Azido­(methanol)[N,N′-(o-phenyl­ene)bis­(pyridine-2-carboxamidato)]manganese(III)

Feng, Y.; Liao, D.

doi:10.1107/S1600536807059211

Azido(methanol)[N,N′-(o-phenylene)bis(pyridine-2-carboxamidato)]manganese(III)

In the title complex, [Mn(C₁₈H₁₂N₄O₂)(N₃)(CH₄O)], the Mn^III ion is in a distorted octahedral coordination environment. In the crystal structure, intermolecular O—H

O hydrogen bonds connect molecules into centrosymmetric dimers.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059211/lh2555sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059211/lh2555Isup2.hkl Contains datablock I

CCDC reference: 643369

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.060
wR factor = 0.159
Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N6
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.849(10) ......       3.00 su-Ra
              O3   -H       1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.849(10) ......       3.00 su-Ra
              O3   -H       1.555   1.555

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   4 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The planar tetradentate ligand bpb^2-, bpb = 1,2-bis(pyridine-2-carboxamido)benzene, can coordinate four equatorial sites of six-coordinated paramagnetic cations, leaving two free axial positions to be occupied by bridging ligands. It is hence, one of the ideal candidates to act as a co-ligand for constructing expanded structures (Colacio et al., 2005; Ni, Kou, Zheng et al., 2005; Ni, Kou, Zhang et al., 2005; Ni, Kou, Zhao et al., 2005; Dominguez-Vera et al., 2005; Havranek et al., 1999; Lin et al., 2003; Liang et al., 2007; Zhang et al., 2006). Mn(III) compounds, with a high-spin ground state related to the Mn(III) ion (S = 2) and an apparent magnetic anisotropy of hexacoordinated Mn(III) centres due to Jahn—Teller distortion, usually display appealing magnetic properties (Lecren et al., 2007).

We originally attempted to synthesize complexes featuring azido-bridged Mn(III) metal chains by reaction of the [Mn(III)(bpb)]^2- building blocks with NaN₃. But, we fortuitously obtained title compound (I), and we report herein its crystal structure.

Related literature top

For general background, see: Ni, Kou, Zheng et al. (2005); Ni, Kou, Zhang et al. (2005); Ni, Kou, Zhao et al. (2005); Colacio et al. (2005); Dominguez-Vera et al. (2005); For bond-length data, see: Havranek et al. (1999); Lin et al. (2003); Liang et al. (2007). For related literature, see: Lecren et al. (2007); Zhang et al. (2006).

Experimental top

To a solution of [Mn(bpb)Cl(H₂O)] (0.425 g, 1 mmol) in 20 ml of methanol was added a solution of NaN₃ (0.065 g, 1 mmol) in a minimum volume of H₂O. After stirring for 30 min at room temperature, the dark brown solution was filtered and allowed to stand for about one month at room temperature to form dark brown crystals of 1, [Mn(bpb)(N₃)(CH₃OH)]. The crystals were collected by suction filtration, washed with a minimum amount of water, and dried in vacuo. Elemental analysis: C₁₉H₁₆MnN₇O₂, Calcd: C 51.25%, H 3.62%, N 22.02%, Found: C 51.68%, H 3.87%, N 22.35%.. IR (KBr): 2035 cm^-1 (N₃^-), 1622 cm^-1 (C=O).

Structure description top

Computing details top

Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker (1997); software used to prepare material for publication: CrystalStructure (Rigaku, 2001).

Figures top

	Fig. 1. The molecular structure with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A centrostmmetric hydrogen-bonded dimer with the donor-acceptor distances shown as dashed lines [symmetry code: (A) -x, -y + 1, -z].

Azido(methanol)[N,N'-(o-phenylene)bis(pyridine-2-carboxamidato)]manganese(III) top

Crystal data top

[Mn(C₁₈H₁₂N₄O₂)(N₃)(CH₄O)]	F(000) = 912
M_r = 445.33	D_x = 1.543 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 3879 reflections
a = 12.115 (2) Å	θ = 1.2–27.8°
b = 9.4987 (19) Å	µ = 0.73 mm⁻¹
c = 16.748 (3) Å	T = 293 K
β = 95.94 (3)°	Prim, red
V = 1917.0 (6) Å³	0.14 × 0.14 × 0.14 mm
Z = 4

