{N,N′-Bis­[(5-chloro-2-hydroxy­phenyl)­phenyl­methyl­ene]­ethyl­endiaminato}nickel(II)

In the title complex, [Ni(C₂₈H₂₀Cl₂N₂O₂)], the Ni^II atom exists in a square-planar environment, coordinated by four atoms from the tetradentate ligand. Molecules are held together by intermolecular C—H...O hydrogen bonds, which link the mol­ecules in a chain along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.058
• wR factor = 0.148
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.620     0.898
            Tmin' and Tmax expected:      0.821     0.898
            RR' =      0.755
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.75
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          5
            N1  -NI1 -O2  -C14    99.90  1.50   1.555   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

{N,N'-Bis[(5-chloro-2-hydroxyphenyl)phenylmethylene]ethylendiaminato}nickel(II)

Crystal data

[Ni(C28H20Cl2N2O2)]	Z = 2
Mr = 546.07	F(000) = 560
Triclinic, P1	Dx = 1.532 Mg m^−3
a = 10.168 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.945 (5) Å	Cell parameters from 840 reflections
c = 11.492 (6) Å	θ = 3.3–25.1°
α = 68.232 (7)°	µ = 1.08 mm^−1
β = 89.066 (8)°	T = 293 K
γ = 85.532 (8)°	Prism, red
V = 1184.0 (10) Å^3	0.18 × 0.12 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	4133 independent reflections
Radiation source: fine-focus sealed tube	2641 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→6
Tmin = 0.620, Tmax = 0.898	k = −13→13
6084 measured reflections	l = −13→12

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.148	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.074P)^2] where P = (Fo^2 + 2Fc^2)/3
4133 reflections	(Δ/σ)max = 0.002
316 parameters	Δρmax = 0.73 e Å^−3
0 restraints	Δρmin = −0.46 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.25830 (6)	0.54090 (6)	−0.00439 (7)	0.0299 (2)
Cl1	−0.23268 (14)	0.24641 (16)	0.44933 (15)	0.0545 (4)
Cl2	0.74402 (16)	0.61205 (17)	−0.48104 (16)	0.0614 (5)
O1	0.1787 (3)	0.3874 (3)	0.0737 (3)	0.0385 (9)
O2	0.3469 (3)	0.4513 (3)	−0.0918 (3)	0.0358 (9)
N1	0.1529 (4)	0.6340 (4)	0.0733 (4)	0.0313 (10)
N2	0.3520 (4)	0.6892 (4)	−0.0739 (4)	0.0292 (10)
C1	−0.1369 (5)	0.7493 (5)	0.1420 (6)	0.0400 (14)
H1	−0.1719	0.7261	0.0795	0.048*
C2	−0.2046 (5)	0.8426 (5)	0.1782 (6)	0.0435 (15)
H2	−0.2855	0.8815	0.1406	0.052*
C3	−0.1543 (5)	0.8785 (6)	0.2685 (6)	0.0469 (15)
