Di­azido{N,N'-bis­[2-(2-pyridyl)­ethyl­ene]-1,3-di­amino­propane}nickel(II) monohydrate

The crystal structure of yellow [Ni(L)(N₃)₂]·H₂O, where L is N,N'-bis­[2-(2-pyridyl)­ethyl­ene]-1,3-di­amino­propane (C₁₅H₁₆N₄), containing six-coordinate nickel(II) with an octahedral [Ni^IIN₆] core, is reported. Four N atoms of the Schiff base ligand form the equatorial plane and two N atoms of two azide ligands occupy the axial positions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.100
• Data-to-parameter ratio = 17.1

checkCIF results

No syntax errors found



ADDSYM reports no extra symmetry

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL, SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL, DENZO (Otwinowski & Minor, 1997) and maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

[Ni(C15H16N4)(N3)2]·H2O	Dx = 1.509 Mg m^−3
Mr = 413.10	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 48907 reflections
a = 13.5783 (3) Å	θ = 3.5–27.9°
b = 15.2608 (3) Å	µ = 1.10 mm^−1
c = 17.5449 (4) Å	T = 293 K
V = 3635.58 (14) Å^3	Block, yellow
Z = 8	0.24 × 0.20 × 0.18 mm
F(000) = 1712

Data collection

Nonius KappaCCD diffractometer	4317 independent reflections
Radiation source: fine-focus sealed tube	2828 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 0.76 pixels mm^-1	θmax = 27.9°, θmin = 3.5°
CCD scans	h = −17→17
Absorption correction: empirical (using intensity measurements) (Blessing, 1995, 1997)	k = −20→20
Tmin = 0.710, Tmax = 0.821	l = −23→23
48907 measured reflections

