Aqua-azido-{2,2'-[o-phenylenebis(nitrilo-methyl-idyne)]diphenolato}manganese(III) hemihydrate.

In the title compound, [Mn(C(20)H(14)N(2)O(2))(N(3))(H(2)O)]·0.5H(2)O, the Mn(III) ion is chelated by the N,N',O,O'-tetra-dentate Schiff base ligand and further coordinated by one azide ion and one water mol-ecule in trans positions, resulting in a distorted fac-MnN(3)O(3) octa-hedral arrangement. The O atom of the uncoordinated water mol-ecule lies on a crystallographic twofold axis. In the crystal, O-H⋯O and O-H⋯N hydrogen bonds help to establish the packing.

Related literature

For background to salicylaldehyde complexes, see: Alam et al. (2003 ▶); Zelewsky & von Knof (1999 ▶).

Experimental

Crystal data

[Mn(C20H14N2O2)(N3)(H2O)]·0.5H2O

M = 438.33

Monoclinic,

a = 25.100 (10) Å

b = 11.478 (5) Å

c = 12.599 (5) Å

β = 94.175 (3)°

V = 3620 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.77 mm−1

T = 293 K

0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.914, T max = 0.941

11927 measured reflections

3162 independent reflections

2371 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.086

S = 1.00

3162 reflections

280 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020200/hb2977sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020200/hb2977Isup2.hkl

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

[Mn(C20H14N2O2)(N3)(H2O)]·0.5H2O	F(000) = 1808
Mr = 438.33	Dx = 1.612 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2yc	Cell parameters from 3162 reflections
a = 25.10 (1) Å	θ = 3.0–25.0°
b = 11.478 (5) Å	µ = 0.77 mm−1
c = 12.599 (5) Å	T = 293 K
β = 94.175 (3)°	Block, pink
V = 3620 (3) Å3	0.12 × 0.10 × 0.08 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	3162 independent reflections
Radiation source: fine-focus sealed tube	2371 reflections with I > 2σ(I)
graphite	Rint = 0.082
φ and ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −27→29
Tmin = 0.914, Tmax = 0.941	k = −13→13
11927 measured reflections	l = −14→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.03P)2] where P = (Fo2 + 2Fc2)/3
3162 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.32 e Å−3
4 restraints	Δρmin = −0.38 e Å−3

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	0.204685 (15)	0.09791 (3)	0.87813 (3)	0.00903 (13)
C1	0.11631 (10)	0.2543 (2)	0.90445 (18)	0.0102 (6)
C2	0.09780 (10)	0.3688 (2)	0.90882 (19)	0.0124 (6)
H2	0.1219	0.4301	0.9061	0.015*
C3	0.04451 (10)	0.3928 (2)	0.91706 (19)	0.0156 (6)
H3	0.0332	0.4699	0.9196	0.019*
C4	0.00719 (10)	0.3029 (2)	0.9217 (2)	0.0180 (6)
H4	−0.0288	0.3197	0.9260	0.022*
C5	0.02444 (10)	0.1897 (2)	0.9198 (2)	0.0161 (6)
H5	−0.0002	0.1297	0.9238	0.019*
C6	0.07880 (10)	0.1623 (2)	0.91183 (18)	0.0110 (6)
C7	0.09346 (10)	0.0426 (2)	0.91314 (18)	0.0114 (6)
H7	0.0662	−0.0115	0.9188	0.014*
C8	0.15275 (10)	−0.1198 (2)	0.91053 (18)	0.0092 (6)
C9	0.11626 (10)	−0.2052 (2)	0.93648 (19)	0.0123 (6)
H9	0.0819	−0.1844	0.9525	0.015*
C10	0.13142 (10)	−0.3207 (2)	0.93819 (18)	0.0123 (6)
H10	0.1071	−0.3777	0.9553	0.015*
C11	0.18272 (10)	−0.3529 (2)	0.91454 (18)	0.0124 (6)
H11	0.1925	−0.4311	0.9157	0.015*
C12	0.21902 (10)	−0.2690 (2)	0.88938 (18)	0.0109 (6)
H12	0.2533	−0.2906	0.8736	0.013*
C13	0.20450 (10)	−0.1518 (2)	0.88751 (18)	0.0096 (5)
C14	0.28922 (10)	−0.0719 (2)	0.84750 (19)	0.0110 (6)
H14	0.3007	−0.1480	0.8385	0.013*
C15	0.32741 (10)	0.0188 (2)	0.83746 (18)	0.0111 (6)
C16	0.38034 (10)	−0.0164 (2)	0.82023 (18)	0.0145 (6)
H16	0.3878	−0.0954	0.8143	0.017*
C17	0.42059 (10)	0.0627 (2)	0.81212 (19)	0.0155 (6)
H17	0.4548	0.0377	0.7998	0.019*
C18	0.40976 (10)	0.1809 (2)	0.82255 (18)	0.0142 (6)
H18	0.4371	0.2350	0.8181	0.017*
C19	0.35893 (10)	0.2184 (2)	0.83938 (19)	0.0136 (6)
H19	0.3525	0.2978	0.8462	0.016*
C20	0.31675 (10)	0.1395 (2)	0.84649 (18)	0.0094 (6)
N1	0.23943 (8)	−0.05699 (18)	0.86829 (15)	0.0098 (5)
N2	0.14151 (8)	0.00196 (18)	0.90708 (15)	0.0092 (5)
N3	0.17896 (8)	0.07150 (19)	0.70029 (16)	0.0131 (5)
N4	0.13255 (9)	0.05323 (19)	0.67637 (16)	0.0136 (5)
N5	0.08768 (9)	0.0341 (2)	0.65186 (17)	0.0234 (6)
O1	0.16772 (7)	0.23708 (15)	0.89293 (13)	0.0127 (4)
O2	0.26797 (6)	0.18073 (15)	0.85790 (12)	0.0113 (4)
O1W	0.23229 (7)	0.08568 (17)	1.05761 (13)	0.0138 (4)
O2W	0.0000	−0.0960 (3)	0.7500	0.0383 (8)
H1W	0.2366 (10)	0.1525 (7)	1.0796 (16)	0.023 (9)*
H2W	0.2189 (11)	0.0413 (15)	1.0991 (14)	0.037 (10)*
H3W	0.0224 (11)	−0.056 (3)	0.723 (3)	0.064 (13)*

