Bis(2-chloro­benzoato-κO)bis­(phenazone-κO)zinc(II) 0.612-hydrate

The title compound, [Zn(C₇H₄ClO₂)₂(C₁₁H₁₂N₂O)₂].0.612H₂O, is a mononuclear zinc(II) compound. The Zn atom lies on a crystallographic twofold rotation axis. It is coordinated in a distorted tetra­hedral arrangement by two O atoms of two phenazone mol­ecules and one carboxyl­ate O atom from each of two 2-chloro­benzoate anions. Intra­molecular O—H...O hydrogen bonds may be effective in the stabilization of the structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.008 Å
• Disorder in solvent or counterion
• R factor = 0.064
• wR factor = 0.138
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      31.00 Perc.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C13    -C18           1.37 Ang.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT415_ALERT_2_C Short Inter D-H..H-X       H3     ..  H1W     ..       2.13 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 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
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Bis(2-chlorobenzoato-κO)bis(phenazone-κO)zinc(II) 0.612-hydrate

Crystal data

[Zn(C7H4ClO2)2(C11H12N2O)2]·0.612H2O	F(000) = 1573
Mr = 763.97	Dx = 1.392 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 27.986 (3) Å	θ = 4.5–8.6°
b = 9.6403 (12) Å	µ = 0.87 mm^−1
c = 14.513 (4) Å	T = 294 K
β = 111.746 (11)°	Prism, colorless
V = 3636.8 (12) Å^3	0.80 × 0.50 × 0.50 mm
Z = 4

Data collection

Siemens P4 diffractometer	1981 reflections with I > 2σ(I)
Radiation source: large-focus sealed tube	Rint = 0.067
Graphite monochromator	θmax = 27.0°, θmin = 2.8°
2θ/ω scans	h = −1→35
Absorption correction: ψ scan (XEMP; Siemens, 1990)	k = −1→12
Tmin = 0.554, Tmax = 0.646	l = −18→17
4553 measured reflections	3 standard reflections every 97 reflections
3853 independent reflections	intensity decay: 8.1%