Data collection top

Rigaku Saturn diffractometer	3406 independent reflections
Radiation source: fine-focus sealed tube	2957 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.1°, θ_min = 2.5°
ω scans	h = −14→14
Absorption correction: multi-scan (Jacobson, 1998)	k = −11→11
T_min = 0.905, T_max = 0.905	l = −19→19
15658 measured reflections

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0859P)² + 0.7977P] where P = (F_o² + 2F_c²)/3
3406 reflections	(Δ/σ)_max < 0.001
269 parameters	Δρ_max = 0.47 e Å⁻³
7 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Mn(C₁₈H₁₂N₄O₂)(N₃)(CH₄O)]	V = 1917.0 (6) Å³
M_r = 445.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.115 (2) Å	µ = 0.73 mm⁻¹
b = 9.4987 (19) Å	T = 293 K
c = 16.748 (3) Å	0.14 × 0.14 × 0.14 mm
β = 95.94 (3)°

Data collection top

Rigaku Saturn diffractometer	3406 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	2957 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.905	R_int = 0.061
15658 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	7 restraints
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.47 e Å⁻³
3406 reflections	Δρ_min = −0.52 e Å⁻³
269 parameters

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

	x	y	z	U_iso*/U_eq
Mn1	0.28436 (4)	0.43236 (5)	0.07581 (3)	0.0426 (2)
N1	0.4102 (2)	0.2866 (3)	0.09158 (17)	0.0457 (7)
N2	0.2637 (2)	0.3704 (3)	0.18327 (17)	0.0475 (7)
N3	0.1504 (2)	0.5370 (3)	0.08979 (18)	0.0457 (7)
N4	0.2560 (2)	0.5208 (3)	−0.03746 (17)	0.0446 (7)
N5	0.4047 (3)	0.5963 (4)	0.10720 (19)	0.0547 (6)
N6	0.3766 (3)	0.7072 (4)	0.12232 (18)	0.0547 (6)
N7	0.3505 (5)	0.8221 (5)	0.1379 (3)	0.1030 (15)
O1	0.3481 (3)	0.2476 (3)	0.29189 (17)	0.0692 (8)
O2	0.0275 (2)	0.7020 (3)	0.03047 (18)	0.0723 (9)
O3	0.1885 (3)	0.2409 (3)	0.01209 (19)	0.0651 (8)
H	0.1217 (19)	0.269 (7)	0.008 (4)	0.14 (3)*
C19	0.1894 (5)	0.0937 (5)	0.0353 (4)	0.0912 (17)
H19A	0.1415	0.0413	−0.0031	0.137*
H19B	0.1637	0.0848	0.0874	0.137*
H19C	0.2636	0.0575	0.0369	0.137*
C17	0.2895 (4)	0.5841 (4)	−0.1701 (2)	0.0584 (10)
H17A	0.3309	0.5721	−0.2134	0.070*
C14	0.1715 (3)	0.6137 (4)	−0.0417 (2)	0.0479 (9)
C9	0.0439 (4)	0.4628 (4)	0.3157 (3)	0.0624 (11)
H9A	0.0212	0.4431	0.3659	0.075*
C2	0.5578 (3)	0.1396 (4)	0.0584 (3)	0.0574 (10)
H2A	0.6032	0.1086	0.0204	0.069*
C4	0.5005 (3)	0.1313 (4)	0.1897 (2)	0.0536 (10)
H4A	0.5073	0.0953	0.2416	0.064*
C8	0.1394 (4)	0.4006 (4)	0.2927 (3)	0.0579 (10)
H8A	0.1815	0.3406	0.3276	0.069*
C6	0.3408 (3)	0.2842 (4)	0.2216 (2)	0.0479 (9)
C10	−0.0179 (4)	0.5543 (4)	0.2643 (3)	0.0638 (12)
H10A	−0.0815	0.5957	0.2803	0.077*
C16	0.2034 (4)	0.6788 (5)	−0.1744 (3)	0.0659 (12)
H16A	0.1859	0.7320	−0.2206	0.079*
C15	0.1430 (4)	0.6940 (4)	−0.1093 (3)	0.0629 (11)
