Download citation
Download citation
link to html
The title compound, [CoCl2(CH4N2S)2].2C11H6N2O, consists of the tetrahedral cobalt(II) complex and free 4,5-di­aza­fluoren-9-one (dafone). Dafone links to the complex through hydrogen bonding between N atoms. The carbonyl bridge in dafone distorts the bi­pyridine moiety. The longer N...N separations of 3.068 (3) and 3.064 (3) Å in dafone are considered to be the reason for the weaker chelating ability of dafone.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802007778/ww6014sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802007778/ww6014Isup2.hkl
Contains datablock I

CCDC reference: 189287

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.033
  • wR factor = 0.099
  • Data-to-parameter ratio = 15.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1985); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997).

(I) top
Crystal data top
[CoCl2(CH4N2S)2]·2C11H6N2OZ = 2
Mr = 646.45F(000) = 658
Triclinic, P1Dx = 1.532 Mg m3
a = 7.3902 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.9763 (12) ÅCell parameters from 20 reflections
c = 15.1615 (18) Åθ = 4.5–10.2°
α = 89.111 (10)°µ = 0.99 mm1
β = 78.107 (11)°T = 298 K
γ = 80.045 (10)°Prism, blue
V = 1401.0 (3) Å30.56 × 0.32 × 0.14 mm
Data collection top
Rigaku AFC-7S
diffractometer
Rint = 0.023
ω/2θ scansθmax = 26°, θmin = 2.1°
Absorption correction: ψ scan
(North et. al., 1968)
h = 98
Tmin = 0.69, Tmax = 0.87k = 150
5748 measured reflectionsl = 1818
5495 independent reflections3 standard reflections every 100 reflections
3653 reflections with I > 2σ(I) intensity decay: 0.2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0459P)2 + 0.2616P]
where P = (Fo2 + 2Fc2)/3
5495 reflections(Δ/σ)max < 0.001
352 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.31 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2485 (4)0.0196 (2)0.14120 (18)0.0437 (6)
C20.0158 (4)0.5134 (2)0.15577 (17)0.0417 (6)
C30.4956 (4)0.3445 (2)0.11229 (19)0.0539 (7)
H90.54980.31660.05840.065*
C40.5399 (4)0.4507 (2)0.1223 (2)0.0553 (7)
H100.62070.49220.07620.066*
C50.4637 (4)0.4953 (2)0.20154 (19)0.0517 (7)
H110.49120.56680.21050.062*
C60.3453 (4)0.4288 (2)0.26660 (17)0.0419 (6)
C70.2383 (4)0.4481 (2)0.35809 (19)0.0481 (6)
C80.1364 (4)0.3430 (2)0.39445 (18)0.0447 (6)
C90.0212 (4)0.3123 (2)0.47678 (18)0.0520 (7)
H120.00760.36030.52140.062*
C100.0493 (4)0.2068 (3)0.48963 (19)0.0551 (7)
H130.12710.18190.54410.066*
C110.0040 (4)0.1382 (2)0.42119 (18)0.0511 (7)
