Poly[(μ₂-4,4′-bipyridine)tris­[μ₄-(E)-4,4′-(ethene-1,2-di­yl)dibenzoato]zinc(II)]

One of the two independent Zn atoms of the polymeric title compound, [Zn₃(C₁₆H₁₀O₄)₃(C₁₀H₈N₂)]_n, lies on a special position of site symmetry 3 and the other on a special position of site symmetry . The carboxylate ends of the 4,4′-(ethene-1,2-di­yl)dibenzoate dianion, which lies on a special position of site symmetry , each bridge these two independent Zn atoms. The bipyridine-coordinated Zn atom on the threefold axis has a tetra­hedral geometry, whereas the other Zn atom is coordin­ated by the O atoms of six different dianions in an octa­hedral geometry.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.062
• wR factor = 0.194
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.421     0.791
            Tmin(prime) and Tmax expected:      0.657     0.781
            RR(prime) =      0.633
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.62
PLAT301_ALERT_3_B Main Residue  Disorder .........................      27.00 Perc.

Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       3.25 Sigma
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       3.00 Ratio
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Zn1
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C58 H38 N2 O12 Zn3
            Atom count from the _atom_site data:  C57.92 H37.92 N2 O12 Zn3
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: check formula stoichiometry or atom site occupancies.
           From the CIF: _cell_formula_units_Z    3
           From the CIF: _chemical_formula_sum  C58 H38 N2 O12 Zn3
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        174.00    173.76    0.24
           H        114.00    113.76    0.24
           N          6.00      6.00    0.00
           O         36.00     36.00    0.00
           Zn         9.00      9.00    0.00
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K

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

   7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2006).

Poly[(µ₂-4,4'-bipyridine)tris[µ₄-(E)-4,4'-(ethene-1,2- diyl)dibenzoato]zinc(II)]

Crystal data

[Zn3(C16H10O4)(C10H8N2)]	Dx = 1.401 Mg m^−3
Mr = 1151.01	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 7459 reflections
Hall symbol: -R 3	θ = 3.1–27.4°
a = 16.134 (1) Å	µ = 1.37 mm^−1
c = 18.162 (1) Å	T = 293 K
V = 4094.1 (3) Å^3	Prism, colorless
Z = 3	0.30 × 0.24 × 0.18 mm
F(000) = 1758

Data collection

Rigaku R-AXIS RAPID IP diffractometer	2086 independent reflections
Radiation source: fine-focus sealed tube	1249 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
ω scans	θmax = 27.4°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −20→20
Tmin = 0.421, Tmax = 0.791	k = −20→20
13477 measured reflections	l = −21→23