H3	−0.1991	0.9442	0.2902	0.056*
C4	−0.0364 (6)	0.8177 (6)	0.3281 (6)	0.0508 (16)
H4	−0.0028	0.8405	0.3915	0.061*
C5	0.0309 (5)	0.7229 (6)	0.2928 (6)	0.0462 (15)
H5	0.1095	0.6809	0.3335	0.055*
C6	−0.0171 (5)	0.6896 (5)	0.1980 (5)	0.0304 (12)
C7	0.0599 (5)	0.5925 (5)	0.1554 (5)	0.0302 (12)
C8	0.0268 (5)	0.4578 (5)	0.2030 (5)	0.0315 (12)
C9	−0.0735 (5)	0.4188 (5)	0.2927 (5)	0.0345 (13)
H9	−0.1178	0.4811	0.3193	0.041*
C10	−0.1060 (5)	0.2928 (5)	0.3404 (5)	0.0371 (13)
C11	−0.0381 (5)	0.1961 (6)	0.3072 (6)	0.0444 (15)
H11	−0.0579	0.1086	0.3443	0.053*
C12	0.0588 (6)	0.2307 (5)	0.2190 (6)	0.0476 (16)
H12	0.1038	0.1659	0.1962	0.057*
C13	0.0914 (5)	0.3619 (5)	0.1624 (5)	0.0337 (13)
C14	0.4318 (5)	0.4961 (5)	−0.1819 (5)	0.0320 (12)
C15	0.4691 (5)	0.4159 (5)	−0.2514 (5)	0.0380 (13)
H15	0.4296	0.3375	−0.2348	0.046*
C16	0.5628 (5)	0.4524 (5)	−0.3431 (5)	0.0418 (14)
H16	0.5858	0.3994	−0.3887	0.050*
C17	0.6223 (5)	0.5681 (5)	−0.3668 (5)	0.0376 (13)
C18	0.5870 (5)	0.6507 (5)	−0.3061 (5)	0.0363 (13)
H18	0.6279	0.7288	−0.3250	0.044*
C19	0.4877 (5)	0.6179 (5)	−0.2138 (5)	0.0295 (12)
C20	0.4447 (5)	0.7116 (5)	−0.1570 (5)	0.0294 (12)
C21	0.5082 (5)	0.8399 (4)	−0.1963 (5)	0.0292 (12)
C22	0.4687 (5)	0.9414 (5)	−0.3063 (6)	0.0435 (14)
H22	0.4057	0.9290	−0.3578	0.052*
C23	0.5227 (6)	1.0616 (6)	−0.3400 (6)	0.0530 (17)
H23	0.4958	1.1306	−0.4138	0.064*
C24	0.6164 (6)	1.0784 (6)	−0.2636 (7)	0.0536 (18)
H24	0.6528	1.1592	−0.2860	0.064*
C25	0.6565 (6)	0.9780 (6)	−0.1555 (6)	0.0504 (16)
H25	0.7201	0.9903	−0.1045	0.060*
C26	0.6029 (5)	0.8582 (5)	−0.1217 (6)	0.0404 (14)
H26	0.6309	0.7895	−0.0481	0.049*
C27	0.3150 (5)	0.7860 (5)	−0.0155 (5)	0.0396 (14)
H27A	0.3275	0.8744	−0.0743	0.048*
H27B	0.3704	0.7685	0.0577	0.048*
C28	0.1744 (5)	0.7756 (5)	0.0216 (6)	0.0436 (15)
H28A	0.1557	0.8143	0.0841	0.052*
H28B	0.1170	0.8214	−0.0506	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0344 (4)	0.0246 (4)	0.0308 (4)	−0.0052 (3)	0.0042 (3)	−0.0099 (3)
Cl1	0.0461 (9)	0.0663 (10)	0.0476 (10)	−0.0211 (7)	0.0145 (7)	−0.0143 (8)
Cl2	0.0655 (10)	0.0655 (11)	0.0558 (12)	−0.0131 (8)	0.0291 (9)	−0.0250 (9)
O1	0.047 (2)	0.030 (2)	0.042 (3)	−0.0129 (16)	0.0160 (18)	−0.0161 (18)
O2	0.043 (2)	0.0257 (19)	0.043 (3)	−0.0096 (16)	0.0139 (18)	−0.0164 (18)
N1	0.031 (2)	0.025 (2)	0.037 (3)	−0.0020 (18)	0.006 (2)	−0.010 (2)
N2	0.034 (2)	0.024 (2)	0.032 (3)	−0.0014 (18)	0.0042 (19)	−0.012 (2)