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0475P)^2] where P = (Fo^2 + 2Fc^2)/3
3853 reflections	(Δ/σ)max < 0.001
240 parameters	Δρmax = 0.44 e Å^−3
3 restraints	Δρmin = −0.44 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)
Zn1	0.0000	0.26041 (8)	0.2500	0.0457 (2)
Cl1	0.20334 (5)	0.16661 (18)	0.39740 (12)	0.0963 (5)
O1	0.04830 (11)	0.1677 (3)	0.2015 (2)	0.0628 (8)
O2	0.09125 (13)	0.1079 (4)	0.3560 (3)	0.0899 (12)
O3	0.03865 (10)	0.3989 (3)	0.35061 (19)	0.0555 (8)
O1W	0.0244 (5)	−0.0420 (12)	0.4249 (8)	0.078 (5)	0.306 (10)
N1	0.08382 (13)	0.4819 (4)	0.5057 (2)	0.0518 (9)
N2	0.08702 (14)	0.4593 (4)	0.6019 (2)	0.0580 (10)
C1	0.08643 (16)	0.1159 (4)	0.2691 (4)	0.0527 (11)
C2	0.12747 (16)	0.0562 (4)	0.2353 (3)	0.0513 (11)
C3	0.1124 (2)	−0.0186 (5)	0.1478 (4)	0.0699 (14)
H3	0.0774	−0.0251	0.1096	0.084*
C4	0.1470 (3)	−0.0842 (6)	0.1147 (5)	0.0910 (18)
H4	0.1357	−0.1342	0.0557	0.109*
C5	0.1990 (3)	−0.0732 (7)	0.1723 (6)	0.0950 (19)
H5	0.2229	−0.1197	0.1532	0.114*
C6	0.2153 (2)	0.0054 (6)	0.2571 (5)	0.0860 (17)
H6	0.2504	0.0164	0.2929	0.103*
C7	0.17954 (17)	0.0692 (5)	0.2899 (4)	0.0620 (12)
C8	0.04795 (14)	0.3951 (4)	0.4429 (3)	0.0441 (10)
C9	0.02841 (16)	0.3187 (4)	0.5028 (3)	0.0492 (10)
H9	0.0031	0.2507	0.4811	0.059*
C10	0.05251 (18)	0.3603 (5)	0.5976 (3)	0.0580 (12)
C11	0.1183 (2)	0.5433 (7)	0.6828 (4)	0.105 (2)
H11A	0.1002	0.5612	0.7265	0.157*
H11B	0.1257	0.6296	0.6579	0.157*
H11C	0.1498	0.4957	0.7185	0.157*
C12	0.0450 (2)	0.3137 (6)	0.6898 (4)	0.0851 (17)
H12A	0.0748	0.2632	0.7311	0.128*
H12B	0.0153	0.2548	0.6722	0.128*
H12C	0.0401	0.3932	0.7252	0.128*
C13	0.11923 (16)	0.5687 (5)	0.4810 (3)	0.0507 (11)
C14	0.1119 (2)	0.7102 (5)	0.4715 (4)	0.0710 (14)
H14	0.0847	0.7512	0.4834	0.085*
C15	0.1453 (2)	0.7900 (6)	0.4445 (4)	0.0900 (19)
H15	0.1406	0.8856	0.4378	0.108*
C16	0.1847 (2)	0.7299 (8)	0.4276 (4)	0.0949 (19)
H16	0.2072	0.7843	0.4095	0.114*
C17	0.1919 (2)	0.5900 (8)	0.4367 (4)	0.0903 (18)
H17	0.2192	0.5497	0.4247	0.108*
C18	0.15846 (19)	0.5068 (5)	0.4641 (4)	0.0711 (14)
H18	0.1631	0.4112	0.4705	0.085*
H1W	0.047 (5)	0.015 (14)	0.452 (9)	0.107*	0.306 (10)
H2W	0.014 (6)	−0.035 (18)	0.3643 (11)	0.107*	0.306 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0421 (4)	0.0539 (5)	0.0408 (4)	0.000	0.0149 (3)	0.000
Cl1	0.0661 (8)	0.1165 (12)	0.1012 (11)	−0.0071 (8)	0.0252 (8)	−0.0296 (10)
O1	0.0471 (17)	0.073 (2)	0.065 (2)	0.0143 (16)	0.0171 (15)	−0.0087 (17)
O2	0.095 (3)	0.120 (3)	0.074 (2)	0.046 (2)	0.054 (2)	0.035 (2)
O3	0.0643 (18)	0.0613 (19)	0.0404 (16)	−0.0135 (16)	0.0186 (14)	−0.0015 (14)
O1W	0.086 (10)	0.074 (9)	0.074 (8)	−0.004 (6)	0.031 (7)	0.017 (7)
N1	0.051 (2)	0.064 (2)	0.0390 (19)	−0.0067 (19)	0.0141 (16)	−0.0060 (18)
N2	0.067 (2)	0.069 (3)	0.039 (2)	0.010 (2)	0.0201 (19)	−0.0082 (19)
C1	0.045 (3)	0.044 (3)	0.070 (3)	0.006 (2)	0.023 (2)	0.004 (2)
C2	0.050 (3)	0.048 (3)	0.063 (3)	0.007 (2)	0.030 (2)	0.011 (2)
C3	0.067 (3)	0.075 (4)	0.076 (3)	0.001 (3)	0.035 (3)	−0.003 (3)
C4	0.109 (5)	0.084 (4)	0.109 (5)	−0.005 (4)	0.075 (4)	−0.026 (4)
C5	0.096 (5)	0.089 (5)	0.135 (6)	0.015 (4)	0.085 (4)	−0.001 (4)
C6	0.061 (3)	0.093 (4)	0.122 (5)	0.007 (3)	0.055 (3)	0.001 (4)
C7	0.056 (3)	0.062 (3)	0.077 (3)	0.007 (2)	0.035 (3)	0.006 (3)
C8	0.045 (2)	0.047 (2)	0.040 (2)	0.004 (2)	0.0148 (19)	0.001 (2)
C9	0.052 (2)	0.052 (3)	0.050 (3)	0.002 (2)	0.026 (2)	−0.001 (2)
C10	0.068 (3)	0.063 (3)	0.049 (3)	0.015 (3)	0.028 (2)	0.001 (2)
C11	0.108 (4)	0.155 (6)	0.050 (3)	−0.029 (4)	0.027 (3)	−0.039 (4)
C12	0.118 (4)	0.100 (4)	0.057 (3)	0.011 (3)	0.054 (3)	0.002 (3)
C13	0.049 (3)	0.050 (3)	0.046 (2)	0.001 (2)	0.010 (2)	−0.006 (2)
C14	0.065 (3)	0.056 (3)	0.086 (4)	0.010 (3)	0.021 (3)	−0.002 (3)
C15	0.084 (4)	0.059 (4)	0.106 (5)	−0.013 (3)	0.012 (4)	0.009 (3)
C16	0.077 (4)	0.106 (6)	0.097 (4)	−0.031 (4)	0.026 (3)	0.015 (4)
C17	0.063 (4)	0.107 (5)	0.110 (5)	−0.006 (4)	0.044 (3)	−0.012 (4)
C18	0.071 (3)	0.055 (3)	0.099 (4)	0.006 (3)	0.045 (3)	−0.004 (3)

