catena-Poly[[[2-(2-fur­yl)-1H-imidazo[4,5-f][1,10]phenanthroline]zinc(II)]-μ-benzene-1,2-dicarboxyl­ato]

Li, C.-B.; Li, Y.-W.; Fang, W.; Liu, B.; Li, D.-Q.

doi:10.1107/S1600536806049592

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catena-Poly[[[2-(2-furyl)-1H-imidazo[4,5-f][1,10]phenanthroline]zinc(II)]-μ-benzene-1,2-dicarboxylato]

C.-B. Li, Y.-W. Li, W. Fang, B. Liu and D.-Q. Li

In the title compound, [Zn(C₈H₄O₄)(C₁₇H₁₀N₄O)]_n, the Zn^II atom is five-coordinated by two N atoms from the phenanthroline-derived ligand and three O atoms from one bidentate and one monodentate benzene-1,2-dicarboxylate (1,2-BDC) dianions in a distorted trigonal–bipyramidal geometry. The Zn^II atoms are bridged by the 1,2-BDC ligands to form a single-chain structure. Neighboring chains interact through π–π interactions, leading to a two-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049592/hb2213sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049592/hb2213Isup2.hkl Contains datablock I

CCDC reference: 629896

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.050
wR factor = 0.159
Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.90 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

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
   8 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

Computing details top

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: SHELXTL (Bruker, 1998??? or Sheldrick, 1990); software used to prepare material for publication: SHELXTL.

catena-Poly[[(2-(2-furyl)-1H-imidazo[4,5-f][1,10]phenanthroline)zinc(II)]- µ-benzene-1,2-dicarboxylato] top

Crystal data top

[Zn(C₈H₄O₄)(C₁₇H₁₀N₄O)]	F(000) = 2096
M_r = 515.77	D_x = 1.633 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2069 reflections
a = 31.852 (13) Å	θ = 1.3–26.1°
b = 9.772 (4) Å	µ = 1.22 mm⁻¹
c = 13.657 (6) Å	T = 293 K
β = 99.285 (7)°	Block, yellow
V = 4195 (3) Å³	0.46 × 0.14 × 0.12 mm
Z = 8

