trans-Bis{2-[3-(cyclo­hexyl­amino)­propyl­imino­methyl]­phenolato}nickel(II) dinitrate

You, Z.-L.; Lin, Y.-S.; Zhu, H.-L.; Liu, W.-S.

doi:10.1107/S1600536804012851

trans-Bis{2-[3-(cyclohexylamino)propyliminomethyl]phenolato}nickel(II) dinitrate

Z.-L. You, Y.-S. Lin, H.-L. Zhu and W.-S. Liu

The title compound, [Ni(C₁₆H₂₄N₂O)₂](NO₃)₂, is a mononuclear nickel(II) compound. The Ni^II atom is coordinated by two N atoms and two O atoms from the Schiff base ligands. The four atoms around the metal are coplanar, constituting a slightly distorted square-planar geometry. The complex is located on an inversion center. All of the nitrate O atoms and all amine N atoms in the Schiff base ligands contribute to hydrogen bonds, leading to the formation of a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804012851/ac6103sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804012851/ac6103Isup2.hkl Contains datablock I

CCDC reference: 242296

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.063
wR factor = 0.148
Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.01
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O1      ..       5.68 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         O1
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....         N3
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            O1  -NI1 -O1  -C2     32.00100.00   3.666   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          6
            N1  -NI1 -N1  -C7    -79.00100.00   3.666   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          9
            N1  -NI1 -N1  -C8    100.00100.00   3.666   1.555   1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.93(3), Rep   0.932(10) ......       3.00 su-Rat
              N2   -H2B     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.93(3), Rep   0.932(10) ......       3.00 su-Rat
              N2   -H2B     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.93(3), Rep   0.932(10) ......       3.00 su-Rat
              N2   -H2B     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.93(3), Rep   0.932(10) ......       3.00 su-Rat
              N2   -H2B     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.54(3), Rep   2.542(12) ......       2.50 su-Rat
              H2B  -N3      1.555   4.576

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

   7 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
   5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

trans-Bis{2-[3-(Cyclohexylamino)propyliminomethyl]phenolato}nickel(II) dinitrate top

Crystal data top

[Ni(C₁₆H₂₄N₂O)₂](NO₃)₂	F(000) = 748
M_r = 703.47	D_x = 1.351 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.444 (2) Å	Cell parameters from 1144 reflections
b = 22.946 (5) Å	θ = 2.5–19.9°
c = 11.961 (2) Å	µ = 0.62 mm⁻¹
β = 102.02 (3)°	T = 293 K
V = 1729.9 (6) Å³	Block, green
Z = 2	0.18 × 0.15 × 0.13 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	3573 independent reflections
Radiation source: fine-focus sealed tube	1985 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
φ and ω scans	θ_max = 26.5°, θ_min = 1.8°
Absorption correction: multi-scan sadabs, (Blessing, 1995)	h = −8→4
T_min = 0.897, T_max = 0.924	k = −28→27
7948 measured reflections	l = −14→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0601P)²] where P = (F_o² + 2F_c²)/3
3573 reflections	(Δ/σ)_max < 0.001
222 parameters	Δρ_max = 0.48 e Å⁻³
3 restraints	Δρ_min = −0.24 e Å⁻³

Special details top

Experimental. C, H and N elemental analyses were performed on a Perkin-Elmer elemental analyzer.

