Bis[(2-pyrid­yl)(2-pyridyl­amino)­methano­lato]manganese(III) nitrate

Ding, S.; Xia, C.; Ji, Y.; Liu, Z.; Ding, Y.

doi:10.1107/S1600536811014371

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages m622-m623

doi:10.1107/S1600536811014371

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Bis[(2-pyridyl)(2-pyridylamino)methanolato]manganese(III) nitrate

Shuai Ding,^a Congjun Xia,^b Yufei Ji,^a Zhiliang Liu ^a ^* and Yong Ding ^b

^aCollege of Chemistry and Chemical Engineering, Inner Mongolia University, Hohhot 010021, People's Republic of China, and ^bYanzhou Coal Mining Logistics Company Ltd, People's Republic of China
^*Correspondence e-mail: cezlliu@imu.edu.cn

(Received 15 March 2011; accepted 16 April 2011; online 22 April 2011)

The Mn^III atom in the title complex, [Mn(C₁₁H₁₀N₃O)₂]NO₃, is coordinated by the two tridentate (2-pyridyl)(2-pyridylamino)methanolate ligands, forming a six-coordinate environment. The four pyridyl N atoms constitute the equatorial plane on which the manganese(III) ion lies; the coordination plane suffers a slight distortion as indicated by the average plane deviation of 0.058 Å. The methanolate O atoms occupy the axial positions. The coordination geometry is thus octahedral. In the title compound, the cations are linked by nitrate anions via N—H⋯O hydrogen bonds to form one-dimensional chains. Moreover, the one-dimensional structure is stabilized by intermolecular edge-to-face aromatic π–π interactions with a center-of-inversion at a distance of ca 4.634 Å.

Related literature

For related structures, see: Adams et al. (2005 ); Liu et al. (2008 ); Arulsamy & Hongson (1994 ).

Experimental

Crystal data

[Mn(C₁₁H₁₀N₃O)₂]NO₃
M_r = 517.39
Monoclinic, P 2₁ /c
a = 12.889 (3) Å
b = 10.931 (2) Å
c = 19.309 (6) Å
β = 123.34 (2)°
V = 2272.7 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 153 K
0.10 × 0.05 × 0.05 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.963, T_max = 0.969
16544 measured reflections
5743 independent reflections
4648 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.166
S = 1.07
5743 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 1.12 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn1—O2	1.8428 (17)
Mn1—O1	1.8488 (17)
Mn1—N6	2.111 (2)
Mn1—N4	2.139 (2)
Mn1—N3	2.179 (2)
Mn1—N5	2.202 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.86	2.08	2.931 (4)	171
N2—H2⋯O4ⁱⁱ	0.86	2.07	2.902 (4)	164
Symmetry codes: (i) x+1, y, z; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2006 ) and XP (Siemens, 1994 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014371/zk2005sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014371/zk2005Isup2.hkl

checkCIF report

Comment top

Selected bond distances and angles are given in Table 1. (2-pyridyl)(2-pyridylamino)-methanolato is a transmutative ligand. There is only four complexes with this ligand reported, such as those of Mn^III (Liu et al. 2008), Co^III (Adams et al. 2005) and Mn^III, Fe^III (Arulsamy & Hongson 1994). We report herein the synthesis and structure of the title compound. The crystal structure of the complex cation shows two tridentate (2-pyridyl)bis(2-pyridylamino)-methanolate ligands coordinated facially to the Mn^III ion to form a distorted octahedral geometry. The Mn^III resides on a pseudo-twofold axis of symmetry and on an equatorial plane formed by the pyridyl N atoms of the two ligands (Fig. 2, Table 2).

Related literature top

For related structures, see: Adams et al. (2005); Liu et al. (2008); Arulsamy & Hongson (1994).

Experimental top

L¹ was synthesized following literature procedures (Arulsamy & Hongson 1994). 50% Mn(NO₃)₂ (0.356 g, 1 mmol) was added to a solution of L¹ (0.277 g, 1 mmol) in ehanol (20 ml); a brown solution formed over time with continuous stirring at room temperature. This solution was left to evaporate slowly at room temperature. After one week, brown block crystals of the title compound were isolated (yield: 0.1662 g, 60%). Microanalysis found: C 50.91, H 3.89, N 18.90%; calculated for C₂₂H₂₀MnN₇O₅ (Mr = 517.39): C 51.02, H 3.86, N 18.94%.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2006) and XP (Siemens, 1994); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids.
	Fig. 2. Part of the crystal structure of the title compound showing hydrogen bond as dashed lines.
	Fig. 3. The formation of the title compound.

