In the molecule of the title complex, [CoCl
2(C
27H
18N
2O)], the coordination polyhedron about the cobalt(II) center is best described as a distorted tetrahedron. Weak intermolecular C—H
O hydrogen-bonding interactions link the molecules, forming infinite chains.
Supporting information
CCDC reference: 605087
Key indicators
- Single-crystal X-ray study
- T = 180 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.106
- Data-to-parameter ratio = 24.1
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.78 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).
Dichloro(2,5-diphenyl-3,4-di-2-pyridylcyclopenta-2,4-dienone)cobalt(II)
top
Crystal data top
[CoCl2(C27H18N2O)] | F(000) = 1052 |
Mr = 516.26 | Dx = 1.456 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8076 reflections |
a = 7.2884 (3) Å | θ = 2.9–32.0° |
b = 15.2580 (8) Å | µ = 0.98 mm−1 |
c = 21.5709 (9) Å | T = 180 K |
β = 101.001 (4)° | Box, dark green |
V = 2354.7 (2) Å3 | 0.37 × 0.30 × 0.23 mm |
Z = 4 | |
Data collection top
Oxford Diffraction XCALIBUR diffractometer | 7176 independent reflections |
Radiation source: fine-focus sealed tube | 5404 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 8.2632 pixels mm-1 | θmax = 30.4°, θmin = 3.1° |
ω and φ scans | h = −10→10 |
Absorption correction: multi-scan (Blessing, 1995) | k = −21→20 |
Tmin = 0.704, Tmax = 0.792 | l = −30→30 |
22412 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.055P)2 + 0.0498P] where P = (Fo2 + 2Fc2)/3 |
7176 reflections | (Δ/σ)max = 0.001 |
298 parameters | Δρmax = 0.68 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
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 | Uiso*/Ueq | |
Co1 | 0.23649 (3) | 0.352805 (15) | 0.384184 (10) | 0.02366 (8) | |
Cl1 | 0.27916 (7) | 0.21229 (3) | 0.36511 (3) | 0.04108 (13) | |
Cl2 | 0.48263 (6) | 0.44184 (3) | 0.39806 (2) | 0.03778 (12) | |
N1 | 0.11668 (18) | 0.36814 (9) | 0.46120 (6) | 0.0217 (3) | |
N2 | 0.03444 (18) | 0.41588 (9) | 0.32051 (6) | 0.0237 (3) | |
O4 | −0.33689 (18) | 0.08992 (8) | 0.33625 (6) | 0.0351 (3) | |
C1 | −0.1402 (2) | 0.27939 (10) | 0.40690 (7) | 0.0211 (3) | |
C2 | −0.1865 (2) | 0.30399 (11) | 0.33792 (7) | 0.0221 (3) | |
C3 | −0.2763 (2) | 0.23775 (11) | 0.30446 (7) | 0.0240 (3) | |
C4 | −0.2848 (2) | 0.16355 (12) | 0.34976 (8) | 0.0265 (3) | |
C5 | −0.1969 (2) | 0.19704 (11) | 0.41472 (7) | 0.0242 (3) | |
C11 | −0.0563 (2) | 0.33607 (10) | 0.45991 (7) | 0.0206 (3) | |
C12 | −0.1526 (2) | 0.35230 (11) | 0.50842 (8) | 0.0247 (3) | |
H12 | −0.2760 | 0.3307 | 0.5060 | 0.030* | |
C13 | −0.0665 (3) | 0.40036 (11) | 0.56022 (8) | 0.0286 (4) | |
H13 | −0.1301 | 0.4119 | 0.5939 | 0.034* | |
C14 | 0.1125 (3) | 0.43142 (11) | 0.56255 (8) | 0.0283 (4) | |
H14 | 0.1749 | 0.4636 | 0.5981 | 0.034* | |
C15 | 0.1989 (2) | 0.41466 (11) | 0.51222 (8) | 0.0253 (3) | |
