.1536 | 0.108* | |
C21 | 0.4129 (6) | 0.7950 (6) | 0.6425 (4) | 0.1003 (17) | |
H21A | 0.4127 | 0.8616 | 0.6791 | 0.150* | |
H21B | 0.4220 | 0.8290 | 0.5760 | 0.150* | |
H21C | 0.4980 | 0.7091 | 0.6537 | 0.150* | |
C22 | 0.5636 (6) | 1.0004 (5) | 0.8526 (5) | 0.118 (2) | |
H22A | 0.5028 | 0.9640 | 0.9024 | 0.177* | |
H22B | 0.5588 | 0.9771 | 0.7926 | 0.177* | |
H22C | 0.5247 | 1.0993 | 0.8507 | 0.177* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0506 (4) | 0.0454 (3) | 0.0389 (3) | −0.0156 (3) | −0.0108 (2) | −0.0012 (2) |
Cl1 | 0.0821 (8) | 0.0473 (6) | 0.0639 (6) | −0.0256 (5) | −0.0129 (6) | −0.0079 (5) |
Cl2 | 0.0492 (6) | 0.1008 (9) | 0.0613 (7) | −0.0161 (6) | −0.0116 (5) | 0.0040 (6) |
N1 | 0.0466 (19) | 0.0405 (17) | 0.0457 (17) | −0.0131 (15) | −0.0121 (14) | −0.0028 (13) |
N2 | 0.0467 (19) | 0.0462 (18) | 0.0384 (16) | −0.0137 (15) | −0.0107 (14) | −0.0013 (13) |
N3 | 0.057 (2) | 0.104 (3) | 0.051 (2) | −0.018 (2) | −0.0218 (18) | −0.0040 (19) |
N4 | 0.0463 (18) | 0.0482 (18) | 0.0388 (16) | −0.0209 (15) | −0.0084 (14) | −0.0033 (13) |
N5 | 0.0527 (19) | 0.0428 (17) | 0.0413 (16) | −0.0222 (15) | −0.0124 (14) | −0.0005 (13) |
N6 | 0.109 (3) | 0.069 (2) | 0.055 (2) | −0.045 (2) | −0.034 (2) | −0.0028 (17) |
O1 | 0.065 (2) | 0.101 (2) | 0.080 (2) | −0.0100 (19) | −0.0094 (17) | −0.0327 (18) |
O2 | 0.073 (2) | 0.132 (3) | 0.074 (2) | −0.046 (2) | −0.0337 (18) | 0.0206 (19) |
C1 | 0.049 (2) | 0.0359 (19) | 0.045 (2) | −0.0161 (17) | −0.0083 (18) | −0.0013 (16) |
C2 | 0.057 (3) | 0.050 (2) | 0.054 (3) | −0.018 (2) | −0.015 (2) | −0.0012 (18) |
C3 | 0.078 (3) | 0.068 (3) | 0.039 (2) | −0.026 (2) | −0.016 (2) | −0.0006 (19) |
C4 | 0.081 (3) | 0.063 (3) | 0.041 (2) | −0.031 (2) | 0.007 (2) | −0.0085 (19) |
C5 | 0.060 (3) | 0.044 (2) | 0.044 (2) | −0.0191 (19) | −0.007 (2) | −0.0045 (17) |
C6 | 0.061 (3) | 0.047 (2) | 0.067 (3) | −0.023 (2) | 0.004 (2) | −0.008 (2) |
C7 | 0.043 (2) | 0.066 (3) | 0.077 (3) | −0.017 (2) | −0.002 (2) | −0.010 (2) |
C8 | 0.050 (3) | 0.050 (2) | 0.067 (3) | −0.019 (2) | −0.017 (2) | −0.0002 (19) |
C9 | 0.070 (3) | 0.084 (3) | 0.081 (3) | −0.032 (3) | 0.024 (3) | −0.021 (3) |
C10 | 0.059 (3) | 0.092 (3) | 0.083 (3) | −0.026 (3) | −0.032 (2) | 0.007 (3) |
