(4,5-Diaza-fluoren-9-one-κN,N')bis-(1H-imidazole-κN)bis-(thio-cyanato-κN)cobalt(II).

In the title complex, [Co(NCS)(2)(C(3)H(4)N(2))(2)(C(11)H(6)N(2)O)], the Co(II) atom has a distorted octa-hedral coordination with the N atoms of the 4,5-diaza-fluoren-9-one ligand and two N atoms from imidazole ligands in the equatorial positions and the axial sites occupied by two N atoms of the thio-cyanate ligand. Inter-molecular N-H⋯O hydrogen bonding forms a one-dimensional motif parallel to the cell ab diagonal.

Related literature

For related structures, see: Notash et al. (2011 ▶); Xu et al. (2009 ▶). For general background to metal complexes with n class="Chemical">diazafluoren-9-one ligands, see: Biju & Rajasekharan (2008 ▶); Zhang & Li (2009 ▶). For a related structure, see: Yang et al. (2004 ▶).

Experimental

Crystal data

[Co(NCS)2(C3H4N2)2(C11n class="Species">H6N2O)]

M = 493.43

Triclinic,

a = 9.2239 (9) Å

b = 10.920 (1) Å

c = 11.9441 (12) Å

α = 71.578 (1)°

β = 70.582 (1)°

γ = 73.931 (2)°

V = 1056.48 (18) Å3

Z = 2

Mo Kα radiation

μ = 1.04 mm−1

T = 298 K

0.35 × 0.33 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.712, T max = 0.746

5357 measured reflections

3633 independent reflections

2208 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.192

S = 1.06

3633 reflections

280 parameters

H-atom parameters constrained

Δρmax = 1.10 e Å−3

Δρmin = −0.50 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536811029060/qm2016sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029060/qm2016Isup2.hkl

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

[Co(NCS)2(C3H4N2)2(C11H6N2O)]	Z = 2
Mr = 493.43	F(000) = 502
Triclinic, P1	Dx = 1.551 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2239 (9) Å	Cell parameters from 1602 reflections
b = 10.920 (1) Å	θ = 2.4–22.9°
c = 11.9441 (12) Å	µ = 1.04 mm−1
α = 71.578 (1)°	T = 298 K
β = 70.582 (1)°	Block, red
γ = 73.931 (2)°	0.35 × 0.33 × 0.30 mm
V = 1056.48 (18) Å3

Bruker SMART CCD area-detector diffractometer	3633 independent reflections
Radiation source: fine-focus sealed tube	2208 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.712, Tmax = 0.746	k = −12→10
5357 measured reflections	l = −14→11