H15 | 0.3214 | 0.4368 | 0.5135 | 0.030* | |
C21 | −0.1453 (2) | 0.38858 (11) | 0.31019 (7) | 0.0215 (3) | |
C22 | −0.2864 (2) | 0.43596 (11) | 0.27177 (8) | 0.0267 (3) | |
H22 | −0.4123 | 0.4163 | 0.2654 | 0.032* | |
C23 | −0.2416 (3) | 0.51180 (12) | 0.24303 (8) | 0.0323 (4) | |
H23 | −0.3360 | 0.5452 | 0.2169 | 0.039* | |
C24 | −0.0565 (3) | 0.53839 (12) | 0.25296 (8) | 0.0332 (4) | |
H24 | −0.0220 | 0.5899 | 0.2332 | 0.040* | |
C25 | 0.0764 (3) | 0.48942 (12) | 0.29165 (8) | 0.0286 (4) | |
H25 | 0.2029 | 0.5082 | 0.2983 | 0.034* | |
C311 | −0.3491 (2) | 0.23484 (11) | 0.23577 (8) | 0.0268 (3) | |
C312 | −0.2338 (3) | 0.25346 (12) | 0.19327 (8) | 0.0328 (4) | |
H312 | −0.1039 | 0.2624 | 0.2082 | 0.039* | |
C313 | −0.3063 (3) | 0.25908 (14) | 0.12912 (9) | 0.0437 (5) | |
H313 | −0.2264 | 0.2718 | 0.1003 | 0.052* | |
C314 | −0.4943 (4) | 0.24616 (17) | 0.10730 (10) | 0.0539 (6) | |
H314 | −0.5445 | 0.2510 | 0.0634 | 0.065* | |
C315 | −0.6104 (3) | 0.22617 (17) | 0.14903 (11) | 0.0554 (6) | |
H315 | −0.7400 | 0.2168 | 0.1336 | 0.066* | |
C316 | −0.5388 (3) | 0.21974 (14) | 0.21337 (9) | 0.0399 (5) | |
H316 | −0.6186 | 0.2051 | 0.2419 | 0.048* | |
C511 | −0.1669 (3) | 0.14433 (11) | 0.47268 (8) | 0.0299 (4) | |
C512 | −0.3149 (3) | 0.10076 (13) | 0.49105 (10) | 0.0420 (5) | |
H512 | −0.4375 | 0.1057 | 0.4666 | 0.050* | |
C513 | −0.2826 (4) | 0.04992 (15) | 0.54541 (11) | 0.0553 (6) | |
H513 | −0.3840 | 0.0207 | 0.5584 | 0.066* | |
C514 | −0.1056 (4) | 0.04150 (15) | 0.58063 (10) | 0.0572 (7) | |
H514 | −0.0851 | 0.0060 | 0.6175 | 0.069* | |
C515 | 0.0434 (4) | 0.08446 (15) | 0.56269 (10) | 0.0502 (6) | |
H515 | 0.1659 | 0.0785 | 0.5871 | 0.060* | |
C516 | 0.0124 (3) | 0.13603 (12) | 0.50902 (9) | 0.0363 (4) | |
H516 | 0.1139 | 0.1661 | 0.4968 | 0.044* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.01961 (12) | 0.02794 (13) | 0.02303 (12) | 0.00083 (9) | 0.00308 (8) | −0.00389 (9) |
Cl1 | 0.0414 (3) | 0.0322 (2) | 0.0520 (3) | 0.00660 (19) | 0.0150 (2) | −0.0092 (2) |
Cl2 | 0.0241 (2) | 0.0515 (3) | 0.0373 (2) | −0.01074 (19) | 0.00478 (17) | −0.0068 (2) |
N1 | 0.0227 (6) | 0.0209 (6) | 0.0202 (6) | 0.0000 (5) | 0.0008 (5) | −0.0018 (5) |
N2 | 0.0236 (7) | 0.0265 (7) | 0.0209 (6) | −0.0030 (6) | 0.0044 (5) | −0.0032 (5) |
O4 | 0.0393 (7) | 0.0256 (6) | 0.0374 (7) | −0.0062 (5) | −0.0005 (6) | −0.0059 (5) |
C1 | 0.0213 (7) | 0.0243 (8) | 0.0172 (7) | −0.0011 (6) | 0.0024 (5) | −0.0015 (6) |
C2 | 0.0205 (7) | 0.0253 (8) | 0.0198 (7) | −0.0005 (6) | 0.0020 (6) | −0.0028 (6) |
C3 | 0.0239 (7) | 0.0256 (8) | 0.0219 (7) | −0.0014 (6) | 0.0026 (6) | −0.0018 (6) |
C4 | 0.0233 (8) | 0.0275 (9) | 0.0279 (8) | −0.0020 (6) | 0.0033 (6) | −0.0036 (7) |
C5 | 0.0245 (8) | 0.0255 (8) | 0.0222 (7) | −0.0016 (6) | 0.0033 (6) | −0.0040 (6) |
C11 | 0.0238 (7) | 0.0181 (7) | 0.0187 (7) | 0.0006 (6) | 0.0013 (6) | 0.0006 (6) |
