Tris­(benz­imidazole)(iminodiacetato)­nickel(II) dihydrate

The title complex, [Ni(C₄H₅NO₄)(C₇H₆N₂)₃]·2H₂O, assumes a distorted octahedral geometry about Ni^II, involving one imino­di­acetate dianion and three benz­imidazole mol­ecules. The tridentate imino­di­acetate dianion chelates the Ni^II atom in the facial mode. The crystal packing is influenced by O—H...O and N—H...O hydrogen bonds and C—H...π interactions, the latter occurring between neighboring benz­imidazole ring systems.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.093
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni     -   O1      ..       6.73 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni     -   O3      ..       9.93 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni     -   N3      ..       5.21 su
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I)

Crystal data

[Ni(C4H5NO4)(C7H6N2)3]·2H2O	F(000) = 1208
Mr = 580.25	Dx = 1.483 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12159 reflections
a = 13.4711 (5) Å	θ = 2.5–26.0°
b = 10.2873 (4) Å	µ = 0.80 mm^−1
c = 19.2982 (6) Å	T = 295 K
β = 103.719 (1)°	Prism, green
V = 2598.07 (16) Å^3	0.31 × 0.20 × 0.10 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	5941 independent reflections
Radiation source: fine-focus sealed tube	4681 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 10.0 pixels mm^-1	θmax = 27.5°, θmin = 1.6°
ω scans	h = −17→17
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
Tmin = 0.84, Tmax = 0.92	l = −23→25
24193 measured reflections

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)] = 0.043	Hydrogen site location: difmap (O-H) and geom (N-H and C-H)
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0393P)^2 + 1.3635P] where P = (Fo^2 + 2Fc^2)/3
5941 reflections	(Δ/σ)max < 0.001
352 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.31 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
Ni	0.250822 (19)	0.24244 (3)	0.227622 (13)	0.02440 (8)
O1	0.22223 (11)	0.18691 (16)	0.32356 (8)	0.0332 (4)
O2	0.10134 (14)	0.1269 (2)	0.37729 (9)	0.0498 (5)
O3	0.26719 (11)	0.03960 (15)	0.20706 (8)	0.0337 (4)
O4	0.18611 (15)	−0.11955 (17)	0.14022 (11)	0.0545 (5)
O1W	0.00882 (15)	−0.1029 (2)	0.40916 (10)	0.0586 (5)
O2W	0.0566 (2)	−0.2877 (3)	0.04626 (14)	0.1130 (12)
N3	0.09497 (14)	0.18969 (19)	0.19069 (9)	0.0306 (4)
H3	0.0608	0.2548	0.1631	0.037*
