Azido-(methanol)[N,N'-(o-phenyl-ene)bis-(pyridine-2-carboxamidato)]manganese(III).

In the title complex, [Mn(C(18)H(12)N(4)O(2))(N(3))(CH(4)O)], the Mn(III) ion is in a distorted octa-hedral coordination environment. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds connect mol-ecules into centrosymmetric dimers.

Related literature

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

Crystal data

[Mn(C18H12N4O2)(N3)(CH4O)]

M = 445.33

Monoclinic,

a = 12.115 (2) Å

b = 9.4987 (19) Å

c = 16.748 (3) Å

β = 95.94 (3)°

V = 1917.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.73 mm−1

T = 293 (2) K

0.14 × 0.14 × 0.14 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (Jacobson, 1998 ▶) T min = 0.905, T max = 0.905

15658 measured reflections

3406 independent reflections

2957 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.159

S = 1.07

3406 reflections

269 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.52 e Å−3

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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807059211/lh2555sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807059211/lh2555Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Mn(C18H12N4O2)(N3)(CH4O)]	F000 = 912
Mr = 445.33	Dx = 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 = 1.2–27.8º
b = 9.4987 (19) Å	µ = 0.73 mm−1
c = 16.748 (3) Å	T = 293 (2) K
β = 95.94 (3)º	Prim, red
V = 1917.0 (6) Å3	0.14 × 0.14 × 0.14 mm
Z = 4

Rigaku Saturn diffractometer	3406 independent reflections
Radiation source: fine-focus sealed tube	2957 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.061
Detector resolution: 7.31 pixels mm-1	θmax = 25.1º
T = 293(2) K	θmin = 2.5º
ω scans	h = −14→14
Absorption correction: multi-scan(Jacobson, 1998)	k = −11→11
Tmin = 0.905, Tmax = 0.905	l = −19→19
15658 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.0859P)2 + 0.7977P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3406 reflections	Δρmax = 0.47 e Å−3
269 parameters	Δρmin = −0.52 e Å−3
7 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
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)

	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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H···O2i	0.849 (10)	1.88 (2)	2.696 (4)	162 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H⋯O2i	0.849 (10)	1.88 (2)	2.696 (4)	162 (6)

Symmetry code: (i) .