The Co(II) ion in the title compound, [CoCl(phen)
2(H
2O)]Cl·C(NH
2)
2S [phen = 1,10-phenanthroline, (C
12H
8N
2)], has a distorted octahedral coordination formed by one Cl atom, one water molecule, and four N atoms of two phen ligands. Ions and molecules are linked into a three-dimensional framework by N—H
S, N—H
Cl and O—H
Cl hydrogen bonds. The supramolecular network structure is consolidated by π–π stacking interactions and hydrogen bonds.
Supporting information
CCDC reference: 1195260
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.008 Å
- R factor = 0.048
- wR factor = 0.181
- Data-to-parameter ratio = 16.1
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C25
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT420_ALERT_2_C D-H Without Acceptor N6 - H6B ... ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
2 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: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: APEX2; software used to prepare material for publication: APEX2.
Crystal data top
[CoCl(C12H8N2)2(H2O)]Cl·(NH2)2CS | Z = 2 |
Mr = 584.38 | F(000) = 598 |
Triclinic, P1 | Dx = 1.536 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8147 (9) Å | Cell parameters from 2467 reflections |
b = 11.3517 (11) Å | θ = 2.6–25.0° |
c = 12.8454 (12) Å | µ = 1.01 mm−1 |
α = 64.223 (1)° | T = 273 K |
β = 86.947 (1)° | Block, pink |
γ = 78.748 (1)° | 0.21 × 0.20 × 0.09 mm |
V = 1263.2 (2) Å3 | |
Data collection top
Bruker APEX-II area-detector diffractometer | 5320 independent reflections |
Radiation source: fine-focus sealed tube | 3160 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 26.9°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −12→12 |
Tmin = 0.815, Tmax = 0.915 | k = −14→14 |
8804 measured reflections | l = −16→15 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.181 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.101P)2 + 0.010P] where P = (Fo2 + 2Fc2)/3 |
5320 reflections | (Δ/σ)max < 0.001 |
330 parameters | Δρmax = 1.17 e Å−3 |
0 restraints | Δρmin = −0.80 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 | |
C1 | 0.1929 (5) | −0.0629 (5) | 0.1418 (4) | 0.0563 (13) | |
H1 | 0.2796 | −0.0711 | 0.1100 | 0.068* | |
C2 | 0.0953 (5) | −0.1286 (6) | 0.1268 (5) | 0.0667 (15) | |
H2 | 0.1170 | −0.1781 | 0.0844 | 0.080* | |
C3 | −0.0305 (5) | −0.1208 (6) | 0.1732 (5) | 0.0608 (14) | |
H3 | −0.0962 | −0.1644 | 0.1633 | 0.073* | |
C4 | −0.0607 (4) | −0.0448 (5) | 0.2376 (4) | 0.0470 (11) | |
C5 | 0.0421 (4) | 0.0187 (4) | 0.2489 (3) | 0.0408 (10) | |
