Diaquabis{2-[(5-méthylpyrazol-3-yl)méthyl]benzimidazole}nickel(II) dichloride dihydrate

In the structure of the title compound, [Ni(C₁₂H₁₂N₄)₂(H₂O)₂]Cl₂·2H₂O, the Ni atom is linked to four N atoms and two water molecules in a distorted octahedral coordination geometry. The coordinated water molecules are engaged in hydrogen bonds with two other water molecules.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.116
• Data-to-parameter ratio = 15.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



PLAT_601  Alert A Structure Contains Solvent Accessible VOIDS of     271.00 A   3


 Alert Level C:



CRYSC_01  Alert C The word below has not been recognised as a standard
          identifier.
          bleu

CRYSC_01  Alert C No recognised colour has been given for crystal colour.

REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.36
         From the CIF: _reflns_number_total               6075
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         6533
         Completeness (_total/calc)             92.99%
          Alert C: < 95% complete

General Notes



FORMU_01  There is a discrepancy between the atom counts in the
          _chemical_formula_sum and _chemical_formula_moiety. This is
          usually due to the moiety formula being in the wrong format.
          Atom count from _chemical_formula_sum:   C24 H32 Cl2 N8 Ni1 O4
          Atom count from _chemical_formula_moiety:C25 H32 N8 Ni1 O4


 1 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

---

Computing details

Data collection: KappaCCD (Nonius, 1998); cell refinement: DENZO SCALEPACK (Otwinoski & Minor, 1997); data reduction: DENZO SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson,1996); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C24H32CL2N8NiO4	F(000) = 1304
Mr = 626.19	Dx = 1.300 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 46051 reflections
a = 12.152 (1) Å	θ = 3.0–26.4°
b = 19.192 (2) Å	µ = 0.81 mm^−1
c = 13.797 (1) Å	T = 293 K
β = 95.961 (1)°	Prisme, bleu
V = 3200.4 (5) Å^3	0.3 × 0.2 × 0.15 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	5458 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 26.4°, θmin = 3.0°
φ scans	h = −15→14
46051 measured reflections	k = 0→23
6075 independent reflections	l = 0→17

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) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0661P)^2 + 1.7273P] where P = (Fo^2 + 2Fc^2)/3
6075 reflections	(Δ/σ)max = 0.005
383 parameters	Δρmax = 0.25 e Å^−3
12 restraints	Δρmin = −0.37 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
C3	0.4847 (2)	0.40377 (12)	0.41758 (17)	0.0376 (5)
C4	0.47917 (18)	0.47134 (12)	0.38485 (16)	0.0380 (5)
H4	0.4324	0.5062	0.4033	0.046*
C5	0.55732 (17)	0.47741 (11)	0.31860 (15)	0.0311 (4)
C6	0.5846 (2)	0.54105 (11)	0.26346 (16)	0.0377 (5)
H6A	0.5218	0.5725	0.2599	0.045*
H6B	0.6465	0.5645	0.2997	0.045*
C7	0.61307 (18)	0.52763 (11)	0.16259 (16)	0.0330 (4)
C9	0.68099 (18)	0.48474 (11)	0.03607 (15)	0.0340 (4)
C10	0.7319 (2)	0.44478 (13)	−0.03080 (16)	0.0410 (5)
H10	0.7682	0.4034	−0.0125	0.049*
C11	0.7262 (2)	0.46926 (16)	−0.12571 (18)	0.0515 (6)
H11	0.7593	0.4437	−0.1720	0.062*
C12	0.6722 (2)	0.53120 (17)	−0.15356 (18)	0.0564 (7)
H12	0.6715	0.5463	−0.2177	0.068*
C13	0.6198 (2)	0.57059 (16)	−0.08890 (19)	0.0539 (7)
H13	0.5828	0.6116	−0.1077	0.065*
C14	0.6253 (2)	0.54583 (13)	0.00624 (17)	0.0405 (5)
C16	0.4227 (2)	0.36649 (16)	0.4895 (2)	0.0560 (7)
H16A	0.3898	0.3251	0.4601	0.084*
H16B	0.3657	0.3963	0.5093	0.084*
H16C	0.4725	0.3540	0.5454	0.084*
C23	1.0088 (2)	0.35664 (15)	0.0659 (2)	0.0486 (6)
C24	1.0298 (2)	0.42590 (14)	0.08170 (18)	0.0457 (6)
H24	1.0853	0.4522	0.0577	0.055*
C25	0.95115 (18)	0.44927 (12)	0.14098 (15)	0.0351 (5)
C26	0.9329 (2)	0.52174 (12)	0.17739 (17)	0.0396 (5)
H26A	0.9998	0.5488	0.1734	0.047*
H26B	0.8741	0.5435	0.1350	0.047*
C27	0.90339 (18)	0.52402 (11)	0.27958 (16)	0.0334 (4)
C29	0.83637 (17)	0.50170 (11)	0.41562 (15)	0.0325 (4)
C30	0.78654 (19)	0.47272 (13)	0.49272 (16)	0.0393 (5)
H30	0.7401	0.4342	0.4837	0.047*
C31	0.8090 (2)	0.50349 (15)	0.58316 (18)	0.0476 (6)
H31	0.7774	0.4848	0.6360	0.057*
C32	0.8773 (2)	0.56166 (15)	0.59782 (19)	0.0533 (7)
H32	0.8890	0.5812	0.6597	0.064*
C33	0.9276 (2)	0.59070 (13)	0.5228 (2)	0.0485 (6)
H33	0.9740	0.6292	0.5326	0.058*
C34	0.90586 (19)	0.55973 (12)	0.43147 (17)	0.0372 (5)
C36	1.0620 (3)	0.3028 (2)	0.0077 (3)	0.0804 (11)
H36A	1.0711	0.2604	0.0446	0.121*
