Bis(7-amino-2,4-dimethyl-1,8-naph­thy­ridine)dichlorido­manganese(II) methanol disolvate

Jin, S.; Wang, D.

doi:10.1107/S1600536807055262

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Bis(7-amino-2,4-dimethyl-1,8-naphthyridine)dichloridomanganese(II) methanol disolvate

S. Jin and D. Wang

In the title compound, [MnCl₂(C₁₀H₁₁N₃)₂]·2CH₃OH, both naphthyridine ligands coordinate to the Mn^II ion via two N atoms in a bidentate chelating mode. The Mn^II centre is furthermore coordinated by two Cl ligands to form an octahedral geometry. In addition, there are two methanol molecules in the asymmetric unit. The crystal packing is stabilized by O—H

Cl, N—H

O and N—H

Cl hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055262/bt2572sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055262/bt2572Isup2.hkl Contains datablock I

CCDC reference: 672672

checkCIF report

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

Comment top

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₎2_Cl2) (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(CH₃O_H) 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.

Related literature top

For related literature, see: Bayer (1979); Gavrilova & Bosnich (2004); Jin et al. (2007); Mintert & Sheldrick (1995a,b); Oskui et al. (1999); Oskui & Sheldrick (1999).

Experimental top

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 C₂₂H₃₀Cl₂Mn_N6_O2: C, 49.22; H, 5.59; N, 15.66. Found: C, 49.17; H, 5.50; N, 15.62.

Computing details top

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).

Figures top

	Fig. 1. The structure of the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Three dimensional network structure connected via pi-pi interaction and hydrogen bonds.

Bis(7-amino-2,4-dimethyl-1,8-naphthyridine)dichloridomanganese(II) methanol disolvate top

Crystal data top

[MnCl₂(C₁₀H₁₁N₃)₂]·2CH₃OH	Z = 2
M_r = 536.36	F(000) = 558
Triclinic, P1	D_x = 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

Data collection top

Siemens SMART CCD area-detector diffractometer	4597 independent reflections
Radiation source: fine-focus sealed tube	2867 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
T_min = 0.753, T_max = 0.885	k = −12→11
6933 measured reflections	l = −17→16

Refinement top

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(F_o²) + (0.0535P)² + 0.4067P] where P = (F_o² + 2F_c²)/3
4597 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[MnCl₂(C₁₀H₁₁N₃)₂]·2CH₃OH	γ = 65.894 (4)°
M_r = 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)°

Data collection top

Siemens SMART CCD area-detector diffractometer	4597 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2867 reflections with I > 2σ(I)
T_min = 0.753, T_max = 0.885	R_int = 0.020
6933 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.02	Δρ_max = 0.31 e Å⁻³
4597 reflections	Δρ_min = −0.24 e Å⁻³
298 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.753, 0.885
No. of measured, independent and observed [I > 2σ(I)] reflections	6933, 4597, 2867
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.24

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

Hydrogen-bond geometry (Å, º) top

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.

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