C6 | 0.0161 (4) | 0.0952 (4) | 0.3148 (3) | 0.0388 (10) | |
C7 | −0.1899 (5) | −0.0359 (5) | 0.2944 (4) | 0.0549 (12) | |
H7 | −0.2595 | −0.0761 | 0.2852 | 0.066* | |
C8 | −0.2111 (4) | 0.0310 (5) | 0.3619 (4) | 0.0521 (12) | |
H8 | −0.2933 | 0.0320 | 0.4013 | 0.063* | |
C9 | −0.1082 (4) | 0.1004 (4) | 0.3732 (4) | 0.0425 (10) | |
C10 | −0.1259 (5) | 0.1722 (5) | 0.4391 (4) | 0.0494 (11) | |
H10 | −0.2063 | 0.1764 | 0.4801 | 0.059* | |
C11 | −0.0239 (5) | 0.2358 (5) | 0.4427 (4) | 0.0513 (12) | |
H11 | −0.0350 | 0.2859 | 0.4848 | 0.062* | |
C12 | 0.0980 (5) | 0.2260 (5) | 0.3829 (4) | 0.0462 (11) | |
H12 | 0.1673 | 0.2692 | 0.3873 | 0.055* | |
C13 | 0.1201 (5) | 0.3156 (5) | −0.0115 (4) | 0.0489 (11) | |
H13 | 0.0853 | 0.2408 | −0.0010 | 0.059* | |
C14 | 0.0788 (5) | 0.4323 (6) | −0.1095 (4) | 0.0581 (14) | |
H14 | 0.0164 | 0.4355 | −0.1631 | 0.070* | |
C15 | 0.1292 (5) | 0.5427 (5) | −0.1278 (4) | 0.0599 (14) | |
H15 | 0.1032 | 0.6210 | −0.1948 | 0.072* | |
C16 | 0.2210 (5) | 0.5379 (5) | −0.0450 (4) | 0.0491 (12) | |
C17 | 0.2583 (4) | 0.4167 (4) | 0.0522 (4) | 0.0409 (10) | |
C18 | 0.3521 (4) | 0.4038 (4) | 0.1399 (4) | 0.0381 (9) | |
C19 | 0.2773 (5) | 0.6491 (5) | −0.0554 (5) | 0.0622 (14) | |
H19 | 0.2540 | 0.7303 | −0.1201 | 0.075* | |
C20 | 0.3649 (6) | 0.6371 (5) | 0.0288 (5) | 0.0638 (15) | |
H20 | 0.3993 | 0.7112 | 0.0211 | 0.077* | |
C21 | 0.4051 (4) | 0.5146 (5) | 0.1282 (4) | 0.0489 (11) | |
C22 | 0.4974 (5) | 0.4981 (5) | 0.2164 (5) | 0.0584 (13) | |
H22 | 0.5368 | 0.5684 | 0.2115 | 0.070* | |
C23 | 0.5271 (5) | 0.3763 (6) | 0.3089 (5) | 0.0590 (13) | |
H23 | 0.5858 | 0.3638 | 0.3687 | 0.071* | |
C24 | 0.4706 (4) | 0.2709 (5) | 0.3146 (4) | 0.0466 (11) | |
H24 | 0.4936 | 0.1887 | 0.3783 | 0.056* | |
C25 | 0.2482 (12) | 0.4413 (11) | 0.5281 (8) | 0.127 (3) | |
Cl1 | 0.42462 (11) | −0.05267 (12) | 0.38482 (9) | 0.0500 (3) | |
Cl2 | 0.37942 (13) | 0.18632 (13) | 0.85438 (11) | 0.0586 (4) | |
Co1 | 0.29819 (5) | 0.12891 (6) | 0.22383 (5) | 0.0369 (2) | |
N1 | 0.1673 (4) | 0.0111 (4) | 0.2000 (3) | 0.0437 (9) | |
N2 | 0.1187 (3) | 0.1579 (3) | 0.3204 (3) | 0.0386 (8) | |
N3 | 0.3846 (3) | 0.2829 (3) | 0.2324 (3) | 0.0376 (8) | |
N4 | 0.2074 (3) | 0.3056 (3) | 0.0685 (3) | 0.0396 (8) | |
N5 | 0.1724 (9) | 0.4020 (8) | 0.6134 (7) | 0.171 (4) | |
H5A | 0.2093 | 0.3500 | 0.6812 | 0.206* | |
H5B | 0.0836 | 0.4272 | 0.6043 | 0.206* | |
N6 | 0.3857 (10) | 0.3916 (14) | 0.5588 (10) | 0.247 (7) | |
H6A | 0.4106 | 0.3399 | 0.6298 | 0.296* | |