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)] = 0.062	H-atom parameters constrained
wR(F^2) = 0.194	w = 1/[σ^2(Fo^2) + (0.0927P)^2 + 8.7373P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.001
2086 reflections	Δρmax = 0.62 e Å^−3
139 parameters	Δρmin = −0.88 e Å^−3
138 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: 0.0013 (4)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	1.0000	0.0000	0.80699 (5)	0.0509 (4)
Zn2	1.0000	0.0000	1.0000	0.0456 (4)
O1	1.0030 (3)	0.1204 (3)	0.82481 (19)	0.0658 (10)
O2	0.9378 (3)	0.0597 (2)	0.93358 (18)	0.0579 (9)
C1	0.9736 (4)	0.1270 (3)	0.8884 (3)	0.0576 (13)
C2	0.9822 (3)	0.2205 (3)	0.9083 (2)	0.0607 (14)
C5	1.0008 (4)	0.3949 (3)	0.9483 (3)	0.086 (2)
C3	1.0506 (6)	0.3040 (6)	0.8738 (5)	0.056 (2)	0.50
H3	1.0900	0.3014	0.8376	0.067*	0.50
C4	1.0595 (7)	0.3910 (9)	0.8940 (4)	0.070 (3)	0.50
H4	1.1050	0.4470	0.8711	0.084*	0.50
C6	0.9321 (7)	0.3107 (6)	0.9821 (6)	0.081 (3)	0.50
H6	0.8923	0.3133	1.0180	0.097*	0.50
C7	0.9225 (7)	0.2232 (9)	0.9626 (4)	0.068 (3)	0.50
H7	0.8769	0.1671	0.9854	0.082*	0.50
C3'	1.0228 (6)	0.2971 (6)	0.8597 (6)	0.056 (2)	0.50
H3'	1.0437	0.2899	0.8136	0.067*	0.50
C4'	1.0324 (7)	0.3845 (9)	0.8796 (4)	0.070 (3)	0.50
H4'	1.0598	0.4359	0.8471	0.084*	0.50
C6'	0.9606 (7)	0.3186 (7)	0.9973 (6)	0.081 (3)	0.50
H6'	0.9401	0.3260	1.0435	0.097*	0.50
C7'	0.9510 (7)	0.2313 (9)	0.9772 (4)	0.068 (3)	0.50
H7'	0.9238	0.1799	1.0097	0.082*	0.50
C8	1.0152 (6)	0.4905 (4)	0.9684 (3)	0.097 (2)
H8	1.0474	0.5404	0.9351	0.117*
N1	1.0000	0.0000	0.6929 (4)	0.069 (2)
C9	0.9567 (12)	−0.0831 (7)	0.6559 (7)	0.079 (4)	0.33
H9	0.9267	−0.1404	0.6820	0.095*	0.33
C10	0.9558 (13)	−0.0854 (6)	0.5797 (7)	0.083 (4)	0.33
H10	0.9259	−0.1436	0.5548	0.100*	0.33
C11	1.0000	0.0000	0.54121 (14)	0.080 (3)
C10'	1.0455 (13)	0.0858 (6)	0.5798 (7)	0.083 (4)	0.33
H10'	1.0765	0.1438	0.5547	0.100*	0.33
C9'	1.0444 (13)	0.0841 (7)	0.6563 (7)	0.079 (4)	0.33
H9'	1.0743	0.1413	0.6824	0.095*	0.33

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0574 (5)	0.0574 (5)	0.0380 (5)	0.0287 (2)	0.000	0.000
Zn2	0.0500 (6)	0.0500 (6)	0.0368 (7)	0.0250 (3)	0.000	0.000
O1	0.086 (3)	0.072 (3)	0.049 (2)	0.047 (2)	−0.0004 (18)	0.0021 (17)
O2	0.062 (2)	0.057 (2)	0.058 (2)	0.0321 (19)	−0.0034 (17)	0.0080 (16)
C1	0.065 (3)	0.068 (3)	0.048 (3)	0.039 (3)	−0.011 (2)	−0.001 (2)
C2	0.080 (4)	0.053 (3)	0.055 (3)	0.038 (3)	0.006 (3)	0.006 (2)
C5	0.125 (5)	0.062 (4)	0.079 (4)	0.053 (4)	0.020 (4)	0.007 (3)
C3	0.064 (5)	0.061 (3)	0.049 (4)	0.037 (4)	−0.011 (4)	−0.003 (3)
C4	0.084 (6)	0.063 (4)	0.059 (4)	0.034 (4)	0.000 (4)	0.007 (3)
C6	0.106 (6)	0.071 (4)	0.070 (5)	0.048 (4)	0.013 (4)	0.004 (3)
C7	0.089 (6)	0.064 (4)	0.060 (4)	0.044 (4)	0.004 (4)	0.006 (3)
C3'	0.064 (5)	0.061 (3)	0.049 (4)	0.037 (4)	−0.011 (4)	−0.003 (3)
C4'	0.084 (6)	0.063 (4)	0.059 (4)	0.034 (4)	0.000 (4)	0.007 (3)
C6'	0.106 (6)	0.071 (4)	0.070 (5)	0.048 (4)	0.013 (4)	0.004 (3)
C7'	0.089 (6)	0.064 (4)	0.060 (4)	0.044 (4)	0.004 (4)	0.006 (3)
C8	0.141 (6)	0.067 (4)	0.089 (4)	0.056 (4)	0.028 (4)	0.010 (3)
N1	0.085 (4)	0.085 (4)	0.037 (4)	0.0427 (19)	0.000	0.000
C9	0.096 (7)	0.064 (6)	0.057 (5)	0.025 (5)	−0.003 (4)	0.000 (5)
C10	0.107 (7)	0.068 (6)	0.057 (5)	0.029 (5)	0.003 (5)	0.007 (5)
C11	0.094 (4)	0.094 (4)	0.052 (5)	0.047 (2)	0.000	0.000
C10'	0.107 (7)	0.068 (6)	0.057 (5)	0.029 (5)	0.003 (5)	0.007 (5)
C9'	0.096 (7)	0.064 (6)	0.057 (5)	0.025 (5)	−0.003 (4)	0.000 (5)

