Diaqua­(2,2′-bipyridine)(ethyl­enediamine)nickel(II) dichloride

The Ni^II ion of the title compound, [Ni(C₂H₈N₂)(C₁₀H₈N₂)(H₂O)₂]Cl₂, is coordinated by four N atoms and two water mol­ecules in a distorted octa­hedral geometry. π–π Stacking of pyridine rings from adjacent complexes leads to a one-dimensional supra­molecular ribbon along the b axis. The chloride anions are hydrogen bonded with complex cations, resulting in a three-dimensional supra­molecular architecture.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.035
• wR factor = 0.092
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C121
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N41
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N42
PLAT301_ALERT_3_C Main Residue  Disorder .........................      17.00 Perc.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3C    ..  CL1     ..       2.88 Ang.

   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

   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Diaqua(2,2'-bipyridine)(ethylenediamine)nickel(II) dichloride

Crystal data

[Ni(C2H8N2)(C10H8N2)(H2O)2]Cl2	F(000) = 792
Mr = 381.93	Dx = 1.541 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2969 reflections
a = 14.132 (5) Å	θ = 2.6–25.8°
b = 8.371 (3) Å	µ = 1.51 mm^−1
c = 15.454 (6) Å	T = 298 K
β = 115.734 (5)°	Block, grey
V = 1646.8 (11) Å^3	0.50 × 0.48 × 0.37 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2889 independent reflections
Radiation source: fine-focus sealed tube	2219 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −16→16
Tmin = 0.490, Tmax = 0.572	k = −9→9
8258 measured reflections	l = −16→18