C12 | 0.0269 (8) | 0.0253 (8) | 0.0223 (7) | −0.0021 (6) | 0.0058 (6) | 0.0000 (6) |
C13 | 0.0378 (9) | 0.0268 (9) | 0.0223 (8) | −0.0003 (7) | 0.0082 (7) | −0.0022 (7) |
C14 | 0.0381 (9) | 0.0247 (8) | 0.0207 (8) | −0.0019 (7) | 0.0018 (7) | −0.0043 (6) |
C15 | 0.0245 (8) | 0.0246 (8) | 0.0243 (8) | −0.0022 (6) | −0.0016 (6) | −0.0010 (6) |
C21 | 0.0237 (7) | 0.0233 (8) | 0.0172 (7) | 0.0004 (6) | 0.0034 (6) | −0.0045 (6) |
C22 | 0.0255 (8) | 0.0293 (9) | 0.0242 (8) | 0.0034 (7) | 0.0020 (6) | −0.0039 (7) |
C23 | 0.0395 (10) | 0.0277 (9) | 0.0271 (8) | 0.0064 (8) | 0.0002 (7) | 0.0005 (7) |
C24 | 0.0485 (11) | 0.0245 (9) | 0.0267 (9) | −0.0040 (8) | 0.0072 (8) | 0.0009 (7) |
C25 | 0.0327 (9) | 0.0285 (9) | 0.0247 (8) | −0.0068 (7) | 0.0055 (7) | −0.0020 (7) |
C311 | 0.0335 (9) | 0.0226 (8) | 0.0222 (8) | −0.0040 (7) | −0.0002 (6) | −0.0048 (6) |
C312 | 0.0419 (10) | 0.0314 (9) | 0.0249 (8) | 0.0001 (8) | 0.0064 (7) | −0.0060 (7) |
C313 | 0.0688 (14) | 0.0357 (11) | 0.0273 (9) | −0.0001 (10) | 0.0112 (9) | −0.0058 (8) |
C314 | 0.0750 (16) | 0.0560 (14) | 0.0232 (10) | −0.0063 (12) | −0.0094 (10) | −0.0066 (9) |
C315 | 0.0503 (13) | 0.0651 (16) | 0.0409 (12) | −0.0139 (11) | −0.0160 (10) | −0.0089 (11) |
C316 | 0.0400 (11) | 0.0446 (12) | 0.0317 (10) | −0.0146 (9) | −0.0017 (8) | −0.0073 (8) |
C511 | 0.0423 (10) | 0.0213 (8) | 0.0259 (8) | −0.0035 (7) | 0.0059 (7) | −0.0012 (7) |
C512 | 0.0566 (13) | 0.0342 (11) | 0.0354 (10) | −0.0139 (10) | 0.0091 (9) | 0.0007 (8) |
C513 | 0.0863 (19) | 0.0389 (12) | 0.0430 (13) | −0.0192 (12) | 0.0179 (12) | 0.0055 (10) |
C514 | 0.105 (2) | 0.0346 (12) | 0.0308 (11) | −0.0006 (13) | 0.0089 (12) | 0.0084 (9) |
C515 | 0.0720 (16) | 0.0384 (12) | 0.0337 (11) | 0.0117 (11) | −0.0060 (10) | 0.0017 (9) |
C516 | 0.0461 (11) | 0.0298 (10) | 0.0306 (9) | 0.0029 (8) | 0.0013 (8) | 0.0009 (8) |
Geometric parameters (Å, º) top
Co1—N1 | 2.0325 (13) | C22—H22 | 0.9500 |
Co1—N2 | 2.0517 (14) | C23—C24 | 1.386 (3) |
Co1—Cl1 | 2.2161 (5) | C23—H23 | 0.9500 |
Co1—Cl2 | 2.2245 (5) | C24—C25 | 1.373 (3) |
N1—C11 | 1.348 (2) | C24—H24 | 0.9500 |
N1—C15 | 1.350 (2) | C25—H25 | 0.9500 |
N2—C25 | 1.346 (2) | C311—C312 | 1.386 (2) |
N2—C21 | 1.352 (2) | C311—C316 | 1.394 (3) |
O4—C4 | 1.204 (2) | C312—C313 | 1.387 (3) |
C1—C5 | 1.343 (2) | C312—H312 | 0.9500 |
C1—C11 | 1.470 (2) | C313—C314 | 1.375 (3) |
C1—C2 | 1.509 (2) | C313—H313 | 0.9500 |
C2—C3 | 1.338 (2) | C314—C315 | 1.382 (3) |
C2—C21 | 1.477 (2) | C314—H314 | 0.9500 |
C3—C311 | 1.476 (2) | C315—C316 | 1.390 (3) |
C3—C4 | 1.504 (2) | C315—H315 | 0.9500 |
C4—C5 | 1.514 (2) | C316—H316 | 0.9500 |
C5—C511 | 1.467 (2) | C511—C512 | 1.387 (3) |
C11—C12 | 1.389 (2) | C511—C516 | 1.395 (3) |
C12—C13 | 1.383 (2) | C512—C513 | 1.388 (3) |
C12—H12 | 0.9500 | C512—H512 | 0.9500 |