H36B	1.1330	0.3192	−0.0069	0.121*
H36C	1.0160	0.2942	−0.0520	0.121*
Cl1	0.88814 (7)	0.18306 (4)	0.23110 (6)	0.0670 (2)
Cl2	0.56383 (7)	0.20868 (3)	0.43529 (5)	0.0588 (2)
N1	0.60997 (14)	0.41727 (9)	0.31055 (13)	0.0307 (4)
N2	0.56410 (15)	0.37274 (9)	0.37146 (13)	0.0339 (4)
H2	0.5834	0.3299	0.3796	0.041*
N8	0.67311 (15)	0.47515 (9)	0.13584 (12)	0.0318 (4)
N15	0.58268 (17)	0.57132 (10)	0.08798 (14)	0.0415 (4)
H15	0.5436	0.6085	0.0909	0.050*
N21	0.88546 (16)	0.39718 (9)	0.16143 (14)	0.0357 (4)
N22	0.92203 (17)	0.34095 (10)	0.11486 (15)	0.0433 (5)
H22	0.8932	0.3001	0.1164	0.052*
N28	0.83512 (14)	0.48081 (9)	0.31823 (12)	0.0314 (4)
N35	0.94600 (16)	0.57215 (10)	0.34364 (14)	0.0396 (4)
H35	0.9907	0.6050	0.3317	0.047*
Ni1	0.74715 (2)	0.403366 (12)	0.235747 (19)	0.02699 (10)
O40	0.81071 (18)	0.32336 (10)	0.32910 (14)	0.0505 (5)
O41	0.67249 (17)	0.32034 (9)	0.15175 (13)	0.0441 (4)
O42	0.7882 (2)	0.20903 (13)	0.01433 (17)	0.0802 (7)
O43	0.6230 (3)	0.18930 (14)	0.2193 (2)	0.0835 (7)
H40A	0.839 (3)	0.2891 (14)	0.312 (3)	0.069 (11)*
H40B	0.808 (3)	0.314 (2)	0.3844 (16)	0.080 (12)*
H41A	0.653 (3)	0.2839 (12)	0.171 (2)	0.058 (9)*
H41B	0.633 (3)	0.325 (2)	0.1034 (19)	0.077 (12)*
H42A	0.820 (4)	0.195 (2)	0.079 (2)	0.127 (9)*
H42B	0.723 (3)	0.239 (2)	0.005 (3)	0.127 (9)*
H43A	0.699 (3)	0.172 (3)	0.223 (4)	0.127 (9)*
H43B	0.611 (4)	0.191 (3)	0.288 (2)	0.127 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C3	0.0358 (12)	0.0466 (13)	0.0315 (11)	−0.0017 (9)	0.0084 (10)	−0.0020 (9)
C4	0.0372 (12)	0.0434 (12)	0.0343 (11)	0.0087 (9)	0.0077 (10)	−0.0036 (9)
C5	0.0317 (11)	0.0326 (10)	0.0288 (10)	0.0044 (8)	0.0031 (8)	−0.0018 (8)
C6	0.0441 (13)	0.0315 (11)	0.0381 (11)	0.0078 (9)	0.0075 (10)	0.0009 (9)
C7	0.0337 (11)	0.0292 (10)	0.0357 (11)	0.0024 (8)	0.0023 (9)	0.0043 (8)
C9	0.0338 (11)	0.0394 (11)	0.0283 (10)	−0.0078 (8)	−0.0001 (9)	0.0033 (8)
C10	0.0418 (13)	0.0475 (13)	0.0339 (11)	−0.0090 (10)	0.0049 (10)	−0.0046 (9)
C11	0.0515 (15)	0.0705 (18)	0.0326 (12)	−0.0193 (13)	0.0055 (11)	−0.0070 (11)
C12	0.0571 (17)	0.082 (2)	0.0292 (12)	−0.0164 (14)	−0.0008 (12)	0.0105 (12)
C13	0.0536 (16)	0.0647 (17)	0.0414 (14)	−0.0043 (13)	−0.0045 (12)	0.0210 (12)