C1	0.042 (3)	0.035 (3)	0.044 (4)	−0.004 (2)	−0.002 (3)	−0.015 (3)
C2	0.035 (3)	0.034 (3)	0.060 (4)	0.002 (2)	0.000 (3)	−0.017 (3)
C3	0.049 (4)	0.042 (4)	0.057 (4)	−0.002 (3)	0.010 (3)	−0.028 (3)
C4	0.057 (4)	0.055 (4)	0.053 (4)	0.005 (3)	−0.004 (3)	−0.037 (4)
C5	0.049 (3)	0.043 (4)	0.050 (4)	0.007 (3)	−0.010 (3)	−0.021 (3)
C6	0.034 (3)	0.030 (3)	0.028 (3)	−0.008 (2)	0.004 (2)	−0.011 (2)
C7	0.029 (3)	0.030 (3)	0.033 (3)	0.000 (2)	0.001 (2)	−0.013 (2)
C8	0.035 (3)	0.026 (3)	0.028 (3)	−0.004 (2)	0.000 (2)	−0.004 (2)
C9	0.036 (3)	0.035 (3)	0.034 (3)	−0.006 (2)	0.002 (2)	−0.013 (3)
C10	0.034 (3)	0.043 (3)	0.031 (3)	−0.010 (2)	0.002 (2)	−0.008 (3)
C11	0.050 (3)	0.034 (3)	0.047 (4)	−0.019 (3)	0.014 (3)	−0.009 (3)
C12	0.057 (4)	0.032 (3)	0.061 (5)	−0.014 (3)	0.015 (3)	−0.023 (3)
C13	0.034 (3)	0.035 (3)	0.035 (4)	−0.010 (2)	0.003 (2)	−0.016 (3)
C14	0.033 (3)	0.030 (3)	0.032 (3)	0.000 (2)	−0.007 (2)	−0.010 (3)
C15	0.049 (3)	0.026 (3)	0.041 (4)	−0.005 (2)	0.009 (3)	−0.014 (3)
C16	0.057 (4)	0.032 (3)	0.037 (4)	0.002 (3)	0.004 (3)	−0.014 (3)
C17	0.041 (3)	0.037 (3)	0.031 (3)	0.001 (2)	0.008 (2)	−0.009 (3)
C18	0.036 (3)	0.032 (3)	0.039 (4)	0.000 (2)	0.004 (2)	−0.011 (3)
C19	0.030 (3)	0.026 (3)	0.033 (3)	−0.005 (2)	0.001 (2)	−0.011 (2)
C20	0.029 (3)	0.025 (3)	0.033 (3)	−0.002 (2)	−0.006 (2)	−0.009 (2)
C21	0.034 (3)	0.019 (3)	0.032 (3)	−0.006 (2)	0.008 (2)	−0.005 (2)
C22	0.044 (3)	0.038 (3)	0.046 (4)	−0.007 (3)	0.004 (3)	−0.013 (3)
C23	0.069 (4)	0.035 (3)	0.042 (4)	−0.006 (3)	0.013 (3)	0.002 (3)
C24	0.061 (4)	0.034 (4)	0.071 (5)	−0.021 (3)	0.023 (4)	−0.023 (4)
C25	0.055 (4)	0.042 (4)	0.058 (5)	−0.015 (3)	0.004 (3)	−0.021 (3)
C26	0.045 (3)	0.029 (3)	0.047 (4)	−0.007 (2)	−0.001 (3)	−0.013 (3)
C27	0.055 (3)	0.025 (3)	0.041 (4)	−0.004 (2)	0.009 (3)	−0.014 (3)
C28	0.050 (3)	0.024 (3)	0.055 (4)	−0.006 (2)	0.011 (3)	−0.013 (3)

Geometric parameters (Å, º)

Ni1—O1	1.831 (3)	C11—H11	0.9300
Ni1—O2	1.830 (3)	C12—C13	1.403 (7)
Ni1—N1	1.859 (4)	C12—H12	0.9300
Ni1—N2	1.854 (4)	C14—C19	1.409 (6)
Cl1—C10	1.749 (5)	C14—C15	1.418 (7)
Cl2—C17	1.749 (5)	C15—C16	1.375 (7)
O1—C13	1.304 (6)	C15—H15	0.9300
O2—C14	1.310 (6)	C16—C17	1.380 (7)
N1—C7	1.308 (6)	C16—H16	0.9300
N1—C28	1.473 (6)	C17—C18	1.357 (7)
N2—C20	1.301 (6)	C18—C19	1.419 (7)
N2—C27	1.473 (6)	C18—H18	0.9300
C1—C2	1.373 (7)	C19—C20	1.444 (7)
C1—C6	1.384 (7)	C20—C21	1.501 (6)
C1—H1	0.9300	C21—C26	1.374 (7)
C2—C3	1.357 (8)	C21—C22	1.378 (7)