Bis[(2-pyridyl)(2-pyridylamino)methanolato]manganese(III) nitrate top

Crystal data top

[Mn(C₁₁H₁₀N₃O)₂]NO₃	F(000) = 1064
M_r = 517.39	D_x = 1.512 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.889 (3) Å	Cell parameters from 3732 reflections
b = 10.931 (2) Å	θ = 1.9–27.9°
c = 19.309 (6) Å	µ = 0.63 mm⁻¹
β = 123.34 (2)°	T = 153 K
V = 2272.7 (10) Å³	Block, brown
Z = 4	0.1 × 0.05 × 0.05 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5743 independent reflections
Radiation source: fine-focus sealed tube	4648 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 7.31 pixels mm^-1	θ_max = 28.5°, θ_min = 1.9°
ω and ϕ scans	h = −13→17
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −13→14
T_min = 0.963, T_max = 0.969	l = −25→25
16544 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.166	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.091P)² + 1.2493P] where P = (F_o² + 2F_c²)/3
5743 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 1.12 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Mn(C₁₁H₁₀N₃O)₂]NO₃	V = 2272.7 (10) Å³
M_r = 517.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.889 (3) Å	µ = 0.63 mm⁻¹
b = 10.931 (2) Å	T = 153 K
c = 19.309 (6) Å	0.1 × 0.05 × 0.05 mm
β = 123.34 (2)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	5743 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	4648 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.969	R_int = 0.021
16544 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.166	H-atom parameters constrained
S = 1.07	Δρ_max = 1.12 e Å⁻³
5743 reflections	Δρ_min = −0.47 e Å⁻³
316 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	0.91585 (3)	0.67947 (3)	0.65817 (2)	0.04290 (14)
O1	1.01651 (17)	0.54585 (15)	0.67793 (11)	0.0507 (4)
O2	0.81804 (17)	0.81050 (16)	0.64742 (13)	0.0530 (4)
N1	1.2075 (2)	0.6381 (2)	0.72255 (14)	0.0541 (5)
H1	1.2780	0.6098	0.7351	0.065*
N2	0.6572 (2)	0.7950 (2)	0.50627 (16)	0.0608 (6)
H2	0.5951	0.8410	0.4732	0.073*
N3	0.7563 (2)	0.5819 (2)	0.64167 (13)	0.0501 (5)
N4	0.8165 (2)	0.66973 (18)	0.52595 (14)	0.0485 (5)
N5	1.0588 (2)	0.79115 (19)	0.65910 (12)	0.0459 (4)
N6	1.0294 (2)	0.68841 (18)	0.78880 (13)	0.0461 (4)
C1	1.0262 (3)	0.9030 (2)	0.62310 (17)	0.0554 (6)
H1A	0.9486	0.9339	0.6065	0.066*
C2	1.1011 (3)	0.9718 (3)	0.6102 (2)	0.0674 (8)
H2A	1.0760	1.0486	0.5857	0.081*
C3	1.2157 (3)	0.9253 (3)	0.6342 (2)	0.0710 (8)
H3	1.2687	0.9709	0.6257	0.085*
C4	1.2511 (3)	0.8141 (3)	0.6699 (2)	0.0597 (7)
H4	1.3276	0.7816	0.6852	0.072*
C5	1.1708 (2)	0.7481 (2)	0.68361 (15)	0.0474 (5)
C6	1.1368 (2)	0.5659 (2)	0.74488 (15)	0.0479 (5)
H6	1.1777	0.4864	0.7648	0.058*
C7	1.1348 (2)	0.6272 (2)	0.81495 (15)	0.0453 (5)
C8	1.2290 (3)	0.6237 (3)	0.89677 (17)	0.0557 (6)
H8	1.3017	0.5810	0.9138	0.067*
C9	1.2149 (3)	0.6842 (3)	0.95381 (19)	0.0637 (7)
H9	1.2775	0.6820	1.0099	0.076*
C10	1.1077 (3)	0.7475 (3)	0.92669 (19)	0.0670 (8)
H10	1.0966	0.7894	0.9641	0.080*
C11	1.0163 (3)	0.7485 (3)	0.84341 (18)	0.0571 (6)
H11	0.9437	0.7923	0.8249	0.068*
C12	0.8687 (3)	0.6069 (3)	0.49241 (18)	0.0605 (7)
H12	0.9378	0.5586	0.5273	0.073*
C13	0.8261 (3)	0.6101 (3)	0.4106 (2)	0.0727 (9)
H13	0.8643	0.5650	0.3898	0.087*
C14	0.7234 (4)	0.6832 (3)	0.3591 (2)	0.0752 (9)
H14	0.6922	0.6884	0.3028	0.090*
C15	0.6696 (3)	0.7461 (3)	0.39065 (18)	0.0637 (7)
H15	0.6019	0.7963	0.3565	0.076*
C16	0.7153 (2)	0.7364 (2)	0.47519 (16)	0.0507 (6)
C17	0.6923 (2)	0.7859 (3)	0.59136 (18)	0.0541 (6)
H17	0.6442	0.8464	0.5999	0.065*
C18	0.6618 (3)	0.6604 (3)	0.60818 (18)	0.0539 (6)
C19	0.5459 (3)	0.6273 (4)	0.5890 (2)	0.0768 (9)
H19	0.4810	0.6834	0.5665	0.092*
C20	0.5287 (4)	0.5062 (4)	0.6047 (3)	0.0914 (12)
H20	0.4521	0.4810	0.5935	0.110*
C21	0.6239 (4)	0.4266 (4)	0.6359 (2)	0.0792 (10)
H21	0.6129	0.3454	0.6449	0.095*
C22	0.7368 (3)	0.4663 (3)	0.65425 (18)	0.0625 (7)
H22	0.8023	0.4110	0.6763	0.075*
O3	0.4514 (3)	0.5305 (4)	0.7831 (3)	0.1256 (13)
O4	0.4849 (5)	0.5147 (5)	0.9012 (3)	0.193 (3)
O5	0.5144 (4)	0.3663 (4)	0.8475 (3)	0.1308 (13)
N7	0.4830 (2)	0.4735 (3)	0.84692 (19)	0.0689 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0444 (2)	0.0363 (2)	0.0444 (2)	0.00432 (13)	0.02212 (17)	−0.00227 (13)
O1	0.0534 (9)	0.0371 (8)	0.0504 (9)	0.0062 (7)	0.0214 (8)	−0.0026 (7)
O2	0.0506 (9)	0.0411 (9)	0.0653 (11)	0.0031 (7)	0.0306 (9)	−0.0091 (8)
N1	0.0540 (12)	0.0532 (12)	0.0613 (13)	0.0145 (10)	0.0357 (11)	0.0103 (10)
N2	0.0547 (12)	0.0543 (13)	0.0662 (14)	0.0160 (10)	0.0287 (11)	0.0123 (11)
N3	0.0530 (11)	0.0481 (11)	0.0484 (11)	0.0031 (9)	0.0274 (9)	−0.0006 (9)
N4	0.0534 (11)	0.0406 (10)	0.0499 (11)	0.0042 (8)	0.0275 (10)	−0.0014 (8)
N5	0.0535 (11)	0.0407 (10)	0.0449 (10)	0.0065 (8)	0.0278 (9)	0.0018 (8)
N6	0.0521 (11)	0.0401 (10)	0.0481 (10)	0.0009 (8)	0.0288 (9)	0.0025 (8)
C1	0.0655 (16)	0.0454 (13)	0.0576 (14)	0.0096 (12)	0.0353 (13)	0.0061 (11)
C2	0.089 (2)	0.0502 (15)	0.0748 (19)	0.0079 (15)	0.0525 (18)	0.0130 (14)
C3	0.089 (2)	0.0633 (18)	0.084 (2)	−0.0020 (16)	0.062 (2)	0.0081 (16)
C4	0.0639 (16)	0.0626 (17)	0.0637 (17)	0.0020 (13)	0.0420 (14)	−0.0004 (13)
C5	0.0548 (13)	0.0470 (13)	0.0433 (12)	0.0044 (10)	0.0288 (10)	−0.0025 (9)
C6	0.0503 (12)	0.0384 (11)	0.0491 (12)	0.0090 (10)	0.0234 (10)	0.0040 (9)
C7	0.0508 (12)	0.0366 (11)	0.0483 (12)	−0.0019 (9)	0.0271 (10)	0.0040 (9)
C8	0.0529 (14)	0.0542 (15)	0.0511 (14)	−0.0022 (12)	0.0229 (11)	0.0059 (11)
C9	0.0701 (18)	0.0674 (18)	0.0454 (14)	−0.0106 (14)	0.0266 (13)	−0.0023 (12)
C10	0.087 (2)	0.0666 (19)	0.0558 (16)	−0.0055 (16)	0.0444 (16)	−0.0067 (14)
C11	0.0685 (16)	0.0524 (15)	0.0614 (16)	0.0036 (12)	0.0427 (14)	0.0024 (12)
C12	0.0697 (17)	0.0561 (16)	0.0582 (15)	0.0077 (13)	0.0368 (14)	−0.0045 (12)
C13	0.086 (2)	0.075 (2)	0.0596 (17)	0.0011 (17)	0.0414 (17)	−0.0122 (15)
C14	0.090 (2)	0.076 (2)	0.0496 (16)	−0.0095 (18)	0.0321 (16)	−0.0040 (14)
C15	0.0597 (16)	0.0601 (17)	0.0523 (15)	−0.0043 (13)	0.0187 (13)	0.0059 (12)
C16	0.0476 (12)	0.0407 (12)	0.0546 (14)	−0.0023 (10)	0.0222 (11)	0.0037 (10)
C17	0.0489 (13)	0.0466 (13)	0.0672 (16)	0.0091 (11)	0.0322 (12)	−0.0013 (12)
C18	0.0505 (13)	0.0545 (14)	0.0566 (14)	0.0037 (11)	0.0293 (12)	−0.0015 (11)
C19	0.0529 (16)	0.081 (2)	0.092 (2)	0.0022 (16)	0.0371 (17)	0.0055 (19)
C20	0.072 (2)	0.091 (3)	0.112 (3)	−0.022 (2)	0.050 (2)	−0.004 (2)
C21	0.086 (2)	0.067 (2)	0.074 (2)	−0.0146 (18)	0.0376 (18)	0.0082 (16)
C22	0.0710 (18)	0.0527 (15)	0.0560 (15)	0.0021 (13)	0.0300 (14)	0.0075 (12)
O3	0.088 (2)	0.123 (3)	0.140 (3)	0.014 (2)	0.046 (2)	0.044 (2)
O4	0.228 (5)	0.236 (5)	0.214 (5)	−0.173 (4)	0.183 (4)	−0.163 (4)
O5	0.141 (3)	0.109 (3)	0.160 (4)	0.031 (2)	0.094 (3)	0.033 (3)
N7	0.0434 (12)	0.0718 (18)	0.0776 (18)	−0.0087 (12)	0.0245 (12)	0.0023 (14)

Geometric parameters (Å, º) top

Mn1—O2	1.8428 (17)	C6—H6	0.9800
Mn1—O1	1.8488 (17)	C7—C8	1.365 (4)
Mn1—N6	2.111 (2)	C8—C9	1.380 (4)
Mn1—N4	2.139 (2)	C8—H8	0.9300
Mn1—N3	2.179 (2)	C9—C10	1.366 (5)
Mn1—N5	2.202 (2)	C9—H9	0.9300
O1—C6	1.385 (3)	C10—C11	1.375 (4)
O2—C17	1.393 (3)	C10—H10	0.9300
N1—C5	1.358 (3)	C11—H11	0.9300
N1—C6	1.439 (3)	C12—C13	1.358 (4)
N1—H1	0.8600	C12—H12	0.9300
N2—C16	1.352 (4)	C13—C14	1.390 (5)
N2—C17	1.448 (4)	C13—H13	0.9300
N2—H2	0.8601	C14—C15	1.338 (5)
N3—C18	1.332 (3)	C14—H14	0.9300
N3—C22	1.336 (4)	C15—C16	1.402 (4)
N4—C16	1.337 (3)	C15—H15	0.9300
N4—C12	1.351 (3)	C17—C18	1.511 (4)
N5—C5	1.333 (3)	C17—H17	0.9800
N5—C1	1.354 (3)	C18—C19	1.376 (4)
N6—C11	1.329 (3)	C19—C20	1.401 (6)
N6—C7	1.339 (3)	C19—H19	0.9300
C1—C2	1.350 (4)	C20—C21	1.346 (6)
C1—H1A	0.9300	C20—H20	0.9300
C2—C3	1.380 (5)	C21—C22	1.365 (5)
C2—H2A	0.9300	C21—H21	0.9300
C3—C4	1.348 (4)	C22—H22	0.9300
C3—H3	0.9300	O3—N7	1.233 (4)
C4—C5	1.401 (4)	O4—N7	1.129 (4)
C4—H4	0.9300	O5—N7	1.237 (5)
C6—C7	1.523 (3)

