Di­azido­bis(2,2′-dipyridyl­amine)­nickel(II) monohydrate

Villanueva, M.; Urtiaga, M.K.; Mesa, J.L.; Arriortua, M.I.

doi:10.1107/S1600536804017532

Diazidobis(2,2'-dipyridylamine)nickel(II) monohydrate

M. Villanueva, M. K. Urtiaga, J. L. Mesa and M. I. Arriortua

The coordination environment of the Ni atom in the title compound, [Ni(N₃)₂(dpa)₂(N₃)₂]·H₂O (dpa = 2,2'-dipyridylamine, C₁₀H₉N₃), is that of an octahedron, with the two azide ligands in a cis arrangement. The crystal structure of the complex is stabilized by hydrogen bonds involving the water molecule, resulting in a two-dimensional network in the (001) plane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804017532/tk6177sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804017532/tk6177Isup2.hkl Contains datablock I

CCDC reference: 248753

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
R factor = 0.035
wR factor = 0.093
Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...         16
PLAT352_ALERT_3_C Short   N-H Bond (0.87A)   N2     -   H21    ...       0.75 Ang.

   0 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

   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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top

Crystal data top

[Ni(N₃)₂(C₁₀H₉N₃)₂]·H₂O	Z = 2
M_r = 503.17	F(000) = 520
Triclinic, P1	D_x = 1.530 Mg m⁻³ D_m = 1.55 Mg m⁻³ D_m measured by flotation in CH₂Cl₂/CCl₄
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 7.651 (3) Å	Cell parameters from 25 reflections
b = 9.268 (2) Å	θ = 8.1–13.3°
c = 16.721 (4) Å	µ = 0.93 mm⁻¹
α = 79.36 (2)°	T = 293 K
β = 84.17 (2)°	Prism, green
γ = 69.78 (2)°	0.16 × 0.14 × 0.10 mm
V = 1092.6 (6) Å³

Data collection top

Enraf-Nonius CAD-4 diffractometer	4806 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.017
Graphite monochromator	θ_max = 30.0°, θ_min = 1.2°
ω/2θ scans	h = −2→10
Absorption correction: psi scan (North et al., 1968)	k = −12→13
T_min = 0.863, T_max = 0.914	l = −23→23
7053 measured reflections	2 standard reflections every 100 reflections
6337 independent reflections	intensity decay: 1.8%

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Only H-atom coordinates refined
R[F² > 2σ(F²)] = 0.035	w = 1/[σ²(F_o²) + (0.0449P)² + 0.159P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.093	(Δ/σ)_max = 0.027
S = 1.01	Δρ_max = 0.44 e Å⁻³
6337 reflections	Δρ_min = −0.27 e Å⁻³
368 parameters