Geometric parameters (Å, º)

Zn1—O1	1.946 (4)	C3'—C4'	1.388 (5)
Zn1—O1^i	1.946 (4)	C6'—C7'	1.387 (5)
Zn1—O1^ii	1.946 (4)	C8—C8^vi	1.342 (5)
Zn1—N1	2.071 (7)	N1—C9	1.342 (5)
Zn2—O2	2.087 (3)	N1—C9'	1.352 (5)
Zn2—O2^i	2.087 (3)	C9—C10	1.384 (5)
Zn2—O2^ii	2.087 (3)	C10—C11	1.384 (5)
Zn2—O2^iii	2.087 (3)	C11—C10'	1.390 (5)
Zn2—O2^iv	2.087 (3)	C11—C11^vii	1.497 (5)
Zn2—O2^v	2.087 (3)	C10'—C9'	1.388 (5)
O1—C1	1.273 (6)	C3—H3	0.9300
O2—C1	1.249 (6)	C4—H4	0.9300
C1—C2	1.489 (4)	C6—H6	0.9300
C2—C3'	1.388 (5)	C7—H7	0.9300
C2—C7'	1.391 (5)	C3'—H3'	0.9300
C2—C3	1.392 (5)	C4'—H4'	0.9300
C2—C7	1.393 (5)	C6'—H6'	0.9300
C5—C4'	1.389 (5)	C7'—H7'	0.9300
C5—C6'	1.390 (5)	C8—H8	0.9300
C5—C4	1.390 (5)	C9—H9	0.9300
C5—C6	1.394 (5)	C10—H10	0.9300
C5—C8	1.486 (4)	C10'—H10'	0.9300
C3—C4	1.387 (5)	C9'—H9'	0.9300
C6—C7	1.388 (5)
O1^i—Zn1—O1	117.3 (1)	C3—C4—H4	119.8
O1^i—Zn1—O1^ii	117.3 (1)	C5—C4—H4	119.8
O1—Zn1—O1^ii	117.3 (1)	C7—C6—C5	120.6 (11)
O1^i—Zn1—N1	99.6 (1)	C7—C6—H6	119.7
O1—Zn1—N1	99.6 (1)	C5—C6—H6	119.7
O1^ii—Zn1—N1	99.6 (1)	C6—C7—C2	119.0 (11)
O2^iv—Zn2—O2^i	180	C6—C7—H7	120.5
O2^iv—Zn2—O2^v	89.9 (1)	C2—C7—H7	120.5
O2^i—Zn2—O2^v	90.1 (1)	C4'—C3'—C2	120.1 (11)
O2^iv—Zn2—O2^ii	90.1 (1)	C4'—C3'—H3'	119.9
O2^i—Zn2—O2^ii	89.9 (1)	C2—C3'—H3'	119.9
O2^v—Zn2—O2^ii	180	C3'—C4'—C5	119.7 (11)
O2^iv—Zn2—O2	90.1 (1)	C3'—C4'—H4'	120.1
O2^i—Zn2—O2	89.9 (1)	C5—C4'—H4'	120.1
O2^v—Zn2—O2	90.1 (1)	C7'—C6'—C5	119.7 (11)
O2^ii—Zn2—O2	89.9 (1)	C7'—C6'—H6'	120.1
O2^iv—Zn2—O2^iii	89.9 (1)	C5—C6'—H6'	120.1
O2^i—Zn2—O2^iii	90.1 (1)	C6'—C7'—C2	120.0 (11)
O2^v—Zn2—O2^iii	89.9 (1)	C6'—C7'—H7'	120.0
O2^ii—Zn2—O2^iii	90.1 (1)	C2—C7'—H7'	120.0