H140.05610.06780.43130.061*
C120.1774 (3)0.2685 (2)0.33002 (17)0.0395 (6)
C130.3076 (3)0.3221 (2)0.24984 (17)0.0395 (6)
C140.1581 (5)0.8859 (3)0.1402 (2)0.0594 (8)
H150.07400.86750.08590.071*
C150.2405 (5)0.9908 (3)0.1556 (2)0.0672 (9)
H160.21051.04010.11230.081*
C160.3666 (5)1.0213 (2)0.2351 (2)0.0659 (9)
H170.42341.09080.24690.079*
C170.4046 (4)0.9445 (2)0.2962 (2)0.0518 (7)
C180.5294 (4)0.9471 (2)0.3874 (2)0.0571 (8)
C190.4998 (4)0.8389 (2)0.42034 (19)0.0504 (7)
C200.5695 (4)0.7954 (3)0.5007 (2)0.0595 (8)
H180.65220.83570.54710.071*
C210.5115 (4)0.6892 (3)0.5098 (2)0.0609 (8)
H190.55360.65640.56320.073*
C220.3896 (4)0.6325 (2)0.4381 (2)0.0555 (7)
H200.35370.56110.44530.067*
C230.3748 (4)0.7754 (2)0.35220 (18)0.0438 (6)
C240.3149 (4)0.8412 (2)0.27524 (18)0.0454 (6)
N10.3304 (4)0.07016 (18)0.10086 (17)0.0606 (7)
H10.32350.12760.12940.073*
H20.39080.07150.04590.073*
N20.1572 (3)0.02008 (18)0.22491 (15)0.0531 (6)
H30.15140.03790.25270.064*
H40.10290.07840.25210.064*
N30.0156 (3)0.60683 (17)0.12131 (15)0.0525 (6)
H50.04660.66110.15240.063*
H60.07780.61370.06760.063*
N40.0802 (3)0.50473 (18)0.23800 (15)0.0524 (6)
H70.14180.55970.26830.063*
H80.08130.44400.26150.063*
N50.3792 (3)0.27765 (17)0.17479 (14)0.0460 (5)
N60.1108 (3)0.16635 (17)0.34072 (14)0.0453 (5)
N70.1930 (3)0.81010 (18)0.19917 (15)0.0492 (6)
N80.3196 (3)0.67337 (17)0.35878 (15)0.0481 (5)
O10.2361 (3)0.53086 (17)0.39568 (15)0.0713 (6)
O20.6349 (3)1.02200 (18)0.42620 (17)0.0804 (7)
S10.27114 (12)0.13338 (6)0.08358 (5)0.0632 (2)
S20.14841 (11)0.40653 (5)0.09429 (5)0.0558 (2)
Cl10.22205 (12)0.26074 (7)0.06530 (6)0.0666 (2)
Cl20.09294 (13)0.25432 (6)0.29010 (5)0.0705 (2)
Co0.01017 (5)0.26196 (3)0.13882 (2)0.04409 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0430 (14)0.0396 (14)0.0460 (15)0.0047 (11)0.0058 (12)0.0039 (11)
C20.0431 (14)0.0408 (14)0.0397 (14)0.0066 (11)0.0053 (11)0.0054 (11)
C30.0576 (17)0.0513 (17)0.0445 (16)0.0083 (14)0.0073 (13)0.0014 (13)
C40.0519 (17)0.0523 (17)0.0523 (17)0.0002 (14)0.0039 (13)0.0089 (13)
C50.0550 (17)0.0392 (14)0.0564 (17)0.0020 (13)0.0065 (14)0.0008 (12)
C60.0438 (14)0.0398 (14)0.0421 (14)0.0071 (11)0.0090 (11)0.0028 (11)
C70.0500 (16)0.0467 (16)0.0471 (16)0.0071 (13)0.0105 (12)0.0062 (12)
C80.0419 (14)0.0493 (15)0.0414 (14)0.0060 (12)0.0067 (11)0.0027 (12)
C90.0498 (16)0.0647 (19)0.0383 (15)0.0082 (14)0.0040 (12)0.0089 (13)
C100.0488 (16)0.071 (2)0.0381 (15)0.0011 (15)0.0008 (12)0.0073 (14)