Special details top

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
Ni	0.24073 (3)	0.01951 (3)	0.218654 (14)	0.02420 (7)
N1	0.0115 (2)	0.21927 (16)	0.18253 (9)	0.0263 (3)
C1	0.0157 (3)	0.3610 (2)	0.18989 (12)	0.0323 (4)
C2	−0.1387 (3)	0.4925 (2)	0.18445 (14)	0.0401 (5)
C3	−0.3073 (3)	0.4814 (2)	0.16894 (14)	0.0423 (5)
C4	−0.3140 (3)	0.3413 (2)	0.15684 (13)	0.0355 (4)
C5	−0.1500 (2)	0.2107 (2)	0.16381 (10)	0.0263 (3)
N2	−0.1612 (2)	0.07085 (18)	0.15105 (10)	0.0291 (3)
C6	−0.0220 (2)	−0.04832 (19)	0.11913 (10)	0.0256 (3)
C7	−0.0756 (3)	−0.1441 (2)	0.07825 (12)	0.0335 (4)
C8	0.0607 (3)	−0.2610 (2)	0.04525 (13)	0.0389 (4)
C9	0.2472 (3)	−0.2777 (2)	0.05097 (13)	0.0387 (4)
C10	0.2879 (3)	−0.1801 (2)	0.09231 (12)	0.0314 (4)
N3	0.1571 (2)	−0.06956 (17)	0.12933 (9)	0.0266 (3)
N4	0.0725 (2)	−0.06934 (17)	0.30895 (9)	0.0287 (3)
C11	0.0479 (3)	−0.2045 (2)	0.30322 (13)	0.0356 (4)
C12	−0.0864 (3)	−0.2550 (3)	0.34811 (14)	0.0429 (5)
C13	−0.1990 (3)	−0.1662 (3)	0.40297 (15)	0.0461 (5)
C14	−0.1705 (3)	−0.0331 (3)	0.41352 (13)	0.0400 (4)
C15	−0.0322 (2)	0.0127 (2)	0.36528 (11)	0.0291 (3)
N5	−0.0093 (2)	0.1493 (2)	0.37651 (11)	0.0347 (4)
C16	0.1469 (3)	0.1937 (2)	0.36211 (11)	0.0289 (3)
C17	0.1495 (3)	0.3164 (2)	0.39954 (13)	0.0393 (4)
C18	0.3033 (4)	0.3620 (3)	0.38744 (15)	0.0475 (5)
C19	0.4542 (3)	0.2827 (3)	0.34049 (14)	0.0455 (5)
C20	0.4411 (3)	0.1660 (3)	0.30533 (13)	0.0368 (4)
N6	0.2868 (2)	0.12345 (18)	0.31266 (9)	0.0293 (3)
N7	0.4272 (2)	0.1000 (2)	0.13560 (10)	0.0347 (3)
N8	0.3690 (2)	0.2002 (2)	0.07918 (10)	0.0347 (4)
N9	0.3158 (3)	0.2993 (3)	0.02485 (14)	0.0630 (6)
N10	0.4696 (2)	−0.1864 (2)	0.25251 (11)	0.0393 (4)
N11	0.4859 (2)	−0.26714 (18)	0.31589 (11)	0.0332 (3)
N12	0.5071 (3)	−0.3501 (3)	0.37853 (13)	0.0550 (5)
O1	0.7247 (3)	0.3539 (2)	0.47326 (12)	0.0569 (5)
H10	0.408 (4)	−0.185 (3)	0.0982 (15)	0.0478 (16)*
H1	0.132 (4)	0.363 (3)	0.2040 (15)	0.0478 (16)*
H11	0.129 (4)	−0.260 (3)	0.2637 (16)	0.0478 (16)*
H9	0.341 (4)	−0.354 (3)	0.0263 (15)	0.0478 (16)*
H8	0.024 (3)	−0.321 (3)	0.0202 (15)	0.0478 (16)*
H31	−0.088 (4)	0.198 (3)	0.4082 (16)	0.0478 (16)*
H13	−0.290 (4)	−0.193 (3)	0.4328 (16)	0.0478 (16)*
H4	−0.422 (4)	0.337 (3)	0.1438 (16)	0.0478 (16)*
H7	−0.201 (4)	−0.120 (3)	0.0728 (15)	0.0478 (16)*
H2	−0.128 (3)	0.582 (3)	0.1917 (15)	0.0478 (16)*
H40	0.669 (4)	0.421 (3)	0.4452 (18)	0.0478 (16)*
H17	0.051 (4)	0.362 (3)	0.4326 (16)	0.0478 (16)*
H20	0.545 (4)	0.109 (3)	0.2736 (16)	0.0478 (16)*
H14	−0.242 (4)	0.023 (3)	0.4533 (16)	0.0478 (16)*
H41	0.674 (4)	0.333 (3)	0.5130 (18)	0.0478 (16)*
H12	−0.098 (4)	−0.344 (3)	0.3397 (16)	0.0478 (16)*
H19	0.558 (4)	0.306 (3)	0.3349 (15)	0.0478 (16)*
H18	0.303 (4)	0.438 (3)	0.4133 (15)	0.0478 (16)*
