Aqua­bis­[2-(2-pyridyl)-1H-benzimidazolato]­zinc(II)

In the title compound, [Zn(C₁₂H₈N₃)₂(H₂O)], the Zn atom is chelated by two heterocycles, and the coordinating N atoms comprise the basal plane of the square-pyramidal environment. The apical position is occupied by an aqua ligand. The complexes are linked by O—H...O hydrogen bonds into a ribbon structure along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.048
• wR factor = 0.131
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.76
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O1W  -H1W1    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O1W  -H1#     1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Aquabis[2-(2-pyridyl)-1H-benzimidazolato]zinc(II)

Crystal data

[Zn(C12H8N3)2(H2O)]	F(000) = 968
Mr = 471.81	Dx = 1.470 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3351 reflections
a = 12.5448 (8) Å	θ = 3.0–25.4°
b = 13.0525 (8) Å	µ = 1.18 mm^−1
c = 13.3493 (9) Å	T = 295 K
β = 102.731 (1)°	Block, colorless
V = 2132.1 (2) Å^3	0.36 × 0.18 × 0.11 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	4812 independent reflections
Radiation source: fine-focus sealed tube	3727 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −16→16
Tmin = 0.676, Tmax = 0.881	k = −10→16
12542 measured reflections	l = −16→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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0743P)^2 + 0.521P] where P = (Fo^2 + 2Fc^2)/3
4812 reflections	(Δ/σ)max = 0.001
297 parameters	Δρmax = 0.58 e Å^−3
2 restraints	Δρmin = −0.21 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Zn1	0.77122 (2)	0.54100 (2)	0.55659 (2)	0.04440 (14)
O1w	0.73887 (16)	0.4226 (2)	0.45939 (19)	0.0634 (6)
H1w1	0.781 (2)	0.398 (2)	0.424 (2)	0.062 (10)*
H1w2	0.6750 (13)	0.399 (2)	0.441 (2)	0.068 (10)*
N1	0.92465 (17)	0.55839 (17)	0.63461 (18)	0.0435 (5)
N2	1.09546 (17)	0.61715 (19)	0.6356 (2)	0.0521 (6)
N3	0.84516 (18)	0.62390 (18)	0.44168 (19)	0.0495 (6)
N4	0.64527 (16)	0.63475 (16)	0.55799 (17)	0.0410 (5)
N5	0.47012 (17)	0.64655 (17)	0.57787 (17)	0.0426 (5)
N6	0.67943 (19)	0.45294 (17)	0.65498 (19)	0.0455 (5)
C1	0.9918 (2)	0.5314 (2)	0.7278 (2)	0.0481 (7)
C2	0.9705 (3)	0.4805 (3)	0.8120 (3)	0.0639 (9)
H2	0.9007	0.4573	0.8132	0.077*
C3	1.0581 (4)	0.4655 (3)	0.8948 (3)	0.0815 (12)
H3	1.0472	0.4296	0.9519	0.098*
