{N,N′-Bis[3-(2-nitro­phen­yl)allyl­idene]ethane-1,2-diamine-κ²N,N′}dichloro­cobalt(II)

In the title complex, [CoCl₂(C₂₀H₁₈N₄O₄)₂], the Co^II atom has a distorted tetra­hedral coordination. The organic ligand is bidentate, coordinating the Co^II atom via two imine N atoms.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.066
• wR factor = 0.176
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: P3/PC (Siemens, 1989); cell refinement: P3/PC; data reduction: P3/PC; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.

{N,N'-Bis[3-(2-nitrophenyl)allylidene]ethane-1,2-diamine- κ²N,N'}dichlorocobalt(II)

Crystal data

[CoCl2(C20H18N4O4)]	F(000) = 1036
Mr = 508.21	Dx = 1.547 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 24 reflections
a = 7.8387 (16) Å	θ = 12.0–13.0°
b = 16.048 (3) Å	µ = 1.07 mm^−1
c = 17.633 (4) Å	T = 173 K
β = 100.27 (3)°	Prism, blue
V = 2182.6 (8) Å^3	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection

Upgraded Syntex P21/Siemens P3 four-circle diffractometer	Rint = 0.059
Radiation source: normal-focus sealed tube	θmax = 27.0°, θmin = 2.7°
Graphite monochromator	h = −10→9
ω scans	k = −8→20
4931 measured reflections	l = −22→22
4627 independent reflections	2 standard reflections every 98 reflections
2974 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.176	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.096P)^2] where P = (Fo^2 + 2Fc^2)/3
4627 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.58 e Å^−3
0 restraints	Δρmin = −0.63 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	0.13609 (7)	0.17604 (4)	0.57573 (4)	0.0282 (2)
Cl1	0.27603 (16)	0.14202 (8)	0.48034 (9)	0.0481 (4)
Cl2	0.28313 (18)	0.25215 (9)	0.67082 (9)	0.0524 (4)
O1	0.4181 (4)	−0.2342 (2)	0.6499 (2)	0.0447 (9)
O2	0.5865 (5)	−0.3003 (2)	0.7404 (3)	0.0530 (10)
O3	−0.3806 (5)	0.5625 (3)	0.4684 (2)	0.0488 (10)
O4	−0.4562 (5)	0.6267 (3)	0.5644 (3)	0.0631 (12)
N1	0.0205 (4)	0.0701 (2)	0.6060 (2)	0.0277 (8)
N2	−0.1114 (4)	0.2135 (2)	0.5400 (2)	0.0269 (8)
N3	0.5366 (5)	−0.2365 (2)	0.7052 (3)	0.0378 (10)
N4	−0.3489 (5)	0.5925 (2)	0.5332 (2)	0.0307 (9)
C1	0.3512 (6)	−0.0737 (3)	0.6913 (3)	0.0276 (9)
H1A	0.2792	−0.1193	0.6995	0.033*
C2	0.2764 (6)	−0.0055 (3)	0.6556 (3)	0.0289 (10)
H2A	0.3475	0.0388	0.6438	0.035*
C3	0.0900 (6)	0.0018 (3)	0.6347 (3)	0.0289 (10)
H3A	0.0184	−0.0441	0.6422	0.035*
C4	−0.1708 (5)	0.0777 (3)	0.5889 (3)	0.0314 (10)
H4A	−0.2141	0.0979	0.6351	0.038*
H4B	−0.2240	0.0228	0.5742	0.038*
C5	−0.2186 (5)	0.1396 (3)	0.5227 (3)	0.0329 (11)
H5A	−0.1985	0.1142	0.4739	0.040*
H5B	−0.3428	0.1547	0.5168	0.040*
C6	−0.1821 (5)	0.2864 (3)	0.5386 (3)	0.0292 (10)
H6A	−0.3040	0.2911	0.5227	0.035*
C7	−0.0833 (6)	0.3606 (3)	0.5602 (3)	0.0286 (9)
H7A	0.0386	0.3572	0.5768	0.034*
C8	−0.1631 (6)	0.4345 (3)	0.5571 (3)	0.0285 (10)
H8A	−0.2837	0.4357	0.5368	0.034*
C9	0.5396 (6)	−0.0813 (3)	0.7184 (3)	0.0281 (10)
C10	0.6271 (5)	−0.1579 (3)	0.7299 (3)	0.0269 (9)