O2—Zn2—O2^iii	180	C8^vi—C8—C5	124.1 (6)
C1—O1—Zn1	114.2 (3)	C8^vi—C8—H8	117.9
C1—O2—Zn2	131.4 (3)	C5—C8—H8	117.9
O2—C1—O1	123.5 (4)	C9—N1—C9'	120.4 (10)
O2—C1—C2	119.4 (4)	C9—N1—Zn1	120.1 (7)
O1—C1—C2	117.1 (4)	C9^ii—N1—Zn1	120.1 (7)
C3'—C2—C7'	120.0 (11)	C9^i—N1—Zn1	120.1 (7)
C7'—C2—C3	116.4 (5)	C9'^i—N1—Zn1	119.5 (7)
C3'—C2—C7	116.7 (5)	C9'—N1—Zn1	119.5 (7)
C3—C2—C7	121.0 (11)	C9'^ii—N1—Zn1	119.5 (7)
C3'—C2—C1	120.7 (6)	N1—C9—C10	121.4 (13)
C7'—C2—C1	119.2 (6)	N1—C9—H9	119.3
C3—C2—C1	119.8 (6)	C10—C9—H9	119.3
C7—C2—C1	119.2 (6)	C11—C10—C9	119.0 (12)
C4'—C5—C6'	120.4 (11)	C11—C10—H10	120.5
C6'—C5—C4	116.2 (5)	C9—C10—H10	120.5
C4—C5—C6	119.7 (11)	C10—C11—C10'	119.3 (8)
C4'—C5—C8	118.0 (6)	C10—C11—C11^vii	120.4 (6)
C6'—C5—C8	121.6 (7)	C10'—C11—C11^vii	120.3 (6)
C4—C5—C8	117.7 (6)	C9'—C10'—C11	119.3 (12)
C6—C5—C8	122.6 (7)	C9'—C10'—H10'	120.3
C4—C3—C2	119.4 (11)	C11—C10'—H10'	120.3
C4—C3—H3	120.3	N1—C9'—C10'	120.5 (12)
C2—C3—H3	120.3	N1—C9'—H9'	119.7
C3—C4—C5	120.4 (11)	C10'—C9'—H9'	119.7
O1^i—Zn1—O1—C1	52.9 (4)	C8—C5—C4'—C3'	178.1 (6)
O1^ii—Zn1—O1—C1	−95.0 (3)	C4'—C5—C6'—C7'	−0.6 (8)
N1—Zn1—O1—C1	158.9 (3)	C4—C5—C6'—C7'	−22.5 (9)
O2^iv—Zn2—O2—C1	71.7 (3)	C6—C5—C6'—C7'	83 (3)
O2^i—Zn2—O2—C1	−108.3 (3)	C8—C5—C6'—C7'	−178.1 (7)
O2^v—Zn2—O2—C1	161.6 (4)	C5—C6'—C7'—C2	0.3 (8)
O2^ii—Zn2—O2—C1	−18.4 (4)	C3'—C2—C7'—C6'	0.0 (6)
Zn2—O2—C1—O1	74.7 (7)	C3—C2—C7'—C6'	22.3 (8)
Zn2—O2—C1—C2	−106.0 (5)	C7—C2—C7'—C6'	−86 (3)
Zn1—O1—C1—O2	−6.1 (7)	C1—C2—C7'—C6'	178.4 (6)
Zn1—O1—C1—C2	174.6 (3)	C4'—C5—C8—C8^vi	177.2 (10)
O2—C1—C2—C3'	179.1 (5)	C6'—C5—C8—C8^vi	−5.4 (15)
O1—C1—C2—C3'	−1.6 (7)	C4—C5—C8—C8^vi	−160.6 (10)