C13—C14 | 1.380 (2) | C513—C514 | 1.373 (4) |
C13—H13 | 0.9500 | C513—H513 | 0.9500 |
C14—C15 | 1.379 (2) | C514—C515 | 1.385 (4) |
C14—H14 | 0.9500 | C514—H514 | 0.9500 |
C15—H15 | 0.9500 | C515—C516 | 1.382 (3) |
C21—C22 | 1.394 (2) | C515—H515 | 0.9500 |
C22—C23 | 1.381 (3) | C516—H516 | 0.9500 |
| | | |
N1—Co1—N2 | 97.34 (5) | C21—C22—H22 | 120.3 |
N1—Co1—Cl1 | 111.13 (4) | C22—C23—C24 | 118.86 (17) |
N2—Co1—Cl1 | 115.96 (4) | C22—C23—H23 | 120.6 |
N1—Co1—Cl2 | 106.32 (4) | C24—C23—H23 | 120.6 |
N2—Co1—Cl2 | 105.13 (4) | C25—C24—C23 | 119.19 (17) |
Cl1—Co1—Cl2 | 118.53 (2) | C25—C24—H24 | 120.4 |
C11—N1—C15 | 118.41 (13) | C23—C24—H24 | 120.4 |
C11—N1—Co1 | 119.17 (10) | N2—C25—C24 | 122.59 (16) |
C15—N1—Co1 | 122.26 (11) | N2—C25—H25 | 118.7 |
C25—N2—C21 | 118.63 (15) | C24—C25—H25 | 118.7 |
C25—N2—Co1 | 120.21 (11) | C312—C311—C316 | 119.40 (17) |
C21—N2—Co1 | 120.99 (11) | C312—C311—C3 | 120.70 (15) |
C5—C1—C11 | 123.00 (14) | C316—C311—C3 | 119.72 (16) |
C5—C1—C2 | 109.89 (13) | C311—C312—C313 | 120.59 (18) |
C11—C1—C2 | 127.01 (14) | C311—C312—H312 | 119.7 |
C3—C2—C21 | 123.90 (14) | C313—C312—H312 | 119.7 |
C3—C2—C1 | 109.77 (14) | C314—C313—C312 | 119.9 (2) |
C21—C2—C1 | 126.31 (13) | C314—C313—H313 | 120.1 |
C2—C3—C311 | 127.54 (15) | C312—C313—H313 | 120.1 |
C2—C3—C4 | 107.12 (14) | C313—C314—C315 | 120.2 (2) |
C311—C3—C4 | 125.31 (15) | C313—C314—H314 | 119.9 |
O4—C4—C3 | 126.53 (16) | C315—C314—H314 | 119.9 |
O4—C4—C5 | 126.67 (16) | C314—C315—C316 | 120.4 (2) |
C3—C4—C5 | 106.54 (14) | C314—C315—H315 | 119.8 |
C1—C5—C511 | 128.33 (15) | C316—C315—H315 | 119.8 |
C1—C5—C4 | 106.58 (14) | C315—C316—C311 | 119.56 (19) |
C511—C5—C4 | 124.85 (15) | C315—C316—H316 | 120.2 |
N1—C11—C12 | 121.66 (14) | C311—C316—H316 | 120.2 |
N1—C11—C1 | 118.56 (13) | C512—C511—C516 | 119.44 (18) |
C12—C11—C1 | 119.73 (14) | C512—C511—C5 | 120.56 (17) |
C13—C12—C11 | 119.13 (15) | C516—C511—C5 | 119.98 (17) |
C13—C12—H12 | 120.4 | C511—C512—C513 | 119.6 (2) |
C11—C12—H12 | 120.4 | C511—C512—H512 | 120.2 |
C14—C13—C12 | 119.44 (15) | C513—C512—H512 | 120.2 |
C14—C13—H13 | 120.3 | C514—C513—C512 | 120.7 (2) |
C12—C13—H13 | 120.3 | C514—C513—H513 | 119.7 |
C15—C14—C13 | 118.57 (16) | C512—C513—H513 | 119.7 |
C15—C14—H14 | 120.7 | C513—C514—C515 | 120.3 (2) |
C13—C14—H14 | 120.7 | C513—C514—H514 | 119.8 |
N1—C15—C14 | 122.76 (15) | C515—C514—H514 | 119.8 |
N1—C15—H15 | 118.6 | C516—C515—C514 | 119.4 (2) |
C14—C15—H15 | 118.6 | C516—C515—H515 | 120.3 |
N2—C21—C22 | 121.33 (15) | C514—C515—H515 | 120.3 |
N2—C21—C2 | 117.91 (14) | C515—C516—C511 | 120.6 (2) |
C22—C21—C2 | 120.66 (14) | C515—C516—H516 | 119.7 |
C23—C22—C21 | 119.38 (16) | C511—C516—H516 | 119.7 |
C23—C22—H22 | 120.3 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···O4i | 0.95 | 2.53 | 3.432 (2) | 158 |
Symmetry code: (i) −x−1, y+1/2, −z+1/2. |