C11 | 0.040 (2) | 0.044 (2) | 0.040 (2) | −0.0179 (17) | −0.0021 (16) | −0.0032 (16) |
C12 | 0.056 (2) | 0.056 (2) | 0.044 (2) | −0.026 (2) | −0.0086 (18) | −0.0068 (18) |
C13 | 0.061 (3) | 0.068 (3) | 0.040 (2) | −0.024 (2) | −0.0177 (19) | 0.0034 (19) |
C14 | 0.056 (3) | 0.053 (2) | 0.048 (2) | −0.014 (2) | −0.0062 (19) | 0.0090 (18) |
C15 | 0.050 (2) | 0.043 (2) | 0.045 (2) | −0.0143 (18) | −0.0051 (18) | 0.0002 (17) |
C16 | 0.057 (3) | 0.047 (2) | 0.061 (3) | −0.019 (2) | 0.002 (2) | −0.0045 (19) |
C17 | 0.061 (3) | 0.048 (2) | 0.071 (3) | −0.025 (2) | 0.003 (2) | −0.018 (2) |
C18 | 0.048 (2) | 0.058 (3) | 0.054 (2) | −0.024 (2) | −0.0019 (18) | −0.0147 (19) |
C19 | 0.098 (4) | 0.047 (3) | 0.088 (3) | −0.026 (3) | −0.012 (3) | 0.002 (2) |
C20 | 0.069 (3) | 0.091 (3) | 0.072 (3) | −0.037 (3) | −0.015 (2) | −0.025 (2) |
C21 | 0.083 (4) | 0.107 (4) | 0.108 (4) | −0.027 (3) | −0.017 (3) | −0.023 (3) |
C22 | 0.090 (4) | 0.080 (4) | 0.190 (7) | −0.035 (3) | −0.058 (4) | 0.014 (4) |
Mn1—N2 | 2.231 (3) | C7—C8 | 1.395 (5) |
Mn1—N5 | 2.267 (3) | C7—H7 | 0.9300 |
Mn1—N4 | 2.344 (3) | C8—C10 | 1.495 (5) |
Mn1—Cl2 | 2.4166 (14) | C9—H9A | 0.9600 |
Mn1—N1 | 2.453 (3) | C9—H9B | 0.9600 |
Mn1—Cl1 | 2.4699 (12) | C9—H9C | 0.9600 |
N1—C8 | 1.327 (5) | C10—H10A | 0.9600 |
N1—C1 | 1.353 (4) | C10—H10B | 0.9600 |
N2—C2 | 1.331 (4) | C10—H10C | 0.9600 |
N2—C1 | 1.347 (4) | C11—C15 | 1.403 (5) |
N3—C2 | 1.332 (5) | C12—C13 | 1.426 (5) |
N3—H3A | 0.8600 | C13—C14 | 1.333 (5) |
N3—H3B | 0.8600 | C13—H13 | 0.9300 |
N4—C18 | 1.322 (4) | C14—C15 | 1.422 (5) |
N4—C11 | 1.341 (4) | C14—H14 | 0.9300 |
N5—C12 | 1.326 (4) | C15—C16 | 1.396 (5) |
N5—C11 | 1.359 (4) | C16—C17 | 1.374 (5) |
N6—C12 | 1.332 (4) | C16—C19 | 1.505 (5) |
N6—H6A | 0.8600 | C17—C18 | 1.392 (5) |
N6—H6B | 0.8600 | C17—H17 | 0.9300 |
O1—C21 | 1.396 (5) | C18—C20 | 1.501 (5) |
O1—H1 | 0.8200 | C19—H19A | 0.9600 |
O2—C22 | 1.371 (5) | C19—H19B | 0.9600 |
O2—H2 | 0.8200 | C19—H19C | 0.9600 |
C1—C5 | 1.398 (5) | C20—H20A | 0.9600 |
C2—C3 | 1.424 (5) | C20—H20B | 0.9600 |
C3—C4 | 1.338 (5) | C20—H20C | 0.9600 |
C3—H3 | 0.9300 | C21—H21A | 0.9600 |
C4—C5 | 1.420 (5) | C21—H21B | 0.9600 |
C4—H4 | 0.9300 | C21—H21C | 0.9600 |
C5—C6 | 1.405 (5) | C22—H22A | 0.9600 |
