{2,6-Bis[(dimethyl­amino)meth­yl]phenyl-κ²N,C¹,N′}chloro­nickel(II)

The title complex, [Ni(C₁₂H₁₉N₂)Cl], consists of a slightly distorted square-planar Ni^II center coordinated by an anionic terdentate NCN pincer-type ligand, where both N atoms are trans to each other, and by a chloride ion. It is isostructural with two platinum analogues.

Key indicators

• Single-crystal X-ray study
• T = 473 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.093
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............       0.00 Deg.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.00
PLAT037_ALERT_1_A _diffrn_reflns_theta_full .......... Not Given .          ?
PLAT038_ALERT_1_A _diffrn_measured_fraction_theta_max  Not Given .          ?
PLAT039_ALERT_1_A _diffrn_measured_fraction_theta_full Not Given .          ?
PLAT095_ALERT_1_A No Residual Density Maximum Given ..............          ?
PLAT096_ALERT_1_A No Residual Density Minimum Given ..............          ?

Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni     -   Cl      ..       5.89 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni     -   C1      ..       6.36 su

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

   5 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
   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: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); 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: UdMX (Maris, 2004).

{2,6-Bis[(dimethylamino)methyl]phenyl-κ²N,C¹,N'}chloronickel(II)

Crystal data

[Ni(C12H19N2)Cl]	F(000) = 600
Mr = 285.45	Dx = 1.478 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 12652 reflections
a = 13.0386 (7) Å	θ = 3.7–68.9°
b = 9.0976 (5) Å	µ = 3.88 mm^−1
c = 11.6950 (7) Å	T = 473 K
β = 112.329 (2)°	Block, orange
V = 1283.24 (12) Å^3	0.16 × 0.14 × 0.12 mm
Z = 4

Data collection

Bruker SMART 2000 diffractometer	2347 independent reflections
Radiation source: X-ray Sealed Tube	2222 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 5.5 pixels mm^-1	θmax = 68.9°, θmin = 3.7°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
Tmin = 0.546, Tmax = 0.628	l = −14→14
17426 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0641P)^2 + 0.3203P] where P = (Fo^2 + 2Fc^2)/3
2347 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = please provide e Å^−3
0 restraints	Δρmin = please provide e Å^−3

Special details

Experimental. X-ray crystallographic data for I were collected from a single-crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 2 K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu—Kα radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8 Å resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis.

