Bis(2-{[2-(2-hy-droxy-benzyl-amino)-eth-yl]amino-meth-yl}phenolato-κN,N',O)cobalt(III) nitrate monohydrate.

In the title compound, [Co(C(16)H(19)N(2)O(2))(2)]NO(3)·H(2)O, the Co(III) ion is located on an inversion center and is six-coordinated by two phenolate O atoms and four amino N atoms from two diamine ligands, forming an octa-hedral geometry. The water mol-ecule and the nitrate anion are located close to an inversion center, and are thus equally disordered by symmetry. The crystal packing is stabilized by inter-molecular O-H⋯O hydrogen bonds involving the uncoordinated water mol-ecule and the free phenol hydroxyl group with the nitrate anion. N-H⋯O hydrogen bonds involving the amino groups and the nitrate anions connect the complex mol-ecules along the c axis.

Related literature

For related structures, see: Zhou (2009 ▶); Zhang (2010 ▶); Khalaji et al. (2010 ▶).

Experimental

Crystal data

[Co(C16H19N2O2)2]NO3·H2O

M = 681.62

Triclinic,

a = 8.989 (3) Å

b = 9.032 (3) Å

c = 10.621 (4) Å

α = 106.680 (2)°

β = 99.950 (3)°

γ = 109.720 (2)°

V = 742.0 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.64 mm−1

T = 293 K

0.42 × 0.14 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.640, T max = 0.930

16124 measured reflections

2694 independent reflections

2303 reflections with I > 2σigma(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.126

S = 1.10

2689 reflections

234 parameters

29 restraints

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.48 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶) and DENZO (Otwinowski & Minor, 1997 ▶); cell refinement: COLLECT and DENZO; data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and CRYSTALBUILDER (Welter, 2006 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055851/bh2406sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055851/bh2406Isup2.hkl

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

[Co(C16H19N2O2)2]NO3·H2O	Z = 1
Mr = 681.62	F(000) = 358
Triclinic, P1	Dx = 1.525 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71070 Å
a = 8.989 (3) Å	Cell parameters from 2525 reflections
b = 9.032 (3) Å	θ = 0.4–25.4°
c = 10.621 (4) Å	µ = 0.64 mm−1
α = 106.680 (2)°	T = 293 K
β = 99.950 (3)°	Parallelepipedic stick, brown
γ = 109.720 (2)°	0.42 × 0.14 × 0.12 mm
V = 742.0 (4) Å3