C110.0495 (16)0.0514 (17)0.0464 (16)0.0033 (13)0.0055 (13)0.0069 (13)
C120.0375 (13)0.0417 (14)0.0394 (14)0.0067 (11)0.0081 (11)0.0000 (11)
C130.0386 (13)0.0405 (14)0.0391 (14)0.0073 (11)0.0067 (11)0.0006 (11)
C140.066 (2)0.0604 (19)0.0535 (18)0.0159 (16)0.0131 (15)0.0023 (15)
C150.079 (2)0.0531 (19)0.076 (2)0.0200 (17)0.0235 (19)0.0095 (16)
C160.072 (2)0.0438 (17)0.087 (3)0.0037 (15)0.0308 (19)0.0067 (16)
C170.0529 (17)0.0416 (15)0.0620 (18)0.0001 (13)0.0208 (14)0.0078 (13)
C180.0500 (17)0.0536 (18)0.0658 (19)0.0050 (14)0.0174 (14)0.0223 (15)
C190.0441 (15)0.0519 (16)0.0528 (17)0.0002 (13)0.0109 (13)0.0160 (13)
C200.0464 (16)0.075 (2)0.0509 (18)0.0023 (15)0.0018 (13)0.0185 (15)
C210.0556 (18)0.073 (2)0.0494 (17)0.0085 (16)0.0015 (14)0.0015 (15)
C220.0561 (17)0.0532 (17)0.0540 (18)0.0050 (14)0.0075 (14)0.0001 (14)
C230.0402 (14)0.0446 (15)0.0461 (15)0.0015 (12)0.0119 (11)0.0114 (12)
C240.0450 (15)0.0423 (15)0.0495 (16)0.0041 (12)0.0137 (12)0.0079 (12)
N10.0771 (17)0.0380 (13)0.0549 (15)0.0004 (12)0.0055 (13)0.0008 (11)
N20.0631 (15)0.0401 (12)0.0489 (14)0.0014 (11)0.0016 (11)0.0062 (10)
N30.0658 (15)0.0376 (12)0.0462 (13)0.0034 (11)0.0018 (11)0.0006 (10)
N40.0659 (15)0.0383 (12)0.0426 (13)0.0011 (11)0.0068 (11)0.0053 (10)
N50.0497 (13)0.0386 (12)0.0437 (12)0.0070 (10)0.0033 (10)0.0005 (9)
N60.0475 (13)0.0423 (12)0.0416 (12)0.0017 (10)0.0039 (10)0.0011 (9)
N70.0522 (14)0.0465 (13)0.0472 (13)0.0066 (11)0.0075 (11)0.0058 (10)
N80.0506 (13)0.0445 (13)0.0457 (13)0.0013 (11)0.0071 (10)0.0081 (10)
O10.0924 (17)0.0491 (12)0.0631 (14)0.0054 (12)0.0015 (12)0.0194 (11)
O20.0817 (16)0.0611 (14)0.0847 (17)0.0213 (13)0.0118 (13)0.0255 (12)
S10.0707 (5)0.0423 (4)0.0567 (5)0.0075 (4)0.0171 (4)0.0115 (3)
S20.0659 (5)0.0394 (4)0.0505 (4)0.0105 (3)0.0167 (3)0.0101 (3)
Cl10.0678 (5)0.0616 (5)0.0731 (5)0.0130 (4)0.0198 (4)0.0060 (4)
Cl20.0999 (6)0.0578 (5)0.0384 (4)0.0038 (4)0.0125 (4)0.0034 (3)
Co0.0555 (2)0.03447 (19)0.03606 (19)0.00296 (16)0.00080 (15)0.00095 (14)
Geometric parameters (Å, º) top
C1—N21.309 (3)C15—C161.380 (5)
C1—N11.313 (3)C15—H160.9300
C1—S11.719 (3)C16—C171.376 (4)
C2—N31.312 (3)C16—H170.9300
C2—N41.315 (3)C17—C241.398 (4)
C2—S21.717 (3)C17—C181.492 (4)
C3—N51.350 (3)C18—O21.210 (3)
C3—C41.373 (4)C18—C191.478 (4)
C3—H90.9300C19—C201.374 (4)
C4—C51.381 (4)C19—C231.404 (4)
C4—H100.9300C20—C211.384 (4)
C5—C61.376 (4)C20—H180.9300
C5—H110.9300C21—C221.389 (4)
C6—C131.394 (3)C21—H190.9300
C6—C71.489 (4)C22—N81.346 (4)
C7—O11.209 (3)C22—H200.9300