	U11	U22	U33	U12	U13	U23
Mn1	0.0082 (2)	0.0069 (2)	0.0122 (2)	−0.00022 (17)	0.00244 (16)	−0.00015 (16)
C1	0.0133 (14)	0.0136 (14)	0.0037 (13)	0.0011 (11)	0.0004 (10)	0.0013 (11)
C2	0.0163 (14)	0.0085 (14)	0.0124 (14)	0.0000 (11)	0.0008 (11)	0.0017 (11)
C3	0.0190 (15)	0.0117 (15)	0.0162 (15)	0.0046 (12)	0.0017 (12)	0.0029 (11)
C4	0.0105 (14)	0.0172 (16)	0.0271 (16)	0.0050 (12)	0.0059 (12)	0.0031 (13)
C5	0.0130 (14)	0.0117 (15)	0.0239 (16)	−0.0027 (11)	0.0035 (12)	0.0033 (12)
C6	0.0149 (14)	0.0083 (14)	0.0101 (14)	0.0023 (11)	0.0031 (11)	0.0004 (11)
C7	0.0121 (14)	0.0118 (15)	0.0105 (14)	−0.0045 (11)	0.0024 (11)	−0.0004 (11)
C8	0.0129 (14)	0.0080 (14)	0.0064 (13)	−0.0001 (11)	−0.0005 (10)	−0.0019 (10)
C9	0.0119 (14)	0.0114 (15)	0.0138 (14)	−0.0013 (11)	0.0035 (11)	−0.0016 (11)
C10	0.0159 (14)	0.0119 (15)	0.0092 (14)	−0.0046 (11)	0.0014 (11)	0.0001 (11)
C11	0.0205 (15)	0.0067 (14)	0.0093 (13)	0.0021 (11)	−0.0028 (11)	0.0002 (11)
C12	0.0129 (14)	0.0145 (15)	0.0052 (13)	0.0043 (11)	0.0005 (10)	−0.0027 (10)
C13	0.0124 (14)	0.0120 (14)	0.0042 (13)	−0.0028 (11)	−0.0007 (10)	−0.0015 (11)
C14	0.0142 (14)	0.0106 (15)	0.0082 (13)	0.0035 (11)	0.0011 (11)	0.0006 (10)
C15	0.0128 (14)	0.0144 (14)	0.0062 (13)	−0.0007 (11)	0.0016 (10)	0.0010 (11)
C16	0.0170 (15)	0.0162 (15)	0.0104 (14)	0.0038 (12)	0.0021 (11)	0.0012 (11)
C17	0.0069 (14)	0.0278 (17)	0.0119 (14)	0.0028 (12)	0.0011 (11)	0.0015 (12)
C18	0.0107 (14)	0.0240 (17)	0.0077 (14)	−0.0048 (12)	−0.0008 (11)	0.0009 (12)
C19	0.0193 (15)	0.0119 (15)	0.0095 (14)	−0.0023 (12)	−0.0006 (11)	−0.0023 (11)
C20	0.0082 (13)	0.0175 (15)	0.0026 (12)	0.0006 (11)	0.0005 (10)	0.0020 (11)
N1	0.0135 (12)	0.0086 (12)	0.0073 (11)	0.0005 (9)	0.0014 (9)	0.0004 (9)
N2	0.0118 (11)	0.0070 (12)	0.0088 (11)	0.0010 (9)	0.0018 (9)	0.0002 (9)
N3	0.0097 (12)	0.0190 (14)	0.0108 (12)	−0.0020 (9)	0.0013 (9)	0.0014 (9)
N4	0.0198 (14)	0.0138 (13)	0.0078 (12)	0.0027 (10)	0.0047 (10)	0.0002 (9)
N5	0.0122 (13)	0.0395 (17)	0.0183 (13)	0.0007 (12)	−0.0002 (10)	0.0000 (11)
O1	0.0099 (9)	0.0074 (10)	0.0213 (10)	−0.0001 (7)	0.0038 (7)	−0.0005 (8)
O2	0.0114 (9)	0.0097 (10)	0.0133 (10)	−0.0007 (8)	0.0037 (7)	0.0011 (8)
O1W	0.0192 (11)	0.0090 (11)	0.0133 (10)	−0.0039 (8)	0.0027 (8)	−0.0004 (9)
O2W	0.025 (2)	0.028 (2)	0.063 (2)	0.000	0.0130 (18)	0.000