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 (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.5000	0.5000	0.0478 (2)
O1	0.3655 (4)	0.44625 (10)	0.5725 (3)	0.0716 (8)
O2	0.0869 (7)	0.74798 (17)	0.3169 (4)	0.1217 (14)
O3	0.3720 (6)	0.72569 (14)	0.2676 (3)	0.0915 (10)
O4	0.1234 (6)	0.7596 (2)	0.1444 (3)	0.1352 (17)
N1	0.3334 (5)	0.56320 (12)	0.5391 (3)	0.0481 (7)
N2	0.4661 (5)	0.75360 (13)	0.5247 (3)	0.0534 (8)
N3	0.1909 (8)	0.74479 (17)	0.2439 (4)	0.0761 (11)
C1	0.1280 (6)	0.50630 (16)	0.6477 (3)	0.0523 (9)
C2	0.2203 (6)	0.45221 (16)	0.6331 (3)	0.0532 (10)
C3	0.1500 (7)	0.40313 (17)	0.6844 (4)	0.0654 (11)
H3	0.2102	0.3670	0.6761	0.078*
C4	−0.0019 (8)	0.4073 (2)	0.7452 (4)	0.0726 (13)
H4	−0.0434	0.3738	0.7788	0.087*
C5	−0.0980 (7)	0.4590 (2)	0.7595 (4)	0.0796 (13)
H5	−0.2055	0.4610	0.8005	0.096*
C6	−0.0311 (7)	0.50820 (19)	0.7114 (4)	0.0726 (12)
H6	−0.0936	0.5438	0.7215	0.087*
C7	0.1905 (6)	0.55839 (16)	0.5970 (3)	0.0545 (10)
H7	0.1182	0.5923	0.6079	0.065*
C8	0.3665 (6)	0.62420 (14)	0.5034 (3)	0.0515 (10)
H8A	0.2373	0.6465	0.4991	0.062*
H8B	0.4014	0.6242	0.4283	0.062*
C9	0.5458 (6)	0.65181 (14)	0.5895 (3)	0.0609 (11)
H9A	0.4961	0.6590	0.6595	0.073*
H9B	0.6615	0.6241	0.6072	0.073*
C10	0.6311 (6)	0.70810 (15)	0.5521 (4)	0.0655 (12)
H10A	0.7446	0.7221	0.6125	0.079*
H10B	0.6902	0.7008	0.4852	0.079*
C11	0.5512 (6)	0.81509 (14)	0.5228 (3)	0.0546 (10)
H11	0.6340	0.8242	0.5992	0.066*
C12	0.3626 (7)	0.85595 (16)	0.4975 (4)	0.0783 (14)
H12A	0.2827	0.8528	0.5576	0.094*
H12B	0.2700	0.8448	0.4260	0.094*
C13	0.4350 (8)	0.91869 (17)	0.4896 (5)	0.0883 (16)
H13A	0.3119	0.9438	0.4689	0.106*
H13B	0.5153	0.9311	0.5635	0.106*
C14	0.5700 (9)	0.92435 (18)	0.4022 (4)	0.0930 (17)
H14A	0.6189	0.9643	0.4005	0.112*
H14B	0.4863	0.9150	0.3272	0.112*
C15	0.7582 (8)	0.88403 (18)	0.4298 (4)	0.0835 (14)
H15A	0.8486	0.8961	0.5014	0.100*
H15B	0.8397	0.8872	0.3705	0.100*
C16	0.6934 (6)	0.82061 (16)	0.4397 (3)	0.0604 (11)
H16A	0.6205	0.8065	0.3654	0.072*
H16B	0.8191	0.7969	0.4649	0.072*
H2A	0.389 (5)	0.7438 (17)	0.4528 (13)	0.085 (16)*
H2B	0.374 (4)	0.7525 (16)	0.575 (2)	0.073 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0538 (4)	0.0331 (3)	0.0583 (4)	−0.0014 (3)	0.0157 (3)	0.0036 (3)
O1	0.083 (2)	0.0426 (15)	0.099 (2)	0.0021 (14)	0.0417 (18)	0.0067 (14)
O2	0.144 (4)	0.128 (3)	0.114 (3)	−0.003 (2)	0.076 (3)	−0.019 (2)
O3	0.078 (2)	0.101 (2)	0.089 (2)	−0.008 (2)	0.003 (2)	0.0032 (19)
O4	0.082 (3)	0.243 (5)	0.077 (3)	0.039 (3)	0.012 (2)	0.026 (3)
N1	0.0503 (19)	0.0414 (17)	0.0526 (19)	−0.0048 (14)	0.0112 (16)	−0.0001 (14)
N2	0.057 (2)	0.0416 (18)	0.064 (2)	−0.0021 (16)	0.018 (2)	0.0049 (16)
N3	0.081 (3)	0.080 (3)	0.069 (3)	−0.014 (2)	0.020 (3)	−0.010 (2)
C1	0.058 (2)	0.048 (2)	0.049 (2)	−0.0071 (19)	0.0076 (19)	−0.0030 (19)
C2	0.057 (2)	0.053 (2)	0.051 (2)	−0.0073 (19)	0.016 (2)	−0.0006 (19)
C3	0.082 (3)	0.051 (2)	0.066 (3)	−0.003 (2)	0.022 (3)	0.005 (2)
C4	0.088 (3)	0.070 (3)	0.064 (3)	−0.023 (3)	0.025 (3)	0.011 (2)
C5	0.078 (3)	0.096 (4)	0.076 (3)	−0.007 (3)	0.040 (3)	−0.001 (3)
C6	0.082 (3)	0.067 (3)	0.073 (3)	0.006 (2)	0.028 (3)	−0.009 (2)
C7	0.063 (3)	0.045 (2)	0.054 (2)	0.0020 (19)	0.009 (2)	−0.0046 (18)
C8	0.059 (3)	0.0361 (19)	0.058 (2)	0.0033 (17)	0.010 (2)	0.0065 (17)
C9	0.074 (3)	0.036 (2)	0.066 (3)	−0.0049 (19)	0.000 (2)	0.0067 (18)
C10	0.054 (3)	0.051 (2)	0.085 (3)	0.0008 (19)	−0.002 (2)	0.005 (2)
C11	0.072 (3)	0.0337 (19)	0.060 (3)	−0.0069 (18)	0.018 (2)	−0.0025 (17)
C12	0.088 (4)	0.043 (2)	0.113 (4)	0.006 (2)	0.042 (3)	0.002 (2)
C13	0.121 (4)	0.042 (2)	0.107 (4)	0.012 (2)	0.033 (4)	0.000 (3)
C14	0.150 (5)	0.036 (2)	0.095 (4)	−0.004 (3)	0.030 (4)	0.009 (2)
C15	0.105 (4)	0.061 (3)	0.088 (4)	−0.022 (3)	0.027 (3)	0.014 (2)
C16	0.070 (3)	0.050 (2)	0.064 (3)	−0.0047 (19)	0.019 (2)	0.0059 (19)