C7—C81.492 (4)C23—N81.325 (3)
C8—C91.379 (4)C23—C241.474 (4)
C8—C121.390 (4)C24—N71.329 (3)
C9—C101.379 (4)N1—H10.8600
C9—H120.9300N1—H20.8600
C10—C111.383 (4)N2—H30.8600
C10—H130.9300N2—H40.8600
C11—N61.350 (3)N3—H50.8600
C11—H140.9300N3—H60.8600
C12—N61.332 (3)N4—H70.8600
C12—C131.483 (3)N4—H80.8600
C13—N51.321 (3)S1—Co2.3387 (9)
C14—N71.341 (4)S2—Co2.3147 (8)
C14—C151.393 (4)Cl1—Co2.2330 (10)
C14—H150.9300Cl2—Co2.2692 (8)
N2—C1—N1119.1 (2)C16—C17—C24119.1 (3)
N2—C1—S1121.9 (2)C16—C17—C18132.5 (3)
N1—C1—S1118.9 (2)C24—C17—C18108.4 (3)
N3—C2—N4119.0 (2)O2—C18—C19126.9 (3)
N3—C2—S2119.3 (2)O2—C18—C17127.2 (3)
N4—C2—S2121.7 (2)C19—C18—C17105.9 (2)
N5—C3—C4124.9 (3)C20—C19—C23119.5 (3)
N5—C3—H9117.6C20—C19—C18132.2 (3)
C4—C3—H9117.6C23—C19—C18108.3 (3)
C3—C4—C5119.5 (3)C19—C20—C21117.3 (3)
C3—C4—H10120.3C19—C20—H18121.3
C5—C4—H10120.3C21—C20—H18121.3
C6—C5—C4116.8 (3)C20—C21—C22119.0 (3)
C6—C5—H11121.6C20—C21—H19120.5
C4—C5—H11121.6C22—C21—H19120.5
C5—C6—C13119.5 (2)N8—C22—C21124.7 (3)
C5—C6—C7131.9 (2)N8—C22—H20117.6
C13—C6—C7108.7 (2)C21—C22—H20117.6
O1—C7—C6127.5 (3)N8—C23—C19124.3 (3)
O1—C7—C8127.1 (3)N8—C23—C24126.8 (2)
C6—C7—C8105.3 (2)C19—C23—C24108.9 (2)
C9—C8—C12119.7 (3)N7—C24—C17124.8 (3)
C9—C8—C7131.4 (3)N7—C24—C23126.7 (2)
C12—C8—C7108.9 (2)C17—C24—C23108.4 (2)
C10—C9—C8116.7 (3)C1—N1—H1120.0
C10—C9—H12121.6C1—N1—H2120.0
C8—C9—H12121.6H1—N1—H2120.0
C9—C10—C11119.8 (3)C1—N2—H3120.0
C9—C10—H13120.1C1—N2—H4120.0
C11—C10—H13120.1H3—N2—H4120.0
N6—C11—C10124.5 (3)C2—N3—H5120.0
N6—C11—H14117.8C2—N3—H6120.0
C10—C11—H14117.8H5—N3—H6120.0
N6—C12—C8124.7 (2)C2—N4—H7120.0
N6—C12—C13126.8 (2)C2—N4—H8120.0
C8—C12—C13108.5 (2)H7—N4—H8120.0
N5—C13—C6124.8 (2)C13—N5—C3114.6 (2)
N5—C13—C12126.6 (2)C12—N6—C11114.6 (2)
C6—C13—C12108.7 (2)C24—N7—C14115.3 (3)
N7—C14—C15123.8 (3)C23—N8—C22115.1 (2)
N7—C14—H15118.1C1—S1—Co109.43 (9)
C15—C14—H15118.1C2—S2—Co108.26 (9)
C16—C15—C14119.8 (3)Cl1—Co—Cl2111.42 (4)
C16—C15—H16120.1Cl1—Co—S2108.24 (3)
C14—C15—H16120.1Cl2—Co—S2113.81 (3)
C17—C16—C15117.1 (3)Cl1—Co—S1112.26 (4)
C17—C16—H17121.4Cl2—Co—S1112.76 (3)
C15—C16—H17121.4S2—Co—S197.59 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N50.862.062.894 (3)164
N1—H2···S1i0.862.843.606 (3)149
N2—H3···N60.862.142.993 (3)171
N2—H4···Cl20.862.493.321 (2)163
N3—H5···N70.862.102.944 (3)167
N3—H6···Cl1ii0.862.733.502 (2)150
N4—H7···N80.862.112.953 (3)169
N4—H8···Cl20.862.513.345 (2)165
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds