Bis[2-(1H-imidazol-2-yl)phenolato-κ²N,O]zinc(II) methanol solvate

In the title complex, [Zn(C₁₈H₁₄N₄O₂)]·CH₃OH, two anionic 2-(1H-imidazol-2-yl)phenolate bidentate ligands coordinate through the phenolate O and imidazolyl N atoms to the central Zn^II atom to give a four-coordinate tetra­hedral geometry.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.013 Å
• R factor = 0.086
• wR factor = 0.214
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Datablock: global



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         13
PLAT352_ALERT_3_C Short   N-H Bond (0.87A)   N2     -   H20    ...       0.74 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 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-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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).

Bis[2-(1H-imidazol-2-yl)phenolato-κ²N,O]zinc(II) methanol solvate

Crystal data

[Zn(C9H7N2O)2]·CH4O	F(000) = 1712
Mr = 415.74	Dx = 1.501 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2963 reflections
a = 9.6943 (19) Å	θ = 2.6–27.9°
b = 14.775 (3) Å	µ = 1.36 mm^−1
c = 25.693 (5) Å	T = 293 K
V = 3680.1 (13) Å^3	Prism, yellow
Z = 8	0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1K CCD diffractometer	3307 independent reflections
Radiation source: fine-focus sealed tube	1837 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.092
φ and ω scans	θmax = 25.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −11→11
Tmin = 0.762, Tmax = 0.769	k = −17→17
21238 measured reflections	l = −30→30

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.086	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.214	w = 1/[σ^2(Fo^2) + (0.031P)^2 + 33.0999P] where P = (Fo^2 + 2Fc^2)/3
S = 1.17	(Δ/σ)max < 0.001
3307 reflections	Δρmax = 0.61 e Å^−3
255 parameters	Δρmin = −0.59 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (4)