H15A	0.0842	0.7572	−0.1110	0.075*
C3	0.5692 (3)	0.0850 (4)	0.1344 (3)	0.0592 (11)
H3A	0.6230	0.0171	0.1487	0.071*
C18	0.3139 (3)	0.5069 (4)	−0.1007 (2)	0.0519 (9)
H18A	0.3725	0.4433	−0.0978	0.062*
C12	0.1084 (3)	0.5218 (4)	0.1652 (2)	0.0470 (8)
C1	0.4782 (3)	0.2411 (4)	0.0387 (2)	0.0543 (10)
H1A	0.4714	0.2791	−0.0127	0.065*
C11	0.0140 (3)	0.5842 (4)	0.1899 (3)	0.0577 (10)
H11A	−0.0275	0.6464	0.1560	0.069*
C13	0.1080 (3)	0.6216 (4)	0.0299 (2)	0.0518 (9)
C7	0.1716 (3)	0.4288 (4)	0.2169 (2)	0.0463 (9)
C5	0.4215 (3)	0.2321 (4)	0.1666 (2)	0.0438 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0434 (4)	0.0411 (4)	0.0427 (4)	0.0090 (2)	0.0012 (2)	0.0035 (2)
N1	0.0429 (16)	0.0452 (17)	0.0479 (17)	0.0029 (13)	−0.0007 (13)	0.0035 (14)
N2	0.0507 (18)	0.0436 (17)	0.0488 (17)	0.0073 (14)	0.0079 (14)	0.0056 (14)
N3	0.0446 (16)	0.0414 (16)	0.0502 (17)	0.0054 (13)	0.0002 (13)	0.0015 (13)
N4	0.0480 (17)	0.0396 (16)	0.0438 (16)	0.0042 (13)	−0.0074 (13)	0.0001 (13)
N5	0.0579 (14)	0.0584 (15)	0.0468 (13)	−0.0053 (13)	0.0012 (10)	0.0014 (13)
N6	0.0579 (14)	0.0584 (15)	0.0468 (13)	−0.0053 (13)	0.0012 (10)	0.0014 (13)
N7	0.125 (3)	0.075 (3)	0.111 (3)	0.007 (3)	0.020 (3)	−0.013 (2)
O1	0.079 (2)	0.076 (2)	0.0525 (17)	0.0197 (16)	0.0103 (14)	0.0191 (15)
O2	0.0586 (18)	0.075 (2)	0.081 (2)	0.0288 (16)	−0.0044 (15)	0.0049 (16)
O3	0.0572 (18)	0.0463 (16)	0.088 (2)	0.0060 (14)	−0.0097 (15)	0.0000 (14)
C19	0.073 (3)	0.066 (3)	0.128 (5)	0.010 (3)	−0.019 (3)	0.010 (3)
C17	0.072 (3)	0.055 (2)	0.047 (2)	−0.004 (2)	−0.0016 (19)	0.0044 (18)
C14	0.050 (2)	0.0401 (19)	0.051 (2)	0.0023 (16)	−0.0084 (16)	0.0009 (16)
C9	0.064 (3)	0.056 (2)	0.071 (3)	−0.010 (2)	0.026 (2)	−0.011 (2)
C2	0.050 (2)	0.054 (2)	0.069 (3)	0.0123 (19)	0.0077 (18)	0.001 (2)
C4	0.054 (2)	0.047 (2)	0.056 (2)	0.0082 (18)	−0.0080 (18)	0.0097 (18)
C8	0.064 (3)	0.048 (2)	0.064 (3)	−0.0072 (19)	0.017 (2)	−0.0005 (19)
C6	0.052 (2)	0.043 (2)	0.048 (2)	0.0008 (17)	0.0005 (16)	0.0045 (17)
C10	0.056 (3)	0.060 (3)	0.079 (3)	−0.005 (2)	0.022 (2)	−0.021 (2)
C16	0.079 (3)	0.060 (3)	0.054 (2)	−0.002 (2)	−0.014 (2)	0.014 (2)
C15	0.062 (3)	0.055 (2)	0.066 (3)	0.010 (2)	−0.014 (2)	0.010 (2)
C3	0.050 (2)	0.053 (2)	0.073 (3)	0.0150 (18)	−0.003 (2)	0.005 (2)
C18	0.062 (2)	0.048 (2)	0.044 (2)	0.0049 (18)	−0.0006 (17)	−0.0006 (17)
C12	0.046 (2)	0.0369 (18)	0.057 (2)	−0.0031 (16)	0.0029 (16)	−0.0060 (17)
C1	0.054 (2)	0.059 (2)	0.050 (2)	0.0104 (19)	0.0058 (17)	0.0071 (18)
C11	0.052 (2)	0.050 (2)	0.072 (3)	0.0041 (18)	0.007 (2)	−0.012 (2)
C13	0.043 (2)	0.045 (2)	0.064 (2)	0.0045 (17)	−0.0071 (17)	0.0008 (18)
C7	0.048 (2)	0.041 (2)	0.052 (2)	−0.0008 (15)	0.0109 (16)	−0.0039 (15)
C5	0.0442 (19)	0.0398 (19)	0.0458 (19)	−0.0010 (15)	−0.0032 (15)	0.0020 (15)