C14	0.0402 (13)	0.0442 (13)	0.0363 (11)	−0.0029 (9)	0.0007 (10)	0.0084 (9)
C16	0.0615 (17)	0.0585 (16)	0.0531 (15)	0.0001 (13)	0.0294 (14)	0.0034 (13)
C23	0.0418 (13)	0.0575 (15)	0.0489 (14)	0.0053 (11)	0.0159 (12)	−0.0057 (11)
C24	0.0398 (13)	0.0577 (15)	0.0416 (13)	−0.0068 (11)	0.0145 (11)	−0.0011 (11)
C25	0.0325 (11)	0.0420 (12)	0.0316 (10)	−0.0053 (9)	0.0063 (9)	0.0016 (9)
C26	0.0440 (13)	0.0374 (12)	0.0384 (12)	−0.0115 (9)	0.0093 (10)	0.0010 (9)
C27	0.0339 (11)	0.0295 (10)	0.0368 (11)	−0.0040 (8)	0.0040 (9)	−0.0012 (8)
C29	0.0317 (11)	0.0336 (10)	0.0314 (10)	0.0029 (8)	0.0003 (9)	−0.0038 (8)
C30	0.0360 (12)	0.0480 (13)	0.0342 (11)	0.0030 (9)	0.0052 (10)	−0.0002 (9)
C31	0.0441 (14)	0.0651 (16)	0.0338 (12)	0.0128 (12)	0.0046 (11)	−0.0032 (11)
C32	0.0551 (16)	0.0638 (17)	0.0389 (13)	0.0143 (13)	−0.0047 (12)	−0.0177 (12)
C33	0.0500 (15)	0.0437 (13)	0.0498 (15)	0.0008 (10)	−0.0049 (12)	−0.0166 (11)
C34	0.0354 (12)	0.0360 (11)	0.0394 (11)	0.0021 (9)	−0.0001 (10)	−0.0058 (9)
C36	0.077 (2)	0.083 (2)	0.088 (2)	0.0088 (18)	0.041 (2)	−0.0262 (19)
Cl1	0.0816 (5)	0.0564 (4)	0.0646 (4)	0.0299 (4)	0.0148 (4)	−0.0024 (3)
Cl2	0.0781 (5)	0.0376 (3)	0.0578 (4)	−0.0074 (3)	−0.0059 (4)	0.0052 (3)
N1	0.0304 (9)	0.0303 (8)	0.0324 (9)	0.0001 (7)	0.0077 (7)	0.0013 (7)
N2	0.0353 (10)	0.0325 (9)	0.0352 (9)	−0.0014 (7)	0.0097 (8)	0.0031 (7)
N8	0.0350 (10)	0.0325 (9)	0.0280 (8)	0.0007 (7)	0.0039 (7)	0.0019 (7)
N15	0.0456 (11)	0.0372 (10)	0.0415 (10)	0.0088 (8)	0.0041 (9)	0.0103 (8)
N21	0.0360 (10)	0.0318 (9)	0.0410 (10)	0.0004 (7)	0.0124 (9)	−0.0020 (7)
N22	0.0450 (11)	0.0348 (10)	0.0530 (12)	0.0017 (8)	0.0192 (10)	−0.0056 (8)
N28	0.0320 (9)	0.0334 (9)	0.0290 (8)	−0.0048 (7)	0.0032 (7)	−0.0017 (7)
N35	0.0402 (11)	0.0340 (9)	0.0444 (11)	−0.0097 (8)	0.0038 (9)	−0.0042 (8)
Ni1	0.02805 (17)	0.02532 (15)	0.02813 (16)	0.00003 (9)	0.00537 (11)	−0.00006 (9)
O40	0.0727 (13)	0.0399 (10)	0.0399 (10)	0.0190 (9)	0.0104 (9)	0.0077 (8)
O41	0.0584 (12)	0.0340 (9)	0.0389 (9)	−0.0089 (8)	−0.0002 (9)	−0.0029 (7)
O42	0.109 (2)	0.0789 (16)	0.0530 (12)	0.0330 (14)	0.0093 (13)	−0.0121 (11)
O43	0.0950 (19)	0.0756 (16)	0.0803 (17)	−0.0158 (14)	0.0112 (16)	0.0099 (14)