H6B | 0.4473 | 0.4119 | 0.5070 | 0.296* | |
O1 | 0.4540 (3) | 0.0967 (4) | 0.1127 (3) | 0.0489 (8) | |
H1A | 0.4233 | 0.1352 | 0.0456 | 0.073* | |
S1 | 0.1732 (3) | 0.5482 (3) | 0.3936 (2) | 0.1518 (11) | |
H1B | 0.510 (5) | 0.019 (5) | 0.148 (4) | 0.052 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.053 (3) | 0.072 (4) | 0.060 (3) | −0.019 (3) | 0.012 (2) | −0.042 (3) |
C2 | 0.066 (3) | 0.085 (4) | 0.082 (4) | −0.031 (3) | 0.018 (3) | −0.061 (4) |
C3 | 0.063 (3) | 0.069 (4) | 0.068 (3) | −0.030 (3) | 0.007 (3) | −0.039 (3) |
C4 | 0.043 (2) | 0.053 (3) | 0.046 (3) | −0.015 (2) | 0.001 (2) | −0.019 (2) |
C5 | 0.039 (2) | 0.043 (3) | 0.035 (2) | −0.0072 (19) | 0.0002 (18) | −0.0124 (19) |
C6 | 0.037 (2) | 0.038 (2) | 0.034 (2) | −0.0057 (18) | −0.0026 (17) | −0.0086 (18) |
C7 | 0.040 (2) | 0.061 (3) | 0.063 (3) | −0.013 (2) | −0.006 (2) | −0.024 (3) |
C8 | 0.034 (2) | 0.056 (3) | 0.052 (3) | −0.007 (2) | 0.004 (2) | −0.011 (2) |
C9 | 0.038 (2) | 0.039 (3) | 0.038 (2) | −0.0016 (19) | −0.0020 (19) | −0.0075 (19) |
C10 | 0.045 (3) | 0.049 (3) | 0.042 (2) | −0.001 (2) | 0.004 (2) | −0.012 (2) |
C11 | 0.061 (3) | 0.050 (3) | 0.041 (2) | 0.005 (2) | 0.001 (2) | −0.024 (2) |
C12 | 0.048 (2) | 0.045 (3) | 0.043 (2) | −0.003 (2) | −0.001 (2) | −0.019 (2) |
C13 | 0.049 (3) | 0.051 (3) | 0.045 (3) | −0.002 (2) | −0.008 (2) | −0.021 (2) |
C14 | 0.056 (3) | 0.070 (4) | 0.041 (3) | 0.010 (3) | −0.011 (2) | −0.024 (3) |
C15 | 0.066 (3) | 0.050 (3) | 0.038 (2) | 0.011 (3) | −0.001 (2) | −0.004 (2) |
C16 | 0.048 (3) | 0.042 (3) | 0.041 (2) | 0.004 (2) | 0.009 (2) | −0.009 (2) |
C17 | 0.039 (2) | 0.037 (2) | 0.039 (2) | −0.0019 (19) | 0.0067 (18) | −0.0112 (19) |
C18 | 0.034 (2) | 0.037 (2) | 0.044 (2) | −0.0072 (18) | 0.0035 (18) | −0.019 (2) |
C19 | 0.065 (3) | 0.035 (3) | 0.067 (3) | −0.001 (2) | 0.013 (3) | −0.009 (2) |
C20 | 0.068 (3) | 0.041 (3) | 0.081 (4) | −0.017 (3) | 0.023 (3) | −0.024 (3) |
C21 | 0.042 (2) | 0.041 (3) | 0.062 (3) | −0.010 (2) | 0.013 (2) | −0.020 (2) |
C22 | 0.049 (3) | 0.056 (3) | 0.085 (4) | −0.019 (2) | 0.009 (3) | −0.042 (3) |
C23 | 0.049 (3) | 0.070 (4) | 0.072 (3) | −0.006 (3) | −0.010 (2) | −0.044 (3) |
C24 | 0.047 (3) | 0.047 (3) | 0.048 (3) | −0.006 (2) | −0.009 (2) | −0.023 (2) |
C25 | 0.138 (8) | 0.156 (9) | 0.093 (6) | −0.011 (7) | 0.032 (6) | −0.070 (6) |
Cl1 | 0.0509 (7) | 0.0503 (7) | 0.0393 (6) | −0.0054 (5) | −0.0022 (5) | −0.0122 (5) |
Cl2 | 0.0631 (8) | 0.0576 (8) | 0.0594 (7) | −0.0054 (6) | −0.0027 (6) | −0.0313 (6) |