Geometric parameters (Å, º) top

Mn1—N2	1.934 (3)	C14—C15	1.379 (5)
Mn1—N3	1.937 (3)	C14—C13	1.493 (6)
Mn1—N1	2.056 (3)	C9—C10	1.387 (6)
Mn1—N4	2.070 (3)	C9—C8	1.390 (6)
Mn1—N5	2.161 (3)	C9—H9A	0.9300
Mn1—O3	2.354 (3)	C2—C3	1.369 (6)
N1—C1	1.341 (5)	C2—C1	1.380 (5)
N1—C5	1.353 (4)	C2—H2A	0.9300
N2—C6	1.352 (5)	C4—C3	1.380 (6)
N2—C7	1.414 (5)	C4—C5	1.380 (5)
N3—C13	1.345 (5)	C4—H4A	0.9300
N3—C12	1.417 (5)	C8—C7	1.392 (5)
N4—C18	1.336 (5)	C8—H8A	0.9300
N4—C14	1.348 (5)	C6—C5	1.496 (5)
N5—N6	1.143 (4)	C10—C11	1.371 (6)
N6—N7	1.174 (5)	C10—H10A	0.9300
O1—C6	1.222 (4)	C16—C15	1.382 (6)
O2—C13	1.239 (4)	C16—H16A	0.9300
O3—C19	1.451 (5)	C15—H15A	0.9300
O3—H	0.849 (10)	C3—H3A	0.9300
C19—H19A	0.9600	C18—H18A	0.9300
C19—H19B	0.9600	C12—C11	1.389 (5)
C19—H19C	0.9600	C12—C7	1.408 (5)
C17—C16	1.374 (6)	C1—H1A	0.9300
C17—C18	1.380 (5)	C11—H11A	0.9300
C17—H17A	0.9300

