In the molecule of the title compound,
cis-[CoCl
2(C
12H
8N
2)
2], the Co
II atom has a distorted octahedral coordination formed by four N atoms from two 1,10-phenanthroline ligands and two Cl atoms. In the crystal structure, molecules are linked into a three-dimensional framework by C—H
Cl hydrogen bonds. The supramolecular network is also consolidated by π–π stacking interactions.
Supporting information
CCDC reference: 1211226
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.005 Å
- R factor = 0.044
- wR factor = 0.151
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Co1 - Cl1 .. 10.71 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Co1 - Cl2 .. 12.24 su
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
2 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.
cis-Dichlorobis(1,10-phenanthroline)cobalt(II)
top
Crystal data top
[CuCl2(C12H8N2)2] | F(000) = 996 |
Mr = 490.24 | Dx = 1.578 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6341 reflections |
a = 9.4644 (3) Å | θ = 2.7–28.2° |
b = 15.1972 (5) Å | µ = 1.11 mm−1 |
c = 14.5250 (5) Å | T = 273 K |
β = 98.905 (1)° | Block, pink |
V = 2063.98 (12) Å3 | 0.26 × 0.26 × 0.26 mm |
Z = 4 | |
Data collection top
Bruker APEX-II area-detector diffractometer | 4710 independent reflections |
Radiation source: fine-focus sealed tube | 3486 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
φ and ω scans | θmax = 27.8°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→11 |
Tmin = 0.761, Tmax = 0.761 | k = −19→19 |
15028 measured reflections | l = −19→19 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.745P] where P = (Fo2 + 2Fc2)/3 |
4710 reflections | (Δ/σ)max < 0.001 |
280 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.78 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 | 0.74528 (4) | 0.22921 (3) | 0.04863 (3) | 0.03995 (16) | |
Cl1 | 0.68637 (8) | 0.13026 (5) | 0.16926 (5) | 0.0473 (2) | |
Cl2 | 0.54135 (8) | 0.21626 (5) | −0.07685 (5) | 0.0475 (2) | |
N1 | 0.8270 (3) | 0.35285 (15) | −0.02410 (16) | 0.0379 (5) | |
N2 | 0.6709 (2) | 0.35339 (16) | 0.11772 (15) | 0.0380 (5) | |
N3 | 0.9832 (3) | 0.22752 (14) | 0.12866 (16) | 0.0365 (5) | |
N4 | 0.8812 (2) | 0.14171 (14) | −0.03172 (15) | 0.0319 (5) | |
C1 | 0.9046 (4) | 0.3531 (2) | −0.0921 (2) | 0.0470 (7) | |
H1 | 0.9410 | 0.2995 | −0.1087 | 0.056* | |
C2 | 0.9358 (4) | 0.4267 (2) | −0.1403 (2) | 0.0563 (9) | |
H2 | 0.9912 | 0.4228 | −0.1878 | 0.068* | |
C3 | 0.8828 (4) | 0.5062 (2) | −0.1163 (2) | 0.0598 (10) | |
H3 | 0.9025 | 0.5571 | −0.1475 | 0.072* | |
C4 | 0.7993 (4) | 0.5107 (2) | −0.0448 (2) | 0.0501 (8) | |
C5 | 0.7376 (4) | 0.5897 (2) | −0.0173 (3) | 0.0624 (10) | |
H5 | 0.7526 | 0.6419 | −0.0477 | 0.075* | |
C6 | 0.6575 (4) | 0.5905 (2) | 0.0519 (3) | 0.0653 (11) | |