N11	0.40318 (14)	0.26936 (17)	0.27664 (9)	0.0288 (4)
N13	0.55810 (14)	0.35600 (19)	0.30796 (10)	0.0364 (4)
H13	0.6075	0.4094	0.3086	0.044*
N21	0.22050 (15)	0.44350 (18)	0.24491 (10)	0.0326 (4)
N23	0.21868 (18)	0.6554 (2)	0.22100 (12)	0.0446 (5)
H23	0.2186	0.7256	0.1968	0.054*
N31	0.27321 (13)	0.26892 (17)	0.12416 (9)	0.0289 (4)
N33	0.23743 (15)	0.2993 (2)	0.00659 (10)	0.0345 (4)
H33	0.2040	0.3220	−0.0353	0.041*
C1	0.13233 (18)	0.1587 (2)	0.32333 (12)	0.0336 (5)
C2	0.05237 (19)	0.1723 (3)	0.25345 (13)	0.0471 (7)
H2A	0.0096	0.0953	0.2465	0.057*
H2B	0.0092	0.2462	0.2570	0.057*
C4	0.09193 (18)	0.0713 (2)	0.14697 (13)	0.0389 (6)
H4A	0.0801	0.0961	0.0972	0.047*
H4B	0.0349	0.0177	0.1522	0.047*
C5	0.18971 (18)	−0.0085 (2)	0.16717 (12)	0.0334 (5)
C12	0.46255 (17)	0.3657 (2)	0.26737 (12)	0.0324 (5)
H12	0.4406	0.4339	0.2358	0.039*
C14	0.63857 (19)	0.1905 (3)	0.40242 (13)	0.0429 (6)
H14	0.7024	0.2292	0.4176	0.052*
C15	0.6143 (2)	0.0775 (3)	0.43195 (14)	0.0472 (7)
H15	0.6632	0.0392	0.4684	0.057*
C16	0.5192 (2)	0.0174 (3)	0.40953 (13)	0.0425 (6)
H16	0.5070	−0.0608	0.4303	0.051*
C17	0.44303 (19)	0.0722 (2)	0.35711 (12)	0.0344 (5)
H17	0.3794	0.0328	0.3422	0.041*
C18	0.46517 (16)	0.1890 (2)	0.32734 (11)	0.0285 (5)
C19	0.56246 (17)	0.2445 (2)	0.34839 (11)	0.0326 (5)
C22	0.2209 (2)	0.5335 (2)	0.19681 (13)	0.0407 (6)
H22	0.2225	0.5143	0.1500	0.049*
C24	0.2137 (2)	0.7423 (3)	0.34196 (16)	0.0548 (7)
H24	0.2136	0.8303	0.3310	0.066*
C25	0.2109 (3)	0.6999 (4)	0.40873 (17)	0.0666 (9)
H25	0.2093	0.7606	0.4441	0.080*
C26	0.2105 (3)	0.5683 (3)	0.42486 (15)	0.0637 (9)
H26	0.2081	0.5432	0.4707	0.076*
C27	0.2134 (2)	0.4736 (3)	0.37470 (13)	0.0464 (6)
H27	0.2132	0.3858	0.3861	0.056*
C28	0.21680 (16)	0.5139 (2)	0.30669 (12)	0.0329 (5)
C29	0.21671 (18)	0.6472 (2)	0.29147 (13)	0.0378 (5)
C32	0.20635 (18)	0.3123 (2)	0.06743 (12)	0.0329 (5)
H32	0.1438	0.3484	0.0694	0.039*
C34	0.4011 (2)	0.2106 (2)	−0.01731 (13)	0.0387 (6)
H34	0.3858	0.2254	−0.0662	0.046*
C35	0.4917 (2)	0.1561 (2)	0.01751 (14)	0.0427 (6)
H35	0.5394	0.1338	−0.0083	0.051*
C36	0.51441 (19)	0.1331 (2)	0.09104 (14)	0.0416 (6)
H36	0.5767	0.0952	0.1128	0.050*
C37	0.44728 (18)	0.1648 (2)	0.13187 (12)	0.0344 (5)
H37	0.4628	0.1483	0.1806	0.041*
C38	0.35500 (17)	0.2229 (2)	0.09770 (11)	0.0275 (4)
C39	0.33291 (17)	0.2427 (2)	0.02380 (11)	0.0305 (4)
H1A	0.0474	−0.0306	0.3958	0.050*
H1B	0.0374	−0.1161	0.4576	0.050*