Geometric parameters (Å, º)

Zn1—O1^i	1.956 (3)	C6—C7	1.401 (6)
Zn1—O1	1.956 (3)	C6—H6	0.9300
Zn1—O3	1.979 (3)	C8—C9	1.397 (5)
Zn1—O3^i	1.979 (3)	C9—C10	1.349 (6)
Cl1—C7	1.729 (5)	C9—H9	0.9300
O1—C1	1.255 (5)	C10—C12	1.499 (6)
O2—C1	1.221 (5)	C11—H11A	0.9600
O3—C8	1.266 (4)	C11—H11B	0.9600
O1W—H1W	0.82 (1)	C11—H11C	0.9600
O1W—H2W	0.82 (1)	C12—H12A	0.9600
N1—C8	1.365 (5)	C12—H12B	0.9600
N1—N2	1.383 (5)	C12—H12C	0.9600
N1—C13	1.440 (5)	C13—C18	1.349 (6)
N2—C10	1.343 (5)	C13—C14	1.379 (6)
N2—C11	1.428 (6)	C14—C15	1.374 (7)
C1—C2	1.519 (6)	C14—H14	0.9300
C2—C7	1.383 (6)	C15—C16	1.347 (8)
C2—C3	1.383 (6)	C15—H15	0.9300
C3—C4	1.383 (7)	C16—C17	1.362 (8)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.388 (8)	C17—C18	1.397 (7)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.371 (8)	C18—H18	0.9300
C5—H5	0.9300
O1^i—Zn1—O1	125.65 (19)	N1—C8—C9	105.5 (4)
O1^i—Zn1—O3	107.71 (12)	C10—C9—C8	108.3 (4)
O1—Zn1—O3	108.19 (12)	C10—C9—H9	125.8
O1^i—Zn1—O3^i	108.19 (12)	C8—C9—H9	125.8
O1—Zn1—O3^i	107.71 (12)	N2—C10—C9	109.8 (4)
O3—Zn1—O3^i	95.11 (17)	N2—C10—C12	120.5 (4)
C1—O1—Zn1	113.6 (3)	C9—C10—C12	129.7 (5)
C8—O3—Zn1	127.0 (3)	N2—C11—H11A	109.5
H1W—O1W—H2W	111 (3)	N2—C11—H11B	109.5
C8—N1—N2	109.5 (3)	H11A—C11—H11B	109.5
C8—N1—C13	126.4 (3)	N2—C11—H11C	109.5
N2—N1—C13	123.4 (3)	H11A—C11—H11C	109.5
C10—N2—N1	106.7 (3)	H11B—C11—H11C	109.5
C10—N2—C11	130.7 (4)	C10—C12—H12A	109.5
N1—N2—C11	122.1 (4)	C10—C12—H12B	109.5
O2—C1—O1	124.7 (4)	H12A—C12—H12B	109.5
O2—C1—C2	120.2 (4)	C10—C12—H12C	109.5
O1—C1—C2	115.1 (4)	H12A—C12—H12C	109.5
C7—C2—C3	118.2 (4)	H12B—C12—H12C	109.5
C7—C2—C1	122.9 (4)	C18—C13—C14	121.3 (5)
C3—C2—C1	118.9 (4)	C18—C13—N1	118.0 (4)
C4—C3—C2	122.8 (5)	C14—C13—N1	120.6 (4)
C4—C3—H3	118.6	C15—C14—C13	119.4 (5)
C2—C3—H3	118.6	C15—C14—H14	120.3
C3—C4—C5	118.0 (5)	C13—C14—H14	120.3
C3—C4—H4	121.0	C16—C15—C14	119.9 (5)