C6—C7 | 1.359 (6) | C22—H22B | 0.9600 |
C6—C9 | 1.509 (5) | C22—H22C | 0.9600 |
N2—Mn1—N5 | 140.98 (10) | C6—C9—H9B | 109.5 |
N2—Mn1—N4 | 97.82 (10) | H9A—C9—H9B | 109.5 |
N5—Mn1—N4 | 58.08 (9) | C6—C9—H9C | 109.5 |
N2—Mn1—Cl2 | 97.46 (8) | H9A—C9—H9C | 109.5 |
N5—Mn1—Cl2 | 113.38 (8) | H9B—C9—H9C | 109.5 |
N4—Mn1—Cl2 | 94.45 (8) | C8—C10—H10A | 109.5 |
N2—Mn1—N1 | 56.89 (10) | C8—C10—H10B | 109.5 |
N5—Mn1—N1 | 89.71 (10) | H10A—C10—H10B | 109.5 |
N4—Mn1—N1 | 88.28 (9) | C8—C10—H10C | 109.5 |
Cl2—Mn1—N1 | 154.31 (8) | H10A—C10—H10C | 109.5 |
N2—Mn1—Cl1 | 105.51 (8) | H10B—C10—H10C | 109.5 |
N5—Mn1—Cl1 | 93.36 (7) | N4—C11—N5 | 112.1 (3) |
N4—Mn1—Cl1 | 151.42 (8) | N4—C11—C15 | 123.8 (3) |
Cl2—Mn1—Cl1 | 98.59 (5) | N5—C11—C15 | 124.1 (3) |
N1—Mn1—Cl1 | 90.77 (7) | N5—C12—N6 | 118.4 (3) |
C8—N1—C1 | 117.8 (3) | N5—C12—C13 | 120.6 (3) |
C8—N1—Mn1 | 151.8 (3) | N6—C12—C13 | 121.0 (3) |
C1—N1—Mn1 | 90.4 (2) | C14—C13—C12 | 120.3 (3) |
C2—N2—C1 | 119.0 (3) | C14—C13—H13 | 119.9 |
C2—N2—Mn1 | 140.4 (3) | C12—C13—H13 | 119.9 |
C1—N2—Mn1 | 100.6 (2) | C13—C14—C15 | 120.9 (3) |
C2—N3—H3A | 120.0 | C13—C14—H14 | 119.5 |
C2—N3—H3B | 120.0 | C15—C14—H14 | 119.5 |
H3A—N3—H3B | 120.0 | C16—C15—C11 | 117.6 (3) |
C18—N4—C11 | 118.2 (3) | C16—C15—C14 | 127.2 (3) |
C18—N4—Mn1 | 148.4 (2) | C11—C15—C14 | 115.2 (3) |
C11—N4—Mn1 | 93.44 (19) | C17—C16—C15 | 117.4 (3) |
C12—N5—C11 | 118.8 (3) | C17—C16—C19 | 120.7 (4) |
C12—N5—Mn1 | 144.8 (2) | C15—C16—C19 | 121.8 (4) |
C11—N5—Mn1 | 96.3 (2) | C16—C17—C18 | 121.6 (3) |
C12—N6—H6A | 120.0 | C16—C17—H17 | 119.2 |
C12—N6—H6B | 120.0 | C18—C17—H17 | 119.2 |
H6A—N6—H6B | 120.0 | N4—C18—C17 | 121.3 (4) |
C21—O1—H1 | 109.5 | N4—C18—C20 | 116.9 (3) |
C22—O2—H2 | 109.5 | C17—C18—C20 | 121.7 (4) |
N2—C1—N1 | 112.1 (3) | C16—C19—H19A | 109.5 |
N2—C1—C5 | 124.4 (3) | C16—C19—H19B | 109.5 |
N1—C1—C5 | 123.5 (3) | H19A—C19—H19B | 109.5 |
N2—C2—N3 | 118.2 (4) | C16—C19—H19C | 109.5 |
N2—C2—C3 | 120.7 (4) | H19A—C19—H19C | 109.5 |
N3—C2—C3 | 121.1 (4) | H19B—C19—H19C | 109.5 |
C4—C3—C2 | 119.5 (4) | C18—C20—H20A | 109.5 |
C4—C3—H3 | 120.2 | C18—C20—H20B | 109.5 |
C2—C3—H3 | 120.2 | H20A—C20—H20B | 109.5 |
C3—C4—C5 | 121.5 (4) | C18—C20—H20C | 109.5 |
