Di­azido­bis(2,2'-bi­pyridine)­zinc(II) monohydrate

In the title compound, [Zn(N₃)₂(C₁₀H₈N₂)₂]·H₂O, the zinc(II) ion is coordinated by two N atoms from two azide groups and four N atoms from two 2,2'-bi­pyridine ligands. The coordination geometry of the zinc(II) ion is slightly distorted octahedral. In the solid state, the title compound forms a network structure via hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.039
• wR factor = 0.084
• Data-to-parameter ratio = 10.3

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
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       3.10 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N8     -   N9      ..       5.77 su
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N6
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N9
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 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
   4 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SHELXTL (Sheldrick, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Diazidobis(2,2'-bipyridine)zinc(II) monohydrate

Crystal data

[Zn(N3)2(C10H8N2)2]·H2O	Z = 2
Mr = 479.81	F(000) = 492
Triclinic, P1	Dx = 1.505 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3030 (17) Å	Cell parameters from 25 reflections
b = 10.334 (2) Å	θ = 2–11°
c = 13.251 (3) Å	µ = 1.20 mm^−1
α = 83.74 (3)°	T = 293 K
β = 86.98 (3)°	Block, yellow
γ = 69.58 (3)°	0.20 × 0.20 × 0.10 mm
V = 1059.0 (4) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3710 independent reflections
Radiation source: fine-focus sealed tube	2736 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 25.3°, θmin = 1.6°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = 0→9
Tmin = 0.793, Tmax = 0.887	k = −11→12
3995 measured reflections	l = −15→15