O2—C1—C2—C7'	0.7 (8)	C6—C5—C8—C8^vi	18.9 (15)
O1—C1—C2—C7'	180.0 (6)	O1^i—Zn1—N1—C9	−29.9 (10)
O2—C1—C2—C3	156.1 (5)	O1—Zn1—N1—C9	−149.9 (10)
O1—C1—C2—C3	−24.6 (7)	O1^ii—Zn1—N1—C9	90.1 (10)
O2—C1—C2—C7	−22.5 (7)	O1^i—Zn1—N1—C9^ii	90.1 (10)
O1—C1—C2—C7	156.8 (6)	O1—Zn1—N1—C9^ii	−29.9 (10)
C3'—C2—C3—C4	83 (3)	O1^ii—Zn1—N1—C9^ii	−149.9 (10)
C7'—C2—C3—C4	−22.5 (6)	O1^i—Zn1—N1—C9^i	−149.9 (10)
C7—C2—C3—C4	0.1 (3)	O1—Zn1—N1—C9^i	90.1 (10)
C1—C2—C3—C4	−178.5 (4)	O1^ii—Zn1—N1—C9^i	−29.9 (10)
C2—C3—C4—C5	0.2 (3)	O1^i—Zn1—N1—C9'^i	30.6 (10)
C4'—C5—C4—C3	−85 (3)	O1—Zn1—N1—C9'^i	−89.4 (10)
C6'—C5—C4—C3	22.3 (7)	O1^ii—Zn1—N1—C9'^i	150.6 (10)
C6—C5—C4—C3	−0.6 (6)	O1^i—Zn1—N1—C9'	150.6 (10)
C8—C5—C4—C3	178.8 (6)	O1—Zn1—N1—C9'	30.6 (10)
C4'—C5—C6—C7	22.6 (9)	O1^ii—Zn1—N1—C9'	−89.4 (10)
C6'—C5—C6—C7	−85 (3)	O1^i—Zn1—N1—C9'^ii	−89.4 (10)
C4—C5—C6—C7	0.8 (8)	O1—Zn1—N1—C9'^ii	150.6 (10)
C8—C5—C6—C7	−178.7 (7)	O1^ii—Zn1—N1—C9'^ii	30.6 (10)
C5—C6—C7—C2	−0.5 (8)	C9'—N1—C9—C10	−0.2 (3)
C3'—C2—C7—C6	−22.2 (8)	Zn1—N1—C9—C10	−179.78 (15)
C7'—C2—C7—C6	83 (3)	N1—C9—C10—C11	−0.4 (3)
C3—C2—C7—C6	0.0 (6)	C9—C10—C11—C10^i	49.0 (5)
C1—C2—C7—C6	178.6 (6)	C9—C10—C11—C10^ii	−48.6 (5)
C7'—C2—C3'—C4'	−0.1 (3)	C9—C10—C11—C10'	1.1 (6)
C3—C2—C3'—C4'	−85 (3)	C9—C10—C11—C10'^i	−73.3 (9)
C7—C2—C3'—C4'	22.6 (6)	C9—C10—C11—C10'^ii	74.3 (9)
C1—C2—C3'—C4'	−178.5 (5)	C9—C10—C11—C11^vii	−179.79 (14)
C2—C3'—C4'—C5	−0.2 (3)	C9—N1—C9'—C10'	0.2 (7)
C6'—C5—C4'—C3'	0.6 (6)	Zn1—N1—C9'—C10'	179.8 (5)
C4—C5—C4'—C3'	84 (3)	C11—C10'—C9'—N1	0.4 (9)
C6—C5—C4'—C3'	−22.2 (7)

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