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.192	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0844P)2 + 0.3689P] where P = (Fo2 + 2Fc2)/3
3633 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 1.10 e Å−3
0 restraints	Δρmin = −0.50 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
Co1	0.20940 (9)	0.77893 (7)	0.26794 (7)	0.0446 (3)
N1	0.3058 (5)	0.5787 (4)	0.3693 (4)	0.0460 (12)
N2	0.4108 (6)	0.7047 (5)	0.1105 (4)	0.0478 (12)
N3	0.0422 (6)	0.8171 (5)	0.4280 (5)	0.0497 (12)
N4	−0.1818 (7)	0.8644 (6)	0.5558 (6)	0.0788 (18)
H4	−0.2815	0.8844	0.5855	0.095*
N5	0.1501 (6)	0.9610 (5)	0.1485 (4)	0.0491 (12)
N6	0.0312 (10)	1.1390 (7)	0.0524 (7)	0.127 (3)
H6	−0.0451	1.1975	0.0306	0.152*
N7	0.3778 (6)	0.8478 (5)	0.2960 (5)	0.0529 (13)
N8	0.0626 (6)	0.6936 (5)	0.2310 (4)	0.0545 (13)
O1	0.7400 (6)	0.2887 (5)	0.1886 (5)	0.0799 (15)
S1	0.5575 (2)	1.00788 (17)	0.30595 (16)	0.0623 (5)
S2	−0.0800 (3)	0.5262 (2)	0.19374 (19)	0.0811 (6)
C1	0.6403 (7)	0.3839 (6)	0.2030 (6)	0.0544 (16)
C2	0.4267 (7)	0.5249 (5)	0.2920 (5)	0.0438 (14)
C3	0.5196 (7)	0.4031 (6)	0.3187 (6)	0.0504 (15)
C4	0.4827 (8)	0.3284 (6)	0.4362 (6)	0.0604 (18)
H4A	0.5395	0.2441	0.4589	0.072*
C5	0.3613 (8)	0.3810 (6)	0.5177 (6)	0.0618 (17)
H5	0.3358	0.3333	0.5989	0.074*
C6	0.2745 (8)	0.5030 (6)	0.4839 (6)	0.0596 (17)
H6A	0.1901	0.5349	0.5429	0.071*
C7	0.4808 (6)	0.5879 (5)	0.1624 (5)	0.0428 (13)
C8	0.6092 (7)	0.5069 (6)	0.1082 (6)	0.0524 (15)
C9	0.6755 (8)	0.5511 (7)	−0.0145 (6)	0.0619 (18)
H9	0.7641	0.5015	−0.0564	0.074*
C10	0.6061 (9)	0.6712 (7)	−0.0729 (6)	0.0664 (19)
H10	0.6483	0.7043	−0.1561	0.080*
C11	0.4755 (8)	0.7435 (6)	−0.0107 (6)	0.0569 (17)
H11	0.4294	0.8231	−0.0543	0.068*
C12	−0.1081 (8)	0.8433 (7)	0.4456 (6)	0.0650 (18)
H12	−0.1580	0.8470	0.3883	0.078*
C13	−0.0723 (11)	0.8488 (8)	0.6116 (7)	0.080 (2)
H13	−0.0890	0.8560	0.6906	0.096*
C14	0.0648 (9)	0.8211 (7)	0.5327 (6)	0.0653 (18)
H14	0.1619	0.8066	0.5472	0.078*
C15	0.0177 (10)	1.0259 (8)	0.1344 (8)	0.101 (3)
H15	−0.0766	0.9975	0.1763	0.121*
C16	0.1769 (11)	1.1482 (8)	0.0101 (7)	0.081 (2)
H16	0.2211	1.2159	−0.0501	0.097*
C17	0.2483 (9)	1.0393 (7)	0.0720 (7)	0.073 (2)
H17	0.3557	1.0192	0.0633	0.088*
C18	0.4548 (7)	0.9133 (6)	0.2987 (5)	0.0457 (14)
C19	0.0036 (7)	0.6238 (6)	0.2169 (5)	0.0453 (14)