Mn1—O1	1.8636 (18)	C10—H10	0.9300
Mn1—O2	1.8844 (18)	C11—C12	1.379 (3)
Mn1—N2	1.986 (2)	C11—H11	0.9300
Mn1—N1	1.988 (2)	C12—C13	1.393 (3)
Mn1—N3	2.306 (2)	C12—H12	0.9300
Mn1—O1W	2.321 (2)	C13—N1	1.430 (3)
C1—O1	1.324 (3)	C14—N1	1.307 (3)
C1—C2	1.397 (3)	C14—C15	1.427 (3)
C1—C6	1.422 (3)	C14—H14	0.9300
C2—C3	1.377 (3)	C15—C20	1.418 (4)
C2—H2	0.9300	C15—C16	1.420 (3)
C3—C4	1.398 (4)	C16—C17	1.367 (4)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.371 (4)	C17—C18	1.392 (4)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.411 (3)	C18—C19	1.378 (3)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.422 (4)	C19—C20	1.401 (3)
C7—N2	1.301 (3)	C19—H19	0.9300
C7—H7	0.9300	C20—O2	1.330 (3)
C8—C9	1.397 (3)	N3—N4	1.200 (3)
C8—C13	1.401 (3)	N4—N5	1.167 (3)
C8—N2	1.425 (3)	O1W—H1W	0.820 (11)
C9—C10	1.379 (4)	O1W—H2W	0.82 (2)
C9—H9	0.9300	O2W—H3W	0.82 (3)
C10—C11	1.393 (3)
O1—Mn1—O2	90.68 (8)	C11—C10—H10	119.7
O1—Mn1—N2	92.69 (8)	C12—C11—C10	120.0 (2)
O2—Mn1—N2	175.37 (8)	C12—C11—H11	120.0
O1—Mn1—N1	175.33 (8)	C10—C11—H11	120.0
O2—Mn1—N1	93.71 (8)	C11—C12—C13	120.1 (2)
N2—Mn1—N1	82.83 (9)	C11—C12—H12	119.9
O1—Mn1—N3	95.95 (8)	C13—C12—H12	119.9
O2—Mn1—N3	96.55 (7)	C12—C13—C8	119.7 (2)
N2—Mn1—N3	86.26 (8)	C12—C13—N1	125.1 (2)
N1—Mn1—N3	85.12 (8)	C8—C13—N1	115.1 (2)
O1—Mn1—O1W	94.00 (7)	N1—C14—C15	125.5 (2)
O2—Mn1—O1W	88.14 (7)	N1—C14—H14	117.2
N2—Mn1—O1W	88.47 (7)	C15—C14—H14	117.2
N1—Mn1—O1W	84.58 (7)	C20—C15—C16	118.3 (2)
N3—Mn1—O1W	168.94 (7)	C20—C15—C14	125.0 (2)
O1—C1—C2	118.3 (2)	C16—C15—C14	116.6 (2)
O1—C1—C6	123.5 (2)	C17—C16—C15	121.8 (3)
C2—C1—C6	118.2 (2)	C17—C16—H16	119.1
C3—C2—C1	121.3 (2)	C15—C16—H16	119.1
C3—C2—H2	119.4	C16—C17—C18	119.3 (2)
C1—C2—H2	119.4	C16—C17—H17	120.3
C2—C3—C4	120.9 (3)	C18—C17—H17	120.3
C2—C3—H3	119.6	C19—C18—C17	120.6 (2)
C4—C3—H3	119.6	C19—C18—H18	119.7
C5—C4—C3	119.1 (2)	C17—C18—H18	119.7
C5—C4—H4	120.5	C18—C19—C20	121.3 (3)
C3—C4—H4	120.5	C18—C19—H19	119.3
C4—C5—C6	121.4 (2)	C20—C19—H19	119.3
C4—C5—H5	119.3	O2—C20—C19	118.9 (2)
C6—C5—H5	119.3	O2—C20—C15	122.5 (2)
C5—C6—C1	119.2 (2)	C19—C20—C15	118.6 (2)
C5—C6—C7	117.7 (2)	C14—N1—C13	122.8 (2)
C1—C6—C7	123.1 (2)	C14—N1—Mn1	124.04 (18)
N2—C7—C6	125.9 (2)	C13—N1—Mn1	113.16 (16)
N2—C7—H7	117.1	C7—N2—C8	122.2 (2)
C6—C7—H7	117.1	C7—N2—Mn1	124.61 (18)
C9—C8—C13	119.9 (2)	C8—N2—Mn1	112.96 (15)
C9—C8—N2	124.3 (2)	N4—N3—Mn1	117.69 (16)
C13—C8—N2	115.8 (2)	N5—N4—N3	178.8 (3)
C10—C9—C8	119.6 (2)	C1—O1—Mn1	129.44 (16)
C10—C9—H9	120.2	C20—O2—Mn1	128.82 (16)
C8—C9—H9	120.2	Mn1—O1W—H1W	107.2 (17)
C9—C10—C11	120.7 (2)	Mn1—O1W—H2W	123.5 (18)
C9—C10—H10	119.7	H1W—O1W—H2W	114.6 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···N3i	0.82 (2)	2.12 (2)	2.937 (3)	176 (3)
O1W—H1W···O2ii	0.82 (1)	2.08 (1)	2.885 (3)	169 (2)
O2W—H3W···N5	0.82 (3)	2.18 (3)	3.000 (3)	173 (4)

Table 1

Selected bond lengths (Å)

Mn1—O1	1.8636 (18)
Mn1—O2	1.8844 (18)
Mn1—N2	1.986 (2)
Mn1—N1	1.988 (2)
Mn1—N3	2.306 (2)
Mn1—O1W	2.321 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W⋯N3i	0.82 (2)	2.12 (2)	2.937 (3)	176 (3)
O1W—H1W⋯O2ii	0.820 (11)	2.076 (6)	2.885 (3)	169 (2)
O2W—H3W⋯N5	0.82 (3)	2.18 (3)	3.000 (3)	173 (4)

Symmetry codes: (i) ; (ii) .