H2C	0.0894	−0.2173	0.0669	0.050*
H2D	0.0062	−0.2933	0.0635	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.02585 (13)	0.02462 (14)	0.02220 (13)	−0.00046 (12)	0.00467 (9)	0.00095 (11)
O1	0.0292 (8)	0.0407 (9)	0.0282 (8)	−0.0052 (7)	0.0040 (6)	0.0038 (7)
O2	0.0481 (10)	0.0700 (13)	0.0325 (9)	−0.0226 (10)	0.0118 (8)	0.0027 (9)
O3	0.0293 (8)	0.0335 (8)	0.0350 (8)	0.0039 (7)	0.0014 (7)	0.0008 (7)
O4	0.0597 (12)	0.0291 (9)	0.0656 (12)	0.0031 (8)	−0.0034 (10)	−0.0091 (9)
O1W	0.0530 (12)	0.0628 (13)	0.0566 (12)	−0.0196 (10)	0.0065 (10)	−0.0003 (10)
O2W	0.118 (2)	0.159 (3)	0.0695 (16)	−0.089 (2)	0.0371 (16)	−0.0455 (18)
N3	0.0286 (9)	0.0346 (10)	0.0267 (9)	0.0034 (8)	0.0031 (7)	0.0015 (8)
N11	0.0313 (9)	0.0285 (9)	0.0259 (8)	−0.0032 (8)	0.0054 (7)	0.0005 (7)
N13	0.0290 (10)	0.0362 (11)	0.0425 (11)	−0.0078 (8)	0.0055 (8)	−0.0014 (9)
N21	0.0367 (10)	0.0305 (10)	0.0303 (9)	−0.0002 (8)	0.0072 (8)	−0.0028 (8)
N23	0.0596 (14)	0.0270 (10)	0.0482 (12)	0.0037 (9)	0.0147 (11)	0.0015 (9)
N31	0.0316 (9)	0.0304 (10)	0.0251 (8)	0.0022 (8)	0.0075 (7)	0.0012 (8)
N33	0.0398 (11)	0.0404 (11)	0.0213 (9)	0.0009 (9)	0.0032 (8)	0.0015 (8)
C1	0.0351 (12)	0.0362 (12)	0.0292 (11)	−0.0076 (10)	0.0072 (9)	−0.0005 (10)
C2	0.0315 (13)	0.0742 (19)	0.0360 (13)	−0.0037 (13)	0.0084 (10)	0.0005 (13)
C4	0.0337 (12)	0.0361 (12)	0.0422 (13)	−0.0013 (10)	−0.0006 (10)	−0.0051 (11)
C5	0.0407 (13)	0.0249 (11)	0.0337 (11)	−0.0001 (10)	0.0072 (10)	0.0033 (10)
C12	0.0333 (12)	0.0310 (11)	0.0319 (11)	−0.0031 (10)	0.0060 (9)	0.0007 (9)
C14	0.0319 (12)	0.0546 (16)	0.0393 (13)	0.0068 (11)	0.0024 (10)	−0.0049 (12)
C15	0.0460 (15)	0.0534 (16)	0.0390 (13)	0.0209 (13)	0.0038 (12)	0.0040 (12)
C16	0.0515 (15)	0.0384 (13)	0.0392 (13)	0.0128 (12)	0.0138 (12)	0.0061 (11)
C17	0.0383 (12)	0.0325 (12)	0.0339 (11)	0.0029 (10)	0.0112 (10)	0.0001 (10)
C18	0.0304 (11)	0.0323 (11)	0.0230 (10)	0.0041 (9)	0.0066 (9)	−0.0039 (9)
C19	0.0316 (11)	0.0374 (12)	0.0287 (10)	0.0016 (10)	0.0066 (8)	−0.0053 (10)
C22	0.0577 (16)	0.0299 (12)	0.0363 (12)	0.0015 (11)	0.0146 (12)	−0.0001 (10)
C24	0.0553 (16)	0.0425 (15)	0.0595 (17)	0.0134 (13)	−0.0009 (13)	−0.0193 (14)
C25	0.067 (2)	0.072 (2)	0.0546 (18)	0.0192 (17)	0.0025 (15)	−0.0302 (17)
C26	0.076 (2)	0.078 (2)	0.0362 (14)	0.0128 (18)	0.0103 (14)	−0.0121 (15)
C27	0.0508 (16)	0.0516 (16)	0.0354 (13)	0.0039 (13)	0.0077 (12)	−0.0014 (12)
C28	0.0258 (11)	0.0374 (12)	0.0333 (11)	0.0026 (9)	0.0029 (9)	−0.0059 (10)
C29	0.0306 (12)	0.0363 (13)	0.0427 (13)	0.0050 (10)	0.0014 (10)	−0.0069 (11)
C32	0.0315 (11)	0.0348 (12)	0.0319 (11)	0.0024 (10)	0.0064 (9)	−0.0012 (10)
C34	0.0493 (15)	0.0400 (13)	0.0307 (11)	−0.0074 (11)	0.0172 (11)	−0.0045 (10)
C35	0.0466 (15)	0.0409 (13)	0.0484 (15)	−0.0023 (11)	0.0269 (12)	−0.0072 (12)
C36	0.0363 (13)	0.0401 (13)	0.0505 (15)	0.0063 (11)	0.0144 (11)	−0.0003 (12)
C37	0.0366 (12)	0.0330 (12)	0.0327 (11)	0.0032 (10)	0.0068 (10)	0.0019 (10)
C38	0.0338 (11)	0.0248 (10)	0.0254 (10)	−0.0018 (8)	0.0098 (8)	−0.0023 (8)
C39	0.0382 (11)	0.0273 (10)	0.0268 (10)	−0.0042 (10)	0.0090 (9)	−0.0022 (9)

Geometric parameters (Å, º)

Ni—O1	2.0593 (15)	C4—H4A	0.9700
Ni—O3	2.1452 (16)	C4—H4B	0.9700
Ni—N3	2.1214 (18)	C12—H12	0.9300
Ni—N11	2.0648 (18)	C14—C15	1.368 (4)
Ni—N21	2.1496 (19)	C14—C19	1.393 (3)
Ni—N31	2.1065 (17)	C14—H14	0.9300
O1—C1	1.244 (3)	C15—C16	1.396 (4)
O2—C1	1.254 (3)	C15—H15	0.9300
O3—C5	1.243 (3)	C16—C17	1.379 (3)
O4—C5	1.251 (3)	C16—H16	0.9300
O1W—H1A	0.976	C17—C18	1.395 (3)
O1W—H1B	0.933	C17—H17	0.9300
O2W—H2C	0.891	C18—C19	1.399 (3)
O2W—H2D	0.825	C22—H22	0.9300
N3—C2	1.469 (3)	C24—C25	1.369 (5)
N3—C4	1.477 (3)	C24—C29	1.388 (3)
N3—H3	0.9100	C24—H24	0.9300
N11—C12	1.312 (3)	C25—C26	1.390 (5)
N11—C18	1.396 (3)	C25—H25	0.9300
N13—C12	1.342 (3)	C26—C27	1.380 (4)
N13—C19	1.381 (3)	C26—H26	0.9300
N13—H13	0.8600	C27—C28	1.387 (3)
N21—C22	1.312 (3)	C27—H27	0.9300
N21—C28	1.406 (3)	C28—C29	1.402 (3)
N23—C22	1.342 (3)	C32—H32	0.9300
N23—C29	1.369 (3)	C34—C35	1.366 (4)
N23—H23	0.8600	C34—C39	1.389 (3)
N31—C32	1.319 (3)	C34—H34	0.9300
N31—C38	1.402 (3)	C35—C36	1.399 (4)
N33—C32	1.343 (3)	C35—H35	0.9300
N33—C39	1.379 (3)	C36—C37	1.372 (3)
N33—H33	0.8600	C36—H36	0.9300
C1—C2	1.520 (3)	C37—C38	1.396 (3)
C2—H2A	0.9700	C37—H37	0.9300
C2—H2B	0.9700	C38—C39	1.401 (3)
C4—C5	1.522 (3)
O1—Ni—N11	90.16 (6)	N11—C12—H12	123.4
O1—Ni—N31	170.89 (7)	N13—C12—H12	123.4
N11—Ni—N31	93.83 (7)	C15—C14—C19	116.4 (2)
O1—Ni—N3	81.37 (6)	C15—C14—H14	121.8
N11—Ni—N3	170.15 (7)	C19—C14—H14	121.8
N31—Ni—N3	93.86 (7)	C14—C15—C16	122.6 (2)
O1—Ni—O3	86.90 (6)	C14—C15—H15	118.7
N11—Ni—O3	94.62 (6)	C16—C15—H15	118.7
N31—Ni—O3	84.62 (7)	C17—C16—C15	121.0 (2)
N3—Ni—O3	79.98 (7)	C17—C16—H16	119.5
O1—Ni—N21	92.55 (7)	C15—C16—H16	119.5
N11—Ni—N21	90.27 (7)	C16—C17—C18	117.4 (2)
N31—Ni—N21	95.62 (7)	C16—C17—H17	121.3