C2—H2	0.9300	C22—C23	1.383 (7)
C3—C4	1.384 (8)	C22—H22	0.9300
C3—H3	0.9300	C23—C24	1.373 (9)
C4—C5	1.379 (7)	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.361 (9)
C5—C6	1.377 (7)	C24—H24	0.9300
C5—H5	0.9300	C25—C26	1.376 (7)
C6—C7	1.492 (7)	C25—H25	0.9300
C7—C8	1.435 (7)	C26—H26	0.9300
C8—C9	1.411 (7)	C27—C28	1.486 (7)
C8—C13	1.414 (7)	C27—H27A	0.9700
C9—C10	1.348 (7)	C27—H27B	0.9700
C9—H9	0.9300	C28—H28A	0.9700
C10—C11	1.385 (7)	C28—H28B	0.9700
C11—C12	1.372 (7)
O1—Ni1—O2	85.11 (15)	C12—C13—C8	118.4 (5)
O1—Ni1—N1	93.53 (16)	O2—C14—C19	124.4 (5)
O1—Ni1—N2	174.79 (18)	O2—C14—C15	117.3 (4)
O2—Ni1—N1	173.87 (18)	C19—C14—C15	118.3 (5)
O2—Ni1—N2	93.92 (16)	C16—C15—C14	121.0 (5)
N1—Ni1—N2	87.96 (17)	C16—C15—H15	119.5
C13—O1—Ni1	128.4 (3)	C14—C15—H15	119.5
C14—O2—Ni1	127.8 (3)	C15—C16—C17	119.4 (5)
C7—N1—C28	119.1 (4)	C15—C16—H16	120.3
C7—N1—Ni1	129.1 (3)	C17—C16—H16	120.3
C28—N1—Ni1	111.5 (3)	C18—C17—C16	121.9 (5)
C20—N2—C27	120.2 (4)	C18—C17—Cl2	118.9 (4)
C20—N2—Ni1	129.1 (3)	C16—C17—Cl2	119.2 (4)
C27—N2—Ni1	110.6 (3)	C17—C18—C19	120.0 (5)
C2—C1—C6	120.4 (5)	C17—C18—H18	120.0
C2—C1—H1	119.8	C19—C18—H18	120.0
C6—C1—H1	119.8	C14—C19—C18	119.1 (5)
C3—C2—C1	120.5 (5)	C14—C19—C20	121.8 (4)
C3—C2—H2	119.8	C18—C19—C20	119.1 (4)
C1—C2—H2	119.8	N2—C20—C19	122.3 (4)
C2—C3—C4	120.1 (5)	N2—C20—C21	118.9 (4)
C2—C3—H3	119.9	C19—C20—C21	118.8 (4)
C4—C3—H3	119.9	C26—C21—C22	119.7 (5)
C5—C4—C3	119.4 (6)	C26—C21—C20	120.5 (5)
C5—C4—H4	120.3	C22—C21—C20	119.9 (5)
C3—C4—H4	120.3	C21—C22—C23	120.0 (6)
C6—C5—C4	120.8 (5)	C21—C22—H22	120.0
C6—C5—H5	119.6	C23—C22—H22	120.0
C4—C5—H5	119.6	C24—C23—C22	119.5 (6)
C5—C6—C1	118.7 (5)	C24—C23—H23	120.3
C5—C6—C7	120.5 (5)	C22—C23—H23	120.3
C1—C6—C7	120.8 (5)	C25—C24—C23	120.7 (5)
N1—C7—C8	122.3 (4)	C25—C24—H24	119.7
N1—C7—C6	118.7 (4)	C23—C24—H24	119.7
C8—C7—C6	118.9 (4)	C24—C25—C26	120.0 (6)
C9—C8—C13	118.4 (4)	C24—C25—H25	120.0
C9—C8—C7	119.6 (5)	C26—C25—H25	120.0
C13—C8—C7	121.9 (4)	C21—C26—C25	120.2 (6)
C10—C9—C8	121.1 (5)	C21—C26—H26	119.9
C10—C9—H9	119.4	C25—C26—H26	119.9
C8—C9—H9	119.4	N2—C27—C28	108.9 (4)
C9—C10—C11	121.0 (5)	N2—C27—H27A	109.9
C9—C10—Cl1	120.7 (4)	C28—C27—H27A	109.9
C11—C10—Cl1	118.3 (4)	N2—C27—H27B	109.9
C12—C11—C10	119.4 (5)	C28—C27—H27B	109.9
C12—C11—H11	120.3	H27A—C27—H27B	108.3
C10—C11—H11	120.3	N1—C28—C27	106.7 (4)
C11—C12—C13	121.4 (5)	N1—C28—H28A	110.4
C11—C12—H12	119.3	C27—C28—H28A	110.4