H3	−0.415 (4)	0.561 (3)	0.1683 (15)	0.0478 (16)*
H21	−0.259 (4)	0.074 (3)	0.1470 (16)	0.0478 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni	0.02045 (11)	0.02345 (11)	0.02846 (12)	−0.00581 (8)	−0.00136 (8)	−0.00637 (8)
N1	0.0240 (7)	0.0230 (7)	0.0310 (7)	−0.0070 (5)	−0.0009 (6)	−0.0040 (6)
C1	0.0366 (10)	0.0269 (8)	0.0352 (9)	−0.0134 (7)	−0.0032 (8)	−0.0028 (7)
C2	0.0501 (12)	0.0223 (9)	0.0454 (11)	−0.0095 (8)	−0.0054 (9)	−0.0028 (8)
C3	0.0382 (11)	0.0276 (9)	0.0499 (12)	0.0035 (8)	−0.0048 (9)	−0.0051 (8)
C4	0.0246 (9)	0.0320 (9)	0.0445 (11)	−0.0016 (7)	−0.0040 (8)	−0.0066 (8)
C5	0.0231 (8)	0.0258 (8)	0.0274 (8)	−0.0056 (6)	0.0000 (6)	−0.0037 (6)
N2	0.0183 (7)	0.0290 (7)	0.0410 (9)	−0.0071 (6)	−0.0011 (6)	−0.0093 (6)
C6	0.0243 (8)	0.0243 (8)	0.0275 (8)	−0.0075 (6)	−0.0015 (6)	−0.0032 (6)
C7	0.0332 (10)	0.0348 (9)	0.0376 (10)	−0.0163 (8)	−0.0053 (8)	−0.0065 (8)
C8	0.0499 (12)	0.0352 (10)	0.0375 (10)	−0.0170 (9)	−0.0040 (9)	−0.0136 (8)
C9	0.0410 (11)	0.0349 (10)	0.0377 (10)	−0.0048 (8)	0.0006 (8)	−0.0163 (8)
C10	0.0256 (9)	0.0317 (9)	0.0336 (9)	−0.0031 (7)	0.0004 (7)	−0.0100 (7)
N3	0.0233 (7)	0.0254 (7)	0.0295 (7)	−0.0050 (5)	−0.0020 (6)	−0.0067 (6)
N4	0.0292 (7)	0.0257 (7)	0.0313 (8)	−0.0096 (6)	−0.0008 (6)	−0.0039 (6)
C11	0.0401 (11)	0.0278 (9)	0.0392 (10)	−0.0118 (8)	−0.0041 (8)	−0.0036 (8)
C12	0.0492 (12)	0.0362 (11)	0.0476 (12)	−0.0233 (10)	−0.0076 (10)	0.0032 (9)
C13	0.0432 (12)	0.0551 (14)	0.0452 (12)	−0.0290 (11)	−0.0018 (10)	0.0040 (10)
C14	0.0355 (10)	0.0484 (12)	0.0367 (10)	−0.0172 (9)	0.0044 (8)	−0.0051 (9)
C15	0.0256 (8)	0.0317 (9)	0.0292 (8)	−0.0092 (7)	−0.0028 (7)	−0.0029 (7)
N5	0.0327 (8)	0.0352 (8)	0.0384 (9)	−0.0115 (7)	0.0073 (7)	−0.0156 (7)
C16	0.0295 (9)	0.0284 (8)	0.0283 (8)	−0.0084 (7)	−0.0039 (7)	−0.0048 (7)
C17	0.0455 (12)	0.0376 (10)	0.0377 (10)	−0.0127 (9)	−0.0004 (9)	−0.0158 (8)
C18	0.0596 (14)	0.0463 (12)	0.0487 (13)	−0.0268 (11)	−0.0069 (11)	−0.0170 (10)
C19	0.0436 (12)	0.0590 (14)	0.0470 (12)	−0.0299 (11)	−0.0038 (10)	−0.0148 (10)
C20	0.0299 (9)	0.0490 (12)	0.0361 (10)	−0.0166 (9)	−0.0015 (8)	−0.0118 (9)
N6	0.0275 (7)	0.0312 (8)	0.0308 (8)	−0.0099 (6)	−0.0031 (6)	−0.0074 (6)
N7	0.0249 (7)	0.0425 (9)	0.0379 (9)	−0.0141 (7)	−0.0001 (6)	−0.0046 (7)
N8	0.0252 (7)	0.0489 (10)	0.0350 (8)	−0.0185 (7)	0.0023 (6)	−0.0090 (7)
N9	0.0489 (12)	0.0820 (16)	0.0492 (12)	−0.0232 (11)	−0.0074 (10)	0.0169 (11)
N10	0.0324 (9)	0.0348 (9)	0.0404 (9)	0.0030 (7)	−0.0045 (7)	−0.0072 (7)
N11	0.0253 (7)	0.0307 (8)	0.0434 (9)	−0.0076 (6)	−0.0050 (6)	−0.0073 (7)
N12	0.0509 (12)	0.0536 (12)	0.0549 (12)	−0.0208 (10)	−0.0063 (10)	0.0135 (10)
O1	0.0492 (11)	0.0580 (12)	0.0482 (11)	0.0031 (8)	0.0045 (8)	−0.0156 (9)