C3—C4—H4 | 119.3 | H20A—C20—H20C | 109.5 |
C5—C4—H4 | 119.3 | H20B—C20—H20C | 109.5 |
C1—C5—C6 | 117.9 (3) | O1—C21—H21A | 109.5 |
C1—C5—C4 | 115.0 (4) | O1—C21—H21B | 109.5 |
C6—C5—C4 | 127.1 (4) | H21A—C21—H21B | 109.5 |
C7—C6—C5 | 117.5 (4) | O1—C21—H21C | 109.5 |
C7—C6—C9 | 121.1 (4) | H21A—C21—H21C | 109.5 |
C5—C6—C9 | 121.4 (4) | H21B—C21—H21C | 109.5 |
C6—C7—C8 | 121.7 (4) | O2—C22—H22A | 109.5 |
C6—C7—H7 | 119.1 | O2—C22—H22B | 109.5 |
C8—C7—H7 | 119.1 | H22A—C22—H22B | 109.5 |
N1—C8—C7 | 121.6 (4) | O2—C22—H22C | 109.5 |
N1—C8—C10 | 117.0 (4) | H22A—C22—H22C | 109.5 |
C7—C8—C10 | 121.5 (4) | H22B—C22—H22C | 109.5 |
C6—C9—H9A | 109.5 | ||
N2—Mn1—N1—C8 | −177.8 (5) | N3—C2—C3—C4 | −178.5 (4) |
N5—Mn1—N1—C8 | −19.2 (5) | C2—C3—C4—C5 | −0.1 (6) |
N4—Mn1—N1—C8 | −77.3 (5) | N2—C1—C5—C6 | −179.3 (3) |
Cl2—Mn1—N1—C8 | −174.0 (4) | N1—C1—C5—C6 | 0.7 (5) |
Cl1—Mn1—N1—C8 | 74.1 (5) | N2—C1—C5—C4 | 0.2 (5) |
N2—Mn1—N1—C1 | −0.35 (18) | N1—C1—C5—C4 | −179.8 (3) |
N5—Mn1—N1—C1 | 158.21 (19) | C3—C4—C5—C1 | −0.5 (5) |
N4—Mn1—N1—C1 | 100.13 (19) | C3—C4—C5—C6 | 178.9 (4) |
Cl2—Mn1—N1—C1 | 3.4 (3) | C1—C5—C6—C7 | −0.3 (5) |
Cl1—Mn1—N1—C1 | −108.44 (18) | C4—C5—C6—C7 | −179.7 (4) |
N5—Mn1—N2—C2 | 143.0 (3) | C1—C5—C6—C9 | 178.6 (3) |
N4—Mn1—N2—C2 | 95.7 (4) | C4—C5—C6—C9 | −0.8 (6) |
Cl2—Mn1—N2—C2 | 0.2 (4) | C5—C6—C7—C8 | 0.2 (6) |
N1—Mn1—N2—C2 | 178.5 (4) | C9—C6—C7—C8 | −178.8 (4) |
Cl1—Mn1—N2—C2 | −100.9 (4) | C1—N1—C8—C7 | 0.7 (5) |
N5—Mn1—N2—C1 | −35.1 (3) | Mn1—N1—C8—C7 | 177.8 (3) |
N4—Mn1—N2—C1 | −82.4 (2) | C1—N1—C8—C10 | 179.8 (3) |
Cl2—Mn1—N2—C1 | −177.99 (19) | Mn1—N1—C8—C10 | −3.1 (7) |
N1—Mn1—N2—C1 | 0.36 (18) | C6—C7—C8—N1 | −0.3 (6) |
Cl1—Mn1—N2—C1 | 80.9 (2) | C6—C7—C8—C10 | −179.4 (4) |
N2—Mn1—N4—C18 | −35.6 (5) | C18—N4—C11—N5 | −177.5 (3) |
N5—Mn1—N4—C18 | 177.5 (5) | Mn1—N4—C11—N5 | 1.7 (3) |
Cl2—Mn1—N4—C18 | 62.6 (5) | C18—N4—C11—C15 | 2.4 (5) |
N1—Mn1—N4—C18 | −91.8 (5) | Mn1—N4—C11—C15 | −178.4 (3) |
Cl1—Mn1—N4—C18 | 179.8 (4) | C12—N5—C11—N4 | 180.0 (3) |
N2—Mn1—N4—C11 | 145.8 (2) | Mn1—N5—C11—N4 | −1.8 (3) |
N5—Mn1—N4—C11 | −1.12 (19) | C12—N5—C11—C15 | 0.1 (5) |
Cl2—Mn1—N4—C11 | −115.98 (19) | Mn1—N5—C11—C15 | 178.4 (3) |
N1—Mn1—N4—C11 | 89.6 (2) | C11—N5—C12—N6 | 179.7 (3) |