	U11	U22	U33	U12	U13	U23
Co1	0.0439 (5)	0.0449 (5)	0.0449 (5)	−0.0073 (4)	−0.0116 (4)	−0.0120 (4)
N1	0.050 (3)	0.044 (3)	0.041 (3)	−0.006 (2)	−0.012 (2)	−0.009 (2)
N2	0.051 (3)	0.047 (3)	0.044 (3)	−0.017 (2)	−0.010 (2)	−0.007 (2)
N3	0.051 (3)	0.047 (3)	0.053 (3)	−0.008 (2)	−0.011 (2)	−0.020 (2)
N4	0.061 (4)	0.077 (4)	0.083 (5)	−0.012 (3)	0.015 (4)	−0.035 (4)
N5	0.047 (3)	0.049 (3)	0.049 (3)	−0.004 (3)	−0.015 (2)	−0.012 (2)
N6	0.091 (6)	0.097 (6)	0.112 (7)	0.028 (5)	−0.023 (5)	0.036 (5)
N7	0.050 (3)	0.054 (3)	0.058 (3)	−0.010 (3)	−0.019 (3)	−0.013 (3)
N8	0.055 (3)	0.060 (3)	0.052 (3)	−0.015 (3)	−0.013 (3)	−0.017 (3)
O1	0.060 (3)	0.063 (3)	0.109 (4)	0.007 (3)	−0.014 (3)	−0.037 (3)
S1	0.0569 (11)	0.0710 (11)	0.0654 (12)	−0.0240 (9)	−0.0175 (9)	−0.0143 (9)
S2	0.0812 (14)	0.1021 (15)	0.0758 (13)	−0.0518 (12)	−0.0018 (11)	−0.0342 (12)
C1	0.044 (4)	0.053 (4)	0.070 (5)	−0.007 (3)	−0.013 (3)	−0.026 (4)
C2	0.044 (3)	0.043 (3)	0.045 (4)	−0.010 (3)	−0.010 (3)	−0.012 (3)
C3	0.051 (4)	0.045 (3)	0.056 (4)	−0.006 (3)	−0.018 (3)	−0.014 (3)
C4	0.065 (5)	0.045 (4)	0.065 (5)	−0.005 (3)	−0.025 (4)	0.000 (3)
C5	0.070 (5)	0.052 (4)	0.054 (4)	−0.013 (4)	−0.013 (4)	−0.002 (3)
C6	0.065 (4)	0.060 (4)	0.045 (4)	−0.013 (3)	−0.006 (3)	−0.009 (3)
C7	0.043 (3)	0.047 (3)	0.043 (3)	−0.011 (3)	−0.010 (3)	−0.017 (3)
C8	0.043 (4)	0.058 (4)	0.057 (4)	−0.014 (3)	−0.007 (3)	−0.020 (3)
C9	0.056 (4)	0.073 (5)	0.058 (4)	−0.022 (4)	0.005 (3)	−0.032 (4)
C10	0.072 (5)	0.077 (5)	0.053 (4)	−0.037 (4)	−0.002 (4)	−0.015 (4)
C11	0.066 (5)	0.058 (4)	0.048 (4)	−0.026 (3)	−0.012 (3)	−0.008 (3)
C12	0.051 (4)	0.077 (5)	0.066 (5)	−0.009 (4)	−0.010 (4)	−0.027 (4)
C13	0.096 (6)	0.083 (5)	0.057 (5)	−0.014 (5)	−0.003 (5)	−0.033 (4)
C14	0.067 (5)	0.070 (4)	0.063 (5)	−0.006 (4)	−0.020 (4)	−0.026 (4)
C15	0.060 (5)	0.099 (6)	0.090 (6)	0.007 (5)	−0.013 (5)	0.021 (5)
C16	0.089 (6)	0.069 (5)	0.077 (6)	−0.022 (5)	−0.031 (5)	0.008 (4)
C17	0.067 (5)	0.064 (5)	0.081 (5)	−0.021 (4)	−0.027 (4)	0.007 (4)
C18	0.043 (4)	0.051 (4)	0.034 (3)	0.003 (3)	−0.011 (3)	−0.008 (3)
C19	0.051 (4)	0.055 (4)	0.025 (3)	−0.013 (3)	−0.006 (3)	−0.005 (3)