C11	0.8015 (6)	−0.1642 (3)	0.7628 (3)	0.0344 (11)
H11A	0.8558	−0.2172	0.7707	0.041*
C12	0.8940 (6)	−0.0930 (3)	0.7838 (3)	0.0374 (11)
H12A	1.0135	−0.0963	0.8058	0.045*
C13	0.8136 (6)	−0.0162 (3)	0.7728 (3)	0.0355 (11)
H13A	0.8784	0.0331	0.7869	0.043*
C14	0.6391 (6)	−0.0111 (3)	0.7414 (3)	0.0324 (10)
H14A	0.5856	0.0422	0.7353	0.039*
C15	−0.0792 (5)	0.5137 (3)	0.5826 (3)	0.0288 (10)
C16	−0.1693 (5)	0.5896 (3)	0.5764 (3)	0.0297 (10)
C17	−0.1015 (6)	0.6633 (3)	0.6063 (3)	0.0336 (10)
H17A	−0.1708	0.7123	0.6016	0.040*
C18	0.0684 (7)	0.6660 (3)	0.6434 (3)	0.0389 (11)
H18A	0.1185	0.7170	0.6637	0.047*
C19	0.1661 (6)	0.5927 (3)	0.6507 (3)	0.0379 (11)
H19A	0.2840	0.5942	0.6756	0.045*
C20	0.0937 (6)	0.5187 (3)	0.6222 (3)	0.0335 (11)
H20A	0.1619	0.4694	0.6294	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0199 (3)	0.0225 (3)	0.0398 (4)	−0.0010 (2)	−0.0014 (2)	0.0047 (3)
Cl1	0.0421 (7)	0.0395 (7)	0.0675 (10)	0.0072 (6)	0.0228 (6)	0.0076 (6)
Cl2	0.0439 (7)	0.0471 (8)	0.0567 (9)	−0.0152 (6)	−0.0170 (6)	−0.0001 (7)
O1	0.0378 (19)	0.0359 (19)	0.056 (3)	0.0021 (15)	−0.0032 (17)	−0.0095 (17)
O2	0.054 (2)	0.0260 (18)	0.077 (3)	0.0072 (16)	0.005 (2)	0.0131 (19)
O3	0.045 (2)	0.061 (3)	0.037 (2)	0.0016 (18)	−0.0016 (16)	−0.0003 (19)
O4	0.041 (2)	0.067 (3)	0.079 (3)	0.015 (2)	0.004 (2)	−0.021 (2)
N1	0.0235 (18)	0.0246 (18)	0.032 (2)	0.0011 (14)	−0.0046 (15)	0.0002 (16)
N2	0.0206 (17)	0.0265 (18)	0.032 (2)	0.0006 (14)	−0.0009 (15)	0.0009 (16)
N3	0.035 (2)	0.027 (2)	0.053 (3)	0.0028 (17)	0.011 (2)	0.0019 (19)
N4	0.0300 (19)	0.0267 (19)	0.033 (2)	0.0030 (16)	−0.0007 (16)	0.0015 (17)
C1	0.032 (2)	0.020 (2)	0.030 (2)	0.0015 (17)	0.0042 (18)	0.0029 (18)
C2	0.030 (2)	0.022 (2)	0.033 (3)	0.0004 (18)	0.0017 (19)	0.0032 (19)
C3	0.030 (2)	0.023 (2)	0.033 (3)	0.0013 (17)	0.0032 (19)	0.0013 (19)
C4	0.021 (2)	0.025 (2)	0.046 (3)	−0.0025 (17)	0.0026 (19)	0.005 (2)
C5	0.020 (2)	0.026 (2)	0.049 (3)	0.0016 (18)	−0.0028 (19)	−0.002 (2)
C6	0.020 (2)	0.029 (2)	0.037 (3)	0.0035 (17)	0.0022 (18)	0.007 (2)
C7	0.025 (2)	0.030 (2)	0.031 (2)	0.0025 (18)	0.0033 (18)	0.0058 (19)
C8	0.023 (2)	0.028 (2)	0.033 (3)	0.0013 (17)	0.0000 (18)	−0.0001 (19)
C9	0.031 (2)	0.027 (2)	0.026 (2)	0.0032 (18)	0.0034 (18)	−0.0005 (18)
C10	0.030 (2)	0.024 (2)	0.027 (2)	0.0024 (17)	0.0041 (18)	0.0015 (17)
C11	0.029 (2)	0.037 (3)	0.035 (3)	0.0098 (19)	0.0005 (19)	0.007 (2)
C12	0.027 (2)	0.050 (3)	0.034 (3)	0.006 (2)	−0.0007 (19)	0.003 (2)
C13	0.033 (2)	0.039 (3)	0.034 (3)	−0.007 (2)	0.005 (2)	−0.005 (2)
C14	0.035 (2)	0.025 (2)	0.037 (3)	0.0020 (18)	0.005 (2)	0.003 (2)
C15	0.024 (2)	0.030 (2)	0.032 (3)	−0.0004 (17)	0.0023 (18)	0.0031 (19)
C16	0.024 (2)	0.029 (2)	0.034 (3)	0.0007 (18)	0.0003 (18)	0.0035 (19)
C17	0.039 (2)	0.029 (2)	0.034 (3)	−0.0019 (19)	0.010 (2)	−0.002 (2)
C18	0.044 (3)	0.038 (3)	0.033 (3)	−0.011 (2)	0.004 (2)	−0.003 (2)
C19	0.033 (2)	0.046 (3)	0.033 (3)	−0.007 (2)	0.000 (2)	−0.002 (2)
C20	0.027 (2)	0.038 (3)	0.035 (3)	0.0039 (19)	0.0021 (19)	0.010 (2)