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	All H-atom parameters refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.033P)^2 + 0.0239P] where P = (Fo^2 + 2Fc^2)/3
3710 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−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
Zn1	0.20749 (5)	0.22026 (4)	0.28862 (3)	0.03447 (13)
N1	−0.0238 (3)	0.2734 (3)	0.37871 (19)	0.0345 (6)
N2	0.1334 (3)	0.0353 (3)	0.30004 (19)	0.0362 (6)
N3	0.4017 (3)	0.1545 (3)	0.17178 (19)	0.0378 (7)
N4	0.0669 (3)	0.2859 (3)	0.14218 (19)	0.0374 (7)
N5	0.2337 (4)	0.4186 (3)	0.2859 (2)	0.0507 (8)
N6	0.3614 (4)	0.4380 (3)	0.2606 (2)	0.0487 (8)
N7	0.4833 (5)	0.4621 (4)	0.2339 (4)	0.1067 (17)
N8	0.3792 (4)	0.1299 (3)	0.4094 (2)	0.0506 (8)
N9	0.3594 (4)	0.1816 (3)	0.4865 (2)	0.0420 (7)
N10	0.3425 (5)	0.2288 (4)	0.5635 (2)	0.0669 (10)
C1	−0.0907 (5)	0.3934 (4)	0.4210 (3)	0.0420 (9)
C2	−0.2346 (5)	0.4228 (4)	0.4837 (3)	0.0499 (10)
C3	−0.3127 (5)	0.3255 (4)	0.5027 (3)	0.0510 (10)
C4	−0.2459 (4)	0.2012 (4)	0.4595 (3)	0.0457 (9)
C5	−0.0997 (4)	0.1771 (3)	0.3982 (2)	0.0338 (7)
C6	−0.0154 (4)	0.0454 (3)	0.3506 (2)	0.0339 (8)
C7	−0.0811 (5)	−0.0618 (4)	0.3585 (3)	0.0474 (9)
C8	0.0083 (6)	−0.1812 (4)	0.3131 (3)	0.0567 (11)
C9	0.1605 (6)	−0.1932 (4)	0.2634 (3)	0.0556 (11)
C10	0.2191 (5)	−0.0832 (4)	0.2582 (3)	0.0469 (9)
C11	0.5684 (5)	0.0910 (4)	0.1919 (3)	0.0526 (10)
C12	0.6973 (5)	0.0708 (5)	0.1190 (3)	0.0569 (11)
C13	0.6497 (6)	0.1191 (5)	0.0205 (3)	0.0591 (11)
C14	0.4792 (5)	0.1843 (4)	−0.0028 (3)	0.0522 (10)
C15	0.3555 (4)	0.2008 (3)	0.0747 (2)	0.0376 (8)
C16	0.1669 (4)	0.2678 (3)	0.0575 (2)	0.0353 (8)
C17	0.0979 (5)	0.3091 (4)	−0.0383 (3)	0.0480 (9)
C18	−0.0780 (6)	0.3711 (4)	−0.0475 (3)	0.0543 (11)
C19	−0.1802 (6)	0.3900 (4)	0.0382 (3)	0.0540 (10)
C20	−0.1036 (5)	0.3461 (4)	0.1313 (3)	0.0471 (9)
O1W	0.6361 (5)	0.6802 (4)	0.2402 (2)	0.0715 (10)
H3A	−0.414 (4)	0.341 (3)	0.550 (2)	0.051 (10)*
H10A	0.319 (4)	−0.087 (3)	0.230 (2)	0.038 (10)*
H2A	−0.273 (4)	0.510 (3)	0.514 (2)	0.045 (10)*
H13A	0.737 (5)	0.112 (3)	−0.034 (3)	0.058 (11)*
H1A	−0.031 (4)	0.456 (4)	0.406 (2)	0.051 (10)*
H17A	0.164 (4)	0.293 (3)	−0.096 (2)	0.042 (10)*
H18A	−0.134 (4)	0.404 (3)	−0.114 (3)	0.051 (10)*
H9A	0.238 (5)	−0.277 (4)	0.231 (3)	0.065 (12)*
H4A	−0.292 (4)	0.133 (3)	0.471 (2)	0.040 (10)*
H14A	0.444 (4)	0.218 (3)	−0.068 (3)	0.047 (10)*
H12A	0.824 (5)	0.013 (4)	0.140 (3)	0.069 (12)*
H11A	0.594 (5)	0.059 (4)	0.257 (3)	0.055 (11)*
H7A	−0.185 (5)	−0.051 (4)	0.395 (3)	0.063 (12)*
H20A	−0.164 (5)	0.357 (4)	0.190 (3)	0.060 (12)*