Co1—N7	2.060 (5)	C1—C8	1.487 (9)
Co1—N8	2.062 (5)	C1—C3	1.492 (8)
Co1—N3	2.096 (5)	C2—C3	1.374 (8)
Co1—N5	2.100 (5)	C2—C7	1.457 (8)
Co1—N1	2.237 (4)	C3—C4	1.365 (8)
Co1—N2	2.335 (5)	C4—C5	1.344 (9)
N1—C2	1.318 (7)	C4—H4A	0.9300
N1—C6	1.339 (7)	C5—C6	1.365 (9)
N2—C7	1.319 (7)	C5—H5	0.9300
N2—C11	1.345 (7)	C6—H6A	0.9300
N3—C12	1.293 (8)	C7—C8	1.370 (8)
N3—C14	1.350 (8)	C8—C9	1.369 (8)
N4—C12	1.325 (8)	C9—C10	1.367 (10)
N4—C13	1.332 (9)	C9—H9	0.9300
N4—H4	0.8600	C10—C11	1.370 (9)
N5—C15	1.267 (8)	C10—H10	0.9300
N5—C17	1.331 (8)	C11—H11	0.9300
N6—C16	1.289 (10)	C12—H12	0.9300
N6—C15	1.319 (9)	C13—C14	1.325 (10)
N6—H6	0.8600	C13—H13	0.9300
N7—C18	1.152 (7)	C14—H14	0.9300
N8—C19	1.130 (7)	C15—H15	0.9300
O1—C1	1.197 (7)	C16—C17	1.315 (9)
S1—C18	1.619 (7)	C16—H16	0.9300
S2—C19	1.610 (6)	C17—H17	0.9300
N7—Co1—N8	173.1 (2)	C5—C4—C3	117.5 (6)
N7—Co1—N3	93.6 (2)	C5—C4—H4A	121.2
N8—Co1—N3	92.08 (19)	C3—C4—H4A	121.2
N7—Co1—N5	90.24 (19)	C4—C5—C6	121.4 (7)
N8—Co1—N5	92.91 (19)	C4—C5—H5	119.3
N3—Co1—N5	97.45 (19)	C6—C5—H5	119.3
N7—Co1—N1	87.91 (18)	N1—C6—C5	122.8 (6)
N8—Co1—N1	88.00 (19)	N1—C6—H6A	118.6
N3—Co1—N1	91.82 (18)	C5—C6—H6A	118.6
N5—Co1—N1	170.65 (18)	N2—C7—C8	127.8 (6)
N7—Co1—N2	85.39 (18)	N2—C7—C2	122.7 (5)
N8—Co1—N2	88.39 (18)	C8—C7—C2	109.4 (5)
N3—Co1—N2	170.70 (18)	C9—C8—C7	117.2 (6)
N5—Co1—N2	91.80 (18)	C9—C8—C1	134.9 (6)
N1—Co1—N2	78.92 (17)	C7—C8—C1	107.9 (5)
C2—N1—C6	114.3 (5)	C10—C9—C8	117.2 (6)
C2—N1—Co1	108.3 (4)	C10—C9—H9	121.4
C6—N1—Co1	137.4 (4)	C8—C9—H9	121.4
C7—N2—C11	113.5 (5)	C9—C10—C11	121.1 (7)
C7—N2—Co1	105.9 (4)	C9—C10—H10	119.4
C11—N2—Co1	140.5 (4)	C11—C10—H10	119.4
C12—N3—C14	105.3 (6)	N2—C11—C10	123.1 (6)
C12—N3—Co1	125.9 (4)	N2—C11—H11	118.5
C14—N3—Co1	128.8 (4)	C10—C11—H11	118.5
C12—N4—C13	107.0 (6)	N3—C12—N4	111.4 (6)
C12—N4—H4	126.5	N3—C12—H12	124.3
C13—N4—H4	126.5	N4—C12—H12	124.3
C15—N5—C17	103.3 (6)	C14—C13—N4	106.7 (7)
C15—N5—Co1	130.3 (5)	C14—C13—H13	126.6
C17—N5—Co1	126.3 (4)	N4—C13—H13	126.6
C16—N6—C15	109.3 (7)	C13—C14—N3	109.6 (7)
C16—N6—H6	125.3	C13—C14—H14	125.2
C15—N6—H6	125.3	N3—C14—H14	125.2
C18—N7—Co1	164.4 (5)	N5—C15—N6	111.0 (8)
C19—N8—Co1	165.8 (5)	N5—C15—H15	124.5
O1—C1—C8	127.0 (6)	N6—C15—H15	124.5
O1—C1—C3	127.4 (6)	N6—C16—C17	103.7 (7)
C8—C1—C3	105.6 (5)	N6—C16—H16	128.2
N1—C2—C3	126.5 (6)	C17—C16—H16	128.2
N1—C2—C7	124.0 (5)	C16—C17—N5	112.6 (7)
C3—C2—C7	109.5 (5)	C16—C17—H17	123.7
C4—C3—C2	117.5 (6)	N5—C17—H17	123.7