Cl1—Mn1—N4—C11 | 1.2 (3) | Mn1—N5—C12—N6 | 2.7 (7) |
N2—Mn1—N5—C12 | 119.4 (4) | C11—N5—C12—C13 | −0.6 (5) |
N4—Mn1—N5—C12 | 178.5 (5) | Mn1—N5—C12—C13 | −177.6 (3) |
Cl2—Mn1—N5—C12 | −101.3 (4) | N5—C12—C13—C14 | 0.5 (6) |
N1—Mn1—N5—C12 | 90.3 (4) | N6—C12—C13—C14 | −179.8 (4) |
Cl1—Mn1—N5—C12 | −0.5 (4) | C12—C13—C14—C15 | 0.1 (6) |
N2—Mn1—N5—C11 | −58.0 (3) | N4—C11—C15—C16 | 0.2 (5) |
N4—Mn1—N5—C11 | 1.11 (18) | N5—C11—C15—C16 | 180.0 (3) |
Cl2—Mn1—N5—C11 | 81.3 (2) | N4—C11—C15—C14 | −179.4 (3) |
N1—Mn1—N5—C11 | −87.1 (2) | N5—C11—C15—C14 | 0.4 (5) |
Cl1—Mn1—N5—C11 | −177.80 (19) | C13—C14—C15—C16 | 180.0 (4) |
C2—N2—C1—N1 | −179.2 (3) | C13—C14—C15—C11 | −0.5 (5) |
Mn1—N2—C1—N1 | −0.6 (3) | C11—C15—C16—C17 | −1.7 (5) |
C2—N2—C1—C5 | 0.8 (5) | C14—C15—C16—C17 | 177.8 (4) |
Mn1—N2—C1—C5 | 179.5 (3) | C11—C15—C16—C19 | 179.2 (3) |
C8—N1—C1—N2 | 179.1 (3) | C14—C15—C16—C19 | −1.3 (6) |
Mn1—N1—C1—N2 | 0.5 (3) | C15—C16—C17—C18 | 0.9 (6) |
C8—N1—C1—C5 | −0.9 (5) | C19—C16—C17—C18 | 179.9 (4) |
Mn1—N1—C1—C5 | −179.5 (3) | C11—N4—C18—C17 | −3.3 (5) |
C1—N2—C2—N3 | 178.2 (3) | Mn1—N4—C18—C17 | 178.3 (3) |
Mn1—N2—C2—N3 | 0.3 (6) | C11—N4—C18—C20 | 175.6 (3) |
C1—N2—C2—C3 | −1.4 (5) | Mn1—N4—C18—C20 | −2.8 (7) |
Mn1—N2—C2—C3 | −179.4 (3) | C16—C17—C18—N4 | 1.7 (6) |
N2—C2—C3—C4 | 1.1 (6) | C16—C17—C18—C20 | −177.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···Cl1i | 0.82 | 2.35 | 3.162 (3) | 169 |
O1—H1···Cl1ii | 0.82 | 2.41 | 3.183 (3) | 158 |
N6—H6B···O1 | 0.86 | 2.10 | 2.960 (4) | 173 |
N6—H6A···Cl1 | 0.86 | 2.55 | 3.359 (4) | 158 |
N3—H3B···O2iii | 0.86 | 2.04 | 2.895 (4) | 175 |
N3—H3A···Cl2 | 0.86 | 2.49 | 3.318 (4) | 161 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+1; (iii) x−1, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | [MnCl2(C10H11N3)2]·2CH3OH |
Mr | 536.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 9.637 (3), 10.649 (3), 14.442 (4) |
α, β, γ (°) | 79.178 (4), 78.343 (4), 65.894 (4) |
V (Å3) | 1315.7 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.73 |
Crystal size (mm) | 0.41 × 0.22 × 0.17 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.753, 0.885 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6933, 4597, 2867 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.125, 1.02 |