Geometric parameters (Å, º) top

Ni—N1	2.1040 (16)	N4—C15	1.341 (2)
Ni—N3	2.0822 (15)	N4—C11	1.351 (2)
Ni—N4	2.1198 (16)	C11—C12	1.373 (3)
Ni—N6	2.1047 (16)	C11—H11	0.95 (3)
Ni—N7	2.1147 (17)	C12—C13	1.375 (4)
Ni—N10	2.1266 (18)	C12—H12	0.90 (3)
N1—C5	1.336 (2)	C13—C14	1.369 (3)
N1—C1	1.353 (2)	C13—H13	0.90 (3)
C1—C2	1.369 (3)	C14—C15	1.400 (3)
C1—H1	0.95 (3)	C14—H14	0.93 (3)
C2—C3	1.383 (3)	C15—N5	1.384 (2)
C2—H2	0.89 (2)	N5—C16	1.378 (2)
C3—C4	1.369 (3)	N5—H31	0.83 (3)
C3—H3	0.90 (3)	C16—N6	1.338 (2)
C4—C5	1.407 (2)	C16—C17	1.403 (3)
C4—H4	0.89 (3)	C17—C18	1.366 (3)
C5—N2	1.384 (2)	C17—H17	0.91 (3)
N2—C6	1.389 (2)	C18—C19	1.390 (4)
N2—H21	0.75 (3)	C18—H18	0.89 (3)
C6—N3	1.340 (2)	C19—C20	1.359 (3)
C6—C7	1.398 (2)	C19—H19	0.88 (3)
C7—C8	1.375 (3)	C20—N6	1.356 (2)
C7—H7	0.92 (3)	C20—H20	0.96 (3)
C8—C9	1.393 (3)	N7—N8	1.195 (2)
C8—H8	0.88 (3)	N8—N9	1.159 (3)
C9—C10	1.365 (3)	N10—N11	1.169 (2)
C9—H9	0.94 (3)	N11—N12	1.169 (3)
C10—N3	1.354 (2)	O1—H40	0.73 (3)
C10—H10	0.92 (3)	O1—H41	0.76 (3)