Co1 | 0.0375 (3) | 0.0368 (4) | 0.0359 (3) | −0.0087 (2) | 0.0023 (2) | −0.0147 (3) |
N1 | 0.0409 (19) | 0.050 (2) | 0.043 (2) | −0.0121 (17) | 0.0048 (16) | −0.0213 (18) |
N2 | 0.0386 (18) | 0.040 (2) | 0.0325 (18) | −0.0066 (15) | 0.0041 (14) | −0.0124 (16) |
N3 | 0.0371 (18) | 0.037 (2) | 0.0389 (19) | −0.0069 (15) | 0.0011 (15) | −0.0165 (16) |
N4 | 0.0417 (19) | 0.039 (2) | 0.0367 (18) | −0.0060 (16) | 0.0020 (15) | −0.0154 (16) |
N5 | 0.149 (7) | 0.146 (8) | 0.139 (8) | 0.002 (6) | −0.018 (6) | 0.001 (6) |
N6 | 0.158 (8) | 0.46 (2) | 0.240 (12) | −0.087 (11) | 0.092 (9) | −0.260 (14) |
O1 | 0.0492 (18) | 0.047 (2) | 0.0443 (17) | −0.0011 (16) | 0.0056 (15) | −0.0182 (17) |
S1 | 0.187 (3) | 0.150 (2) | 0.1045 (18) | 0.002 (2) | 0.0128 (17) | −0.0575 (17) |
Geometric parameters (Å, º) top
C1—N1 | 1.332 (6) | C16—C19 | 1.426 (7) |
C1—C2 | 1.391 (7) | C17—N4 | 1.375 (6) |
C1—H1 | 0.9300 | C17—C18 | 1.432 (6) |
C2—C3 | 1.347 (7) | C18—N3 | 1.359 (5) |
C2—H2 | 0.9300 | C18—C21 | 1.399 (6) |
C3—C4 | 1.418 (7) | C19—C20 | 1.362 (7) |
C3—H3 | 0.9300 | C19—H19 | 0.9300 |
C4—C5 | 1.397 (6) | C20—C21 | 1.419 (7) |
C4—C7 | 1.437 (6) | C20—H20 | 0.9300 |
C5—N1 | 1.354 (5) | C21—C22 | 1.414 (7) |
C5—C6 | 1.437 (6) | C22—C23 | 1.363 (7) |
C6—N2 | 1.364 (5) | C22—H22 | 0.9300 |
C6—C9 | 1.402 (6) | C23—C24 | 1.387 (7) |
C7—C8 | 1.365 (7) | C23—H23 | 0.9300 |
C7—H7 | 0.9300 | C24—N3 | 1.331 (5) |
C8—C9 | 1.444 (7) | C24—H24 | 0.9300 |
C8—H8 | 0.9300 | C25—N5 | 1.253 (10) |
C9—C10 | 1.393 (6) | C25—N6 | 1.364 (13) |
C10—C11 | 1.357 (7) | C25—S1 | 1.721 (10) |
C10—H10 | 0.9300 | Cl1—Co1 | 2.3733 (12) |
C11—C12 | 1.399 (6) | Co1—O1 | 2.124 (3) |
C11—H11 | 0.9300 | Co1—N3 | 2.131 (3) |
C12—N2 | 1.319 (5) | Co1—N1 | 2.145 (4) |
C12—H12 | 0.9300 | Co1—N2 | 2.156 (3) |
C13—N4 | 1.326 (5) | Co1—N4 | 2.193 (3) |
C13—C14 | 1.378 (6) | N5—H5A | 0.8600 |
C13—H13 | 0.9300 | N5—H5B | 0.8600 |
C14—C15 | 1.358 (7) | N6—H6A | 0.8600 |
C14—H14 | 0.9300 | N6—H6B | 0.8600 |
C15—C16 | 1.408 (7) | O1—H1A | 0.8300 |
C15—H15 | 0.9300 | O1—H1B | 0.88 (6) |
C16—C17 | 1.394 (6) | | |
| | | |
N1—C1—C2 | 122.7 (4) | C16—C19—H19 | 119.8 |
N1—C1—H1 | 118.7 | C19—C20—C21 | 121.7 (5) |
C2—C1—H1 | 118.7 | C19—C20—H20 | 119.1 |
C3—C2—C1 | 120.3 (5) | C21—C20—H20 | 119.1 |
C3—C2—H2 | 119.8 | C18—C21—C22 | 117.9 (4) |
C1—C2—H2 | 119.8 | C18—C21—C20 | 118.9 (4) |
C2—C3—C4 | 118.6 (4) | C22—C21—C20 | 123.2 (5) |
C2—C3—H3 | 120.7 | C23—C22—C21 | 118.2 (4) |
C4—C3—H3 | 120.7 | C23—C22—H22 | 120.9 |
C5—C4—C3 | 117.9 (4) | C21—C22—H22 | 120.9 |