O2—Mn1—O1	175.06 (9)	C7—C6—H6	108.1
O2—Mn1—N6	94.63 (8)	N6—C7—C8	121.6 (2)
O1—Mn1—N6	80.96 (8)	N6—C7—C6	113.2 (2)
O2—Mn1—N4	88.88 (9)	C8—C7—C6	125.2 (2)
O1—Mn1—N4	95.67 (8)	C7—C8—C9	119.1 (3)
N6—Mn1—N4	174.62 (8)	C7—C8—H8	120.5
O2—Mn1—N3	80.32 (8)	C9—C8—H8	120.5
O1—Mn1—N3	98.18 (8)	C10—C9—C8	119.1 (3)
N6—Mn1—N3	100.15 (8)	C10—C9—H9	120.5
N4—Mn1—N3	84.45 (9)	C8—C9—H9	120.5
O2—Mn1—N5	95.03 (8)	C9—C10—C11	119.2 (3)
O1—Mn1—N5	86.97 (8)	C9—C10—H10	120.4
N6—Mn1—N5	86.39 (8)	C11—C10—H10	120.4
N4—Mn1—N5	89.24 (8)	N6—C11—C10	121.5 (3)
N3—Mn1—N5	172.21 (8)	N6—C11—H11	119.2
C6—O1—Mn1	111.44 (14)	C10—C11—H11	119.2
C17—O2—Mn1	111.68 (15)	N4—C12—C13	123.7 (3)
C5—N1—C6	124.5 (2)	N4—C12—H12	118.2
C5—N1—H1	117.9	C13—C12—H12	118.2
C6—N1—H1	117.6	C12—C13—C14	117.7 (3)
C16—N2—C17	124.6 (2)	C12—C13—H13	121.1
C16—N2—H2	117.6	C14—C13—H13	121.1
C17—N2—H2	117.8	C15—C14—C13	119.8 (3)
C18—N3—C22	119.0 (3)	C15—C14—H14	120.1
C18—N3—Mn1	107.03 (18)	C13—C14—H14	120.1
C22—N3—Mn1	133.9 (2)	C14—C15—C16	120.0 (3)
C16—N4—C12	117.9 (2)	C14—C15—H15	120.0
C16—N4—Mn1	123.43 (18)	C16—C15—H15	120.0
C12—N4—Mn1	117.92 (19)	N4—C16—N2	119.2 (2)
C5—N5—C1	118.1 (2)	N4—C16—C15	120.8 (3)
C5—N5—Mn1	123.03 (17)	N2—C16—C15	120.0 (3)
C1—N5—Mn1	118.31 (18)	O2—C17—N2	111.9 (2)
C11—N6—C7	119.5 (2)	O2—C17—C18	109.7 (2)
C11—N6—Mn1	131.58 (19)	N2—C17—C18	110.5 (2)
C7—N6—Mn1	108.72 (16)	O2—C17—H17	108.2
C2—C1—N5	123.1 (3)	N2—C17—H17	108.2
C2—C1—H1A	118.5	C18—C17—H17	108.2
N5—C1—H1A	118.5	N3—C18—C19	121.9 (3)
C1—C2—C3	118.4 (3)	N3—C18—C17	114.4 (2)
C1—C2—H2A	120.8	C19—C18—C17	123.6 (3)
C3—C2—H2A	120.8	C18—C19—C20	117.9 (3)
C4—C3—C2	120.2 (3)	C18—C19—H19	121.1
C4—C3—H3	119.9	C20—C19—H19	121.1
C2—C3—H3	119.9	C21—C20—C19	119.6 (3)
C3—C4—C5	118.9 (3)	C21—C20—H20	120.2
C3—C4—H4	120.6	C19—C20—H20	120.2
C5—C4—H4	120.6	C20—C21—C22	119.3 (3)
N5—C5—N1	119.2 (2)	C20—C21—H21	120.3
N5—C5—C4	121.3 (2)	C22—C21—H21	120.3
N1—C5—C4	119.4 (2)	N3—C22—C21	122.2 (3)
O1—C6—N1	112.0 (2)	N3—C22—H22	118.9
O1—C6—C7	110.0 (2)	C21—C22—H22	118.9
N1—C6—C7	110.3 (2)	O4—N7—O3	123.5 (5)
O1—C6—H6	108.1	O4—N7—O5	122.0 (5)
N1—C6—H6	108.1	O3—N7—O5	114.5 (4)