C13—C12—H12	119.3	N1—C28—H28B	110.4
O1—C13—C12	117.3 (5)	C27—C28—H28B	110.4
O1—C13—C8	124.2 (4)	H28A—C28—H28B	108.6
O2—Ni1—O1—C13	178.9 (5)	C9—C8—C13—O1	174.9 (5)
N1—Ni1—O1—C13	−7.1 (5)	C7—C8—C13—O1	−4.9 (8)
O1—Ni1—O2—C14	177.4 (4)	C9—C8—C13—C12	−4.0 (8)
N2—Ni1—O2—C14	−7.8 (4)	C7—C8—C13—C12	176.2 (5)
N1—Ni1—O2—C14	99.9 (15)	Ni1—O2—C14—C19	11.4 (7)
O1—Ni1—N1—C7	1.3 (5)	Ni1—O2—C14—C15	−168.5 (4)
N2—Ni1—N1—C7	−173.7 (5)	O2—C14—C15—C16	−176.6 (5)
O1—Ni1—N1—C28	−172.4 (4)	C19—C14—C15—C16	3.5 (8)
N2—Ni1—N1—C28	12.6 (4)	C14—C15—C16—C17	0.6 (9)
O2—Ni1—N2—C20	1.1 (5)	C15—C16—C17—C18	−3.0 (9)
N1—Ni1—N2—C20	−173.1 (5)	C15—C16—C17—Cl2	178.6 (4)
O2—Ni1—N2—C27	−174.9 (3)	C16—C17—C18—C19	1.1 (9)
N1—Ni1—N2—C27	10.9 (4)	Cl2—C17—C18—C19	179.5 (4)
C6—C1—C2—C3	0.6 (8)	O2—C14—C19—C18	174.7 (5)
C1—C2—C3—C4	−2.4 (9)	C15—C14—C19—C18	−5.4 (8)
C2—C3—C4—C5	1.6 (9)	O2—C14—C19—C20	−6.6 (8)
C3—C4—C5—C6	0.9 (9)	C15—C14—C19—C20	173.3 (5)
C4—C5—C6—C1	−2.6 (8)	C17—C18—C19—C14	3.2 (8)
C4—C5—C6—C7	176.6 (5)	C17—C18—C19—C20	−175.5 (5)
C2—C1—C6—C5	1.9 (8)	C27—N2—C20—C19	177.8 (5)
C2—C1—C6—C7	−177.3 (5)	Ni1—N2—C20—C19	2.2 (7)
C28—N1—C7—C8	175.3 (5)	C27—N2—C20—C21	−2.9 (7)
Ni1—N1—C7—C8	2.0 (8)	Ni1—N2—C20—C21	−178.6 (4)
C28—N1—C7—C6	−2.7 (7)	C14—C19—C20—N2	−0.3 (8)
Ni1—N1—C7—C6	−176.1 (4)	C18—C19—C20—N2	178.4 (5)
C5—C6—C7—N1	−83.8 (7)	C14—C19—C20—C21	−179.6 (5)
C1—C6—C7—N1	95.3 (6)	C18—C19—C20—C21	−0.9 (7)
C5—C6—C7—C8	98.0 (6)	N2—C20—C21—C26	78.8 (6)
C1—C6—C7—C8	−82.8 (6)	C19—C20—C21—C26	−101.9 (6)
N1—C7—C8—C9	179.2 (5)	N2—C20—C21—C22	−99.4 (6)
C6—C7—C8—C9	−2.7 (7)	C19—C20—C21—C22	79.9 (6)
N1—C7—C8—C13	−1.0 (8)	C26—C21—C22—C23	−1.1 (8)
C6—C7—C8—C13	177.0 (5)	C20—C21—C22—C23	177.1 (5)
C13—C8—C9—C10	1.0 (8)	C21—C22—C23—C24	0.5 (9)
C7—C8—C9—C10	−179.2 (5)	C22—C23—C24—C25	0.1 (9)
C8—C9—C10—C11	2.9 (8)	C23—C24—C25—C26	−0.1 (9)
C8—C9—C10—Cl1	−178.8 (4)	C22—C21—C26—C25	1.1 (8)
C9—C10—C11—C12	−3.8 (9)	C20—C21—C26—C25	−177.1 (5)
Cl1—C10—C11—C12	177.9 (5)	C24—C25—C26—C21	−0.5 (9)
C10—C11—C12—C13	0.6 (9)	C20—N2—C27—C28	151.9 (5)
Ni1—O1—C13—C12	−171.4 (4)	Ni1—N2—C27—C28	−31.7 (5)
Ni1—O1—C13—C8	9.7 (8)	C7—N1—C28—C27	153.2 (5)
C11—C12—C13—O1	−175.7 (6)	Ni1—N1—C28—C27	−32.3 (5)
C11—C12—C13—C8	3.3 (9)	N2—C27—C28—N1	40.5 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1^i	0.93	2.51	3.385 (7)	157
C26—H26···O2^ii	0.93	2.52	3.371 (7)	152

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z.