C5—C4—H4	121.0	C16—C15—H15	120.0
C6—C5—C4	120.7 (5)	C14—C15—H15	120.0
C6—C5—H5	119.7	C15—C16—C17	120.6 (6)
C4—C5—H5	119.7	C15—C16—H16	119.7
C5—C6—C7	120.3 (5)	C17—C16—H16	119.7
C5—C6—H6	119.9	C16—C17—C18	120.5 (6)
C7—C6—H6	119.9	C16—C17—H17	119.8
C2—C7—C6	120.0 (5)	C18—C17—H17	119.8
C2—C7—Cl1	122.6 (3)	C13—C18—C17	118.2 (5)
C6—C7—Cl1	117.4 (4)	C13—C18—H18	120.9
O3—C8—N1	120.1 (4)	C17—C18—H18	120.9
O3—C8—C9	134.4 (4)
O1^i—Zn1—O1—C1	−74.7 (3)	Zn1—O3—C8—N1	166.3 (3)
O3—Zn1—O1—C1	54.3 (3)	Zn1—O3—C8—C9	−15.1 (7)
O3^i—Zn1—O1—C1	156.1 (3)	N2—N1—C8—O3	179.7 (3)
O1^i—Zn1—O3—C8	26.8 (3)	C13—N1—C8—O3	−9.6 (6)
O1—Zn1—O3—C8	−111.7 (3)	N2—N1—C8—C9	0.7 (4)
O3^i—Zn1—O3—C8	137.8 (4)	C13—N1—C8—C9	171.4 (4)
C8—N1—N2—C10	−1.0 (4)	O3—C8—C9—C10	−178.9 (4)
C13—N1—N2—C10	−172.0 (4)	N1—C8—C9—C10	−0.2 (4)
C8—N1—N2—C11	−174.6 (4)	N1—N2—C10—C9	0.9 (5)
C13—N1—N2—C11	14.4 (6)	C11—N2—C10—C9	173.7 (5)
Zn1—O1—C1—O2	8.2 (6)	N1—N2—C10—C12	−178.2 (4)
Zn1—O1—C1—C2	−173.9 (3)	C11—N2—C10—C12	−5.4 (7)
O2—C1—C2—C7	−40.9 (7)	C8—C9—C10—N2	−0.5 (5)
O1—C1—C2—C7	141.2 (4)	C8—C9—C10—C12	178.6 (5)
O2—C1—C2—C3	136.8 (5)	C8—N1—C13—C18	−71.5 (6)
O1—C1—C2—C3	−41.1 (6)	N2—N1—C13—C18	97.9 (5)
C7—C2—C3—C4	2.1 (7)	C8—N1—C13—C14	106.3 (5)
C1—C2—C3—C4	−175.7 (5)	N2—N1—C13—C14	−84.3 (5)
C2—C3—C4—C5	−0.2 (8)	C18—C13—C14—C15	0.0 (8)
C3—C4—C5—C6	−2.8 (9)	N1—C13—C14—C15	−177.7 (4)
C4—C5—C6—C7	3.8 (9)	C13—C14—C15—C16	−0.1 (8)
C3—C2—C7—C6	−1.1 (7)	C14—C15—C16—C17	0.2 (9)
C1—C2—C7—C6	176.6 (4)	C15—C16—C17—C18	−0.1 (9)
C3—C2—C7—Cl1	176.9 (4)	C14—C13—C18—C17	0.1 (7)
C1—C2—C7—Cl1	−5.4 (6)	N1—C13—C18—C17	177.9 (4)
C5—C6—C7—C2	−1.8 (8)	C16—C17—C18—C13	0.0 (8)
C5—C6—C7—Cl1	−179.9 (5)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2	0.82 (1)	2.36 (1)	2.824 (1)	117 (1)
O1W—H2W···O1^i	0.82 (1)	2.56 (2)	2.970 (1)	113 (2)

Symmetry code: (i) −x, y, −z+1/2.