No. of reflections | 4597 |
No. of parameters | 298 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.24 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···Cl1i | 0.82 | 2.35 | 3.162 (3) | 169.3 |
O1—H1···Cl1ii | 0.82 | 2.41 | 3.183 (3) | 157.6 |
N6—H6B···O1 | 0.86 | 2.10 | 2.960 (4) | 172.9 |
N6—H6A···Cl1 | 0.86 | 2.55 | 3.359 (4) | 157.5 |
N3—H3B···O2iii | 0.86 | 2.04 | 2.895 (4) | 174.9 |
N3—H3A···Cl2 | 0.86 | 2.49 | 3.318 (4) | 160.6 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+1; (iii) x−1, y, z−1. |
Molecular structures and chemical properties of transition metal complexes of 1,8-naphthyridine (napy) and its derivatives have received much attention, because the ligands can link to metals with several coordination modes such as monodentate, chelating bidentate, and dinuclear bridging binding fashion (Gavrilova & Bosnich, 2004). 5,7-dimethyl-1,8-naphthyridin-2-amine are potentially tridentate ligands and are capable of linking two to four metal atoms together to form metal aggregates having metal–metal interactions (Oskui et al., 1999; Mintert & Sheldrick, 1995a,b; Oskui & Sheldrick, 1999). The coordination chemistry of 5,7-dimethyl-1,8-naphthyridine-2-amine (L) has not been well studied before although a Mn(II) complex (Mn(L)2Cl2) (Bayer, 1979) was once described in a US patent. As an extension of our work (Jin et al., 2007), the title complex (Mn(L)2(Cl)2)·2(CH3OH) is reported here.
The complex was obtained as colorless crystals by reacting of manganese chloride tetrahydrate and L in methanol. The compound is air stable and light insensitive. The complex does not dissolve in water and common organic solvent. The molecular structure of the compound is shown in Fig. 1. Both of the two L coordinate to the metal with two N atoms in a bidentate chelating fashion. Two chloride anions coordinate to the Mn ion to complete its octahedral geometry. The amine group of 5,7-dimethyl-1,8-naphthyridin-2-amine does not show any bonding interaction with the Mn atoms. The Mn—N bond distances range from 2.231 (3) to 2.453 (3) Å. The Mn—Cl bond distances are 2.4166 (14) and 2.4699 (12) Å. The two naphthyridine rings are almost perpendicular to each other.