O2—Mn1—O1—C6	−62.4 (10)	C1—N5—C5—C4	−2.4 (4)
N6—Mn1—O1—C6	−35.28 (17)	Mn1—N5—C5—C4	168.7 (2)
N4—Mn1—O1—C6	140.48 (17)	C6—N1—C5—N5	−4.3 (4)
N3—Mn1—O1—C6	−134.33 (17)	C6—N1—C5—C4	175.8 (2)
N5—Mn1—O1—C6	51.54 (17)	C3—C4—C5—N5	2.7 (4)
O1—Mn1—O2—C17	−108.0 (10)	C3—C4—C5—N1	−177.4 (3)
N6—Mn1—O2—C17	−134.89 (19)	Mn1—O1—C6—N1	−80.4 (2)
N4—Mn1—O2—C17	49.19 (19)	Mn1—O1—C6—C7	42.7 (2)
N3—Mn1—O2—C17	−35.37 (19)	C5—N1—C6—O1	53.1 (3)
N5—Mn1—O2—C17	138.33 (19)	C5—N1—C6—C7	−69.9 (3)
O2—Mn1—N3—C18	18.63 (18)	C11—N6—C7—C8	0.9 (4)
O1—Mn1—N3—C18	−166.13 (18)	Mn1—N6—C7—C8	176.2 (2)
N6—Mn1—N3—C18	111.65 (18)	C11—N6—C7—C6	−178.6 (2)
N4—Mn1—N3—C18	−71.18 (18)	Mn1—N6—C7—C6	−3.2 (2)
N5—Mn1—N3—C18	−35.1 (6)	O1—C6—C7—N6	−23.8 (3)
O2—Mn1—N3—C22	−165.0 (3)	N1—C6—C7—N6	100.3 (2)
O1—Mn1—N3—C22	10.2 (3)	O1—C6—C7—C8	156.8 (2)
N6—Mn1—N3—C22	−72.0 (3)	N1—C6—C7—C8	−79.1 (3)
N4—Mn1—N3—C22	105.2 (3)	N6—C7—C8—C9	0.3 (4)
N5—Mn1—N3—C22	141.3 (5)	C6—C7—C8—C9	179.6 (3)
O2—Mn1—N4—C16	−7.8 (2)	C7—C8—C9—C10	−0.9 (4)
O1—Mn1—N4—C16	170.3 (2)	C8—C9—C10—C11	0.5 (5)
N6—Mn1—N4—C16	−138.6 (8)	C7—N6—C11—C10	−1.3 (4)
N3—Mn1—N4—C16	72.6 (2)	Mn1—N6—C11—C10	−175.4 (2)
N5—Mn1—N4—C16	−102.8 (2)	C9—C10—C11—N6	0.6 (5)
O2—Mn1—N4—C12	162.2 (2)	C16—N4—C12—C13	1.7 (5)
O1—Mn1—N4—C12	−19.7 (2)	Mn1—N4—C12—C13	−168.8 (3)
N6—Mn1—N4—C12	31.3 (9)	N4—C12—C13—C14	0.5 (5)
N3—Mn1—N4—C12	−117.4 (2)	C12—C13—C14—C15	−0.7 (5)
N5—Mn1—N4—C12	67.1 (2)	C13—C14—C15—C16	−1.2 (5)
O2—Mn1—N5—C5	164.94 (19)	C12—N4—C16—N2	176.5 (3)
O1—Mn1—N5—C5	−10.53 (19)	Mn1—N4—C16—N2	−13.5 (3)
N6—Mn1—N5—C5	70.60 (19)	C12—N4—C16—C15	−3.6 (4)
N4—Mn1—N5—C5	−106.25 (19)	Mn1—N4—C16—C15	166.3 (2)
N3—Mn1—N5—C5	−142.1 (5)	C17—N2—C16—N4	−3.6 (4)
O2—Mn1—N5—C1	−24.0 (2)	C17—N2—C16—C15	176.5 (3)
O1—Mn1—N5—C1	160.53 (19)	C14—C15—C16—N4	3.5 (4)
N6—Mn1—N5—C1	−118.35 (19)	C14—C15—C16—N2	−176.6 (3)
N4—Mn1—N5—C1	64.80 (19)	Mn1—O2—C17—N2	−77.3 (2)
N3—Mn1—N5—C1	28.9 (7)	Mn1—O2—C17—C18	45.6 (3)
O2—Mn1—N6—C11	13.3 (2)	C16—N2—C17—O2	52.2 (4)
O1—Mn1—N6—C11	−164.4 (2)	C16—N2—C17—C18	−70.3 (3)
N4—Mn1—N6—C11	143.9 (8)	C22—N3—C18—C19	2.5 (4)
N3—Mn1—N6—C11	−67.7 (2)	Mn1—N3—C18—C19	179.5 (3)
N5—Mn1—N6—C11	108.1 (2)	C22—N3—C18—C17	−176.0 (2)
O2—Mn1—N6—C7	−161.26 (16)	Mn1—N3—C18—C17	1.0 (3)
O1—Mn1—N6—C7	20.99 (16)	O2—C17—C18—N3	−28.3 (3)
N4—Mn1—N6—C7	−30.6 (9)	N2—C17—C18—N3	95.6 (3)
N3—Mn1—N6—C7	117.77 (16)	O2—C17—C18—C19	153.3 (3)
N5—Mn1—N6—C7	−66.51 (16)	N2—C17—C18—C19	−82.9 (4)
C5—N5—C1—C2	0.8 (4)	N3—C18—C19—C20	−1.0 (5)
Mn1—N5—C1—C2	−170.7 (2)	C17—C18—C19—C20	177.3 (3)
N5—C1—C2—C3	0.6 (5)	C18—C19—C20—C21	−1.3 (6)
C1—C2—C3—C4	−0.2 (5)	C19—C20—C21—C22	2.0 (6)
C2—C3—C4—C5	−1.3 (5)	C18—N3—C22—C21	−1.7 (4)
C1—N5—C5—N1	177.7 (2)	Mn1—N3—C22—C21	−177.7 (2)
Mn1—N5—C5—N1	−11.3 (3)	C20—C21—C22—N3	−0.5 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.08	2.931 (4)	171
N2—H2···O4ⁱⁱ	0.86	2.07	2.902 (4)	164