Geometric parameters (Å, º)

Co1—N1	2.042 (4)	C6—H6A	0.9500
Co1—N2	2.022 (3)	C7—C8	1.337 (6)
Co1—Cl1	2.2335 (16)	C7—H7A	0.9500
Co1—Cl2	2.2233 (15)	C8—C15	1.464 (6)
O1—N3	1.221 (6)	C8—H8A	0.9500
O2—N3	1.225 (5)	C9—C14	1.390 (6)
O3—N4	1.224 (5)	C9—C10	1.405 (6)
O4—N4	1.215 (6)	C10—C11	1.391 (6)
N1—C3	1.287 (5)	C11—C12	1.369 (7)
N1—C4	1.481 (5)	C11—H11A	0.9500
N2—C6	1.293 (6)	C12—C13	1.381 (7)
N2—C5	1.454 (6)	C12—H12A	0.9500
N3—C10	1.474 (6)	C13—C14	1.384 (7)
N4—C16	1.477 (6)	C13—H13A	0.9500
C1—C2	1.344 (6)	C14—H14A	0.9500
C1—C9	1.474 (6)	C15—C16	1.403 (6)
C1—H1A	0.9500	C15—C20	1.412 (6)
C2—C3	1.446 (6)	C16—C17	1.364 (6)
C2—H2A	0.9500	C17—C18	1.375 (7)
C3—H3A	0.9500	C17—H17A	0.9500
C4—C5	1.528 (7)	C18—C19	1.397 (7)
C4—H4A	0.9900	C18—H18A	0.9500
C4—H4B	0.9900	C19—C20	1.373 (7)
C5—H5A	0.9900	C19—H19A	0.9500
C5—H5B	0.9900	C20—H20A	0.9500
C6—C7	1.434 (6)
N2—Co1—N1	83.30 (14)	C8—C7—C6	119.9 (4)
N2—Co1—Cl2	114.29 (12)	C8—C7—H7A	120.0
N1—Co1—Cl2	117.06 (12)	C6—C7—H7A	120.0
N2—Co1—Cl1	114.26 (12)	C7—C8—C15	125.2 (4)
N1—Co1—Cl1	107.07 (12)	C7—C8—H8A	117.4
Cl2—Co1—Cl1	116.37 (6)	C15—C8—H8A	117.4
C3—N1—C4	119.5 (4)	C14—C9—C10	115.7 (4)
C3—N1—Co1	129.5 (3)	C14—C9—C1	120.4 (4)
C4—N1—Co1	111.0 (3)	C10—C9—C1	123.7 (4)
C6—N2—C5	120.3 (3)	C11—C10—C9	122.8 (4)
C6—N2—Co1	131.2 (3)	C11—C10—N3	116.6 (4)
C5—N2—Co1	108.0 (3)	C9—C10—N3	120.6 (4)
O1—N3—O2	123.9 (4)	C12—C11—C10	119.1 (4)
O1—N3—C10	117.9 (4)	C12—C11—H11A	120.5
O2—N3—C10	118.2 (4)	C10—C11—H11A	120.5
O4—N4—O3	124.0 (4)	C11—C12—C13	120.1 (4)
O4—N4—C16	117.0 (4)	C11—C12—H12A	120.0
O3—N4—C16	119.0 (4)	C13—C12—H12A	120.0
C2—C1—C9	123.2 (4)	C12—C13—C14	120.2 (4)
C2—C1—H1A	118.4	C12—C13—H13A	119.9
C9—C1—H1A	118.4	C14—C13—H13A	119.9
C1—C2—C3	121.5 (4)	C13—C14—C9	122.1 (4)
C1—C2—H2A	119.3	C13—C14—H14A	119.0
C3—C2—H2A	119.3	C9—C14—H14A	119.0
N1—C3—C2	120.5 (4)	C16—C15—C20	114.5 (4)
N1—C3—H3A	119.8	C16—C15—C8	122.5 (4)
C2—C3—H3A	119.8	C20—C15—C8	122.7 (4)