Nonius KappaCCD diffractometer	2694 independent reflections
Radiation source: fine-focus sealed tube	2303 reflections with I > 2σigma(I)
horizontally mounted graphite crystal	Rint = 0.019
Detector resolution: 9 pixels mm-1	θmax = 25.7°, θmin = 2.8°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −10→10
Tmin = 0.640, Tmax = 0.930	l = −12→12
16124 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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0583P)2 + 0.3846P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2689 reflections	Δρmax = 0.25 e Å−3
234 parameters	Δρmin = −0.48 e Å−3
29 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.058 (9)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq	Occ. (<1)
Co1	0.5000	0.0000	0.5000	0.0525 (2)
O1	0.5163 (2)	0.1737 (3)	0.4297 (2)	0.0576 (5)
O2	−0.0155 (3)	−0.4955 (3)	0.1901 (3)	0.0811 (7)
H2O	−0.0938	−0.5812	0.1814	0.122*
N1	0.4113 (3)	0.0896 (3)	0.6449 (2)	0.0568 (6)
H1N	0.4568	0.0862	0.7215	0.068*
N2	0.2647 (3)	−0.1449 (3)	0.3863 (2)	0.0568 (6)
H2N	0.2543	−0.2386	0.3935	0.068*
C1	0.4130 (3)	0.2510 (4)	0.4369 (3)	0.0572 (7)
C2	0.3471 (4)	0.2816 (4)	0.3232 (3)	0.0631 (7)
H2	0.3774	0.2503	0.2435	0.076*
C3	0.2380 (4)	0.3575 (4)	0.3273 (4)	0.0705 (8)
H3	0.1945	0.3762	0.2502	0.085*
C4	0.1928 (4)	0.4059 (4)	0.4441 (4)	0.0735 (9)
H4	0.1179	0.4561	0.4461	0.088*
C5	0.2590 (4)	0.3796 (4)	0.5582 (4)	0.0700 (8)
H5	0.2302	0.4149	0.6381	0.084*
C6	0.3679 (4)	0.3016 (4)	0.5563 (3)	0.0602 (7)
C7	0.4394 (4)	0.2700 (4)	0.6785 (3)	0.0649 (8)
H7A	0.5575	0.3400	0.7142	0.078*
H7B	0.3898	0.3029	0.7501	0.078*
C8	0.2337 (3)	−0.0254 (4)	0.6089 (3)	0.0646 (8)
H8A	0.1770	0.0346	0.6580	0.077*
H8B	0.2245	−0.1213	0.6358	0.077*
C9	0.1554 (3)	−0.0863 (4)	0.4564 (3)	0.0632 (8)
H9A	0.0471	−0.1785	0.4286	0.076*
H9B	0.1419	0.0050	0.4320	0.076*
C10	0.2197 (3)	−0.1723 (4)	0.2372 (3)	0.0650 (8)
H10A	0.2601	−0.2527	0.1904	0.078*
H10B	0.2779	−0.0659	0.2277	0.078*
C11	0.0387 (3)	−0.2355 (4)	0.1642 (3)	0.0593 (7)
C12	−0.0188 (4)	−0.1310 (4)	0.1179 (3)	0.0673 (8)
H12	0.0539	−0.0202	0.1376	0.081*
C13	−0.1816 (4)	−0.1876 (5)	0.0434 (3)	0.0698 (8)
H13	−0.2187	−0.1153	0.0138	0.084*
C14	−0.2878 (4)	−0.3500 (4)	0.0135 (3)	0.0670 (8)
H14	−0.3973	−0.3893	−0.0388	0.080*
C15	−0.2359 (4)	−0.4569 (4)	0.0591 (3)	0.0644 (8)
H15	−0.3095	−0.5679	0.0380	0.077*
C16	−0.0727 (4)	−0.3981 (4)	0.1370 (3)	0.0602 (7)
O11	0.7320 (11)	0.1846 (10)	0.1338 (9)	0.123 (3)	0.50
N11	0.5877 (7)	0.0882 (8)	0.0550 (6)	0.0742 (14)	0.50
O12	0.5389 (14)	0.1116 (12)	−0.0485 (10)	0.104 (3)	0.50
O13	0.5023 (13)	−0.0330 (11)	0.0776 (11)	0.097 (3)	0.50
O21	0.7119 (11)	0.2509 (10)	0.2025 (9)	0.111 (3)	0.50
H21O	0.6490	0.1443	0.2054	0.167*	0.50
H22O	0.6628	0.2429	0.1127	0.167*	0.50