H6 | 0.6189 | 0.6433 | 0.0686 | 0.078* | |
C7 | 0.7740 (3) | 0.43068 (17) | 0.00001 (19) | 0.0383 (6) | |
C8 | 0.6899 (3) | 0.43089 (18) | 0.0749 (2) | 0.0390 (6) | |
C9 | 0.6307 (3) | 0.5109 (2) | 0.1004 (2) | 0.0506 (8) | |
C10 | 0.5467 (4) | 0.5075 (3) | 0.1722 (3) | 0.0599 (10) | |
H10 | 0.5039 | 0.5584 | 0.1905 | 0.072* | |
C11 | 0.5282 (4) | 0.4285 (3) | 0.2150 (2) | 0.0589 (10) | |
H11 | 0.4731 | 0.4254 | 0.2627 | 0.071* | |
C12 | 0.5931 (3) | 0.3530 (2) | 0.1862 (2) | 0.0460 (7) | |
H12 | 0.5813 | 0.3002 | 0.2163 | 0.055* | |
C13 | 1.0316 (4) | 0.2659 (2) | 0.2093 (2) | 0.0477 (7) | |
H13 | 0.9678 | 0.2980 | 0.2387 | 0.057* | |
C14 | 1.1745 (4) | 0.2603 (2) | 0.2524 (2) | 0.0573 (9) | |
H14 | 1.2040 | 0.2887 | 0.3089 | 0.069* | |
C15 | 1.2688 (4) | 0.2135 (2) | 0.2114 (3) | 0.0549 (9) | |
H15 | 1.3637 | 0.2093 | 0.2397 | 0.066* | |
C16 | 1.2229 (3) | 0.1708 (2) | 0.1252 (2) | 0.0452 (7) | |
C17 | 1.0774 (3) | 0.17952 (17) | 0.08741 (18) | 0.0350 (6) | |
C18 | 1.0235 (3) | 0.13435 (16) | 0.00230 (18) | 0.0323 (5) | |
C19 | 1.3142 (3) | 0.1199 (2) | 0.0769 (3) | 0.0576 (9) | |
H19 | 1.4108 | 0.1159 | 0.1011 | 0.069* | |
C20 | 1.2649 (3) | 0.0776 (2) | −0.0023 (3) | 0.0532 (8) | |
H20 | 1.3272 | 0.0442 | −0.0317 | 0.064* | |
C21 | 1.1166 (3) | 0.08329 (19) | −0.0425 (2) | 0.0393 (6) | |
C22 | 1.0585 (3) | 0.0387 (2) | −0.1246 (2) | 0.0447 (7) | |
H22 | 1.1164 | 0.0040 | −0.1562 | 0.054* | |
C23 | 0.9168 (3) | 0.04700 (19) | −0.15714 (19) | 0.0436 (7) | |
H23 | 0.8768 | 0.0184 | −0.2116 | 0.052* | |
C24 | 0.8311 (3) | 0.09894 (18) | −0.10820 (18) | 0.0385 (6) | |
H24 | 0.7340 | 0.1033 | −0.1311 | 0.046* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0404 (3) | 0.0379 (2) | 0.0415 (2) | 0.00505 (16) | 0.00639 (17) | 0.00114 (16) |
Cl1 | 0.0380 (4) | 0.0538 (4) | 0.0504 (4) | 0.0044 (3) | 0.0083 (3) | 0.0171 (3) |
Cl2 | 0.0385 (4) | 0.0549 (4) | 0.0463 (4) | 0.0111 (3) | −0.0023 (3) | −0.0034 (3) |
N1 | 0.0441 (13) | 0.0335 (11) | 0.0350 (12) | −0.0014 (10) | 0.0023 (9) | 0.0008 (9) |
N2 | 0.0376 (12) | 0.0390 (12) | 0.0355 (12) | 0.0073 (10) | −0.0004 (9) | −0.0034 (10) |
N3 | 0.0395 (13) | 0.0307 (11) | 0.0380 (12) | −0.0025 (9) | 0.0018 (10) | 0.0007 (9) |
N4 | 0.0300 (11) | 0.0318 (10) | 0.0330 (11) | 0.0047 (9) | 0.0021 (8) | 0.0021 (9) |
C1 | 0.0550 (19) | 0.0445 (16) | 0.0428 (16) | −0.0038 (14) | 0.0112 (13) | 0.0053 (13) |
C2 | 0.065 (2) | 0.060 (2) | 0.0426 (17) | −0.0148 (17) | 0.0066 (14) | 0.0124 (15) |
C3 | 0.070 (2) | 0.0519 (19) | 0.0513 (19) | −0.0201 (17) | −0.0102 (16) | 0.0228 (16) |
C4 | 0.0528 (18) | 0.0380 (15) | 0.0511 (17) | −0.0074 (14) | −0.0186 (14) | 0.0075 (14) |
C5 | 0.074 (2) | 0.0313 (15) | 0.072 (2) | 0.0004 (16) | −0.0222 (19) | 0.0069 (16) |
