Retracted: cis-Dichloro­bis(1,10-phenanthroline)cobalt(II)

In the mol­ecule of the title compound, cis-[CoCl₂(C₁₂H₈N₂)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.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](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

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Computing details

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)

Crystal data

[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) Å^3	0.26 × 0.26 × 0.26 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.745P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cl2^i	0.93	2.63	3.537 (3)	165
C19—H19···Cl1^ii	0.93	2.65	3.573 (3)	172
C22—H22···Cl1^iii	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.