	U11	U22	U33	U12	U13	U23
Co1	0.0430 (3)	0.0580 (4)	0.0498 (3)	0.0179 (2)	0.0079 (2)	0.0177 (2)
O1	0.0520 (11)	0.0630 (12)	0.0589 (11)	0.0241 (9)	0.0139 (8)	0.0252 (9)
O2	0.0661 (14)	0.0758 (16)	0.0986 (18)	0.0311 (12)	0.0078 (13)	0.0361 (14)
N1	0.0479 (12)	0.0637 (15)	0.0515 (13)	0.0188 (11)	0.0079 (10)	0.0201 (11)
N2	0.0479 (12)	0.0655 (15)	0.0518 (13)	0.0213 (11)	0.0100 (10)	0.0201 (11)
C1	0.0450 (14)	0.0562 (16)	0.0628 (17)	0.0167 (12)	0.0093 (12)	0.0204 (13)
C2	0.0539 (16)	0.0654 (19)	0.0664 (18)	0.0210 (14)	0.0105 (13)	0.0281 (15)
C3	0.0584 (18)	0.073 (2)	0.080 (2)	0.0257 (16)	0.0103 (15)	0.0351 (17)
C4	0.0567 (18)	0.072 (2)	0.095 (3)	0.0299 (16)	0.0163 (17)	0.0352 (18)
C5	0.0600 (18)	0.0657 (19)	0.078 (2)	0.0246 (15)	0.0203 (15)	0.0201 (16)
C6	0.0527 (15)	0.0572 (17)	0.0623 (17)	0.0197 (13)	0.0107 (13)	0.0179 (13)
C7	0.0602 (17)	0.069 (2)	0.0585 (17)	0.0270 (15)	0.0133 (13)	0.0152 (14)
C8	0.0470 (15)	0.081 (2)	0.0590 (17)	0.0194 (14)	0.0154 (12)	0.0248 (15)
C9	0.0418 (14)	0.076 (2)	0.0610 (17)	0.0170 (13)	0.0119 (12)	0.0208 (15)
C10	0.0478 (15)	0.080 (2)	0.0512 (16)	0.0180 (14)	0.0062 (12)	0.0179 (14)
C11	0.0480 (15)	0.0691 (19)	0.0486 (15)	0.0186 (14)	0.0071 (11)	0.0158 (13)
C12	0.0589 (17)	0.070 (2)	0.0611 (18)	0.0168 (15)	0.0104 (14)	0.0232 (15)
C13	0.0622 (18)	0.080 (2)	0.0670 (19)	0.0297 (17)	0.0109 (15)	0.0320 (17)
C14	0.0483 (15)	0.087 (2)	0.0565 (17)	0.0240 (16)	0.0074 (13)	0.0230 (16)
C15	0.0514 (16)	0.0666 (19)	0.0599 (17)	0.0169 (14)	0.0086 (13)	0.0155 (14)
C16	0.0531 (16)	0.0650 (18)	0.0565 (16)	0.0243 (14)	0.0101 (12)	0.0178 (14)
O11	0.129 (6)	0.083 (5)	0.122 (7)	0.026 (4)	−0.011 (5)	0.041 (5)
N11	0.070 (3)	0.073 (4)	0.079 (4)	0.027 (3)	0.021 (3)	0.032 (3)
O12	0.113 (7)	0.107 (7)	0.078 (5)	0.028 (6)	0.011 (4)	0.044 (5)
O13	0.094 (5)	0.089 (6)	0.090 (5)	0.012 (4)	0.018 (4)	0.042 (5)
O21	0.100 (5)	0.081 (5)	0.134 (7)	0.017 (4)	0.016 (5)	0.050 (5)