H8A	−0.040 (5)	−0.250 (4)	0.320 (3)	0.058 (11)*
H2W1	0.605 (6)	0.613 (5)	0.248 (4)	0.09 (2)*
H1W1	0.638 (6)	0.708 (4)	0.296 (3)	0.080 (16)*
H19A	−0.297 (6)	0.430 (4)	0.039 (3)	0.092 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0354 (2)	0.0384 (2)	0.0312 (2)	−0.01539 (17)	0.00288 (15)	−0.00337 (16)
N1	0.0344 (16)	0.0355 (16)	0.0347 (15)	−0.0140 (13)	0.0016 (12)	−0.0032 (12)
N2	0.0382 (17)	0.0380 (16)	0.0340 (15)	−0.0152 (14)	0.0013 (13)	−0.0050 (13)
N3	0.0341 (17)	0.0450 (17)	0.0336 (16)	−0.0130 (14)	−0.0007 (13)	−0.0030 (13)
N4	0.0372 (17)	0.0401 (17)	0.0357 (16)	−0.0151 (14)	−0.0029 (13)	0.0004 (13)
N5	0.052 (2)	0.0454 (19)	0.059 (2)	−0.0233 (16)	0.0092 (16)	−0.0093 (16)
N6	0.049 (2)	0.0404 (18)	0.060 (2)	−0.0189 (16)	0.0036 (16)	−0.0074 (15)
N7	0.073 (3)	0.086 (3)	0.183 (5)	−0.054 (3)	0.040 (3)	−0.034 (3)
N8	0.052 (2)	0.058 (2)	0.0367 (17)	−0.0104 (16)	−0.0084 (15)	−0.0092 (15)
N9	0.0413 (18)	0.0445 (18)	0.0458 (19)	−0.0235 (15)	−0.0028 (15)	0.0027 (15)
N10	0.092 (3)	0.080 (3)	0.048 (2)	−0.051 (2)	0.0103 (19)	−0.0235 (19)
C1	0.043 (2)	0.038 (2)	0.045 (2)	−0.0135 (18)	0.0039 (17)	−0.0085 (17)
C2	0.045 (2)	0.048 (2)	0.050 (2)	−0.006 (2)	0.0035 (18)	−0.0108 (19)
C3	0.035 (2)	0.062 (3)	0.051 (2)	−0.011 (2)	0.0079 (18)	−0.006 (2)
C4	0.033 (2)	0.053 (2)	0.053 (2)	−0.0185 (19)	0.0011 (17)	0.0016 (19)
C5	0.0280 (17)	0.0394 (19)	0.0318 (17)	−0.0098 (15)	−0.0043 (14)	0.0016 (15)
C6	0.0376 (19)	0.0379 (19)	0.0271 (17)	−0.0149 (16)	−0.0088 (15)	0.0027 (14)
C7	0.048 (2)	0.047 (2)	0.053 (2)	−0.026 (2)	−0.0074 (19)	0.0063 (19)
C8	0.071 (3)	0.043 (2)	0.066 (3)	−0.031 (2)	−0.017 (2)	0.002 (2)
C9	0.071 (3)	0.042 (2)	0.052 (2)	−0.016 (2)	−0.003 (2)	−0.009 (2)
C10	0.055 (3)	0.042 (2)	0.043 (2)	−0.015 (2)	0.0037 (19)	−0.0069 (18)
C11	0.042 (2)	0.071 (3)	0.040 (2)	−0.014 (2)	0.0001 (19)	−0.003 (2)
C12	0.038 (2)	0.076 (3)	0.051 (3)	−0.013 (2)	0.007 (2)	−0.011 (2)
C13	0.054 (3)	0.080 (3)	0.049 (2)	−0.029 (2)	0.018 (2)	−0.015 (2)
C14	0.061 (3)	0.062 (3)	0.035 (2)	−0.024 (2)	0.008 (2)	−0.0064 (19)
C15	0.047 (2)	0.039 (2)	0.0306 (18)	−0.0188 (17)	0.0015 (16)	−0.0058 (15)
C16	0.046 (2)	0.0301 (18)	0.0328 (18)	−0.0169 (16)	−0.0035 (16)	−0.0035 (14)
C17	0.060 (3)	0.047 (2)	0.039 (2)	−0.019 (2)	−0.007 (2)	−0.0042 (18)
C18	0.072 (3)	0.051 (2)	0.043 (2)	−0.023 (2)	−0.025 (2)	0.0020 (19)
C19	0.048 (3)	0.046 (2)	0.067 (3)	−0.014 (2)	−0.018 (2)	0.002 (2)
C20	0.042 (2)	0.048 (2)	0.050 (2)	−0.0155 (19)	−0.0032 (19)	0.0015 (19)
O1W	0.100 (3)	0.089 (3)	0.0412 (18)	−0.053 (2)	0.0079 (17)	−0.0078 (17)