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0425P)^2 + 1.9396P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
4317 reflections	Δρmax = 0.68 e Å^−3
252 parameters	Δρmin = −0.37 e Å^−3
3 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: 0.0014 (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
O1	0.13664 (16)	0.12665 (12)	0.23559 (12)	0.0652 (6)
Ni1	0.37530 (2)	0.002947 (16)	0.345462 (14)	0.03204 (11)
N1	0.38617 (14)	0.12410 (12)	0.40560 (11)	0.0375 (4)
N2	0.38323 (15)	0.09055 (13)	0.25658 (11)	0.0439 (5)
N3	0.36859 (14)	−0.10221 (12)	0.27297 (10)	0.0374 (4)
N4	0.36751 (13)	−0.10302 (11)	0.42495 (10)	0.0339 (4)
N5	0.22050 (16)	0.01497 (14)	0.35186 (12)	0.0478 (5)
N6	0.18588 (16)	0.01708 (12)	0.41386 (13)	0.0450 (5)
N7	0.1515 (2)	0.01869 (16)	0.47386 (16)	0.0773 (9)
N8	0.53171 (15)	−0.00650 (12)	0.35000 (11)	0.0406 (5)
N9	0.57131 (15)	−0.07339 (13)	0.33263 (11)	0.0400 (5)
N10	0.61005 (18)	−0.13800 (16)	0.31629 (16)	0.0687 (7)
C1	0.38638 (18)	0.14266 (15)	0.47986 (14)	0.0445 (6)
H1	0.3846	0.0965	0.5144	0.053*
C2	0.38913 (19)	0.22733 (16)	0.50802 (17)	0.0540 (7)
H2	0.3896	0.2373	0.5603	0.065*
C3	0.3912 (2)	0.29613 (17)	0.4582 (2)	0.0616 (8)
H3	0.3929	0.3535	0.4760	0.074*
C4	0.39069 (19)	0.27898 (16)	0.38129 (18)	0.0539 (7)
H4	0.3916	0.3246	0.3462	0.065*
C5	0.38876 (17)	0.19283 (15)	0.35698 (15)	0.0432 (6)
C6	0.38864 (18)	0.16990 (16)	0.27580 (16)	0.0501 (7)
H6	0.3925	0.2135	0.2389	0.060*
C7	0.3849 (2)	0.0673 (2)	0.17481 (14)	0.0604 (8)
H7A	0.4219	0.1114	0.1471	0.072*
H7B	0.3180	0.0675	0.1553	0.072*
C8	0.4307 (3)	−0.0218 (2)	0.16067 (14)	0.0664 (9)
H8A	0.4410	−0.0290	0.1063	0.080*
H8B	0.4947	−0.0237	0.1852	0.080*
C9	0.3704 (2)	−0.09681 (18)	0.18903 (13)	0.0533 (7)
H9A	0.3036	−0.0907	0.1704	0.064*
H9B	0.3970	−0.1510	0.1687	0.064*
C10	0.36995 (18)	−0.17618 (15)	0.30474 (14)	0.0432 (6)
H10	0.3725	−0.2271	0.2757	0.052*
C11	0.36742 (16)	−0.18093 (14)	0.38863 (13)	0.0367 (5)
C12	0.36409 (18)	−0.25992 (15)	0.42595 (15)	0.0466 (6)
H12	0.3657	−0.3122	0.3987	0.056*
C13	0.35836 (19)	−0.26074 (16)	0.50465 (15)	0.0502 (7)
H13	0.3553	−0.3133	0.5314	0.060*
C14	0.35738 (18)	−0.18193 (17)	0.54220 (14)	0.0483 (6)
H14	0.3531	−0.1802	0.5951	0.058*
C15	0.36272 (17)	−0.10537 (15)	0.50095 (13)	0.0408 (6)
H15	0.3630	−0.0525	0.5274	0.049*
H1A	0.157 (2)	0.0913 (17)	0.2764 (13)	0.092 (8)*
H1B	0.104 (2)	0.0886 (17)	0.2024 (14)	0.092 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0808 (15)	0.0408 (10)	0.0740 (14)	−0.0021 (10)	−0.0275 (12)	−0.0039 (10)
Ni1	0.03995 (18)	0.02971 (16)	0.02644 (16)	0.00016 (12)	−0.00010 (11)	0.00052 (11)
N1	0.0391 (11)	0.0305 (9)	0.0430 (11)	0.0011 (8)	0.0013 (8)	0.0015 (8)
N2	0.0485 (13)	0.0475 (12)	0.0359 (10)	0.0042 (9)	0.0006 (9)	0.0121 (9)
N3	0.0397 (11)	0.0453 (11)	0.0272 (9)	−0.0025 (8)	−0.0012 (8)	−0.0066 (8)
N4	0.0384 (11)	0.0309 (9)	0.0324 (9)	−0.0033 (8)	−0.0018 (8)	−0.0016 (8)
N5	0.0431 (12)	0.0575 (13)	0.0427 (12)	0.0044 (10)	−0.0010 (9)	0.0001 (10)
N6	0.0473 (13)	0.0307 (10)	0.0571 (14)	0.0001 (9)	0.0060 (10)	0.0013 (9)
N7	0.103 (2)	0.0584 (15)	0.0703 (18)	0.0037 (14)	0.0436 (16)	0.0033 (13)
N8	0.0388 (11)	0.0382 (11)	0.0448 (11)	−0.0023 (9)	0.0006 (9)	−0.0049 (9)
N9	0.0404 (12)	0.0398 (11)	0.0397 (11)	−0.0032 (9)	−0.0011 (9)	−0.0007 (9)
N10	0.0653 (17)	0.0501 (13)	0.0906 (19)	0.0124 (12)	0.0021 (14)	−0.0173 (14)
C1	0.0483 (15)	0.0368 (12)	0.0484 (14)	0.0003 (11)	−0.0015 (11)	−0.0053 (11)
C2	0.0569 (18)	0.0449 (14)	0.0603 (17)	0.0034 (12)	−0.0037 (13)	−0.0144 (13)
C3	0.0616 (19)	0.0320 (13)	0.091 (2)	0.0013 (12)	−0.0014 (16)	−0.0143 (15)
C4	0.0562 (17)	0.0312 (12)	0.074 (2)	−0.0002 (11)	0.0015 (14)	0.0081 (13)
C5	0.0379 (14)	0.0336 (11)	0.0581 (16)	0.0018 (10)	0.0019 (11)	0.0050 (11)
C6	0.0535 (17)	0.0427 (14)	0.0542 (15)	0.0022 (12)	0.0014 (12)	0.0195 (12)
C7	0.082 (2)	0.0660 (18)	0.0330 (12)	0.0080 (16)	0.0003 (13)	0.0127 (13)
C8	0.073 (2)	0.092 (2)	0.0339 (14)	−0.0008 (18)	0.0028 (13)	−0.0004 (14)
C9	0.0619 (18)	0.0695 (18)	0.0285 (12)	−0.0094 (14)	−0.0009 (12)	−0.0107 (12)
C10	0.0512 (15)	0.0376 (12)	0.0408 (13)	−0.0057 (11)	−0.0001 (11)	−0.0112 (11)
C11	0.0382 (13)	0.0313 (11)	0.0408 (12)	−0.0034 (10)	−0.0024 (10)	−0.0034 (10)
C12	0.0547 (16)	0.0315 (12)	0.0536 (15)	−0.0016 (11)	−0.0043 (12)	−0.0016 (11)
C13	0.0599 (18)	0.0388 (13)	0.0518 (15)	−0.0051 (12)	−0.0060 (13)	0.0114 (12)
C14	0.0561 (17)	0.0532 (14)	0.0356 (12)	−0.0026 (12)	−0.0043 (11)	0.0079 (12)
C15	0.0523 (16)	0.0377 (12)	0.0325 (11)	−0.0027 (10)	−0.0031 (10)	−0.0034 (10)

Geometric parameters (Å, º)