N1—Ni—N4	91.09 (6)	C10—C9—C8	118.27 (18)
N1—Ni—N6	90.19 (6)	C10—C9—H9	121.7 (16)
N3—Ni—N4	91.41 (6)	C8—C9—H9	120.0 (15)
N3—Ni—N6	172.30 (6)	N3—C10—C9	123.63 (18)
N7—Ni—N10	87.43 (7)	N3—C10—H10	113.7 (16)
Ni—N7—N8	120.13 (13)	C9—C10—H10	122.6 (16)
Ni—N10—N11	125.79 (14)	C6—N3—C10	117.42 (16)
N7—N8—N9	178.2 (2)	C6—N3—Ni	122.70 (12)
N10—N11—N12	178.1 (2)	C10—N3—Ni	118.29 (12)
N3—Ni—N7	91.91 (7)	C15—N4—C11	117.53 (17)
N3—Ni—N1	83.79 (6)	C15—N4—Ni	122.78 (12)
N1—Ni—N7	92.84 (7)	C11—N4—Ni	119.01 (13)
N6—Ni—N7	93.19 (7)	N4—C11—C12	123.1 (2)
N6—Ni—N4	83.89 (6)	N4—C11—H11	113.7 (15)
N7—Ni—N4	175.11 (6)	C12—C11—H11	123.1 (15)
N3—Ni—N10	94.27 (7)	C11—C12—C13	118.8 (2)
N1—Ni—N10	178.05 (6)	C11—C12—H12	118.2 (17)
N6—Ni—N10	91.72 (7)	C13—C12—H12	123.0 (17)
N4—Ni—N10	88.73 (7)	C14—C13—C12	119.4 (2)
C5—N1—C1	117.61 (15)	C14—C13—H13	118.7 (16)
C5—N1—Ni	122.26 (12)	C12—C13—H13	121.9 (16)
C1—N1—Ni	119.38 (12)	C13—C14—C15	118.9 (2)
N1—C1—C2	123.40 (19)	C13—C14—H14	118.9 (16)
N1—C1—H1	115.8 (15)	C15—C14—H14	122.2 (16)
C2—C1—H1	120.5 (15)	N4—C15—N5	120.54 (16)
C1—C2—C3	118.60 (19)	N4—C15—C14	122.04 (18)
C1—C2—H2	119.4 (17)	N5—C15—C14	117.40 (18)
C3—C2—H2	122.0 (16)	C16—N5—C15	129.33 (16)
C4—C3—C2	119.32 (19)	C16—N5—H31	113.9 (18)
C4—C3—H3	117.6 (16)	C15—N5—H31	114.1 (18)
C2—C3—H3	123.0 (16)	N6—C16—N5	120.41 (16)
C3—C4—C5	118.97 (19)	N6—C16—C17	122.29 (18)
C3—C4—H4	118.4 (16)	N5—C16—C17	117.29 (18)
C5—C4—H4	122.6 (16)	C18—C17—C16	118.8 (2)
N1—C5—N2	120.49 (15)	C18—C17—H17	121.6 (16)
N1—C5—C4	121.93 (17)	C16—C17—H17	119.5 (16)
N2—C5—C4	117.58 (16)	C17—C18—C19	119.1 (2)
C5—N2—C6	127.22 (15)	C17—C18—H18	117.2 (17)
C5—N2—H21	113 (2)	C19—C18—H18	123.5 (17)
C6—N2—H21	116 (2)	C20—C19—C18	118.8 (2)
N3—C6—N2	119.60 (15)	C20—C19—H19	120.7 (17)
N3—C6—C7	122.33 (16)	C18—C19—H19	120.5 (17)
N2—C6—C7	118.06 (16)	N6—C20—C19	123.4 (2)
C8—C7—C6	118.71 (18)	N6—C20—H20	116.7 (15)
C8—C7—H7	124.4 (16)	C19—C20—H20	119.9 (15)
C6—C7—H7	116.7 (16)	C16—N6—C20	117.25 (16)
C7—C8—C9	119.36 (19)	C16—N6—Ni	121.38 (12)
C7—C8—H8	117.4 (16)	C20—N6—Ni	117.58 (13)
C9—C8—H8	123.2 (16)	H40—O1—H41	115 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···N7ⁱ	0.76 (3)	2.34 (3)	3.100 (3)	177 (3)
N5—H31···O1ⁱ	0.84 (3)	2.02 (3)	2.852 (3)	169 (2)
O1—H40···N12ⁱⁱ	0.76 (5)	2.18 (5)	2.928 (4)	168 (5)
O1—H41···N12ⁱⁱⁱ	0.75 (4)	2.17 (4)	2.900 (4)	163 (4)

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

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Di­azido­bis(2,2'-dipyridyl­amine)­nickel(II) monohydrate

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Diazidobis(2,2'-dipyridylamine)nickel(II) monohydrate