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
Ni	0.19004 (2)	0.47941 (3)	−0.05696 (2)	0.02706 (14)
Cl	0.04727 (3)	0.47184 (5)	−0.23963 (4)	0.03582 (15)
N1	0.26941 (10)	0.64436 (15)	−0.09951 (11)	0.0297 (3)
N2	0.14164 (10)	0.31501 (15)	0.02327 (11)	0.0294 (3)
C1	0.30387 (14)	0.49287 (18)	0.09416 (16)	0.0286 (3)
C2	0.39576 (13)	0.57951 (18)	0.10782 (14)	0.0312 (3)
C3	0.48165 (13)	0.5909 (2)	0.22323 (15)	0.0360 (4)
H3	0.5432	0.6491	0.2336	0.043*
C4	0.47440 (16)	0.5141 (2)	0.32305 (17)	0.0378 (4)
H4	0.5321	0.5203	0.4000	0.045*
C5	0.38176 (14)	0.42807 (19)	0.30913 (14)	0.0341 (4)
H5	0.3777	0.3776	0.3765	0.041*
C6	0.29565 (13)	0.41825 (17)	0.19426 (14)	0.0305 (3)
C7	0.26663 (15)	0.6462 (2)	−0.22790 (15)	0.0405 (4)
H7A	0.1912	0.6530	−0.2854	0.061*
H7B	0.2993	0.5574	−0.2430	0.061*
H7C	0.3077	0.7294	−0.2381	0.061*
C8	0.21361 (15)	0.77947 (19)	−0.08138 (17)	0.0391 (4)
H8A	0.2473	0.8641	−0.1018	0.059*
H8B	0.2210	0.7856	0.0033	0.059*
H8C	0.1364	0.7761	−0.1340	0.059*
C9	0.18755 (13)	0.33884 (19)	0.16136 (14)	0.0329 (3)
H9A	0.1363	0.3969	0.1850	0.039*
H9B	0.1989	0.2452	0.2041	0.039*
C10	0.19362 (15)	0.18105 (19)	−0.00409 (16)	0.0389 (4)
H10A	0.1748	0.0973	0.0340	0.058*
H10B	0.2727	0.1929	0.0280	0.058*
H10C	0.1669	0.1665	−0.0919	0.058*
C11	0.02079 (14)	0.2855 (2)	−0.01763 (16)	0.0381 (4)
H11A	−0.0089	0.2621	−0.1042	0.057*
H11B	−0.0158	0.3711	−0.0035	0.057*
H11C	0.0091	0.2042	0.0284	0.057*
C12	0.38906 (12)	0.6475 (2)	−0.01191 (14)	0.0345 (4)
H12A	0.4343	0.5925	−0.0463	0.041*
H12B	0.4158	0.7480	0.0017	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.0258 (2)	0.0313 (2)	0.02068 (19)	−0.00017 (9)	0.00499 (14)	0.00079 (9)
Cl	0.0330 (2)	0.0407 (3)	0.0254 (2)	−0.00193 (15)	0.00177 (18)	0.00007 (14)
N1	0.0268 (6)	0.0360 (7)	0.0238 (6)	0.0006 (5)	0.0067 (5)	0.0027 (5)
N2	0.0302 (6)	0.0320 (7)	0.0239 (6)	−0.0010 (5)	0.0078 (5)	−0.0011 (5)
C1	0.0290 (8)	0.0307 (7)	0.0245 (8)	0.0025 (6)	0.0084 (7)	0.0000 (6)
C2	0.0289 (8)	0.0339 (8)	0.0277 (8)	0.0025 (6)	0.0071 (6)	0.0003 (6)
C3	0.0282 (8)	0.0402 (9)	0.0334 (9)	−0.0023 (7)	0.0046 (7)	−0.0018 (7)
C4	0.0353 (10)	0.0438 (10)	0.0254 (8)	0.0022 (7)	0.0015 (7)	−0.0022 (7)
C5	0.0386 (9)	0.0383 (9)	0.0216 (7)	0.0047 (7)	0.0072 (6)	0.0017 (6)
C6	0.0333 (8)	0.0308 (8)	0.0256 (7)	0.0031 (6)	0.0093 (6)	−0.0013 (6)
C7	0.0398 (9)	0.0548 (11)	0.0264 (8)	−0.0033 (8)	0.0120 (7)	0.0045 (7)
C8	0.0386 (9)	0.0345 (9)	0.0429 (9)	0.0036 (7)	0.0141 (8)	0.0051 (7)
C9	0.0363 (8)	0.0368 (8)	0.0238 (7)	−0.0017 (7)	0.0096 (6)	0.0003 (6)
C10	0.0484 (10)	0.0331 (8)	0.0346 (8)	0.0030 (7)	0.0149 (8)	−0.0019 (7)
C11	0.0327 (8)	0.0428 (9)	0.0359 (8)	−0.0077 (7)	0.0096 (7)	0.0008 (7)
C12	0.0264 (8)	0.0429 (9)	0.0296 (8)	−0.0018 (7)	0.0056 (6)	0.0041 (7)

Geometric parameters (Å, º)