O1—H1A	0.941 (17)	C3—C4	1.375 (4)
O1—H1B	0.937 (17)	C3—H3	0.9300
Ni1—N3	2.0497 (18)	C4—C5	1.382 (3)
Ni1—N2	2.0569 (18)	C4—H4	0.9300
Ni1—N5	2.113 (2)	C5—C6	1.467 (4)
Ni1—N8	2.130 (2)	C6—H6	0.9300
Ni1—N1	2.1339 (18)	C7—C8	1.516 (4)
Ni1—N4	2.1380 (18)	C7—H7A	0.9700
N1—C1	1.333 (3)	C7—H7B	0.9700
N1—C5	1.352 (3)	C8—C9	1.492 (4)
N2—C6	1.259 (3)	C8—H8A	0.9700
N2—C7	1.478 (3)	C8—H8B	0.9700
N3—C10	1.259 (3)	C9—H9A	0.9700
N3—C9	1.475 (3)	C9—H9B	0.9700
N4—C15	1.335 (3)	C10—C11	1.474 (3)
N4—C11	1.349 (3)	C10—H10	0.9300
N5—N6	1.185 (3)	C11—C12	1.373 (3)
N6—N7	1.152 (3)	C12—C13	1.383 (3)
N8—N9	1.193 (2)	C12—H12	0.9300
N9—N10	1.154 (3)	C13—C14	1.371 (4)
C1—C2	1.384 (3)	C13—H13	0.9300
C1—H1	0.9300	C14—C15	1.376 (3)
C2—C3	1.367 (4)	C14—H14	0.9300
C2—H2	0.9300	C15—H15	0.9300
H1A—O1—H1B	105.2 (19)	C5—C4—H4	120.5
N3—Ni1—N2	92.34 (8)	N1—C5—C4	122.9 (3)
N3—Ni1—N5	93.25 (8)	N1—C5—C6	115.3 (2)
N2—Ni1—N5	92.06 (8)	C4—C5—C6	121.8 (2)
N3—Ni1—N8	90.83 (7)	N2—C6—C5	119.3 (2)
N2—Ni1—N8	91.15 (8)	N2—C6—H6	120.3
N5—Ni1—N8	174.70 (8)	C5—C6—H6	120.3
N3—Ni1—N1	171.21 (7)	N2—C7—C8	112.3 (2)
N2—Ni1—N1	78.93 (8)	N2—C7—H7A	109.1
N5—Ni1—N1	88.13 (8)	C8—C7—H7A	109.1
N8—Ni1—N1	88.35 (7)	N2—C7—H7B	109.1
N3—Ni1—N4	79.07 (7)	C8—C7—H7B	109.1
N2—Ni1—N4	171.39 (7)	H7A—C7—H7B	107.9
N5—Ni1—N4	88.96 (7)	C9—C8—C7	114.1 (3)
N8—Ni1—N4	88.50 (7)	C9—C8—H8A	108.7
N1—Ni1—N4	109.65 (7)	C7—C8—H8A	108.7
C1—N1—C5	116.8 (2)	C9—C8—H8B	108.7
C1—N1—Ni1	131.86 (16)	C7—C8—H8B	108.7
C5—N1—Ni1	111.22 (16)	H8A—C8—H8B	107.6
C6—N2—C7	119.3 (2)	N3—C9—C8	112.6 (2)
C6—N2—Ni1	115.16 (17)	N3—C9—H9A	109.1
C7—N2—Ni1	125.51 (17)	C8—C9—H9A	109.1
C10—N3—C9	119.5 (2)	N3—C9—H9B	109.1
C10—N3—Ni1	115.25 (15)	C8—C9—H9B	109.1
C9—N3—Ni1	125.10 (16)	H9A—C9—H9B	107.8
C15—N4—C11	116.61 (19)	N3—C10—C11	119.1 (2)
C15—N4—Ni1	132.37 (15)	N3—C10—H10	120.5
C11—N4—Ni1	111.02 (14)	C11—C10—H10	120.5
N6—N5—Ni1	116.46 (17)	N4—C11—C12	123.3 (2)
N7—N6—N5	179.4 (3)	N4—C11—C10	115.36 (19)
N9—N8—Ni1	119.84 (15)	C12—C11—C10	121.4 (2)
N10—N9—N8	179.5 (3)	C11—C12—C13	119.1 (2)
N1—C1—C2	123.2 (2)	C11—C12—H12	120.5
N1—C1—H1	118.4	C13—C12—H12	120.5
C2—C1—H1	118.4	C14—C13—C12	118.2 (2)
C3—C2—C1	119.3 (3)	C14—C13—H13	120.9
C3—C2—H2	120.3	C12—C13—H13	120.9
C1—C2—H2	120.3	C13—C14—C15	119.4 (2)
C2—C3—C4	118.8 (2)	C13—C14—H14	120.3
C2—C3—H3	120.6	C15—C14—H14	120.3
C4—C3—H3	120.6	N4—C15—C14	123.4 (2)
C3—C4—C5	119.0 (2)	N4—C15—H15	118.3
C3—C4—H4	120.5	C14—C15—H15	118.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N5	0.94 (2)	1.96 (2)	2.892 (3)	171 (3)
O1—H1B···N8^i	0.94 (2)	1.98 (3)	2.901 (3)	169 (2)

Symmetry code: (i) x−1/2, y, −z+1/2.