Geometric parameters (Å, º)

Zn1—N8	2.110 (3)	C6—C7	1.387 (5)
Zn1—N5	2.131 (3)	C7—C8	1.383 (6)
Zn1—N1	2.140 (3)	C7—H7A	0.95 (4)
Zn1—N3	2.159 (3)	C8—C9	1.366 (6)
Zn1—N2	2.192 (3)	C8—H8A	0.93 (3)
Zn1—N4	2.233 (3)	C9—C10	1.379 (5)
N1—C1	1.341 (4)	C9—H9A	1.01 (4)
N1—C5	1.349 (4)	C10—H10A	0.88 (3)
N2—C10	1.345 (4)	C11—C12	1.378 (5)
N2—C6	1.351 (4)	C11—H11A	0.90 (3)
N3—C11	1.336 (4)	C12—C13	1.372 (5)
N3—C15	1.350 (4)	C12—H12A	1.05 (4)
N4—C20	1.341 (4)	C13—C14	1.374 (6)
N4—C16	1.350 (4)	C13—H13A	0.99 (3)
N5—N6	1.172 (4)	C14—C15	1.393 (5)
N6—N7	1.154 (4)	C14—H14A	0.91 (3)
N8—N9	1.183 (4)	C15—C16	1.494 (5)
N9—N10	1.158 (4)	C16—C17	1.382 (5)
C1—C2	1.381 (5)	C17—C18	1.381 (5)
C1—H1A	0.95 (3)	C17—H17A	0.92 (3)
C2—C3	1.371 (5)	C18—C19	1.371 (6)
C2—H2A	0.97 (3)	C18—H18A	0.99 (3)
C3—C4	1.384 (5)	C19—C20	1.375 (5)
C3—H3A	1.00 (3)	C19—H19A	0.91 (4)
C4—C5	1.387 (5)	C20—H20A	0.90 (3)
C4—H4A	0.91 (3)	O1W—H2W1	0.82 (5)
C5—C6	1.489 (4)	O1W—H1W1	0.83 (4)
N8—Zn1—N5	94.27 (13)	N2—C6—C7	121.5 (3)
N8—Zn1—N1	96.86 (11)	N2—C6—C5	115.3 (3)
N5—Zn1—N1	94.83 (11)	C7—C6—C5	123.2 (3)
N8—Zn1—N3	94.38 (11)	C8—C7—C6	118.9 (4)
N5—Zn1—N3	93.09 (11)	C8—C7—H7A	122 (2)
N1—Zn1—N3	165.71 (10)	C6—C7—H7A	119 (2)
N8—Zn1—N2	89.89 (11)	C9—C8—C7	119.9 (4)
N5—Zn1—N2	169.81 (11)	C9—C8—H8A	124 (2)
N1—Zn1—N2	75.42 (10)	C7—C8—H8A	116 (2)
N3—Zn1—N2	95.86 (10)	C8—C9—C10	118.5 (4)
N8—Zn1—N4	168.29 (11)	C8—C9—H9A	126 (2)
N5—Zn1—N4	90.41 (11)	C10—C9—H9A	115 (2)
N1—Zn1—N4	93.43 (10)	N2—C10—C9	123.0 (4)
N3—Zn1—N4	74.62 (10)	N2—C10—H10A	115 (2)
N2—Zn1—N4	87.30 (10)	C9—C10—H10A	122 (2)
C1—N1—C5	118.8 (3)	N3—C11—C12	123.7 (4)
C1—N1—Zn1	123.5 (2)	N3—C11—H11A	116 (2)
C5—N1—Zn1	117.6 (2)	C12—C11—H11A	120 (2)
C10—N2—C6	118.2 (3)	C13—C12—C11	117.5 (4)
C10—N2—Zn1	125.8 (2)	C13—C12—H12A	124 (2)
C6—N2—Zn1	115.9 (2)	C11—C12—H12A	119 (2)
C11—N3—C15	118.5 (3)	C12—C13—C14	120.2 (4)
C11—N3—Zn1	123.0 (2)	C12—C13—H13A	121 (2)
C15—N3—Zn1	117.5 (2)	C14—C13—H13A	119 (2)
C20—N4—C16	118.1 (3)	C13—C14—C15	119.3 (4)
C20—N4—Zn1	126.4 (2)	C13—C14—H14A	122 (2)
C16—N4—Zn1	115.4 (2)	C15—C14—H14A	119 (2)
N6—N5—Zn1	122.6 (3)	N3—C15—C14	120.7 (3)
N7—N6—N5	177.3 (4)	N3—C15—C16	115.6 (3)
N9—N8—Zn1	120.7 (3)	C14—C15—C16	123.6 (3)
N10—N9—N8	178.1 (4)	N4—C16—C17	121.7 (3)
N1—C1—C2	122.8 (4)	N4—C16—C15	115.5 (3)
N1—C1—H1A	115 (2)	C17—C16—C15	122.7 (3)
C2—C1—H1A	122 (2)	C18—C17—C16	119.0 (4)
C3—C2—C1	118.4 (4)	C18—C17—H17A	118 (2)
C3—C2—H2A	123.0 (19)	C16—C17—H17A	123 (2)
C1—C2—H2A	118.5 (19)	C19—C18—C17	119.5 (4)
C2—C3—C4	119.7 (4)	C19—C18—H18A	118.0 (19)
C2—C3—H3A	120.8 (19)	C17—C18—H18A	122.5 (19)
C4—C3—H3A	119.5 (19)	C18—C19—C20	118.7 (4)
C3—C4—C5	119.1 (4)	C18—C19—H19A	125 (3)
C3—C4—H4A	123 (2)	C20—C19—H19A	116 (3)
C5—C4—H4A	118 (2)	N4—C20—C19	123.0 (4)
N1—C5—C4	121.3 (3)	N4—C20—H20A	114 (2)
N1—C5—C6	115.6 (3)	C19—C20—H20A	123 (2)
C4—C5—C6	123.2 (3)	H2W1—O1W—H1W1	109 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···N10^i	0.83 (4)	2.07 (4)	2.895 (4)	177 (4)
O1W—H2W1···N7	0.82 (5)	2.16 (5)	2.957 (6)	165 (5)
C1—H1A···N5	0.94 (4)	2.59 (3)	3.226 (5)	126 (3)
C7—H7A···N10^ii	0.94 (4)	2.60 (4)	3.278 (6)	129 (3)
C11—H11A···N8	0.90 (4)	2.61 (4)	3.205 (5)	124 (3)
C14—H14A···O1W^iii	0.92 (4)	2.43 (4)	3.346 (5)	176 (3)
C17—H17A···O1W^iii	0.91 (3)	2.52 (3)	3.396 (5)	160 (2)

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