Data collection top

Bruker APEX CCD diffractometer	4172 independent reflections
Radiation source: fine-focus sealed tube	2562 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 0 pixels mm^-1	θ_max = 26.1°, θ_min = 1.3°
ω scans	h = −39→35
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −6→12
T_min = 0.813, T_max = 0.864	l = −16→16
11154 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0803P)²] where P = (F_o² + 2F_c²)/3
4172 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.126525 (16)	0.05840 (5)	0.96106 (4)	0.0485 (2)
C11	0.06596 (14)	0.2799 (4)	0.9314 (3)	0.0389 (10)
C1	0.04012 (15)	−0.0776 (4)	0.9018 (3)	0.0507 (12)
H1A	0.0548	−0.1602	0.9098	0.061*
C18	0.15842 (14)	−0.1214 (4)	1.0763 (3)	0.0431 (10)
C6	0.00324 (14)	0.4152 (4)	0.8802 (3)	0.0398 (10)
C19	0.18798 (13)	−0.2119 (4)	1.1431 (3)	0.0424 (10)
C7	0.04760 (14)	0.4098 (4)	0.9178 (3)	0.0420 (10)
C2	−0.00377 (16)	−0.0813 (5)	0.8717 (3)	0.0530 (12)
H2A	−0.0180	−0.1644	0.8617	0.064*
C14	−0.09717 (16)	0.5609 (4)	0.7897 (3)	0.0505 (12)
C4	−0.00313 (14)	0.1631 (4)	0.8745 (3)	0.0417 (10)
C5	−0.02086 (14)	0.2978 (4)	0.8615 (3)	0.0424 (10)
C12	0.04089 (14)	0.1573 (4)	0.9077 (3)	0.0390 (10)
C20	0.19105 (13)	−0.2069 (4)	1.2467 (3)	0.0438 (11)
C13	−0.05959 (15)	0.4805 (5)	0.8244 (3)	0.0462 (11)
C10	0.13216 (16)	0.3721 (5)	0.9884 (3)	0.0540 (13)
H10A	0.1610	0.3597	1.0115	0.065*
C21	0.22315 (15)	−0.2812 (5)	1.3048 (4)	0.0581 (13)
H21A	0.2263	−0.2760	1.3736	0.070*
C3	−0.02557 (15)	0.0398 (4)	0.8571 (3)	0.0456 (11)
H3A	−0.0548	0.0402	0.8359	0.055*
C24	0.21518 (15)	−0.2939 (5)	1.1008 (4)	0.0552 (12)
H24A	0.2128	−0.2983	1.0321	0.066*
C9	0.11623 (16)	0.5046 (5)	0.9775 (4)	0.0575 (13)
H9A	0.1339	0.5797	0.9943	0.069*
C8	0.07411 (16)	0.5218 (4)	0.9414 (3)	0.0510 (12)
H8A	0.0630	0.6097	0.9324	0.061*
C22	0.25021 (16)	−0.3622 (6)	1.2609 (5)	0.0731 (17)
H22A	0.2714	−0.4119	1.3003	0.088*
C23	0.24612 (16)	−0.3702 (6)	1.1599 (5)	0.0706 (16)
H23A	0.2641	−0.4267	1.1308	0.085*
C15	−0.13633 (14)	0.5160 (5)	0.7633 (4)	0.0515 (12)
H15A	−0.1453	0.4254	0.7620	0.062*
C16	−0.1618 (2)	0.6317 (10)	0.7374 (5)	0.107 (3)
H16A	−0.1911	0.6316	0.7168	0.128*
C17	−0.1372 (3)	0.7398 (8)	0.7472 (6)	0.112 (3)
H17A	−0.1465	0.8291	0.7335	0.135*
C25	0.15789 (14)	−0.1371 (4)	1.2958 (3)	0.0438 (11)
O3	0.15796 (10)	0.0046 (3)	1.0950 (2)	0.0533 (8)
O2	0.13730 (11)	−0.1683 (3)	0.9988 (3)	0.0674 (10)
O1	−0.09435 (16)	0.7010 (4)	0.7820 (4)	0.1039 (15)
O5	0.11984 (10)	−0.1442 (3)	1.2567 (2)	0.0523 (8)
O4	0.17038 (10)	−0.0806 (3)	1.3784 (2)	0.0576 (9)
N2	0.10770 (12)	0.2623 (4)	0.9672 (3)	0.0453 (9)
N1	0.06206 (11)	0.0366 (3)	0.9195 (3)	0.0429 (9)
N4	−0.02130 (12)	0.5299 (3)	0.8578 (3)	0.0458 (9)
N3	−0.06106 (11)	0.3415 (4)	0.8251 (2)	0.0448 (9)
H3C	−0.0830	0.2910	0.8063	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0457 (4)	0.0464 (4)	0.0524 (4)	0.0064 (2)	0.0045 (3)	0.0062 (2)
C11	0.045 (3)	0.038 (2)	0.035 (2)	0.0011 (19)	0.0091 (19)	0.0008 (18)
C1	0.054 (3)	0.042 (3)	0.056 (3)	0.010 (2)	0.008 (2)	0.007 (2)
C18	0.040 (3)	0.037 (3)	0.052 (3)	0.000 (2)	0.009 (2)	0.002 (2)
C6	0.048 (3)	0.035 (2)	0.038 (2)	0.0041 (19)	0.010 (2)	−0.0016 (18)
C19	0.035 (2)	0.033 (2)	0.059 (3)	0.0007 (18)	0.006 (2)	0.002 (2)
C7	0.049 (3)	0.039 (2)	0.039 (2)	0.003 (2)	0.010 (2)	−0.0030 (19)
C2	0.057 (3)	0.043 (3)	0.058 (3)	−0.007 (2)	0.006 (2)	0.006 (2)
C14	0.058 (3)	0.039 (3)	0.054 (3)	0.008 (2)	0.011 (2)	0.000 (2)
C4	0.048 (3)	0.042 (2)	0.035 (2)	0.002 (2)	0.008 (2)	−0.0005 (19)
C5	0.046 (3)	0.044 (3)	0.037 (2)	0.005 (2)	0.009 (2)	0.0008 (19)
C12	0.045 (3)	0.037 (2)	0.036 (2)	0.0011 (19)	0.009 (2)	0.0030 (18)
C20	0.035 (3)	0.040 (2)	0.054 (3)	−0.0018 (19)	0.000 (2)	0.004 (2)
C13	0.049 (3)	0.047 (3)	0.045 (3)	0.012 (2)	0.017 (2)	0.001 (2)
C10	0.049 (3)	0.058 (3)	0.053 (3)	−0.009 (2)	0.004 (2)	−0.004 (2)
C21	0.046 (3)	0.056 (3)	0.069 (3)	0.005 (2)	−0.002 (3)	0.015 (3)
C3	0.042 (3)	0.044 (3)	0.050 (3)	−0.003 (2)	0.003 (2)	0.001 (2)
C24	0.044 (3)	0.053 (3)	0.070 (3)	0.004 (2)	0.012 (2)	−0.003 (2)
C9	0.057 (3)	0.046 (3)	0.069 (3)	−0.005 (2)	0.010 (3)	−0.008 (2)
C8	0.060 (3)	0.038 (3)	0.055 (3)	0.000 (2)	0.009 (2)	−0.003 (2)
C22	0.044 (3)	0.061 (3)	0.108 (5)	0.019 (3)	−0.004 (3)	0.018 (3)
C23	0.041 (3)	0.067 (4)	0.106 (5)	0.017 (3)	0.017 (3)	−0.003 (3)
C15	0.035 (3)	0.049 (3)	0.067 (3)	−0.001 (2)	0.001 (2)	0.007 (2)
C16	0.062 (5)	0.161 (8)	0.096 (5)	0.043 (5)	0.008 (4)	0.013 (6)
C17	0.120 (7)	0.094 (6)	0.130 (7)	0.069 (5)	0.040 (6)	0.040 (5)
C25	0.046 (3)	0.034 (2)	0.051 (3)	−0.001 (2)	0.008 (2)	0.003 (2)
O3	0.063 (2)	0.0373 (17)	0.0546 (19)	0.0018 (15)	−0.0063 (16)	0.0008 (15)
O2	0.074 (2)	0.047 (2)	0.072 (2)	0.0069 (17)	−0.017 (2)	−0.0115 (17)
O1	0.121 (4)	0.064 (3)	0.131 (4)	0.009 (3)	0.032 (3)	0.000 (3)
O5	0.0392 (19)	0.060 (2)	0.057 (2)	0.0074 (15)	0.0047 (16)	−0.0020 (15)
O4	0.052 (2)	0.067 (2)	0.055 (2)	−0.0202 (16)	0.0107 (16)	−0.0162 (17)
N2	0.041 (2)	0.047 (2)	0.046 (2)	−0.0021 (18)	0.0036 (17)	−0.0006 (17)
N1	0.047 (2)	0.035 (2)	0.047 (2)	0.0008 (16)	0.0089 (17)	0.0060 (16)
N4	0.048 (2)	0.039 (2)	0.050 (2)	0.0065 (17)	0.0104 (18)	−0.0017 (16)
N3	0.040 (2)	0.047 (2)	0.047 (2)	0.0040 (16)	0.0041 (18)	0.0002 (17)

