{2,2'-[Ethane-1,2-diylbis(nitrilomethylidene)]diphenolato}cobalt(II)

The Co^II atom in the title compound, [Co(C₁₆H₁₄N₂O₂)], has a square-planar coordination.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.037
• wR factor = 0.082
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co     -   O2      ..       6.17 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co     -   N1      ..       6.03 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co     -   N2      ..       6.78 su
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            N2  -CO  -O1  -C1   -111.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          5
            N1  -CO  -O2  -C16   -86.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          9
            O2  -CO  -N1  -C7    -85.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         12
            O2  -CO  -N1  -C8     92.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         14
            O1  -CO  -N2  -C10   -77.00  4.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         17
            O1  -CO  -N2  -C9     99.00  4.00   1.555   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

{2,2'-Ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}cobalt(II)

Crystal data

[Co(C16H14N2O2)]	Dx = 1.605 Mg m^−3
Mr = 325.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 33 reflections
a = 7.471 (1) Å	θ = 5.3–14.7°
b = 13.805 (2) Å	µ = 1.28 mm^−1
c = 26.096 (5) Å	T = 297 K
V = 2691.5 (7) Å^3	Prism, red
Z = 8	0.58 × 0.44 × 0.12 mm
F(000) = 1336

Data collection

Siemens P4 diffractometer	1605 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.013
Graphite monochromator	θmax = 25.5°, θmin = 1.6°
ω scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→16
Tmin = 0.514, Tmax = 0.858	l = −1→31
3059 measured reflections	3 standard reflections every 97 reflections
2497 independent reflections	intensity decay: 2.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.035P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max = 0.001
2497 reflections	Δρmax = 0.31 e Å^−3
191 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0062 (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
Co	0.19052 (5)	0.54793 (2)	0.488555 (15)	0.03025 (15)
O1	0.1170 (3)	0.63715 (13)	0.44032 (8)	0.0414 (6)
O2	0.0963 (3)	0.63360 (13)	0.53592 (8)	0.0405 (5)
N1	0.2896 (3)	0.46416 (17)	0.44137 (10)	0.0386 (6)
N2	0.2576 (4)	0.45852 (17)	0.53706 (11)	0.0406 (6)
C1	0.1252 (4)	0.6285 (2)	0.38991 (12)	0.0375 (8)
C2	0.0351 (5)	0.6972 (2)	0.35996 (13)	0.0451 (9)
H2	−0.0321	0.7452	0.3759	0.054*
C3	0.0446 (5)	0.6949 (2)	0.30704 (14)	0.0564 (10)