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.092	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0433P)^2 + 0.2675P] where P = (Fo^2 + 2Fc^2)/3
2889 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.42 e Å^−3
6 restraints	Δρmin = −0.39 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	Occ. (<1)
Ni1	0.28820 (3)	0.32630 (4)	0.09996 (2)	0.03275 (14)
Cl1	0.38254 (7)	0.82789 (9)	0.09934 (6)	0.0564 (2)
Cl2	0.20130 (7)	0.07407 (11)	0.30761 (6)	0.0583 (3)
N1	0.13201 (18)	0.2558 (3)	0.02937 (16)	0.0361 (6)
N2	0.2247 (2)	0.4345 (3)	0.18387 (17)	0.0405 (6)
N31	0.44165 (18)	0.4127 (3)	0.16953 (17)	0.0461 (6)	0.50
H3A	0.4438	0.5172	0.1568	0.055*	0.50
H3B	0.4667	0.4001	0.2335	0.055*	0.50
N41	0.3445 (2)	0.2124 (3)	0.01129 (18)	0.0437 (6)	0.50
H4A	0.3566	0.1084	0.0272	0.052*	0.50
H4B	0.2968	0.2191	−0.0505	0.052*	0.50
N32	0.44165 (18)	0.4127 (3)	0.16953 (17)	0.0461 (6)	0.50
H3C	0.4413	0.5165	0.1846	0.055*	0.50
H3D	0.4779	0.3576	0.2240	0.055*	0.50
N42	0.3445 (2)	0.2124 (3)	0.01129 (18)	0.0437 (6)	0.50
H4C	0.3250	0.1090	0.0034	0.052*	0.50
H4D	0.3184	0.2595	−0.0468	0.052*	0.50
O1	0.24714 (15)	0.5288 (2)	0.00960 (14)	0.0436 (5)
H13	0.2440	0.5135	−0.0459	0.052*
H14	0.2874	0.6090	0.0319	0.052*
O2	0.33157 (17)	0.1288 (2)	0.19259 (15)	0.0493 (6)
H15	0.3004	0.1074	0.2274	0.059*
H16	0.3304	0.0423	0.1634	0.059*
C1	0.0897 (3)	0.1683 (4)	−0.0502 (2)	0.0476 (8)
H1	0.1335	0.1296	−0.0761	0.057*
C2	−0.0160 (3)	0.1316 (4)	−0.0964 (3)	0.0578 (9)
H2	−0.0427	0.0688	−0.1515	0.069*
C3	−0.0802 (3)	0.1907 (4)	−0.0584 (3)	0.0629 (11)
H3	−0.1518	0.1691	−0.0879	0.075*
C4	−0.0377 (3)	0.2828 (4)	0.0241 (3)	0.0544 (9)
H4	−0.0804	0.3226	0.0509	0.065*
C5	0.0688 (2)	0.3149 (3)	0.0663 (2)	0.0374 (7)
C6	0.1208 (2)	0.4154 (3)	0.1523 (2)	0.0405 (7)
C7	0.0670 (3)	0.4895 (4)	0.1986 (3)	0.0583 (10)
H7	−0.0051	0.4756	0.1764	0.070*
C8	0.1221 (4)	0.5828 (5)	0.2772 (3)	0.0743 (13)
H8	0.0869	0.6349	0.3078	0.089*
C9	0.2266 (4)	0.6000 (5)	0.3104 (3)	0.0729 (12)
H9	0.2645	0.6615	0.3647	0.087*
C10	0.2768 (3)	0.5238 (4)	0.2619 (3)	0.0639 (10)
H10	0.3491	0.5353	0.2846	0.077*
C111	0.5052 (8)	0.3169 (14)	0.1315 (7)	0.061 (3)	0.50
H11A	0.5224	0.2140	0.1635	0.074*	0.50
H11B	0.5703	0.3723	0.1449	0.074*	0.50