C6 | 0.069 (2) | 0.0322 (15) | 0.081 (3) | 0.0140 (16) | −0.029 (2) | −0.0129 (17) |
C7 | 0.0416 (15) | 0.0311 (13) | 0.0373 (14) | −0.0008 (11) | −0.0095 (11) | 0.0022 (11) |
C8 | 0.0386 (15) | 0.0329 (13) | 0.0405 (14) | 0.0071 (11) | −0.0094 (11) | −0.0043 (11) |
C9 | 0.0485 (18) | 0.0402 (15) | 0.0548 (18) | 0.0137 (13) | −0.0187 (14) | −0.0149 (14) |
C10 | 0.0493 (19) | 0.061 (2) | 0.063 (2) | 0.0226 (17) | −0.0100 (16) | −0.0273 (18) |
C11 | 0.0418 (18) | 0.083 (3) | 0.0500 (18) | 0.0122 (17) | 0.0023 (13) | −0.0259 (18) |
C12 | 0.0389 (16) | 0.0572 (18) | 0.0410 (15) | 0.0077 (14) | 0.0034 (12) | −0.0070 (14) |
C13 | 0.060 (2) | 0.0419 (16) | 0.0391 (15) | −0.0055 (14) | 0.0008 (14) | −0.0012 (13) |
C14 | 0.070 (2) | 0.0482 (18) | 0.0460 (17) | −0.0155 (17) | −0.0148 (16) | −0.0002 (15) |
C15 | 0.0431 (18) | 0.0524 (18) | 0.062 (2) | −0.0151 (15) | −0.0154 (15) | 0.0125 (16) |
C16 | 0.0322 (14) | 0.0419 (15) | 0.0584 (18) | −0.0060 (12) | −0.0026 (12) | 0.0123 (14) |
C17 | 0.0328 (14) | 0.0307 (12) | 0.0405 (14) | −0.0033 (11) | 0.0027 (10) | 0.0086 (11) |
C18 | 0.0307 (13) | 0.0306 (12) | 0.0358 (13) | 0.0012 (10) | 0.0059 (10) | 0.0067 (10) |
C19 | 0.0296 (15) | 0.062 (2) | 0.080 (2) | 0.0023 (15) | 0.0034 (15) | 0.0165 (19) |
C20 | 0.0316 (15) | 0.061 (2) | 0.070 (2) | 0.0106 (14) | 0.0164 (14) | 0.0113 (17) |
C21 | 0.0355 (14) | 0.0394 (14) | 0.0452 (15) | 0.0056 (12) | 0.0129 (11) | 0.0092 (12) |
C22 | 0.0510 (18) | 0.0423 (15) | 0.0448 (16) | 0.0111 (14) | 0.0200 (13) | 0.0042 (13) |
C23 | 0.0568 (18) | 0.0401 (15) | 0.0338 (14) | 0.0067 (14) | 0.0069 (12) | −0.0041 (12) |
C24 | 0.0392 (15) | 0.0380 (14) | 0.0364 (14) | 0.0061 (12) | 0.0003 (11) | −0.0005 (12) |
Geometric parameters (Å, º) top
Co1—Cl1 | 2.4381 (8) | C10—H10 | 0.9300 |
Co1—Cl2 | 2.4488 (8) | C11—C12 | 1.396 (4) |
Co1—N1 | 2.345 (2) | C11—H11 | 0.9300 |
Co1—N2 | 2.298 (2) | C12—H12 | 0.9300 |
Co1—N3 | 2.369 (2) | C13—C14 | 1.402 (5) |
Co1—N4 | 2.291 (2) | C13—H13 | 0.9300 |
N1—C1 | 1.319 (4) | C17—C16 | 1.407 (4) |
N1—C7 | 1.352 (4) | C17—C18 | 1.437 (4) |
N2—C12 | 1.326 (4) | C18—C21 | 1.407 (4) |
N2—C8 | 1.357 (4) | C24—C23 | 1.402 (4) |
N3—C13 | 1.325 (4) | C24—H24 | 0.9300 |
N3—C17 | 1.361 (4) | C23—C22 | 1.357 (4) |
N4—C24 | 1.311 (3) | C23—H23 | 0.9300 |
N4—C18 | 1.366 (3) | C5—C6 | 1.350 (6) |
C1—C2 | 1.377 (4) | C5—H5 | 0.9300 |
C1—H1 | 0.9300 | C6—H6 | 0.9300 |
C2—C3 | 1.373 (5) | C14—C15 | 1.351 (6) |
C2—H2 | 0.9300 | C14—H14 | 0.9300 |
C3—C4 | 1.401 (5) | C15—C16 | 1.418 (5) |
C3—H3 | 0.9300 | C15—H15 | 0.9300 |
C4—C7 | 1.417 (4) | C16—C19 | 1.423 (5) |
C4—C5 | 1.419 (5) | C19—C20 | 1.337 (5) |
C7—C8 | 1.443 (5) | C19—H19 | 0.9300 |
C8—C9 | 1.412 (4) | C20—C21 | 1.437 (4) |
C9—C10 | 1.407 (5) | C20—H20 | 0.9300 |