H3	−0.0164	0.7411	0.2878	0.068*
C4	0.1451 (6)	0.6237 (3)	0.28240 (14)	0.0685 (12)
H4	0.1549	0.6237	0.2469	0.082*
C5	0.2288 (5)	0.5545 (3)	0.31059 (13)	0.0597 (11)
H5	0.2938	0.5064	0.2940	0.072*
C6	0.2190 (4)	0.5540 (2)	0.36478 (12)	0.0418 (8)
C7	0.2964 (4)	0.4756 (2)	0.39211 (13)	0.0441 (9)
H7	0.3566	0.4287	0.3732	0.053*
C8	0.3751 (5)	0.3772 (2)	0.46352 (13)	0.0487 (9)
H8A	0.5035	0.3866	0.4660	0.058*
H8B	0.3523	0.3212	0.4420	0.058*
C9	0.2966 (5)	0.3621 (2)	0.51577 (13)	0.0518 (9)
H9A	0.1877	0.3241	0.5135	0.062*
H9B	0.3808	0.3280	0.5375	0.062*
C10	0.2644 (5)	0.4709 (2)	0.58655 (14)	0.0456 (9)
H10	0.3129	0.4214	0.6063	0.055*
C11	0.2024 (5)	0.5555 (2)	0.61231 (12)	0.0425 (8)
C12	0.2175 (5)	0.5598 (3)	0.66635 (14)	0.0597 (11)
H12	0.2807	0.5116	0.6835	0.072*
C13	0.1419 (6)	0.6324 (3)	0.69363 (14)	0.0690 (13)
H13	0.1558	0.6351	0.7290	0.083*
C14	0.0434 (5)	0.7029 (2)	0.66832 (14)	0.0601 (11)
H14	−0.0122	0.7516	0.6871	0.072*
C15	0.0266 (5)	0.7018 (2)	0.61546 (13)	0.0447 (9)
H15	−0.0406	0.7494	0.5992	0.054*
C16	0.1103 (4)	0.6294 (2)	0.58623 (13)	0.0386 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co	0.0375 (2)	0.0241 (2)	0.0292 (2)	−0.00055 (19)	−0.0031 (2)	−0.00047 (19)
O1	0.0586 (15)	0.0375 (12)	0.0280 (12)	0.0044 (11)	0.0011 (12)	0.0015 (10)
O2	0.0531 (14)	0.0385 (11)	0.0299 (12)	0.0055 (11)	−0.0020 (12)	0.0024 (10)
N1	0.0421 (17)	0.0305 (13)	0.0433 (16)	0.0003 (14)	−0.0063 (14)	−0.0026 (12)
N2	0.0433 (15)	0.0343 (13)	0.0442 (16)	−0.0010 (13)	−0.0042 (15)	0.0014 (14)
C1	0.045 (2)	0.0355 (17)	0.0317 (19)	−0.0063 (16)	−0.0010 (16)	−0.0012 (15)
C2	0.059 (2)	0.0423 (18)	0.034 (2)	0.0008 (18)	−0.0047 (19)	−0.0003 (16)
C3	0.071 (3)	0.060 (2)	0.038 (2)	0.003 (2)	−0.007 (2)	0.0050 (19)
C4	0.097 (4)	0.076 (3)	0.032 (2)	0.010 (3)	0.003 (2)	0.000 (2)
C5	0.078 (3)	0.064 (2)	0.037 (2)	0.010 (2)	0.011 (2)	−0.0115 (19)
C6	0.048 (2)	0.0432 (18)	0.0342 (19)	−0.0008 (18)	0.0029 (17)	−0.0027 (16)
C7	0.044 (2)	0.0427 (18)	0.046 (2)	−0.0009 (17)	0.0046 (19)	−0.0113 (16)
C8	0.051 (2)	0.0358 (17)	0.059 (2)	0.0040 (16)	−0.001 (2)	−0.0021 (17)
C9	0.064 (3)	0.0328 (15)	0.059 (2)	0.0092 (18)	−0.005 (2)	0.0052 (17)
C10	0.048 (2)	0.0410 (19)	0.047 (2)	−0.0053 (17)	−0.0096 (19)	0.0093 (17)
C11	0.049 (2)	0.0425 (18)	0.035 (2)	−0.0067 (19)	−0.0042 (17)	0.0046 (16)
C12	0.077 (3)	0.060 (2)	0.042 (2)	−0.001 (2)	−0.009 (2)	0.0095 (19)
C13	0.101 (4)	0.074 (3)	0.032 (2)	−0.008 (3)	−0.001 (2)	−0.002 (2)
C14	0.086 (3)	0.055 (2)	0.039 (2)	−0.008 (2)	0.008 (2)	−0.0097 (19)
C15	0.059 (2)	0.0396 (17)	0.036 (2)	−0.0064 (17)	0.0060 (19)	−0.0050 (16)
C16	0.043 (2)	0.0393 (18)	0.033 (2)	−0.0121 (17)	−0.0020 (17)	0.0048 (15)