C4	1.1617 (3)	0.5033 (4)	0.8941 (3)	0.0867 (12)
H4	1.2182	0.4935	0.9514	0.104*
C5	1.1822 (3)	0.5543 (3)	0.8112 (3)	0.0750 (11)
H5	1.2518	0.5789	0.8113	0.090*
C6	1.0967 (2)	0.5686 (2)	0.7270 (3)	0.0543 (7)
C7	0.9922 (2)	0.60767 (19)	0.5855 (2)	0.0424 (6)
C8	0.9496 (2)	0.6464 (2)	0.4811 (2)	0.0456 (6)
C9	1.0120 (3)	0.7003 (2)	0.4242 (3)	0.0644 (9)
H9	1.0848	0.7158	0.4521	0.077*
C10	0.9632 (3)	0.7301 (3)	0.3256 (3)	0.0733 (10)
H10	1.0032	0.7658	0.2861	0.088*
C11	0.8567 (3)	0.7072 (3)	0.2865 (3)	0.0718 (10)
H11	0.8225	0.7274	0.2204	0.086*
C12	0.8009 (3)	0.6538 (3)	0.3467 (3)	0.0607 (8)
H12	0.7280	0.6375	0.3195	0.073*
C13	0.6018 (2)	0.7241 (2)	0.5122 (2)	0.0408 (6)
C14	0.6474 (2)	0.8013 (2)	0.4628 (2)	0.0533 (7)
H14	0.7197	0.7981	0.4565	0.064*
C15	0.5811 (3)	0.8824 (2)	0.4237 (3)	0.0602 (8)
H15	0.6088	0.9343	0.3891	0.072*
C16	0.4734 (3)	0.8886 (2)	0.4347 (3)	0.0601 (8)
H16	0.4313	0.9448	0.4075	0.072*
C17	0.4282 (2)	0.8149 (2)	0.4841 (2)	0.0529 (7)
H17	0.3563	0.8201	0.4912	0.063*
C18	0.4931 (2)	0.7312 (2)	0.52396 (19)	0.0416 (6)
C19	0.56288 (19)	0.5934 (2)	0.59504 (18)	0.0375 (5)
C20	0.5814 (2)	0.4952 (2)	0.65080 (19)	0.0393 (5)
C21	0.5037 (2)	0.4494 (2)	0.6954 (2)	0.0504 (7)
H21	0.4359	0.4801	0.6910	0.061*
C22	0.5281 (3)	0.3581 (3)	0.7462 (2)	0.0599 (8)
H22	0.4773	0.3262	0.7770	0.072*
C23	0.6281 (3)	0.3148 (2)	0.7509 (2)	0.0596 (8)
H23	0.6468	0.2533	0.7855	0.072*
C24	0.7009 (3)	0.3635 (2)	0.7036 (2)	0.0575 (8)
H24	0.7682	0.3327	0.7056	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02878 (18)	0.0487 (2)	0.0573 (2)	−0.00007 (12)	0.01280 (14)	0.00078 (14)
O1w	0.0341 (11)	0.0767 (15)	0.0863 (16)	−0.0156 (10)	0.0281 (11)	−0.0329 (12)
N1	0.0319 (11)	0.0458 (13)	0.0540 (13)	0.0021 (9)	0.0121 (10)	−0.0006 (10)
N2	0.0316 (12)	0.0559 (15)	0.0706 (17)	−0.0001 (10)	0.0150 (11)	−0.0044 (12)
N3	0.0399 (12)	0.0536 (15)	0.0572 (14)	0.0018 (10)	0.0155 (11)	0.0057 (11)
N4	0.0321 (11)	0.0406 (12)	0.0515 (13)	−0.0010 (9)	0.0120 (9)	0.0015 (9)
N5	0.0331 (11)	0.0502 (13)	0.0459 (12)	−0.0006 (9)	0.0119 (9)	−0.0080 (10)
N6	0.0393 (12)	0.0449 (13)	0.0531 (14)	−0.0005 (9)	0.0117 (10)	0.0037 (10)
C1	0.0426 (15)	0.0495 (17)	0.0512 (16)	0.0086 (12)	0.0082 (13)	−0.0055 (12)
C2	0.061 (2)	0.071 (2)	0.060 (2)	0.0024 (16)	0.0132 (16)	0.0000 (16)
C3	0.094 (3)	0.090 (3)	0.056 (2)	0.014 (2)	0.006 (2)	0.0064 (18)
C4	0.065 (2)	0.109 (3)	0.073 (3)	0.013 (2)	−0.015 (2)	−0.004 (2)
C5	0.0451 (19)	0.090 (3)	0.083 (3)	0.0081 (17)	−0.0020 (18)	−0.006 (2)
C6	0.0358 (14)	0.0576 (18)	0.068 (2)	0.0066 (12)	0.0086 (13)	−0.0121 (15)
C7	0.0315 (13)	0.0376 (14)	0.0614 (17)	0.0013 (10)	0.0175 (12)	−0.0056 (12)
C8	0.0397 (14)	0.0345 (14)	0.0676 (18)	0.0037 (11)	0.0230 (13)	0.0020 (12)
C9	0.0495 (18)	0.0541 (19)	0.095 (3)	−0.0024 (14)	0.0272 (17)	0.0137 (17)
C10	0.077 (2)	0.057 (2)	0.095 (3)	0.0049 (17)	0.040 (2)	0.0304 (19)
C11	0.081 (3)	0.065 (2)	0.073 (2)	0.0146 (18)	0.0258 (19)	0.0233 (18)
C12	0.0540 (18)	0.064 (2)	0.064 (2)	0.0040 (15)	0.0120 (15)	0.0121 (16)
C13	0.0340 (12)	0.0411 (14)	0.0459 (14)	−0.0011 (10)	0.0054 (10)	−0.0043 (11)
C14	0.0425 (15)	0.0461 (17)	0.0704 (19)	−0.0042 (12)	0.0106 (13)	0.0059 (14)
C15	0.0625 (19)	0.0402 (16)	0.073 (2)	−0.0057 (14)	0.0034 (16)	0.0069 (14)
C16	0.0585 (19)	0.0424 (17)	0.070 (2)	0.0067 (14)	−0.0063 (16)	−0.0028 (14)
C17	0.0430 (15)	0.0536 (18)	0.0581 (17)	0.0105 (13)	0.0027 (13)	−0.0068 (14)
C18	0.0376 (13)	0.0443 (15)	0.0417 (14)	−0.0008 (11)	0.0063 (11)	−0.0102 (11)
C19	0.0297 (12)	0.0447 (15)	0.0384 (13)	−0.0034 (10)	0.0082 (10)	−0.0074 (11)
C20	0.0394 (14)	0.0429 (14)	0.0360 (13)	−0.0071 (11)	0.0090 (10)	−0.0057 (11)
C21	0.0435 (16)	0.065 (2)	0.0441 (15)	−0.0072 (13)	0.0133 (12)	0.0017 (13)
C22	0.0596 (19)	0.073 (2)	0.0477 (16)	−0.0175 (16)	0.0128 (14)	0.0112 (15)
C23	0.073 (2)	0.0514 (19)	0.0517 (17)	−0.0072 (15)	0.0067 (15)	0.0115 (14)
C24	0.0568 (18)	0.0515 (18)	0.0632 (19)	0.0039 (14)	0.0108 (15)	0.0056 (14)

Geometric parameters (Å, º)

Zn1—O1w	2.001 (2)	C7—C8	1.467 (4)
Zn1—N1	1.989 (2)	C8—C9	1.395 (4)
Zn1—N3	2.239 (2)	C9—C10	1.379 (5)
Zn1—N4	2.002 (2)	C9—H9	0.9300
Zn1—N6	2.245 (2)	C10—C11	1.356 (5)
O1w—H1w1	0.85 (1)	C10—H10	0.9300
O1w—H1w2	0.84 (1)	C11—C12	1.368 (4)
N1—C7	1.345 (3)	C11—H11	0.9300
N1—C1	1.385 (4)	C12—H12	0.9300
N2—C7	1.326 (3)	C13—C14	1.394 (4)
N2—C6	1.372 (4)	C13—C18	1.410 (3)
N3—C12	1.326 (4)	C14—C15	1.377 (4)
N3—C8	1.333 (3)	C14—H14	0.9300
N4—C19	1.353 (3)	C15—C16	1.392 (4)
N4—C13	1.373 (3)	C15—H15	0.9300
N5—C19	1.331 (3)	C16—C17	1.360 (4)
N5—C18	1.383 (3)	C16—H16	0.9300
N6—C24	1.334 (4)	C17—C18	1.396 (4)
N6—C20	1.338 (3)	C17—H17	0.9300
C1—C2	1.382 (5)	C19—C20	1.474 (4)
C1—C6	1.404 (4)	C20—C21	1.385 (4)
C2—C3	1.390 (5)	C21—C22	1.372 (4)
C2—H2	0.9300	C21—H21	0.9300
C3—C4	1.393 (6)	C22—C23	1.365 (4)
C3—H3	0.9300	C22—H22	0.9300
C4—C5	1.362 (6)	C23—C24	1.375 (4)
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.386 (5)	C24—H24	0.9300
C5—H5	0.9300
O1w—Zn1—N1	117.5 (1)	C9—C8—C7	124.1 (3)
O1w—Zn1—N3	89.1 (1)	C10—C9—C8	118.5 (3)
O1w—Zn1—N4	115.5 (1)	C10—C9—H9	120.7
O1w—Zn1—N6	85.8 (1)	C8—C9—H9	120.7
N1—Zn1—N3	78.7 (1)	C11—C10—C9	119.9 (3)
N1—Zn1—N4	126.9 (1)	C11—C10—H10	120.1
N1—Zn1—N6	108.3 (1)	C9—C10—H10	120.1
N3—Zn1—N4	99.1 (1)	C10—C11—C12	118.3 (3)
N3—Zn1—N6	172.7 (1)	C10—C11—H11	120.8
N4—Zn1—N6	78.5 (1)	C12—C11—H11	120.8
Zn1—O1w—H1w1	126 (2)	N3—C12—C11	123.4 (3)
Zn1—O1w—H1w2	121 (2)	N3—C12—H12	118.3
H1w1—O1w—H1w2	112 (3)	C11—C12—H12	118.3
C7—N1—C1	103.6 (2)	N4—C13—C14	131.3 (2)
C7—N1—Zn1	116.13 (19)	N4—C13—C18	107.8 (2)
C1—N1—Zn1	140.2 (2)	C14—C13—C18	120.9 (2)
C7—N2—C6	102.9 (2)	C15—C14—C13	117.3 (3)
C12—N3—C8	118.8 (3)	C15—C14—H14	121.4
C12—N3—Zn1	130.4 (2)	C13—C14—H14	121.4
C8—N3—Zn1	110.84 (18)	C14—C15—C16	121.6 (3)
C19—N4—C13	104.0 (2)	C14—C15—H15	119.2
C19—N4—Zn1	115.32 (17)	C16—C15—H15	119.2
C13—N4—Zn1	138.76 (17)	C17—C16—C15	121.9 (3)
C19—N5—C18	103.4 (2)	C17—C16—H16	119.1
C24—N6—C20	117.8 (2)	C15—C16—H16	119.1
C24—N6—Zn1	131.1 (2)	C16—C17—C18	117.9 (3)
C20—N6—Zn1	110.47 (17)	C16—C17—H17	121.0
C2—C1—N1	131.6 (3)	C18—C17—H17	121.0
C2—C1—C6	121.5 (3)	N5—C18—C17	130.8 (2)
N1—C1—C6	106.9 (3)	N5—C18—C13	108.9 (2)
C1—C2—C3	117.0 (3)	C17—C18—C13	120.4 (3)
C1—C2—H2	121.5	N5—C19—N4	116.0 (2)
C3—C2—H2	121.5	N5—C19—C20	125.1 (2)
C2—C3—C4	121.4 (4)	N4—C19—C20	118.9 (2)
C2—C3—H3	119.3	N6—C20—C21	122.1 (3)
C4—C3—H3	119.3	N6—C20—C19	114.9 (2)
C5—C4—C3	121.5 (4)	C21—C20—C19	123.0 (2)
C5—C4—H4	119.3	C22—C21—C20	119.1 (3)
C3—C4—H4	119.3	C22—C21—H21	120.5
C4—C5—C6	118.3 (4)	C20—C21—H21	120.5
C4—C5—H5	120.9	C23—C22—C21	119.0 (3)
C6—C5—H5	120.9	C23—C22—H22	120.5
N2—C6—C5	129.7 (3)	C21—C22—H22	120.5
N2—C6—C1	109.9 (3)	C22—C23—C24	119.0 (3)
C5—C6—C1	120.4 (3)	C22—C23—H23	120.5
N2—C7—N1	116.7 (3)	C24—C23—H23	120.5
N2—C7—C8	123.9 (2)	N6—C24—C23	123.0 (3)
N1—C7—C8	119.4 (2)	N6—C24—H24	118.5
N3—C8—C9	121.1 (3)	C23—C24—H24	118.5
N3—C8—C7	114.8 (2)
O1w—Zn1—N1—C7	83.4 (2)	Zn1—N3—C8—C9	−178.5 (2)
N4—Zn1—N1—C7	−92.5 (2)	C12—N3—C8—C7	−178.3 (3)
N3—Zn1—N1—C7	0.45 (18)	Zn1—N3—C8—C7	3.1 (3)
N6—Zn1—N1—C7	178.37 (18)	N2—C7—C8—N3	176.2 (2)
O1w—Zn1—N1—C1	−92.8 (3)	N1—C7—C8—N3	−3.1 (4)
N4—Zn1—N1—C1	91.3 (3)	N2—C7—C8—C9	−2.2 (4)
N3—Zn1—N1—C1	−175.8 (3)	N1—C7—C8—C9	178.6 (3)