N2—Mn1—N3	81.55 (13)	C8—C9—H9A	119.8
N2—Mn1—N1	80.87 (12)	C3—C2—C1	119.2 (4)
N3—Mn1—N1	161.63 (13)	C3—C2—H2A	120.4
N2—Mn1—N4	161.93 (12)	C1—C2—H2A	120.4
N3—Mn1—N4	80.85 (12)	C3—C4—C5	118.8 (4)
N1—Mn1—N4	116.19 (12)	C3—C4—H4A	120.6
N2—Mn1—N5	98.16 (13)	C5—C4—H4A	120.6
N3—Mn1—N5	98.81 (13)	C9—C8—C7	119.4 (4)
N1—Mn1—N5	88.92 (13)	C9—C8—H8A	120.3
N4—Mn1—N5	88.53 (12)	C7—C8—H8A	120.3
N2—Mn1—O3	94.67 (13)	O1—C6—N2	127.4 (4)
N3—Mn1—O3	94.08 (12)	O1—C6—C5	120.8 (3)
N1—Mn1—O3	82.11 (11)	N2—C6—C5	111.8 (3)
N4—Mn1—O3	82.57 (11)	C11—C10—C9	120.6 (4)
N5—Mn1—O3	162.99 (13)	C11—C10—H10A	119.7
C1—N1—C5	118.7 (3)	C9—C10—H10A	119.7
C1—N1—Mn1	129.0 (2)	C17—C16—C15	119.2 (4)
C5—N1—Mn1	112.3 (2)	C17—C16—H16A	120.4
C6—N2—C7	125.6 (3)	C15—C16—H16A	120.4
C6—N2—Mn1	118.4 (2)	C14—C15—C16	118.8 (4)
C7—N2—Mn1	115.8 (2)	C14—C15—H15A	120.6
C13—N3—C12	125.4 (3)	C16—C15—H15A	120.6
C13—N3—Mn1	118.5 (3)	C2—C3—C4	119.6 (4)
C12—N3—Mn1	116.0 (2)	C2—C3—H3A	120.2
C18—N4—C14	118.8 (3)	C4—C3—H3A	120.2
C18—N4—Mn1	129.4 (3)	N4—C18—C17	122.1 (4)
C14—N4—Mn1	111.5 (2)	N4—C18—H18A	119.0
N6—N5—Mn1	120.6 (3)	C17—C18—H18A	119.0
N5—N6—N7	178.3 (5)	C11—C12—C7	119.8 (4)
C19—O3—Mn1	129.3 (3)	C11—C12—N3	127.2 (4)
C19—O3—H	108 (5)	C7—C12—N3	112.9 (3)
Mn1—O3—H	102 (4)	N1—C1—C2	122.0 (4)
O3—C19—H19A	109.5	N1—C1—H1A	119.0
O3—C19—H19B	109.5	C2—C1—H1A	119.0
H19A—C19—H19B	109.5	C10—C11—C12	120.0 (4)
O3—C19—H19C	109.5	C10—C11—H11A	120.0
H19A—C19—H19C	109.5	C12—C11—H11A	120.0
H19B—C19—H19C	109.5	O2—C13—N3	127.1 (4)
C16—C17—C18	119.1 (4)	O2—C13—C14	120.5 (4)
C16—C17—H17A	120.4	N3—C13—C14	112.3 (3)
C18—C17—H17A	120.4	C8—C7—C12	119.8 (4)
N4—C14—C15	122.0 (4)	C8—C7—N2	126.5 (4)
N4—C14—C13	116.3 (3)	C12—C7—N2	113.7 (3)
C15—C14—C13	121.7 (4)	N1—C5—C4	121.8 (3)
C10—C9—C8	120.4 (4)	N1—C5—C6	115.8 (3)
C10—C9—H9A	119.8	C4—C5—C6	122.4 (3)