N1—C4—C5	108.1 (4)	C17—C16—C15	124.5 (4)
N1—C4—H4A	110.1	C17—C16—N4	116.2 (4)
C5—C4—H4A	110.1	C15—C16—N4	119.2 (4)
N1—C4—H4B	110.1	C16—C17—C18	119.2 (4)
C5—C4—H4B	110.1	C16—C17—H17A	120.4
H4A—C4—H4B	108.4	C18—C17—H17A	120.4
N2—C5—C4	108.4 (4)	C17—C18—C19	119.1 (4)
N2—C5—H5A	110.0	C17—C18—H18A	120.5
C4—C5—H5A	110.0	C19—C18—H18A	120.5
N2—C5—H5B	110.0	C20—C19—C18	120.7 (4)
C4—C5—H5B	110.0	C20—C19—H19A	119.6
H5A—C5—H5B	108.4	C18—C19—H19A	119.6
N2—C6—C7	122.5 (4)	C19—C20—C15	121.8 (4)
N2—C6—H6A	118.7	C19—C20—H20A	119.1
C7—C6—H6A	118.7	C15—C20—H20A	119.1
N2—Co1—N1—C3	176.9 (4)	C1—C9—C10—N3	8.3 (7)
Cl2—Co1—N1—C3	−69.2 (4)	O1—N3—C10—C11	−149.0 (4)
Cl1—Co1—N1—C3	63.5 (4)	O2—N3—C10—C11	29.7 (6)
N2—Co1—N1—C4	−1.7 (3)	O1—N3—C10—C9	29.5 (6)
Cl2—Co1—N1—C4	112.2 (3)	O2—N3—C10—C9	−151.7 (5)
Cl1—Co1—N1—C4	−115.1 (3)	C9—C10—C11—C12	−1.3 (7)
N1—Co1—N2—C6	147.1 (5)	N3—C10—C11—C12	177.2 (4)
Cl2—Co1—N2—C6	30.4 (5)	C10—C11—C12—C13	0.6 (7)
Cl1—Co1—N2—C6	−107.2 (4)	C11—C12—C13—C14	0.7 (8)
N1—Co1—N2—C5	−25.1 (3)	C12—C13—C14—C9	−1.4 (8)
Cl2—Co1—N2—C5	−141.8 (3)	C10—C9—C14—C13	0.7 (7)
Cl1—Co1—N2—C5	80.6 (3)	C1—C9—C14—C13	174.8 (4)
C9—C1—C2—C3	−175.6 (4)	C7—C8—C15—C16	178.7 (5)
C4—N1—C3—C2	−176.7 (4)	C7—C8—C15—C20	−7.9 (8)
Co1—N1—C3—C2	4.8 (7)	C20—C15—C16—C17	−0.9 (7)
C1—C2—C3—N1	174.6 (5)	C8—C15—C16—C17	173.0 (5)
C3—N1—C4—C5	−151.9 (4)	C20—C15—C16—N4	177.4 (4)
Co1—N1—C4—C5	26.8 (4)	C8—C15—C16—N4	−8.7 (7)
C6—N2—C5—C4	−126.6 (5)	O4—N4—C16—C17	−50.1 (6)
Co1—N2—C5—C4	46.6 (4)	O3—N4—C16—C17	128.5 (5)
N1—C4—C5—N2	−48.4 (5)	O4—N4—C16—C15	131.5 (5)
C5—N2—C6—C7	175.7 (4)	O3—N4—C16—C15	−50.0 (6)
Co1—N2—C6—C7	4.3 (7)	C15—C16—C17—C18	2.1 (8)
N2—C6—C7—C8	179.4 (5)	N4—C16—C17—C18	−176.3 (4)
C6—C7—C8—C15	175.5 (5)	C16—C17—C18—C19	−1.2 (7)
C2—C1—C9—C14	30.0 (7)	C17—C18—C19—C20	−0.8 (8)
C2—C1—C9—C10	−156.3 (5)	C18—C19—C20—C15	2.0 (8)
C14—C9—C10—C11	0.7 (7)	C16—C15—C20—C19	−1.2 (7)
C1—C9—C10—C11	−173.3 (4)	C8—C15—C20—C19	−175.1 (5)
C14—C9—C10—N3	−177.8 (4)