Geometric parameters (Å, º)

Co—N2	1.838 (3)	C6—C7	1.420 (4)
Co—N1	1.844 (3)	C7—H7	0.9300
Co—O1	1.845 (2)	C8—C9	1.499 (4)
Co—O2	1.850 (2)	C8—H8A	0.9700
O1—C1	1.322 (3)	C8—H8B	0.9700
O2—C16	1.318 (3)	C9—H9A	0.9700
N1—C7	1.296 (4)	C9—H9B	0.9700
N1—C8	1.477 (4)	C10—C11	1.425 (4)
N2—C10	1.304 (4)	C10—H10	0.9300
N2—C9	1.472 (4)	C11—C16	1.407 (4)
C1—C2	1.401 (4)	C11—C12	1.416 (4)
C1—C6	1.406 (4)	C12—C13	1.353 (5)
C2—C3	1.383 (4)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.387 (5)
C3—C4	1.394 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.385 (5)
C4—C5	1.359 (5)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.404 (4)
C5—C6	1.416 (4)	C15—H15	0.9300
C5—H5	0.9300
N2—Co—N1	85.95 (11)	C6—C7—H7	117.5
N2—Co—O1	178.50 (11)	N1—C8—C9	107.5 (3)
N1—Co—O1	94.73 (10)	N1—C8—H8A	110.2
N2—Co—O2	94.18 (11)	C9—C8—H8A	110.2
N1—Co—O2	178.61 (10)	N1—C8—H8B	110.2
O1—Co—O2	85.17 (8)	C9—C8—H8B	110.2
C1—O1—Co	127.21 (19)	H8A—C8—H8B	108.5
C16—O2—Co	127.4 (2)	N2—C9—C8	107.1 (2)
C7—N1—C8	118.0 (3)	N2—C9—H9A	110.3
C7—N1—Co	127.0 (2)	C8—C9—H9A	110.3
C8—N1—Co	114.9 (2)	N2—C9—H9B	110.3
C10—N2—C9	119.0 (3)	C8—C9—H9B	110.3
C10—N2—Co	127.2 (2)	H9A—C9—H9B	108.5
C9—N2—Co	113.7 (2)	N2—C10—C11	124.2 (3)
O1—C1—C2	118.1 (3)	N2—C10—H10	117.9
O1—C1—C6	123.6 (3)	C11—C10—H10	117.9
C2—C1—C6	118.3 (3)	C16—C11—C12	119.4 (3)
C3—C2—C1	121.1 (3)	C16—C11—C10	121.7 (3)
C3—C2—H2	119.4	C12—C11—C10	118.6 (3)
C1—C2—H2	119.4	C13—C12—C11	121.5 (3)
C2—C3—C4	120.3 (3)	C13—C12—H12	119.3
C2—C3—H3	119.9	C11—C12—H12	119.3
C4—C3—H3	119.9	C12—C13—C14	119.4 (4)
C5—C4—C3	119.6 (3)	C12—C13—H13	120.3
C5—C4—H4	120.2	C14—C13—H13	120.3
C3—C4—H4	120.2	C15—C14—C13	121.0 (3)
C4—C5—C6	121.3 (3)	C15—C14—H14	119.5
C4—C5—H5	119.3	C13—C14—H14	119.5
C6—C5—H5	119.3	C14—C15—C16	120.6 (3)
C1—C6—C5	119.2 (3)	C14—C15—H15	119.7
C1—C6—C7	121.8 (3)	C16—C15—H15	119.7
C5—C6—C7	118.9 (3)	O2—C16—C15	118.4 (3)
N1—C7—C6	125.1 (3)	O2—C16—C11	123.5 (3)
N1—C7—H7	117.5	C15—C16—C11	118.1 (3)
N2—Co—O1—C1	−111 (4)	C4—C5—C6—C1	−1.9 (6)
N1—Co—O1—C1	6.0 (3)	C4—C5—C6—C7	174.8 (3)
O2—Co—O1—C1	−175.4 (3)	C8—N1—C7—C6	179.0 (3)
N2—Co—O2—C16	9.6 (3)	Co—N1—C7—C6	−3.5 (5)
N1—Co—O2—C16	−86 (4)	C1—C6—C7—N1	0.0 (5)
O1—Co—O2—C16	−171.8 (3)	C5—C6—C7—N1	−176.7 (3)
N2—Co—N1—C7	179.5 (3)	C7—N1—C8—C9	−160.4 (3)
O1—Co—N1—C7	0.8 (3)	Co—N1—C8—C9	21.7 (3)
O2—Co—N1—C7	−85 (4)	C10—N2—C9—C8	−150.1 (3)
N2—Co—N1—C8	−3.0 (2)	Co—N2—C9—C8	33.2 (3)
O1—Co—N1—C8	178.4 (2)	N1—C8—C9—N2	−33.4 (3)
O2—Co—N1—C8	92 (4)	C9—N2—C10—C11	−169.5 (3)
N1—Co—N2—C10	166.0 (3)	Co—N2—C10—C11	6.6 (5)
O1—Co—N2—C10	−77 (4)	N2—C10—C11—C16	6.8 (5)
O2—Co—N2—C10	−12.6 (3)	N2—C10—C11—C12	179.9 (3)
N1—Co—N2—C9	−17.7 (2)	C16—C11—C12—C13	1.4 (6)
O1—Co—N2—C9	99 (4)	C10—C11—C12—C13	−171.9 (4)
O2—Co—N2—C9	163.7 (2)	C11—C12—C13—C14	1.8 (6)
Co—O1—C1—C2	169.4 (2)	C12—C13—C14—C15	−2.3 (6)
Co—O1—C1—C6	−10.4 (4)	C13—C14—C15—C16	−0.4 (5)
O1—C1—C2—C3	177.2 (3)	Co—O2—C16—C15	−179.4 (2)
C6—C1—C2—C3	−3.0 (5)	Co—O2—C16—C11	−0.4 (4)
C1—C2—C3—C4	−0.2 (5)	C14—C15—C16—O2	−177.4 (3)
C2—C3—C4—C5	2.3 (6)	C14—C15—C16—C11	3.6 (5)
C3—C4—C5—C6	−1.3 (6)	C12—C11—C16—O2	177.0 (3)
O1—C1—C6—C5	−176.2 (3)	C10—C11—C16—O2	−9.9 (5)
C2—C1—C6—C5	4.0 (5)	C12—C11—C16—C15	−4.0 (5)
O1—C1—C6—C7	7.2 (5)	C10—C11—C16—C15	169.1 (3)
C2—C1—C6—C7	−172.7 (3)