Ni—C1	1.8298 (17)	C5—H5	0.93
Ni—N1	1.9904 (13)	C6—C9	1.498 (2)
Ni—N2	1.9914 (13)	C7—H7a	0.96
Ni—Cl	2.2388 (5)	C7—H7b	0.96
N1—C8	1.484 (2)	C7—H7c	0.96
N1—C7	1.4882 (19)	C8—H8a	0.96
N1—C12	1.5065 (19)	C8—H8b	0.96
N2—C11	1.487 (2)	C8—H8c	0.96
N2—C10	1.487 (2)	C9—H9a	0.97
N2—C9	1.5095 (19)	C9—H9b	0.97
C1—C2	1.392 (2)	C10—H10a	0.96
C1—C6	1.392 (2)	C10—H10b	0.96
C2—C3	1.392 (2)	C10—H10c	0.96
C2—C12	1.503 (2)	C11—H11a	0.96
C3—C4	1.394 (3)	C11—H11b	0.96
C3—H3	0.93	C11—H11c	0.96
C4—C5	1.396 (3)	C12—H12a	0.97
C4—H4	0.93	C12—H12b	0.97
C5—C6	1.388 (2)
C1—Ni—N1	83.28 (6)	N1—C7—H7A	109.5
C1—Ni—N2	83.17 (6)	N1—C7—H7B	109.5
N1—Ni—N2	166.41 (5)	H7A—C7—H7B	109.5
C1—Ni—Cl	177.41 (5)	N1—C7—H7C	109.5
N1—Ni—Cl	96.17 (4)	H7A—C7—H7C	109.5
N2—Ni—Cl	97.41 (4)	H7B—C7—H7C	109.5
C8—N1—C7	108.03 (13)	N1—C8—H8A	109.5
C8—N1—C12	108.94 (13)	N1—C8—H8B	109.5
C7—N1—C12	107.93 (12)	H8A—C8—H8B	109.5
C8—N1—Ni	105.01 (10)	N1—C8—H8C	109.5
C7—N1—Ni	116.42 (11)	H8A—C8—H8C	109.5
C12—N1—Ni	110.28 (10)	H8B—C8—H8C	109.5
C11—N2—C10	107.25 (13)	C6—C9—N2	107.21 (12)
C11—N2—C9	108.13 (12)	C6—C9—H9A	110.3
C10—N2—C9	108.66 (12)	N2—C9—H9A	110.3
C11—N2—Ni	118.1 (1)	C6—C9—H9B	110.3
C10—N2—Ni	105.2 (1)	N2—C9—H9B	110.3
C9—N2—Ni	109.17 (10)	H9A—C9—H9B	108.5
C2—C1—C6	121.17 (15)	N2—C10—H10A	109.5
C2—C1—Ni	119.72 (13)	N2—C10—H10B	109.5
C6—C1—Ni	119.09 (13)	H10A—C10—H10B	109.5
C1—C2—C3	119.59 (15)	N2—C10—H10C	109.5
C1—C2—C12	112.54 (14)	H10A—C10—H10C	109.5
C3—C2—C12	127.84 (15)	H10B—C10—H10C	109.5
C2—C3—C4	119.27 (16)	N2—C11—H11A	109.5
C2—C3—H3	120.4	N2—C11—H11B	109.5
C4—C3—H3	120.4	H11A—C11—H11B	109.5
C3—C4—C5	120.95 (16)	N2—C11—H11C	109.5
C3—C4—H4	119.5	H11A—C11—H11C	109.5
C5—C4—H4	119.5	H11B—C11—H11C	109.5
C6—C5—C4	119.66 (16)	C2—C12—N1	107.73 (12)
C6—C5—H5	120.2	C2—C12—H12A	110.2
C4—C5—H5	120.2	N1—C12—H12A	110.2
C5—C6—C1	119.34 (15)	C2—C12—H12B	110.2
C5—C6—C9	128.00 (15)	N1—C12—H12B	110.2
C1—C6—C9	112.63 (14)	H12A—C12—H12B	108.5
C1—Ni—N1—C8	−95.91 (11)	Ni—C1—C2—C3	179.25 (13)
N2—Ni—N1—C8	−100.8 (2)	C6—C1—C2—C12	178.79 (15)
Cl—Ni—N1—C8	81.55 (10)	Ni—C1—C2—C12	−2.59 (19)
C1—Ni—N1—C7	144.68 (12)	C1—C2—C3—C4	0.5 (2)
N2—Ni—N1—C7	139.8 (2)	C12—C2—C3—C4	−177.31 (17)
Cl—Ni—N1—C7	−37.86 (11)	C2—C3—C4—C5	−1.0 (3)
C1—Ni—N1—C12	21.31 (11)	C3—C4—C5—C6	0.2 (3)
N2—Ni—N1—C12	16.4 (3)	C4—C5—C6—C1	0.9 (2)
Cl—Ni—N1—C12	−161.24 (9)	C4—C5—C6—C9	−176.67 (16)
C1—Ni—N2—C11	148.94 (12)	C2—C1—C6—C5	−1.4 (2)
N1—Ni—N2—C11	153.9 (2)	Ni—C1—C6—C5	180.00 (12)
Cl—Ni—N2—C11	−28.52 (11)	C2—C1—C6—C9	176.59 (15)
C1—Ni—N2—C10	−91.50 (11)	Ni—C1—C6—C9	−2.04 (19)
N1—Ni—N2—C10	−86.6 (2)	C5—C6—C9—N2	−160.26 (16)
Cl—Ni—N2—C10	91.04 (9)	C1—C6—C9—N2	22.00 (18)
C1—Ni—N2—C9	24.95 (11)	C11—N2—C9—C6	−160.60 (13)
N1—Ni—N2—C9	29.9 (3)	C10—N2—C9—C6	83.31 (15)
Cl—Ni—N2—C9	−152.51 (9)	Ni—N2—C9—C6	−30.92 (15)
N1—Ni—C1—C2	−10.87 (13)	C1—C2—C12—N1	19.49 (19)
N2—Ni—C1—C2	167.97 (14)	C3—C2—C12—N1	−162.55 (16)
N1—Ni—C1—C6	167.78 (14)	C8—N1—C12—C2	87.90 (16)
N2—Ni—C1—C6	−13.38 (13)	C7—N1—C12—C2	−155.04 (14)
C6—C1—C2—C3	0.6 (2)	Ni—N1—C12—C2	−26.86 (15)