Symmetry codes: (i) x+1, y, z; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Mn(C₁₁H₁₀N₃O)₂]NO₃
M_r	517.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	153
a, b, c (Å)	12.889 (3), 10.931 (2), 19.309 (6)
β (°)	123.34 (2)
V (Å³)	2272.7 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.1 × 0.05 × 0.05

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.963, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	16544, 5743, 4648
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.166, 1.07
No. of reflections	5743
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.12, −0.47

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2006) and XP (Siemens, 1994), publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

Mn1—O2	1.8428 (17)	Mn1—N4	2.139 (2)
Mn1—O1	1.8488 (17)	Mn1—N3	2.179 (2)
Mn1—N6	2.111 (2)	Mn1—N5	2.202 (2)

O2—Mn1—O1	175.06 (9)	N6—Mn1—N3	100.15 (8)
O2—Mn1—N6	94.63 (8)	N4—Mn1—N3	84.45 (9)
O1—Mn1—N6	80.96 (8)	O2—Mn1—N5	95.03 (8)
O2—Mn1—N4	88.88 (9)	O1—Mn1—N5	86.97 (8)
O1—Mn1—N4	95.67 (8)	N6—Mn1—N5	86.39 (8)
N6—Mn1—N4	174.62 (8)	N4—Mn1—N5	89.24 (8)
O2—Mn1—N3	80.32 (8)	N3—Mn1—N5	172.21 (8)
O1—Mn1—N3	98.18 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.08	2.931 (4)	170.5
N2—H2···O4ⁱⁱ	0.86	2.07	2.902 (4)	164.0

Symmetry codes: (i) x+1, y, z; (ii) x, −y+3/2, z−1/2.

Acknowledgements

Financial support by the NSFC (grant Nos. 20761004 and 21061009) and the Inner Mongolia Autonomous Region Fund for Natural Science (grant No. 2010MS0201) is gratefully acknowledged. This work was supported by the `211 project' postgraduate student programme of Inner Mongolia University.

References

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