N3—Ni—N21	95.10 (7)	C18—C17—H17	121.3
O3—Ni—N21	175.08 (7)	C17—C18—N11	130.4 (2)
C1—O1—Ni	116.80 (14)	C17—C18—C19	120.6 (2)
C5—O3—Ni	113.18 (14)	N11—C18—C19	109.0 (2)
H1A—O1W—H1B	104.9	N13—C19—C14	132.8 (2)
H2C—O2W—H2D	104.2	N13—C19—C18	105.28 (19)
C2—N3—C4	114.0 (2)	C14—C19—C18	121.8 (2)
C2—N3—Ni	107.64 (14)	N21—C22—N23	114.2 (2)
C4—N3—Ni	107.10 (14)	N21—C22—H22	122.9
C2—N3—H3	109.3	N23—C22—H22	122.9
C4—N3—H3	109.3	C25—C24—C29	116.6 (3)
Ni—N3—H3	109.3	C25—C24—H24	121.7
C12—N11—C18	105.07 (18)	C29—C24—H24	121.7
C12—N11—Ni	127.64 (15)	C24—C25—C26	121.6 (3)
C18—N11—Ni	127.29 (14)	C24—C25—H25	119.2
C12—N13—C19	107.33 (19)	C26—C25—H25	119.2
C12—N13—H13	126.3	C27—C26—C25	121.9 (3)
C19—N13—H13	126.3	C27—C26—H26	119.1
C22—N21—C28	104.10 (19)	C25—C26—H26	119.1
C22—N21—Ni	122.44 (16)	C26—C27—C28	117.8 (3)
C28—N21—Ni	132.34 (15)	C26—C27—H27	121.1
C22—N23—C29	107.1 (2)	C28—C27—H27	121.1
C22—N23—H23	126.4	C27—C28—C29	119.4 (2)
C29—N23—H23	126.4	C27—C28—N21	131.6 (2)
C32—N31—C38	104.64 (18)	C29—C28—N21	108.9 (2)
C32—N31—Ni	127.39 (15)	N23—C29—C24	131.6 (3)
C38—N31—Ni	127.08 (14)	N23—C29—C28	105.6 (2)
C32—N33—C39	107.33 (18)	C24—C29—C28	122.8 (3)
C32—N33—H33	126.3	N31—C32—N33	113.5 (2)
C39—N33—H33	126.3	N31—C32—H32	123.3
O1—C1—O2	125.0 (2)	N33—C32—H32	123.3
O1—C1—C2	117.8 (2)	C35—C34—C39	116.8 (2)
O2—C1—C2	117.1 (2)	C35—C34—H34	121.6
N3—C2—C1	114.2 (2)	C39—C34—H34	121.6
N3—C2—H2A	108.7	C34—C35—C36	121.6 (2)
C1—C2—H2A	108.7	C34—C35—H35	119.2
N3—C2—H2B	108.7	C36—C35—H35	119.2
C1—C2—H2B	108.7	C37—C36—C35	121.8 (2)
H2A—C2—H2B	107.6	C37—C36—H36	119.1
N3—C4—C5	113.17 (18)	C35—C36—H36	119.1
N3—C4—H4A	108.9	C36—C37—C38	117.7 (2)
C5—C4—H4A	108.9	C36—C37—H37	121.1
N3—C4—H4B	108.9	C38—C37—H37	121.1
C5—C4—H4B	108.9	C37—C38—N31	131.4 (2)
H4A—C4—H4B	107.8	C37—C38—C39	119.6 (2)
O3—C5—O4	124.4 (2)	N31—C38—C39	109.02 (19)
O3—C5—C4	119.5 (2)	N33—C39—C34	132.0 (2)
O4—C5—C4	116.1 (2)	N33—C39—C38	105.51 (19)
N11—C12—N13	113.3 (2)	C34—C39—C38	122.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2	0.98	1.85	2.808 (3)	168
O1W—H1B···O2W^i	0.93	1.94	2.806 (3)	154
O2W—H2C···O4	0.89	1.96	2.797 (3)	156
O2W—H2D···O2^ii	0.83	2.21	2.994 (3)	160
N3—H3···O1W^iii	0.91	2.08	2.990 (3)	173
N13—H13···O3^iv	0.86	2.23	3.084 (2)	171
N23—H23···O4^v	0.86	1.92	2.767 (3)	167
N33—H33···O2^vi	0.86	1.98	2.827 (3)	168

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