Geometric parameters (Å, º) top

Ni1—O1ⁱ	1.827 (3)	C8—C9	1.517 (5)
Ni1—O1	1.827 (3)	C8—H8A	0.9700
Ni1—N1	1.919 (3)	C8—H8B	0.9700
Ni1—N1ⁱ	1.919 (3)	C9—C10	1.508 (5)
O1—C2	1.305 (4)	C9—H9A	0.9700
O2—N3	1.208 (5)	C9—H9B	0.9700
O3—N3	1.223 (5)	C10—H10A	0.9700
O4—N3	1.228 (5)	C10—H10B	0.9700
N1—C7	1.268 (5)	C11—C16	1.491 (5)
N1—C8	1.492 (4)	C11—C12	1.515 (5)
N2—C10	1.477 (5)	C11—H11	0.9800
N2—C11	1.516 (4)	C12—C13	1.522 (5)
N2—H2A	0.926 (10)	C12—H12A	0.9700
N2—H2B	0.932 (10)	C12—H12B	0.9700
C1—C6	1.399 (5)	C13—C14	1.498 (6)
C1—C2	1.403 (5)	C13—H13A	0.9700
C1—C7	1.435 (5)	C13—H13B	0.9700
C2—C3	1.402 (5)	C14—C15	1.506 (6)
C3—C4	1.339 (6)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C4—C5	1.367 (6)	C15—C16	1.525 (5)
C4—H4	0.9300	C15—H15A	0.9700
C5—C6	1.376 (6)	C15—H15B	0.9700
C5—H5	0.9300	C16—H16A	0.9700
C6—H6	0.9300	C16—H16B	0.9700
C7—H7	0.9300

O1ⁱ—Ni1—O1	180.00 (11)	C10—C9—H9A	108.4
O1ⁱ—Ni1—N1	87.15 (12)	C8—C9—H9A	108.4
O1—Ni1—N1	92.85 (12)	C10—C9—H9B	108.4
O1ⁱ—Ni1—N1ⁱ	92.85 (12)	C8—C9—H9B	108.4
O1—Ni1—N1ⁱ	87.15 (12)	H9A—C9—H9B	107.5
N1—Ni1—N1ⁱ	180.00 (17)	N2—C10—C9	112.4 (3)
C2—O1—Ni1	131.2 (2)	N2—C10—H10A	109.1
C7—N1—C8	113.7 (3)	C9—C10—H10A	109.1
C7—N1—Ni1	125.1 (3)	N2—C10—H10B	109.1
C8—N1—Ni1	121.2 (2)	C9—C10—H10B	109.1
C10—N2—C11	114.5 (3)	H10A—C10—H10B	107.9
C10—N2—H2A	105 (2)	C16—C11—C12	113.2 (3)
C11—N2—H2A	110 (2)	C16—C11—N2	111.3 (3)
C10—N2—H2B	111 (2)	C12—C11—N2	107.6 (3)
C11—N2—H2B	109 (2)	C16—C11—H11	108.2
H2A—N2—H2B	108 (2)	C12—C11—H11	108.2
O2—N3—O3	120.1 (5)	N2—C11—H11	108.2
O2—N3—O4	123.1 (5)	C11—C12—C13	110.8 (4)
O3—N3—O4	116.9 (5)	C11—C12—H12A	109.5
C6—C1—C2	118.2 (4)	C13—C12—H12A	109.5
C6—C1—C7	120.4 (4)	C11—C12—H12B	109.5
C2—C1—C7	121.4 (4)	C13—C12—H12B	109.5
O1—C2—C3	119.5 (4)	H12A—C12—H12B	108.1
O1—C2—C1	122.3 (3)	C14—C13—C12	110.8 (4)
C3—C2—C1	118.2 (4)	C14—C13—H13A	109.5
C4—C3—C2	121.3 (4)	C12—C13—H13A	109.5
C4—C3—H3	119.3	C14—C13—H13B	109.5
C2—C3—H3	119.3	C12—C13—H13B	109.5
C3—C4—C5	122.0 (4)	H13A—C13—H13B	108.1
C3—C4—H4	119.0	C13—C14—C15	110.6 (4)
C5—C4—H4	119.0	C13—C14—H14A	109.5
C4—C5—C6	118.1 (4)	C15—C14—H14A	109.5
C4—C5—H5	120.9	C13—C14—H14B	109.5
C6—C5—H5	120.9	C15—C14—H14B	109.5
C5—C6—C1	122.1 (4)	H14A—C14—H14B	108.1
C5—C6—H6	119.0	C14—C15—C16	112.5 (4)
C1—C6—H6	119.0	C14—C15—H15A	109.1
N1—C7—C1	127.1 (4)	C16—C15—H15A	109.1
N1—C7—H7	116.4	C14—C15—H15B	109.1
C1—C7—H7	116.4	C16—C15—H15B	109.1
N1—C8—C9	109.4 (3)	H15A—C15—H15B	107.8
N1—C8—H8A	109.8	C11—C16—C15	110.4 (3)
C9—C8—H8A	109.8	C11—C16—H16A	109.6
N1—C8—H8B	109.8	C15—C16—H16A	109.6
C9—C8—H8B	109.8	C11—C16—H16B	109.6
H8A—C8—H8B	108.3	C15—C16—H16B	109.6
C10—C9—C8	115.4 (3)	H16A—C16—H16B	108.1