Geometric parameters (Å, º)

C3—N2	1.348 (3)	C25—N21	1.328 (3)
C3—C4	1.372 (3)	C25—C26	1.503 (3)
C3—C16	1.490 (3)	C26—C27	1.491 (3)
C4—C5	1.390 (3)	C27—N28	1.324 (3)
C5—N1	1.330 (3)	C27—N35	1.344 (3)
C5—C6	1.494 (3)	C29—C30	1.393 (3)
C6—C7	1.491 (3)	C29—N28	1.401 (3)
C7—N8	1.319 (3)	C29—C34	1.401 (3)
C7—N15	1.349 (3)	C30—C31	1.382 (3)
C9—C10	1.393 (3)	C31—C32	1.393 (4)
C9—C14	1.395 (3)	C32—C33	1.374 (4)
C9—N8	1.402 (3)	C33—C34	1.394 (3)
C10—C11	1.386 (3)	C34—N35	1.373 (3)
C11—C12	1.393 (4)	N1—N2	1.358 (2)
C12—C13	1.375 (4)	N1—Ni1	2.0671 (17)
C13—C14	1.391 (3)	N8—Ni1	2.0857 (17)
C14—N15	1.378 (3)	N21—N22	1.354 (3)
C23—N22	1.344 (3)	N21—Ni1	2.0611 (18)
C23—C24	1.367 (4)	N28—Ni1	2.0962 (17)
C23—C36	1.497 (4)	Ni1—O40	2.0992 (18)
C24—C25	1.395 (3)	Ni1—O41	2.1183 (17)
N2—C3—C4	105.98 (19)	C33—C32—C31	121.4 (2)
N2—C3—C16	122.6 (2)	C32—C33—C34	116.8 (2)
C4—C3—C16	131.4 (2)	N35—C34—C33	132.3 (2)
C3—C4—C5	106.37 (19)	N35—C34—C29	105.30 (19)
N1—C5—C4	110.47 (19)	C33—C34—C29	122.3 (2)
N1—C5—C6	122.20 (18)	C5—N1—N2	105.23 (16)
C4—C5—C6	127.32 (19)	C5—N1—Ni1	125.00 (14)
C7—C6—C5	114.79 (18)	N2—N1—Ni1	129.18 (13)
N8—C7—N15	112.12 (19)	C3—N2—N1	111.94 (18)
N8—C7—C6	125.59 (19)	C7—N8—C9	105.71 (18)
N15—C7—C6	122.23 (19)	C7—N8—Ni1	122.19 (14)
C10—C9—C14	120.2 (2)	C9—N8—Ni1	131.83 (15)
C10—C9—N8	131.2 (2)	C7—N15—C14	107.92 (19)
C14—C9—N8	108.64 (19)	C25—N21—N22	105.37 (18)
C11—C10—C9	117.2 (2)	C25—N21—Ni1	126.98 (15)
C10—C11—C12	121.7 (3)	N22—N21—Ni1	127.34 (14)
C13—C12—C11	121.8 (2)	C23—N22—N21	111.9 (2)
C12—C13—C14	116.4 (3)	C27—N28—C29	105.20 (17)
N15—C14—C13	131.7 (2)	C27—N28—Ni1	122.08 (14)
N15—C14—C9	105.60 (19)	C29—N28—Ni1	132.68 (14)
C13—C14—C9	122.7 (2)	C27—N35—C34	108.24 (18)
N22—C23—C24	106.3 (2)	N21—Ni1—N1	175.87 (7)
N22—C23—C36	121.3 (3)	N21—Ni1—N8	91.57 (7)
C24—C23—C36	132.3 (3)	N1—Ni1—N8	85.97 (7)
C23—C24—C25	106.2 (2)	N21—Ni1—N28	85.11 (7)
N21—C25—C24	110.2 (2)	N1—Ni1—N28	91.70 (7)
N21—C25—C26	120.87 (19)	N8—Ni1—N28	92.93 (7)
C24—C25—C26	128.9 (2)	N21—Ni1—O40	89.77 (8)
C27—C26—C25	113.67 (18)	N1—Ni1—O40	93.01 (7)
N28—C27—N35	112.35 (19)	N8—Ni1—O40	174.08 (8)
N28—C27—C26	125.80 (19)	N28—Ni1—O40	92.93 (8)
N35—C27—C26	121.84 (19)	N21—Ni1—O41	90.55 (7)
C30—C29—N28	131.0 (2)	N1—Ni1—O41	92.78 (7)
C30—C29—C34	120.1 (2)	N8—Ni1—O41	90.26 (7)
N28—C29—C34	108.88 (19)	N28—Ni1—O41	174.68 (7)
C31—C30—C29	117.3 (2)	O40—Ni1—O41	83.96 (8)
C30—C31—C32	122.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl2	0.86	2.47	3.2696 (19)	155
N15—H15···Cl2^i	0.86	2.33	3.179 (2)	169
N22—H22···O42	0.86	2.51	3.242 (4)	144
N22—H22···Cl1	0.86	2.75	3.473 (2)	142
N35—H35···Cl1^ii	0.86	2.33	3.176 (2)	168
O40—H40A···Cl1	0.79 (2)	2.42 (2)	3.198 (2)	167 (3)
O40—H40B···O42^iii	0.79 (2)	1.89 (2)	2.672 (3)	175 (4)
O41—H41A···O43	0.79 (2)	1.98 (2)	2.770 (3)	174 (3)
O41—H41B···Cl2^iv	0.78 (2)	2.47 (3)	3.1865 (19)	153 (4)
O42—H42A···Cl1	0.97 (3)	2.18 (3)	3.148 (3)	170 (4)
O42—H42B···Cl2^iv	0.98 (3)	2.30 (3)	3.241 (3)	161 (4)
O43—H43A···Cl1	0.98 (3)	2.30 (3)	3.211 (3)	155 (4)
O43—H43B···Cl2	0.97 (3)	2.19 (3)	3.159 (3)	171 (4)

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