C121	0.4439 (8)	0.2924 (14)	0.0241 (8)	0.068 (3)	0.50
H12A	0.4293	0.3940	−0.0093	0.082*	0.50
H12B	0.4830	0.2257	−0.0003	0.082*	0.50
C112	0.4909 (8)	0.3923 (11)	0.1018 (8)	0.057 (3)	0.50
H11C	0.5666	0.4029	0.1359	0.068*	0.50
H11D	0.4647	0.4726	0.0516	0.068*	0.50
C122	0.4614 (8)	0.2254 (11)	0.0588 (8)	0.055 (3)	0.50
H12C	0.4893	0.2076	0.0122	0.066*	0.50
H12D	0.4909	0.1455	0.1090	0.066*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0300 (2)	0.0338 (2)	0.0385 (2)	−0.00157 (16)	0.01871 (17)	−0.00341 (16)
Cl1	0.0665 (6)	0.0388 (5)	0.0635 (5)	−0.0005 (4)	0.0279 (5)	−0.0074 (4)
Cl2	0.0659 (6)	0.0700 (6)	0.0427 (5)	−0.0144 (5)	0.0271 (4)	−0.0058 (4)
N1	0.0331 (13)	0.0337 (13)	0.0437 (14)	−0.0040 (11)	0.0187 (12)	0.0001 (12)
N2	0.0492 (16)	0.0384 (15)	0.0432 (14)	−0.0017 (12)	0.0287 (13)	−0.0026 (12)
N31	0.0321 (14)	0.0492 (16)	0.0522 (16)	−0.0053 (12)	0.0139 (12)	−0.0013 (13)
N41	0.0437 (15)	0.0459 (16)	0.0495 (16)	0.0034 (12)	0.0276 (13)	−0.0043 (12)
N32	0.0321 (14)	0.0492 (16)	0.0522 (16)	−0.0053 (12)	0.0139 (12)	−0.0013 (13)
N42	0.0437 (15)	0.0459 (16)	0.0495 (16)	0.0034 (12)	0.0276 (13)	−0.0043 (12)
O1	0.0492 (13)	0.0400 (12)	0.0454 (12)	−0.0026 (10)	0.0240 (10)	−0.0024 (10)
O2	0.0608 (15)	0.0424 (12)	0.0543 (13)	0.0043 (11)	0.0341 (12)	0.0051 (10)
C1	0.047 (2)	0.0449 (19)	0.0488 (19)	−0.0071 (16)	0.0187 (16)	−0.0031 (16)
C2	0.049 (2)	0.053 (2)	0.055 (2)	−0.0129 (17)	0.0066 (18)	0.0077 (17)
C3	0.0314 (19)	0.059 (2)	0.078 (3)	−0.0067 (17)	0.0051 (19)	0.031 (2)
C4	0.0366 (19)	0.055 (2)	0.078 (3)	0.0098 (17)	0.0314 (19)	0.025 (2)
C5	0.0358 (17)	0.0323 (17)	0.0515 (18)	0.0083 (13)	0.0260 (15)	0.0160 (14)
C6	0.052 (2)	0.0289 (16)	0.0553 (19)	0.0084 (14)	0.0375 (17)	0.0114 (15)
C7	0.073 (2)	0.052 (2)	0.077 (3)	0.0197 (19)	0.058 (2)	0.015 (2)
C8	0.126 (4)	0.052 (2)	0.083 (3)	0.023 (3)	0.080 (3)	0.005 (2)
C9	0.121 (4)	0.056 (2)	0.058 (2)	−0.003 (3)	0.055 (3)	−0.016 (2)
C10	0.082 (3)	0.062 (2)	0.057 (2)	−0.018 (2)	0.039 (2)	−0.0195 (19)
C111	0.033 (4)	0.071 (8)	0.082 (7)	0.004 (5)	0.026 (5)	0.008 (6)
C121	0.059 (6)	0.066 (8)	0.095 (9)	0.004 (6)	0.048 (6)	0.000 (6)
C112	0.041 (5)	0.057 (6)	0.083 (7)	−0.001 (5)	0.036 (5)	0.010 (5)
C122	0.052 (6)	0.053 (6)	0.083 (8)	0.007 (5)	0.050 (6)	0.003 (5)