N2—Mn1—N1—C1	174.5 (3)	C10—C9—C8—C7	−1.2 (6)
N3—Mn1—N1—C1	157.5 (4)	C7—N2—C6—O1	−4.0 (6)
N4—Mn1—N1—C1	0.8 (4)	Mn1—N2—C6—O1	171.2 (3)
N5—Mn1—N1—C1	−87.1 (3)	C7—N2—C6—C5	175.3 (3)
O3—Mn1—N1—C1	78.4 (3)	Mn1—N2—C6—C5	−9.6 (4)
N2—Mn1—N1—C5	−5.0 (2)	C8—C9—C10—C11	0.3 (6)
N3—Mn1—N1—C5	−22.0 (5)	C18—C17—C16—C15	−0.3 (6)
N4—Mn1—N1—C5	−178.7 (2)	N4—C14—C15—C16	−0.2 (6)
N5—Mn1—N1—C5	93.5 (2)	C13—C14—C15—C16	−178.2 (4)
O3—Mn1—N1—C5	−101.0 (2)	C17—C16—C15—C14	0.2 (6)
N3—Mn1—N2—C6	−177.0 (3)	C1—C2—C3—C4	0.6 (6)
N1—Mn1—N2—C6	8.3 (3)	C5—C4—C3—C2	0.0 (6)
N4—Mn1—N2—C6	169.9 (3)	C14—N4—C18—C17	−0.3 (6)
N5—Mn1—N2—C6	−79.3 (3)	Mn1—N4—C18—C17	−173.8 (3)
O3—Mn1—N2—C6	89.5 (3)	C16—C17—C18—N4	0.4 (6)
N3—Mn1—N2—C7	−1.4 (3)	C13—N3—C12—C11	3.5 (6)
N1—Mn1—N2—C7	−176.1 (3)	Mn1—N3—C12—C11	−179.5 (3)
N4—Mn1—N2—C7	−14.5 (6)	C13—N3—C12—C7	−178.3 (3)
N5—Mn1—N2—C7	96.4 (3)	Mn1—N3—C12—C7	−1.4 (4)
O3—Mn1—N2—C7	−94.9 (3)	C5—N1—C1—C2	0.8 (6)
N2—Mn1—N3—C13	178.7 (3)	Mn1—N1—C1—C2	−178.6 (3)
N1—Mn1—N3—C13	−164.4 (3)	C3—C2—C1—N1	−1.0 (6)
N4—Mn1—N3—C13	−5.4 (3)	C9—C10—C11—C12	0.6 (6)
N5—Mn1—N3—C13	81.7 (3)	C7—C12—C11—C10	−0.6 (6)
O3—Mn1—N3—C13	−87.2 (3)	N3—C12—C11—C10	177.5 (4)
N2—Mn1—N3—C12	1.5 (3)	C12—N3—C13—O2	1.6 (6)
N1—Mn1—N3—C12	18.5 (5)	Mn1—N3—C13—O2	−175.3 (3)
N4—Mn1—N3—C12	177.5 (3)	C12—N3—C13—C14	179.9 (3)
N5—Mn1—N3—C12	−95.5 (3)	Mn1—N3—C13—C14	3.1 (4)
O3—Mn1—N3—C12	95.7 (3)	N4—C14—C13—O2	−178.5 (3)
N2—Mn1—N4—C18	−166.4 (4)	C15—C14—C13—O2	−0.4 (6)
N3—Mn1—N4—C18	−179.5 (3)	N4—C14—C13—N3	3.0 (5)
N1—Mn1—N4—C18	−6.7 (4)	C15—C14—C13—N3	−178.8 (3)
N5—Mn1—N4—C18	81.3 (3)	C9—C8—C7—C12	1.2 (6)
O3—Mn1—N4—C18	−84.1 (3)	C9—C8—C7—N2	−177.5 (4)
N2—Mn1—N4—C14	19.8 (5)	C11—C12—C7—C8	−0.3 (5)
N3—Mn1—N4—C14	6.7 (2)	N3—C12—C7—C8	−178.6 (3)
N1—Mn1—N4—C14	179.4 (2)	C11—C12—C7—N2	178.5 (3)
N5—Mn1—N4—C14	−92.5 (3)	N3—C12—C7—N2	0.2 (4)
O3—Mn1—N4—C14	102.1 (3)	C6—N2—C7—C8	−4.9 (6)
N2—Mn1—N5—N6	−85.4 (3)	Mn1—N2—C7—C8	179.8 (3)
N3—Mn1—N5—N6	−2.8 (3)	C6—N2—C7—C12	176.3 (3)
N1—Mn1—N5—N6	−166.0 (3)	Mn1—N2—C7—C12	1.1 (4)
N4—Mn1—N5—N6	77.7 (3)	C1—N1—C5—C4	−0.2 (5)
O3—Mn1—N5—N6	136.0 (4)	Mn1—N1—C5—C4	179.3 (3)
N2—Mn1—O3—C19	−39.4 (4)	C1—N1—C5—C6	−178.1 (3)
N3—Mn1—O3—C19	−121.2 (4)	Mn1—N1—C5—C6	1.4 (4)
N1—Mn1—O3—C19	40.7 (4)	C3—C4—C5—N1	−0.3 (6)
N4—Mn1—O3—C19	158.6 (4)	C3—C4—C5—C6	177.5 (4)
N5—Mn1—O3—C19	99.5 (5)	O1—C6—C5—N1	−175.8 (3)
C18—N4—C14—C15	0.3 (6)	N2—C6—C5—N1	4.9 (5)
Mn1—N4—C14—C15	174.8 (3)	O1—C6—C5—C4	6.3 (6)
C18—N4—C14—C13	178.4 (3)	N2—C6—C5—C4	−173.0 (3)
Mn1—N4—C14—C13	−7.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H···O2ⁱ	0.85 (1)	1.88 (2)	2.696 (4)	162 (6)

Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Mn(C₁₈H₁₂N₄O₂)(N₃)(CH₄O)]
M_r	445.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.115 (2), 9.4987 (19), 16.748 (3)
β (°)	95.94 (3)
V (Å³)	1917.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.14 × 0.14 × 0.14

Data collection
Diffractometer	Rigaku Saturn
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.905, 0.905
No. of measured, independent and observed [I > 2σ(I)] reflections	15658, 3406, 2957
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.159, 1.07
No. of reflections	3406
No. of parameters	269
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.52

Computer programs: CrystalClear (Rigaku, 2001), CrystalClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker (1997), CrystalStructure (Rigaku, 2001).