C9—C6 | 1.442 (5) | C21—C22 | 1.408 (4) |
C10—C11 | 1.377 (6) | C22—H22 | 0.9300 |
| | | |
Cl1—Co1—Cl2 | 104.11 (3) | C9—C10—H10 | 120.3 |
Cl1—Co1—N1 | 161.10 (6) | C10—C11—C12 | 119.2 (3) |
Cl1—Co1—N2 | 94.19 (6) | C10—C11—H11 | 120.4 |
Cl1—Co1—N3 | 86.92 (6) | C12—C11—H11 | 120.4 |
Cl1—Co1—N4 | 102.53 (6) | N2—C12—C11 | 122.9 (3) |
Cl2—Co1—N1 | 90.35 (6) | N2—C12—H12 | 118.5 |
Cl2—Co1—N2 | 97.56 (6) | C11—C12—H12 | 118.5 |
Cl2—Co1—N3 | 160.76 (7) | N3—C13—C14 | 123.1 (3) |
Cl2—Co1—N4 | 90.82 (6) | N3—C13—H13 | 118.5 |
N1—Co1—N2 | 71.54 (9) | C14—C13—H13 | 118.5 |
N1—Co1—N3 | 82.81 (8) | N3—C17—C16 | 123.2 (3) |
N1—Co1—N4 | 89.15 (8) | N3—C17—C18 | 117.7 (2) |
N2—Co1—N3 | 97.27 (8) | C16—C17—C18 | 119.1 (3) |
N2—Co1—N4 | 158.89 (9) | N4—C18—C21 | 122.1 (2) |
N3—Co1—N4 | 71.20 (8) | N4—C18—C17 | 118.1 (2) |
C1—N1—C7 | 117.6 (3) | C21—C18—C17 | 119.8 (2) |
C1—N1—Co1 | 126.9 (2) | N4—C24—C23 | 123.2 (3) |
C7—N1—Co1 | 114.99 (19) | N4—C24—H24 | 118.4 |
C12—N2—C8 | 118.4 (3) | C23—C24—H24 | 118.4 |
C12—N2—Co1 | 124.6 (2) | C22—C23—C24 | 119.6 (3) |
C8—N2—Co1 | 116.18 (19) | C22—C23—H23 | 120.2 |
C13—N3—C17 | 117.7 (3) | C24—C23—H23 | 120.2 |
C13—N3—Co1 | 127.0 (2) | C6—C5—C4 | 121.4 (3) |
C17—N3—Co1 | 115.32 (17) | C6—C5—H5 | 119.3 |
C24—N4—C18 | 118.2 (2) | C4—C5—H5 | 119.3 |
C24—N4—Co1 | 124.16 (18) | C5—C6—C9 | 121.2 (3) |
C18—N4—Co1 | 117.60 (17) | C5—C6—H6 | 119.4 |
N1—C1—C2 | 124.8 (3) | C9—C6—H6 | 119.4 |
N1—C1—H1 | 117.6 | C15—C14—C13 | 119.5 (3) |
C2—C1—H1 | 117.6 | C15—C14—H14 | 120.2 |
C3—C2—C1 | 118.0 (3) | C13—C14—H14 | 120.2 |
C3—C2—H2 | 121.0 | C14—C15—C16 | 119.8 (3) |
C1—C2—H2 | 121.0 | C14—C15—H15 | 120.1 |
C2—C3—C4 | 120.1 (3) | C16—C15—H15 | 120.1 |
C2—C3—H3 | 119.9 | C17—C16—C15 | 116.7 (3) |
C4—C3—H3 | 119.9 | C17—C16—C19 | 119.4 (3) |
C3—C4—C7 | 117.0 (3) | C15—C16—C19 | 123.9 (3) |
C3—C4—C5 | 123.7 (3) | C20—C19—C16 | 121.9 (3) |
C7—C4—C5 | 119.4 (4) | C20—C19—H19 | 119.1 |
N1—C7—C4 | 122.4 (3) | C16—C19—H19 | 119.1 |
N1—C7—C8 | 117.9 (2) | C19—C20—C21 | 120.6 (3) |
C4—C7—C8 | 119.8 (3) | C19—C20—H20 | 119.7 |
N2—C8—C9 | 122.7 (3) | C21—C20—H20 | 119.7 |
N2—C8—C7 | 118.1 (2) | C18—C21—C22 | 117.9 (3) |
C9—C8—C7 | 119.1 (3) | C18—C21—C20 | 119.2 (3) |
C10—C9—C8 | 117.2 (3) | C22—C21—C20 | 123.0 (3) |
C10—C9—C6 | 123.7 (3) | C23—C22—C21 | 119.0 (3) |
C8—C9—C6 | 119.2 (3) | C23—C22—H22 | 120.5 |
C11—C10—C9 | 119.5 (3) | C21—C22—H22 | 120.5 |
C11—C10—H10 | 120.3 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···Cl2i | 0.93 | 2.63 | 3.537 (3) | 165 |
C19—H19···Cl1ii | 0.93 | 2.65 | 3.573 (3) | 172 |
C22—H22···Cl1iii | 0.93 | 2.79 | 3.651 (3) | 154 |
C24—H24···Cl2 | 0.93 | 2.71 | 3.361 (3) | 128 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) −x+2, −y, −z. |