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	0.35438 (11)	0.53054 (8)	0.62891 (4)	0.0524 (4)
N1	0.3573 (7)	0.5988 (5)	0.5650 (3)	0.0507 (19)
N2	0.4376 (9)	0.6534 (6)	0.4925 (3)	0.054 (2)
N3	0.2767 (7)	0.5657 (5)	0.6959 (3)	0.0509 (19)
N4	0.1764 (8)	0.5462 (6)	0.7706 (3)	0.056 (2)
C1	0.2499 (10)	0.6364 (7)	0.5366 (4)	0.063 (3)
H1	0.1584	0.6387	0.5475	0.076*
C2	0.2973 (11)	0.6689 (8)	0.4914 (4)	0.069 (3)
H2	0.2465	0.6960	0.4649	0.083*
C3	0.4707 (10)	0.6112 (6)	0.5369 (3)	0.050 (2)
C4	0.6113 (8)	0.5813 (6)	0.5503 (3)	0.042 (2)
C5	0.7183 (9)	0.6001 (6)	0.5149 (3)	0.051 (2)
H5	0.6983	0.6307	0.4842	0.061*
C6	0.8536 (10)	0.5739 (8)	0.5251 (4)	0.066 (3)
H6	0.9235	0.5871	0.5016	0.079*
C7	0.8823 (10)	0.5285 (8)	0.5700 (4)	0.069 (3)
H7	0.9726	0.5107	0.5766	0.082*
C8	0.7824 (8)	0.5084 (7)	0.6055 (4)	0.056 (3)
H8	0.8054	0.4773	0.6358	0.067*
C9	0.6455 (9)	0.5343 (7)	0.5967 (3)	0.048 (2)
C10	0.3239 (11)	0.6299 (7)	0.7308 (4)	0.063 (3)
H10	0.3879	0.6749	0.7231	0.076*
C11	0.2639 (11)	0.6179 (7)	0.7772 (4)	0.063 (3)
H11	0.2787	0.6511	0.8075	0.076*
C12	0.1860 (8)	0.5154 (6)	0.7220 (3)	0.044 (2)
C13	0.1080 (8)	0.4398 (7)	0.7012 (3)	0.050 (2)
C14	−0.0080 (10)	0.4072 (7)	0.7274 (4)	0.056 (3)
H14	−0.0329	0.4346	0.7586	0.068*
C15	−0.0865 (10)	0.3374 (8)	0.7097 (4)	0.068 (3)
H15	−0.1637	0.3183	0.7281	0.082*
C16	−0.0500 (10)	0.2960 (7)	0.6644 (4)	0.063 (3)
H16	−0.1034	0.2483	0.6521	0.076*
C17	0.0637 (10)	0.3229 (7)	0.6364 (4)	0.062 (3)
H17	0.0869	0.2927	0.6059	0.074*
C18	0.1451 (9)	0.3957 (6)	0.6537 (3)	0.046 (2)
O1	0.5525 (6)	0.5156 (5)	0.6338 (2)	0.0619 (18)
O2	0.2540 (6)	0.4182 (4)	0.6259 (2)	0.0580 (17)
O3	0.5697 (8)	0.7099 (6)	0.4025 (3)	0.076 (2)
H22	0.6372	0.6828	0.3912	0.114*
C19	0.4875 (16)	0.7379 (11)	0.3613 (5)	0.123 (6)
H19A	0.4228	0.7824	0.3734	0.185*
H19B	0.4385	0.6869	0.3474	0.185*
H19C	0.5445	0.7639	0.3347	0.185*
H20	0.482 (10)	0.651 (7)	0.469 (4)	0.06 (4)*
H21	0.142 (10)	0.522 (7)	0.796 (4)	0.07 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0438 (6)	0.0731 (8)	0.0402 (6)	−0.0055 (6)	0.0050 (5)	0.0032 (6)
N1	0.039 (4)	0.065 (5)	0.048 (4)	−0.003 (4)	0.005 (4)	−0.001 (4)
N2	0.059 (5)	0.069 (6)	0.033 (5)	0.006 (5)	0.007 (4)	0.007 (4)
N3	0.046 (4)	0.059 (5)	0.047 (4)	−0.008 (4)	0.005 (4)	−0.002 (4)
N4	0.050 (5)	0.078 (6)	0.038 (4)	−0.003 (5)	0.009 (4)	−0.003 (4)
C1	0.044 (5)	0.074 (7)	0.072 (7)	0.015 (5)	−0.001 (5)	0.002 (6)
C2	0.059 (7)	0.098 (9)	0.049 (6)	0.014 (6)	−0.003 (5)	0.012 (6)
C3	0.058 (6)	0.057 (6)	0.036 (5)	−0.001 (5)	0.001 (4)	0.001 (4)
C4	0.037 (5)	0.056 (6)	0.034 (4)	−0.003 (4)	−0.004 (4)	−0.004 (4)
C5	0.056 (6)	0.058 (6)	0.039 (5)	−0.005 (5)	0.007 (4)	−0.004 (4)
C6	0.042 (5)	0.091 (8)	0.066 (7)	0.009 (6)	0.016 (5)	0.012 (6)
C7	0.049 (6)	0.098 (9)	0.059 (6)	0.001 (6)	0.001 (5)	0.008 (6)
C8	0.034 (5)	0.093 (8)	0.041 (5)	−0.003 (5)	−0.004 (4)	0.003 (5)
C9	0.041 (4)	0.069 (6)	0.033 (4)	−0.008 (5)	0.000 (4)	−0.002 (5)
C10	0.067 (7)	0.065 (7)	0.057 (6)	−0.010 (6)	0.010 (5)	−0.001 (5)
C11	0.065 (7)	0.067 (7)	0.057 (6)	−0.001 (6)	0.001 (6)	−0.017 (5)
C12	0.034 (4)	0.062 (6)	0.036 (5)	0.002 (4)	0.000 (4)	−0.004 (4)
C13	0.035 (5)	0.069 (7)	0.045 (5)	−0.001 (4)	0.005 (4)	0.014 (5)
C14	0.062 (6)	0.054 (6)	0.054 (6)	−0.005 (5)	0.006 (5)	−0.001 (5)
C15	0.051 (6)	0.073 (8)	0.081 (8)	−0.010 (6)	0.013 (6)	0.002 (6)
C16	0.056 (6)	0.059 (7)	0.075 (7)	−0.008 (5)	−0.006 (6)	0.001 (6)
C17	0.063 (6)	0.065 (7)	0.057 (6)	0.003 (6)	0.005 (5)	0.004 (5)
C18	0.046 (5)	0.048 (5)	0.045 (5)	0.004 (5)	0.003 (5)	0.003 (4)
O1	0.047 (3)	0.101 (5)	0.038 (3)	−0.009 (4)	−0.007 (3)	0.010 (4)
O2	0.052 (4)	0.070 (4)	0.052 (4)	−0.010 (3)	0.017 (3)	−0.007 (3)
O3	0.068 (5)	0.099 (6)	0.061 (5)	0.010 (5)	0.014 (4)	0.003 (4)
C19	0.144 (13)	0.149 (14)	0.078 (9)	0.056 (12)	−0.022 (9)	0.013 (9)