C5—C4—C7 | 119.7 (4) | C22—C23—C24 | 120.7 (5) |
C3—C4—C7 | 122.3 (4) | C22—C23—H23 | 119.6 |
N1—C5—C4 | 122.5 (4) | C24—C23—H23 | 119.6 |
N1—C5—C6 | 118.0 (4) | N3—C24—C23 | 122.5 (4) |
C4—C5—C6 | 119.5 (4) | N3—C24—H24 | 118.8 |
N2—C6—C9 | 122.2 (4) | C23—C24—H24 | 118.8 |
N2—C6—C5 | 117.1 (4) | N5—C25—N6 | 111.9 (10) |
C9—C6—C5 | 120.7 (4) | N5—C25—S1 | 119.5 (9) |
C8—C7—C4 | 120.4 (4) | N6—C25—S1 | 128.6 (9) |
C8—C7—H7 | 119.8 | O1—Co1—N3 | 92.49 (13) |
C4—C7—H7 | 119.8 | O1—Co1—N1 | 94.99 (13) |
C7—C8—C9 | 121.2 (4) | N3—Co1—N1 | 166.10 (13) |
C7—C8—H8 | 119.4 | O1—Co1—N2 | 171.40 (13) |
C9—C8—H8 | 119.4 | N3—Co1—N2 | 94.03 (13) |
C10—C9—C6 | 118.2 (4) | N1—Co1—N2 | 77.51 (13) |
C10—C9—C8 | 123.4 (4) | O1—Co1—N4 | 85.18 (13) |
C6—C9—C8 | 118.3 (4) | N3—Co1—N4 | 77.09 (13) |
C11—C10—C9 | 118.9 (4) | N1—Co1—N4 | 91.87 (13) |
C11—C10—H10 | 120.5 | N2—Co1—N4 | 90.80 (12) |
C9—C10—H10 | 120.5 | O1—Co1—Cl1 | 89.78 (10) |
C10—C11—C12 | 119.9 (4) | N3—Co1—Cl1 | 97.59 (9) |
C10—C11—H11 | 120.0 | N1—Co1—Cl1 | 94.14 (10) |
C12—C11—H11 | 120.0 | N2—Co1—Cl1 | 94.92 (9) |
N2—C12—C11 | 122.7 (4) | N4—Co1—Cl1 | 172.47 (9) |
N2—C12—H12 | 118.6 | C1—N1—C5 | 117.9 (4) |
C11—C12—H12 | 118.6 | C1—N1—Co1 | 128.2 (3) |
N4—C13—C14 | 122.7 (5) | C5—N1—Co1 | 113.8 (3) |
N4—C13—H13 | 118.6 | C12—N2—C6 | 117.9 (4) |
C14—C13—H13 | 118.6 | C12—N2—Co1 | 128.5 (3) |
C15—C14—C13 | 119.9 (5) | C6—N2—Co1 | 113.6 (3) |
C15—C14—H14 | 120.0 | C24—N3—C18 | 117.9 (4) |
C13—C14—H14 | 120.0 | C24—N3—Co1 | 127.0 (3) |
C14—C15—C16 | 119.7 (4) | C18—N3—Co1 | 115.0 (3) |
C14—C15—H15 | 120.2 | C13—N4—C17 | 118.2 (4) |
C16—C15—H15 | 120.2 | C13—N4—Co1 | 129.0 (3) |
C17—C16—C15 | 117.3 (5) | C17—N4—Co1 | 112.6 (3) |
C17—C16—C19 | 118.9 (5) | C25—N5—H5A | 120.0 |
C15—C16—C19 | 123.8 (5) | C25—N5—H5B | 120.0 |
N4—C17—C16 | 122.1 (4) | H5A—N5—H5B | 120.0 |
N4—C17—C18 | 117.3 (4) | C25—N6—H6A | 120.0 |
C16—C17—C18 | 120.6 (4) | C25—N6—H6B | 120.0 |
N3—C18—C21 | 122.8 (4) | H6A—N6—H6B | 120.0 |
N3—C18—C17 | 117.7 (4) | Co1—O1—H1A | 109.5 |
C21—C18—C17 | 119.5 (4) | Co1—O1—H1B | 112 (3) |
C20—C19—C16 | 120.4 (5) | H1A—O1—H1B | 129.2 |
C20—C19—H19 | 119.8 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···Cl2i | 0.88 (5) | 2.39 (5) | 3.165 (4) | 148 (4) |
O1—H1A···Cl2ii | 0.82 | 2.31 | 3.100 (3) | 162 |
N6—H6A···Cl2 | 0.86 | 2.68 | 3.491 (12) | 157 |
N5—H5B···S1iii | 0.86 | 2.48 | 3.328 (9) | 168 |
N5—H5A···Cl2 | 0.86 | 2.60 | 3.441 (8) | 165 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y, z−1; (iii) −x, −y+1, −z+1. |