Co1—O1i	1.896 (2)	N11—O13	1.222 (9)
Co1—O1	1.896 (2)	N11—O13ii	1.348 (12)
Co1—N1i	1.950 (2)	N11—N11ii	1.728 (12)
Co1—N1	1.950 (2)	N11—O12ii	1.753 (10)
Co1—N2i	1.997 (2)	O12—O13ii	0.627 (11)
Co1—N2	1.997 (2)	O12—N11ii	1.753 (10)
O1—C1	1.337 (3)	O13—O12ii	0.627 (11)
O2—C16	1.358 (4)	O13—N11ii	1.348 (12)
N1—C7	1.484 (4)	O2—H2O	0.8200
N1—C8	1.488 (4)	N1—H1N	0.8595
N2—C9	1.475 (4)	N2—H2N	0.8468
N2—C10	1.490 (4)	C2—H2	0.9300
C1—C2	1.393 (4)	C3—H3	0.9300
C1—C6	1.397 (4)	C4—H4	0.9300
C2—C3	1.373 (4)	C5—H5	0.9300
C3—C4	1.370 (5)	C7—H7A	0.9700
C4—C5	1.375 (5)	C7—H7B	0.9700
C5—C6	1.385 (4)	C8—H8A	0.9700
C6—C7	1.493 (4)	C8—H8B	0.9700
C8—C9	1.502 (4)	C9—H9A	0.9700
C10—C11	1.502 (4)	C9—H9B	0.9700
C11—C12	1.381 (4)	C10—H10A	0.9700
C11—C16	1.381 (4)	C10—H10B	0.9700
C12—C13	1.375 (4)	C12—H12	0.9300
C13—C14	1.359 (5)	C13—H13	0.9300
C14—C15	1.371 (5)	C14—H14	0.9300
C15—C16	1.386 (4)	C15—H15	0.9300
O11—N11	1.259 (9)	O21—H21O	0.9503
N11—O12	1.214 (11)	O21—H22O	0.9504
O1i—Co1—O1	180	O12—N11—O11	118.7 (8)
O1i—Co1—N1i	94.28 (10)	O13—N11—O11	120.6 (8)
O1—Co1—N1i	85.72 (10)	C16—O2—H2O	109.5
O1i—Co1—N1	85.72 (9)	C7—N1—H1N	104.3
O1—Co1—N1	94.28 (10)	C8—N1—H1N	104.2
N1i—Co1—N1	180	Co1—N1—H1N	111.3
O1i—Co1—N2i	93.87 (9)	C9—N2—H2N	107.1
O1—Co1—N2i	86.13 (9)	C10—N2—H2N	108.3
N1i—Co1—N2i	86.32 (10)	Co1—N2—H2N	100.6
N1—Co1—N2i	93.68 (9)	C3—C2—H2	119.6
O1i—Co1—N2	86.13 (9)	C1—C2—H2	119.6
O1—Co1—N2	93.87 (9)	C4—C3—H3	119.8
N1i—Co1—N2	93.68 (9)	C2—C3—H3	119.8
N1—Co1—N2	86.32 (10)	C3—C4—H4	120.3
N2i—Co1—N2	180	C5—C4—H4	120.3
C1—O1—Co1	122.22 (18)	C4—C5—H5	119.4
C7—N1—C8	113.1 (2)	C6—C5—H5	119.4
C7—N1—Co1	114.85 (19)	N1—C7—H7A	109.1
C8—N1—Co1	108.49 (18)	C6—C7—H7A	109.1
C9—N2—C10	112.6 (2)	N1—C7—H7B	109.1
C9—N2—Co1	109.04 (17)	C6—C7—H7B	109.1
C10—N2—Co1	117.92 (18)	H7A—C7—H7B	107.9
O1—C1—C2	119.8 (3)	N1—C8—H8A	109.8
O1—C1—C6	121.5 (3)	C9—C8—H8A	109.8
C2—C1—C6	118.6 (3)	N1—C8—H8B	109.8
C3—C2—C1	120.8 (3)	C9—C8—H8B	109.8
C4—C3—C2	120.5 (3)	H8A—C8—H8B	108.3
C3—C4—C5	119.5 (3)	N2—C9—H9A	110.1
C4—C5—C6	121.2 (3)	C8—C9—H9A	110.1
C5—C6—C1	119.4 (3)	N2—C9—H9B	110.1
C5—C6—C7	122.0 (3)	C8—C9—H9B	110.1
C1—C6—C7	118.7 (3)	H9A—C9—H9B	108.4
N1—C7—C6	112.3 (2)	N2—C10—H10A	108.2
N1—C8—C9	109.2 (2)	C11—C10—H10A	108.2
N2—C9—C8	108.0 (2)	N2—C10—H10B	108.2
N2—C10—C11	116.5 (2)	C11—C10—H10B	108.2
C12—C11—C16	118.2 (3)	H10A—C10—H10B	107.3
C12—C11—C10	119.6 (3)	C13—C12—H12	119.3
C16—C11—C10	122.1 (3)	C11—C12—H12	119.3
C13—C12—C11	121.3 (3)	C14—C13—H13	120.3
C14—C13—C12	119.4 (3)	C12—C13—H13	120.3
C13—C14—C15	121.0 (3)	C13—C14—H14	119.5
C14—C15—C16	119.4 (3)	C15—C14—H14	119.5
O2—C16—C11	117.3 (3)	C14—C15—H15	120.3