Geometric parameters (Å, º)

Zn1—O2	1.926 (6)	C7—H7	0.9300
Zn1—N1	1.928 (7)	C8—C9	1.400 (12)
Zn1—O1	1.937 (6)	C8—H8	0.9300
Zn1—N3	1.950 (7)	C9—O1	1.340 (10)
N1—C3	1.328 (11)	C10—C11	1.340 (13)
N1—C1	1.386 (11)	C10—H10	0.9300
N2—C3	1.339 (11)	C11—H11	0.9300
N2—C2	1.379 (12)	C12—C13	1.451 (13)
N2—H20	0.75 (9)	C13—C14	1.396 (12)
N3—C12	1.332 (11)	C13—C18	1.431 (12)
N3—C10	1.382 (12)	C14—C15	1.360 (13)
N4—C12	1.333 (11)	C14—H14	0.9300
N4—C11	1.368 (13)	C15—C16	1.360 (14)
N4—H21	0.81 (10)	C15—H15	0.9300
C1—C2	1.340 (13)	C16—C17	1.375 (13)
C1—H1	0.9300	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.406 (13)
C3—C4	1.474 (12)	C17—H17	0.9300
C4—C5	1.407 (11)	C18—O2	1.316 (10)
C4—C9	1.420 (11)	O3—C19	1.388 (13)
C5—C6	1.393 (13)	O3—H22	0.8200
C5—H5	0.9300	C19—H19A	0.9600
C6—C7	1.363 (14)	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600
C7—C8	1.363 (12)
O2—Zn1—N1	115.1 (3)	C9—C8—H8	119.8
O2—Zn1—O1	113.9 (3)	O1—C9—C8	117.9 (8)
N1—Zn1—O1	95.8 (3)	O1—C9—C4	122.7 (8)
O2—Zn1—N3	94.0 (3)	C8—C9—C4	119.3 (8)
N1—Zn1—N3	128.2 (3)	C11—C10—N3	110.0 (9)
O1—Zn1—N3	110.9 (3)	C11—C10—H10	125.0
C3—N1—C1	106.3 (8)	N3—C10—H10	125.0
C3—N1—Zn1	123.2 (6)	C10—C11—N4	105.2 (9)
C1—N1—Zn1	130.2 (6)	C10—C11—H11	127.4
C3—N2—C2	109.4 (9)	N4—C11—H11	127.4
C3—N2—H20	122 (8)	N3—C12—N4	109.1 (8)
C2—N2—H20	124 (8)	N3—C12—C13	126.1 (8)
C12—N3—C10	106.0 (7)	N4—C12—C13	124.8 (8)
C12—N3—Zn1	123.4 (6)	C14—C13—C18	117.3 (9)
C10—N3—Zn1	128.8 (6)	C14—C13—C12	120.5 (9)
C12—N4—C11	109.7 (8)	C18—C13—C12	122.2 (8)
C12—N4—H21	129 (8)	C15—C14—C13	123.4 (10)
C11—N4—H21	120 (8)	C15—C14—H14	118.3
C2—C1—N1	110.0 (9)	C13—C14—H14	118.3
C2—C1—H1	125.0	C16—C15—C14	118.8 (10)
N1—C1—H1	125.0	C16—C15—H15	120.6
C1—C2—N2	105.1 (9)	C14—C15—H15	120.6
C1—C2—H2	127.5	C15—C16—C17	121.7 (10)
N2—C2—H2	127.5	C15—C16—H16	119.1
N1—C3—N2	109.2 (8)	C17—C16—H16	119.1
N1—C3—C4	126.7 (8)	C16—C17—C18	120.4 (10)
N2—C3—C4	124.1 (8)	C16—C17—H17	119.8
C5—C4—C9	117.9 (8)	C18—C17—H17	119.8
C5—C4—C3	118.1 (8)	O2—C18—C17	118.2 (8)
C9—C4—C3	124.0 (7)	O2—C18—C13	123.4 (8)
C6—C5—C4	121.2 (9)	C17—C18—C13	118.4 (8)
C6—C5—H5	119.4	C9—O1—Zn1	126.7 (5)
C4—C5—H5	119.4	C18—O2—Zn1	127.0 (6)
C7—C6—C5	119.2 (9)	C19—O3—H22	109.5