Geometric parameters (Å, º)

Ni1—N1	2.078 (2)	C3—C4	1.384 (5)
Ni1—N2	2.078 (2)	C3—H3	0.9300
Ni1—N31	2.087 (2)	C4—C5	1.382 (4)
Ni1—N41	2.090 (2)	C4—H4	0.9300
Ni1—O1	2.111 (2)	C5—C6	1.472 (4)
Ni1—O2	2.097 (2)	C6—C7	1.395 (4)
N1—C1	1.329 (4)	C7—C8	1.368 (5)
N1—C5	1.346 (3)	C7—H7	0.9300
N2—C10	1.336 (4)	C8—C9	1.344 (6)
N2—C6	1.340 (4)	C8—H8	0.9300
N31—C111	1.500 (9)	C9—C10	1.391 (5)
N31—H3A	0.9000	C9—H9	0.9300
N31—H3B	0.9000	C10—H10	0.9300
N41—C121	1.489 (10)	C111—C121	1.516 (13)
N41—H4A	0.9000	C111—H11A	0.9700
N41—H4B	0.9000	C111—H11B	0.9700
O1—H13	0.8499	C121—H12A	0.9700
O1—H14	0.8499	C121—H12B	0.9700
O2—H15	0.8499	C112—C122	1.525 (12)
O2—H16	0.8499	C112—H11C	0.9700
C1—C2	1.382 (5)	C112—H11D	0.9700
C1—H1	0.9300	C122—H12C	0.9700
C2—C3	1.368 (5)	C122—H12D	0.9700
C2—H2	0.9300
N1—Ni1—N2	78.65 (10)	C1—C2—H2	121.1
N1—Ni1—N31	176.22 (10)	C2—C3—C4	119.6 (3)
N2—Ni1—N31	99.28 (10)	C2—C3—H3	120.2
N1—Ni1—N41	98.42 (10)	C4—C3—H3	120.2
N2—Ni1—N41	177.07 (10)	C5—C4—C3	119.4 (3)
N31—Ni1—N41	83.65 (10)	C5—C4—H4	120.3
N1—Ni1—O2	93.64 (9)	C3—C4—H4	120.3
N2—Ni1—O2	89.72 (9)	N1—C5—C4	121.0 (3)
N31—Ni1—O2	89.49 (9)	N1—C5—C6	115.4 (3)
N41—Ni1—O2	90.36 (9)	C4—C5—C6	123.5 (3)
N1—Ni1—O1	87.51 (9)	N2—C6—C7	121.0 (3)
N2—Ni1—O1	89.62 (9)	N2—C6—C5	115.8 (2)
N31—Ni1—O1	89.32 (9)	C7—C6—C5	123.2 (3)
N41—Ni1—O1	90.36 (9)	C8—C7—C6	118.9 (4)
O2—Ni1—O1	178.54 (9)	C8—C7—H7	120.6
C1—N1—C5	118.6 (3)	C6—C7—H7	120.6
C1—N1—Ni1	126.2 (2)	C9—C8—C7	120.5 (3)
C5—N1—Ni1	115.0 (2)	C9—C8—H8	119.7
C10—N2—C6	118.9 (3)	C7—C8—H8	119.7
C10—N2—Ni1	126.1 (2)	C8—C9—C10	118.6 (4)
C6—N2—Ni1	115.0 (2)	C8—C9—H9	120.7
C111—N31—Ni1	106.1 (4)	C10—C9—H9	120.7
C111—N31—H3A	110.5	N2—C10—C9	122.1 (4)
Ni1—N31—H3A	110.5	N2—C10—H10	118.9
C111—N31—H3B	110.5	C9—C10—H10	118.9
Ni1—N31—H3B	110.5	N31—C111—C121	110.3 (7)
H3A—N31—H3B	108.7	N31—C111—H11A	109.6
C121—N41—Ni1	108.2 (5)	C121—C111—H11A	109.6
C121—N41—H4A	110.0	N31—C111—H11B	109.6
Ni1—N41—H4A	110.0	C121—C111—H11B	109.6
C121—N41—H4B	110.0	H11A—C111—H11B	108.1
Ni1—N41—H4B	110.0	N41—C121—C111	105.3 (8)
H4A—N41—H4B	108.4	N41—C121—H12A	110.7
Ni1—O1—H13	115.2	C111—C121—H12A	110.7
Ni1—O1—H14	115.0	N41—C121—H12B	110.7
H13—O1—H14	105.2	C111—C121—H12B	110.7
Ni1—O2—H15	121.4	H12A—C121—H12B	108.8
Ni1—O2—H16	112.1	C122—C112—H11C	110.4
H15—O2—H16	105.2	C122—C112—H11D	110.4
N1—C1—C2	123.5 (3)	H11C—C112—H11D	108.6
N1—C1—H1	118.2	C112—C122—H12C	110.0
C2—C1—H1	118.2	C112—C122—H12D	110.0
C3—C2—C1	117.8 (3)	H12C—C122—H12D	108.4
C3—C2—H2	121.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H13···Cl2^i	0.85	2.20	3.025 (2)	164
O1—H14···Cl1	0.85	2.24	3.090 (2)	174
O2—H15···Cl2	0.85	2.25	3.099 (2)	172
O2—H16···Cl1^ii	0.85	2.32	3.137 (2)	162
N31—H3A···Cl1	0.90	2.76	3.628 (3)	162
N31—H3B···Cl1^iii	0.90	2.61	3.425 (3)	151
N32—H3C···Cl1	0.90	2.88	3.628 (3)	142
N32—H3D···Cl1^iii	0.90	2.59	3.425 (3)	154
N41—H4A···Cl1^ii	0.90	2.56	3.444 (3)	169
N41—H4B···Cl2^i	0.90	2.66	3.416 (3)	143
N42—H4C···Cl1^ii	0.90	2.71	3.444 (3)	139
N42—H4D···Cl2^i	0.90	2.55	3.416 (3)	161
C2—H2···Cl2^iv	0.93	2.75	3.613 (4)	154
C4—H4···O1^v	0.93	2.46	3.191 (4)	135

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, y−1, z; (iii) −x+1, y−1/2, −z+1/2; (iv) −x, −y, −z; (v) −x, −y+1, −z.