C4—C3—C1	135.0 (6)	N7—C18—S1	177.9 (6)
C2—C3—C1	107.5 (6)	N8—C19—S2	178.7 (5)
N7—Co1—N1—C2	−83.4 (4)	C7—C2—C3—C1	0.1 (6)
N8—Co1—N1—C2	91.1 (4)	O1—C1—C3—C4	−0.2 (12)
N3—Co1—N1—C2	−176.9 (4)	C8—C1—C3—C4	178.7 (7)
N2—Co1—N1—C2	2.3 (4)	O1—C1—C3—C2	−178.1 (6)
N7—Co1—N1—C6	95.8 (6)	C8—C1—C3—C2	0.8 (6)
N8—Co1—N1—C6	−89.7 (6)	C2—C3—C4—C5	−2.0 (9)
N3—Co1—N1—C6	2.3 (6)	C1—C3—C4—C5	−179.7 (6)
N2—Co1—N1—C6	−178.5 (6)	C3—C4—C5—C6	2.1 (10)
N7—Co1—N2—C7	86.0 (4)	C2—N1—C6—C5	0.4 (9)
N8—Co1—N2—C7	−91.1 (4)	Co1—N1—C6—C5	−178.7 (4)
N5—Co1—N2—C7	176.1 (4)	C4—C5—C6—N1	−1.4 (11)
N1—Co1—N2—C7	−2.8 (3)	C11—N2—C7—C8	1.4 (8)
N7—Co1—N2—C11	−92.8 (6)	Co1—N2—C7—C8	−177.7 (5)
N8—Co1—N2—C11	90.2 (6)	C11—N2—C7—C2	−177.9 (5)
N5—Co1—N2—C11	−2.7 (6)	Co1—N2—C7—C2	3.0 (6)
N1—Co1—N2—C11	178.5 (6)	N1—C2—C7—N2	−1.1 (9)
N7—Co1—N3—C12	151.9 (5)	C3—C2—C7—N2	178.3 (5)
N8—Co1—N3—C12	−32.0 (6)	N1—C2—C7—C8	179.5 (5)
N5—Co1—N3—C12	61.2 (6)	C3—C2—C7—C8	−1.1 (7)
N1—Co1—N3—C12	−120.1 (5)	N2—C7—C8—C9	0.6 (9)
N7—Co1—N3—C14	−27.4 (6)	C2—C7—C8—C9	−180.0 (5)
N8—Co1—N3—C14	148.7 (5)	N2—C7—C8—C1	−177.8 (5)
N5—Co1—N3—C14	−118.1 (5)	C2—C7—C8—C1	1.6 (6)
N1—Co1—N3—C14	60.6 (5)	O1—C1—C8—C9	−0.6 (12)
N7—Co1—N5—C15	−141.3 (7)	C3—C1—C8—C9	−179.5 (7)
N8—Co1—N5—C15	44.9 (7)	O1—C1—C8—C7	177.4 (6)
N3—Co1—N5—C15	−47.6 (7)	C3—C1—C8—C7	−1.5 (6)
N2—Co1—N5—C15	133.3 (7)	C7—C8—C9—C10	−1.3 (9)
N7—Co1—N5—C17	35.0 (6)	C1—C8—C9—C10	176.6 (6)
N8—Co1—N5—C17	−138.8 (6)	C8—C9—C10—C11	−0.2 (10)
N3—Co1—N5—C17	128.7 (6)	C7—N2—C11—C10	−2.9 (8)
N2—Co1—N5—C17	−50.4 (6)	Co1—N2—C11—C10	175.8 (4)
N3—Co1—N7—C18	−84.9 (19)	C9—C10—C11—N2	2.5 (10)
N5—Co1—N7—C18	12.5 (19)	C14—N3—C12—N4	0.3 (8)
N1—Co1—N7—C18	−176.6 (19)	Co1—N3—C12—N4	−179.2 (4)
N2—Co1—N7—C18	104.3 (19)	C13—N4—C12—N3	−0.9 (9)
N3—Co1—N8—C19	−110 (2)	C12—N4—C13—C14	1.1 (9)
N5—Co1—N8—C19	153 (2)	N4—C13—C14—N3	−1.0 (9)
N1—Co1—N8—C19	−18 (2)	C12—N3—C14—C13	0.5 (8)
N2—Co1—N8—C19	61 (2)	Co1—N3—C14—C13	179.9 (5)
C6—N1—C2—C3	−0.4 (8)	C17—N5—C15—N6	0.5 (10)
Co1—N1—C2—C3	179.0 (5)	Co1—N5—C15—N6	177.5 (6)
C6—N1—C2—C7	178.9 (5)	C16—N6—C15—N5	0.9 (12)
Co1—N1—C2—C7	−1.7 (6)	C15—N6—C16—C17	−1.9 (11)
N1—C2—C3—C4	1.2 (9)	N6—C16—C17—N5	2.3 (10)
C7—C2—C3—C4	−178.2 (5)	C15—N5—C17—C16	−1.8 (9)
N1—C2—C3—C1	179.5 (5)	Co1—N5—C17—C16	−178.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O1i	0.86	2.47	2.980 (10)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯O1i	0.86	2.47	2.980 (10)	119

Symmetry code: (i) .