C7—C6—H6	120.4	O3—C19—H19A	109.5
C5—C6—H6	120.4	O3—C19—H19B	109.5
C6—C7—C8	121.9 (10)	H19A—C19—H19B	109.5
C6—C7—H7	119.0	O3—C19—H19C	109.5
C8—C7—H7	119.0	H19A—C19—H19C	109.5
C7—C8—C9	120.4 (9)	H19B—C19—H19C	109.5
C7—C8—H8	119.8
O2—Zn1—N1—C3	−112.0 (7)	C3—C4—C9—C8	179.6 (9)
O1—Zn1—N1—C3	7.8 (8)	C12—N3—C10—C11	0.7 (11)
N3—Zn1—N1—C3	130.2 (7)	Zn1—N3—C10—C11	−164.2 (7)
O2—Zn1—N1—C1	61.6 (9)	N3—C10—C11—N4	−1.2 (12)
O1—Zn1—N1—C1	−178.6 (8)	C12—N4—C11—C10	1.2 (11)
N3—Zn1—N1—C1	−56.2 (10)	C10—N3—C12—N4	0.0 (10)
O2—Zn1—N3—C12	−0.1 (7)	Zn1—N3—C12—N4	166.0 (6)
N1—Zn1—N3—C12	126.5 (7)	C10—N3—C12—C13	179.3 (8)
O1—Zn1—N3—C12	−117.6 (7)	Zn1—N3—C12—C13	−14.7 (12)
O2—Zn1—N3—C10	162.5 (8)	C11—N4—C12—N3	−0.8 (11)
N1—Zn1—N3—C10	−70.9 (9)	C11—N4—C12—C13	180.0 (9)
O1—Zn1—N3—C10	45.0 (9)	N3—C12—C13—C14	−163.4 (9)
C3—N1—C1—C2	1.7 (12)	N4—C12—C13—C14	15.7 (14)
Zn1—N1—C1—C2	−172.7 (8)	N3—C12—C13—C18	16.4 (14)
N1—C1—C2—N2	−1.8 (13)	N4—C12—C13—C18	−164.5 (9)
C3—N2—C2—C1	1.3 (13)	C18—C13—C14—C15	−0.7 (14)
C1—N1—C3—N2	−0.8 (11)	C12—C13—C14—C15	179.1 (9)
Zn1—N1—C3—N2	174.1 (6)	C13—C14—C15—C16	0.8 (16)
C1—N1—C3—C4	−178.8 (9)	C14—C15—C16—C17	0.0 (16)
Zn1—N1—C3—C4	−3.9 (13)	C15—C16—C17—C18	−1.0 (16)
C2—N2—C3—N1	−0.3 (12)	C16—C17—C18—O2	179.1 (9)
C2—N2—C3—C4	177.8 (9)	C16—C17—C18—C13	1.1 (14)
N1—C3—C4—C5	179.3 (9)	C14—C13—C18—O2	−178.2 (8)
N2—C3—C4—C5	1.6 (14)	C12—C13—C18—O2	2.0 (14)
N1—C3—C4—C9	−0.5 (15)	C14—C13—C18—C17	−0.3 (13)
N2—C3—C4—C9	−178.1 (9)	C12—C13—C18—C17	180.0 (8)
C9—C4—C5—C6	−0.3 (14)	C8—C9—O1—Zn1	−172.3 (7)
C3—C4—C5—C6	180.0 (9)	C4—C9—O1—Zn1	9.8 (13)
C4—C5—C6—C7	0.5 (16)	O2—Zn1—O1—C9	109.7 (8)
C5—C6—C7—C8	−0.4 (18)	N1—Zn1—O1—C9	−11.1 (8)
C6—C7—C8—C9	0.0 (17)	N3—Zn1—O1—C9	−145.8 (7)
C7—C8—C9—O1	−177.7 (9)	C17—C18—O2—Zn1	162.6 (6)
C7—C8—C9—C4	0.3 (15)	C13—C18—O2—Zn1	−19.5 (12)
C5—C4—C9—O1	177.7 (8)	N1—Zn1—O2—C18	−119.0 (7)
C3—C4—C9—O1	−2.5 (14)	O1—Zn1—O2—C18	131.8 (7)
C5—C4—C9—C8	−0.2 (13)	N3—Zn1—O2—C18	16.9 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H20···O3	0.75 (9)	2.09 (10)	2.771 (11)	152 (11)
N4—H21···O1^i	0.81 (10)	2.01 (10)	2.770 (10)	157 (10)
O3—H22···O2^ii	0.82	1.88	2.653 (10)	157

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) −x+1, −y+1, −z+1.