Geometric parameters (Å, º) top

Zn1—O4ⁱ	1.945 (3)	C12—N1	1.355 (5)
Zn1—O3	2.009 (3)	C20—C21	1.393 (6)
Zn1—N1	2.051 (4)	C20—C25	1.502 (6)
Zn1—N2	2.086 (4)	C13—N4	1.322 (6)
Zn1—O2	2.287 (3)	C13—N3	1.359 (5)
Zn1—C18	2.466 (4)	C10—N2	1.331 (6)
C11—N2	1.352 (5)	C10—C9	1.390 (7)
C11—C7	1.397 (6)	C10—H10A	0.9300
C11—C12	1.448 (6)	C21—C22	1.377 (7)
C1—N1	1.319 (5)	C21—H21A	0.9300
C1—C2	1.393 (6)	C3—H3A	0.9300
C1—H1A	0.9300	C24—C23	1.385 (7)
C18—O2	1.246 (5)	C24—H24A	0.9300
C18—O3	1.258 (5)	C9—C8	1.363 (7)
C18—C19	1.491 (6)	C9—H9A	0.9300
C6—N4	1.373 (5)	C8—H8A	0.9300
C6—C5	1.381 (6)	C22—C23	1.368 (8)
C6—C7	1.424 (6)	C22—H22A	0.9300
C19—C24	1.374 (6)	C23—H23A	0.9300
C19—C20	1.403 (6)	C15—C16	1.404 (8)
C7—C8	1.388 (6)	C15—H15A	0.9300
C2—C3	1.370 (6)	C16—C17	1.308 (10)
C2—H2A	0.9300	C16—H16A	0.9300
C14—C15	1.317 (6)	C17—O1	1.424 (8)
C14—O1	1.377 (5)	C17—H17A	0.9300
C14—C13	1.446 (6)	C25—O5	1.245 (5)
C4—C3	1.401 (6)	C25—O4	1.262 (5)
C4—C12	1.403 (6)	O4—Zn1ⁱⁱ	1.945 (3)
C4—C5	1.432 (6)	N3—H3C	0.8600
C5—N3	1.365 (5)