O1ⁱ—Ni1—O1—C2	32 (100)	C7—C1—C6—C5	178.8 (4)
N1—Ni1—O1—C2	−3.7 (4)	C8—N1—C7—C1	−177.1 (3)
N1ⁱ—Ni1—O1—C2	176.3 (4)	Ni1—N1—C7—C1	2.0 (5)
O1ⁱ—Ni1—N1—C7	−179.3 (3)	C6—C1—C7—N1	178.9 (4)
O1—Ni1—N1—C7	0.7 (3)	C2—C1—C7—N1	−2.5 (6)
N1ⁱ—Ni1—N1—C7	−79 (100)	C7—N1—C8—C9	94.6 (4)
O1ⁱ—Ni1—N1—C8	−0.3 (2)	Ni1—N1—C8—C9	−84.6 (3)
O1—Ni1—N1—C8	179.7 (2)	N1—C8—C9—C10	166.7 (3)
N1ⁱ—Ni1—N1—C8	100 (100)	C11—N2—C10—C9	161.8 (3)
Ni1—O1—C2—C3	−177.0 (3)	C8—C9—C10—N2	59.0 (5)
Ni1—O1—C2—C1	4.1 (6)	C10—N2—C11—C16	57.4 (5)
C6—C1—C2—O1	178.1 (4)	C10—N2—C11—C12	−178.2 (4)
C7—C1—C2—O1	−0.5 (6)	C16—C11—C12—C13	−54.4 (5)
C6—C1—C2—C3	−0.9 (5)	N2—C11—C12—C13	−177.8 (4)
C7—C1—C2—C3	−179.5 (3)	C11—C12—C13—C14	55.8 (5)
O1—C2—C3—C4	−178.5 (4)	C12—C13—C14—C15	−57.0 (5)
C1—C2—C3—C4	0.5 (6)	C13—C14—C15—C16	56.4 (5)
C2—C3—C4—C5	0.7 (7)	C12—C11—C16—C15	52.7 (5)
C3—C4—C5—C6	−1.5 (7)	N2—C11—C16—C15	174.0 (3)
C4—C5—C6—C1	1.0 (7)	C14—C15—C16—C11	−53.7 (5)
C2—C1—C6—C5	0.1 (6)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N3ⁱⁱ	0.93 (1)	2.54 (1)	3.458 (6)	168 (3)
N2—H2B···O3ⁱⁱ	0.93 (1)	2.36 (2)	3.125 (5)	139 (3)
N2—H2B···O4ⁱⁱ	0.93 (1)	1.98 (2)	2.887 (5)	164 (3)
N2—H2A···N3	0.93 (1)	2.56 (2)	3.462 (6)	165 (3)
N2—H2A···O2	0.93 (1)	2.26 (2)	3.105 (5)	150 (3)
N2—H2A···O3	0.93 (1)	2.23 (2)	3.076 (5)	151 (3)

Symmetry code: (ii) x, −y+3/2, z+1/2.

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trans-Bis{2-[3-(cyclo­hexyl­amino)­propyl­imino­methyl]­phenolato}nickel(II) dinitrate

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trans-Bis{2-[3-(cyclohexylamino)propyliminomethyl]phenolato}nickel(II) dinitrate