N6—Zn1—N1—C1	2.2 (3)	N3—C8—C9—C10	0.0 (5)
N1—Zn1—N3—C12	179.6 (3)	C7—C8—C9—C10	178.2 (3)
O1w—Zn1—N3—C12	61.3 (3)	C8—C9—C10—C11	0.4 (5)
N4—Zn1—N3—C12	−54.4 (3)	C9—C10—C11—C12	−0.7 (6)
N1—Zn1—N3—C8	−2.06 (18)	C8—N3—C12—C11	−0.3 (5)
O1w—Zn1—N3—C8	−120.38 (19)	Zn1—N3—C12—C11	177.8 (3)
N4—Zn1—N3—C8	123.93 (19)	C10—C11—C12—N3	0.7 (6)
N1—Zn1—N4—C19	−116.85 (18)	C19—N4—C13—C14	178.2 (3)
O1w—Zn1—N4—C19	67.1 (2)	Zn1—N4—C13—C14	−19.5 (5)
N3—Zn1—N4—C19	160.48 (18)	C19—N4—C13—C18	−0.4 (3)
N6—Zn1—N4—C19	−12.54 (18)	Zn1—N4—C13—C18	161.9 (2)
N1—Zn1—N4—C13	82.2 (3)	N4—C13—C14—C15	179.7 (3)
O1w—Zn1—N4—C13	−93.8 (3)	C18—C13—C14—C15	−1.9 (4)
N3—Zn1—N4—C13	−0.4 (3)	C13—C14—C15—C16	1.3 (5)
N6—Zn1—N4—C13	−173.5 (3)	C14—C15—C16—C17	−0.3 (5)
N1—Zn1—N6—C24	−53.0 (3)	C15—C16—C17—C18	−0.3 (5)
O1w—Zn1—N6—C24	64.6 (3)	C19—N5—C18—C17	179.9 (3)
N4—Zn1—N6—C24	−178.3 (3)	C19—N5—C18—C13	−0.4 (3)
N1—Zn1—N6—C20	135.97 (18)	C16—C17—C18—N5	179.3 (3)
O1w—Zn1—N6—C20	−106.39 (19)	C16—C17—C18—C13	−0.3 (4)
N4—Zn1—N6—C20	10.70 (18)	N4—C13—C18—N5	0.5 (3)
C7—N1—C1—C2	179.1 (3)	C14—C13—C18—N5	−178.2 (2)
Zn1—N1—C1—C2	−4.4 (5)	N4—C13—C18—C17	−179.8 (2)
C7—N1—C1—C6	0.5 (3)	C14—C13—C18—C17	1.5 (4)
Zn1—N1—C1—C6	177.0 (2)	C18—N5—C19—N4	0.2 (3)
N1—C1—C2—C3	180.0 (3)	C18—N5—C19—C20	179.9 (2)
C6—C1—C2—C3	−1.5 (5)	C13—N4—C19—N5	0.1 (3)
C1—C2—C3—C4	2.1 (6)	Zn1—N4—C19—N5	−167.05 (17)
C2—C3—C4—C5	−1.6 (7)	C13—N4—C19—C20	−179.6 (2)
C3—C4—C5—C6	0.4 (7)	Zn1—N4—C19—C20	13.3 (3)
C7—N2—C6—C5	−179.5 (3)	C24—N6—C20—C21	0.4 (4)
C7—N2—C6—C1	−0.1 (3)	Zn1—N6—C20—C21	172.7 (2)
C4—C5—C6—N2	179.5 (4)	C24—N6—C20—C19	−179.4 (2)
C4—C5—C6—C1	0.2 (5)	Zn1—N6—C20—C19	−7.1 (3)
C2—C1—C6—N2	−179.1 (3)	N5—C19—C20—N6	177.1 (2)
N1—C1—C6—N2	−0.2 (3)	N4—C19—C20—N6	−3.2 (3)
C2—C1—C6—C5	0.4 (5)	N5—C19—C20—C21	−2.7 (4)
N1—C1—C6—C5	179.2 (3)	N4—C19—C20—C21	177.0 (2)
C6—N2—C7—N1	0.5 (3)	N6—C20—C21—C22	0.5 (4)
C6—N2—C7—C8	−178.8 (3)	C19—C20—C21—C22	−179.7 (3)
C1—N1—C7—N2	−0.6 (3)	C20—C21—C22—C23	−0.3 (5)
Zn1—N1—C7—N2	−178.13 (18)	C21—C22—C23—C24	−0.6 (5)
C1—N1—C7—C8	178.7 (2)	C20—N6—C24—C23	−1.4 (4)
Zn1—N1—C7—C8	1.2 (3)	Zn1—N6—C24—C23	−171.9 (2)
C12—N3—C8—C9	0.0 (4)	C22—C23—C24—N6	1.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···N2^i	0.85 (1)	1.90 (2)	2.713 (3)	160 (3)
O1w—H1w2···N5^ii	0.84 (1)	1.88 (1)	2.713 (3)	170 (3)

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