O4ⁱ—Zn1—O3	105.00 (14)	N3—C13—C14	121.2 (4)
O4ⁱ—Zn1—N1	129.19 (14)	N2—C10—C9	122.5 (5)
O3—Zn1—N1	123.66 (14)	N2—C10—H10A	118.8
O4ⁱ—Zn1—N2	98.92 (14)	C9—C10—H10A	118.8
O3—Zn1—N2	108.53 (13)	C22—C21—C20	120.3 (5)
N1—Zn1—N2	80.13 (14)	C22—C21—H21A	119.8
O4ⁱ—Zn1—O2	98.21 (13)	C20—C21—H21A	119.8
O3—Zn1—O2	60.44 (12)	C2—C3—C4	119.0 (4)
N1—Zn1—O2	93.96 (13)	C2—C3—H3A	120.5
N2—Zn1—O2	161.69 (14)	C4—C3—H3A	120.5
N2—C11—C7	122.0 (4)	C19—C24—C23	120.4 (5)
N2—C11—C12	116.8 (4)	C19—C24—H24A	119.8
C7—C11—C12	121.2 (4)	C23—C24—H24A	119.8
N1—C1—C2	123.6 (4)	C8—C9—C10	118.3 (5)
N1—C1—H1A	118.2	C8—C9—H9A	120.8
C2—C1—H1A	118.2	C10—C9—H9A	120.8
O2—C18—O3	120.7 (4)	C9—C8—C7	120.9 (4)
O2—C18—C19	120.2 (4)	C9—C8—H8A	119.5
O3—C18—C19	118.8 (4)	C7—C8—H8A	119.5
O2—C18—Zn1	67.0 (2)	C23—C22—C21	120.5 (5)
O3—C18—Zn1	54.2 (2)	C23—C22—H22A	119.7
C19—C18—Zn1	165.3 (3)	C21—C22—H22A	119.7
N4—C6—C5	110.9 (4)	C22—C23—C24	120.0 (5)
N4—C6—C7	127.3 (4)	C22—C23—H23A	120.0
C5—C6—C7	121.7 (4)	C24—C23—H23A	120.0
C24—C19—C20	119.9 (4)	C14—C15—C16	106.5 (6)
C24—C19—C18	117.8 (4)	C14—C15—H15A	126.7
C20—C19—C18	122.1 (4)	C16—C15—H15A	126.7
C8—C7—C11	117.3 (4)	C17—C16—C15	108.2 (6)
C8—C7—C6	125.9 (4)	C17—C16—H16A	125.9
C11—C7—C6	116.8 (4)	C15—C16—H16A	125.9
C3—C2—C1	118.8 (4)	C16—C17—O1	110.2 (6)
C3—C2—H2A	120.6	C16—C17—H17A	124.9
C1—C2—H2A	120.6	O1—C17—H17A	124.9
C15—C14—O1	112.4 (4)	O5—C25—O4	123.5 (4)
C15—C14—C13	127.3 (4)	O5—C25—C20	119.3 (4)
O1—C14—C13	120.3 (5)	O4—C25—C20	117.0 (4)
C3—C4—C12	118.4 (4)	C18—O3—Zn1	95.2 (3)
C3—C4—C5	126.1 (4)	C18—O2—Zn1	82.9 (3)
C12—C4—C5	115.5 (4)	C14—O1—C17	102.7 (5)
N3—C5—C6	105.6 (4)	C25—O4—Zn1ⁱⁱ	114.6 (3)
N3—C5—C4	131.4 (4)	C10—N2—C11	118.9 (4)
C6—C5—C4	123.0 (4)	C10—N2—Zn1	128.1 (3)
N1—C12—C4	121.7 (4)	C11—N2—Zn1	112.3 (3)
N1—C12—C11	116.6 (4)	C1—N1—C12	118.4 (4)
C4—C12—C11	121.7 (4)	C1—N1—Zn1	128.0 (3)
C21—C20—C19	118.8 (4)	C12—N1—Zn1	113.6 (3)
C21—C20—C25	119.1 (4)	C13—N4—C6	103.8 (4)
C19—C20—C25	121.7 (4)	C13—N3—C5	106.5 (4)
N4—C13—N3	113.2 (4)	C13—N3—H3C	126.8
N4—C13—C14	125.7 (4)	C5—N3—H3C	126.8

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3C···O5ⁱⁱⁱ	0.86	1.96	2.792 (5)	162

Symmetry code: (iii) −x, −y, −z+2.

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