O2—C16—C15	122.2 (3)	C16—C15—H15	120.3
C11—C16—C15	120.6 (3)	H21O—O21—H22O	104.1
O12—N11—O13	120.6 (8)
N1i—Co1—O1—C1	149.8 (2)	C7—N1—C8—C9	90.2 (3)
N1—Co1—O1—C1	−30.2 (2)	Co1—N1—C8—C9	−38.5 (3)
N2i—Co1—O1—C1	−123.6 (2)	C10—N2—C9—C8	−167.3 (3)
N2—Co1—O1—C1	56.4 (2)	Co1—N2—C9—C8	−34.4 (3)
O1i—Co1—N1—C7	161.25 (19)	N1—C8—C9—N2	48.1 (3)
O1—Co1—N1—C7	−18.75 (19)	C9—N2—C10—C11	−33.9 (4)
N2i—Co1—N1—C7	67.64 (19)	Co1—N2—C10—C11	−162.3 (2)
N2—Co1—N1—C7	−112.36 (19)	N2—C10—C11—C12	112.2 (3)
O1i—Co1—N1—C8	−71.16 (19)	N2—C10—C11—C16	−70.1 (4)
O1—Co1—N1—C8	108.84 (19)	C16—C11—C12—C13	−1.8 (5)
N2i—Co1—N1—C8	−164.77 (19)	C10—C11—C12—C13	176.0 (3)
N2—Co1—N1—C8	15.23 (19)	C11—C12—C13—C14	−0.7 (5)
O1i—Co1—N2—C9	96.9 (2)	C12—C13—C14—C15	1.5 (5)
O1—Co1—N2—C9	−83.1 (2)	C13—C14—C15—C16	0.0 (5)
N1i—Co1—N2—C9	−169.1 (2)	C12—C11—C16—O2	−176.4 (3)
N1—Co1—N2—C9	10.9 (2)	C10—C11—C16—O2	5.8 (4)
O1i—Co1—N2—C10	−133.0 (2)	C12—C11—C16—C15	3.4 (4)
O1—Co1—N2—C10	47.0 (2)	C10—C11—C16—C15	−174.4 (3)
N1i—Co1—N2—C10	−39.0 (2)	C14—C15—C16—O2	177.2 (3)
N1—Co1—N2—C10	141.0 (2)	C14—C15—C16—C11	−2.5 (5)
Co1—O1—C1—C2	−136.5 (2)	O13—N11—O12—O13ii	−29 (3)
Co1—O1—C1—C6	43.1 (3)	O11—N11—O12—O13ii	147 (2)
O1—C1—C2—C3	178.6 (3)	N11ii—N11—O12—O13ii	−18 (2)
C6—C1—C2—C3	−1.0 (5)	O12ii—N11—O12—O13ii	−18 (2)
C1—C2—C3—C4	0.5 (5)	O13—N11—O12—N11ii	−10.6 (13)
C2—C3—C4—C5	0.7 (5)	O11—N11—O12—N11ii	164.8 (9)
C3—C4—C5—C6	−1.5 (5)	O13ii—N11—O12—N11ii	18 (2)
C4—C5—C6—C1	0.9 (5)	O12ii—N11—O12—N11ii	0.0
C4—C5—C6—C7	−179.2 (3)	O12—N11—O13—O12ii	49 (5)
O1—C1—C6—C5	−179.3 (3)	O11—N11—O13—O12ii	−127 (4)
C2—C1—C6—C5	0.3 (4)	O13ii—N11—O13—O12ii	36 (4)
O1—C1—C6—C7	0.8 (4)	N11ii—N11—O13—O12ii	36 (4)
C2—C1—C6—C7	−179.6 (3)	O12—N11—O13—N11ii	12.9 (16)
C8—N1—C7—C6	−67.3 (3)	O11—N11—O13—N11ii	−162.4 (9)
Co1—N1—C7—C6	57.9 (3)	O13ii—N11—O13—N11ii	0.0
C5—C6—C7—N1	126.1 (3)	O12ii—N11—O13—N11ii	−36 (4)
C1—C6—C7—N1	−54.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21O···O12ii	0.95	2.27	3.025 (12)	136.
O21—H22O···O13ii	0.95	2.18	2.922 (13)	134.
O2—H2O···O21iii	0.82	1.99	2.787 (9)	165.
O2—H2O···O11iii	0.82	2.01	2.823 (9)	169.
N1—H1N···O12iv	0.86	2.35	3.185 (10)	165.
N1—H1N···O13i	0.86	2.31	3.145 (11)	163.

Table 1

Selected geometric parameters (Å, °)

Co1—O1	1.896 (2)
Co1—N1	1.950 (2)
Co1—N2	1.997 (2)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O21—H21O⋯O12ii	0.95	2.27	3.025 (12)	136
O21—H22O⋯O13ii	0.95	2.18	2.922 (13)	134
O2—H2O⋯O21iii	0.82	1.99	2.787 (9)	165
O2—H2O⋯O11iii	0.82	2.01	2.823 (9)	169
N1—H1N⋯O12iv	0.86	2.35	3.185 (10)	165
N1—H1N⋯O13i	0.86	2.31	3.145 (11)	163

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .