catena-Poly­[[bis(1H-benz­imidazole-κN³)­zinc(II)]-μ-3-carboxy­phenoxy­acetato-κ²O:O′]

In the title one-dimensional polymer, [Zn(C₉H₆O₅)(C₇H₆N₂)₂]_n, the Zn^II center exhibits a deformed tetrahedral coordination geometry defined by two N atoms from two benz­imidazole mol­ecules and two carboxyl O atoms from two different 4-carboxy­phenoxy­acetate groups. Each 4-carboxy­phenoxy­acetate ligand acts in a bis-monodentate mode to connect two adjacent Zn^II ions, forming a chain structure. Hydrogen bonds serve to connect the chains into a two-dimensional supramolecular network.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.060
• wR factor = 0.151
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

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

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

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: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

catena-Poly[[bis(1H-benzimidazole-κN³)zinc(II)]-µ-3-carboxyphenoxyacetato- κ²O:O']

Crystal data

[Zn(C9H6O5)(C7H6N2)2]	Z = 2
Mr = 495.80	F(000) = 508
Triclinic, P1	Dx = 1.459 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.580 (3) Å	Cell parameters from 8851 reflections
b = 11.356 (3) Å	θ = 3.4–27.5°
c = 11.492 (3) Å	µ = 1.13 mm^−1
α = 116.06 (2)°	T = 295 K
β = 100.32 (2)°	Prism, colorless
γ = 104.936 (14)°	0.37 × 0.26 × 0.18 mm
V = 1128.4 (6) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	5055 independent reflections
Radiation source: fine-focus sealed tube	3129 reflections with I > 2σ(I)'
Graphite monochromator	Rint = 0.045
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −13→13
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −14→14
Tmin = 0.679, Tmax = 0.822	l = −14→14
10127 measured reflections

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0715P)^2 + 0.3509P] where P = (Fo^2 + 2Fc^2)/3
5055 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

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

	x	y	z	Uiso*/Ueq
Zn1	0.74550 (5)	0.89735 (5)	0.68338 (5)	0.05213 (19)
O1	0.8747 (3)	0.8960 (3)	0.8255 (3)	0.0618 (8)
O2	0.8601 (3)	0.6840 (3)	0.6722 (3)	0.0648 (8)
O3	0.9940 (3)	0.6508 (3)	0.8778 (3)	0.0633 (8)
O4	0.7018 (3)	0.0702 (3)	0.7632 (3)	0.0621 (8)
O5	0.9159 (3)	0.1644 (3)	0.7723 (3)	0.0596 (7)
N1	0.5598 (3)	0.7461 (3)	0.6316 (3)	0.0532 (8)
N2	0.3532 (4)	0.5726 (4)	0.5123 (4)	0.0736 (11)
N3	0.7845 (3)	0.8594 (3)	0.5080 (3)	0.0534 (8)
N4	0.9021 (4)	0.8260 (4)	0.3624 (4)	0.0598 (9)
C1	0.4721 (5)	0.6476 (5)	0.5084 (5)	0.0641 (11)
C2	0.4941 (4)	0.7354 (4)	0.7238 (4)	0.0535 (10)
C3	0.5368 (5)	0.8156 (5)	0.8656 (5)	0.0701 (12)
C4	0.4463 (6)	0.7845 (7)	0.9298 (6)	0.0977 (19)
C5	0.3156 (7)	0.6766 (7)	0.8547 (7)	0.0983 (18)
C6	0.2712 (6)	0.5965 (6)	0.7155 (7)	0.0877 (16)
C7	0.3644 (5)	0.6274 (4)	0.6507 (5)	0.0614 (11)
C8	0.8739 (5)	0.8060 (4)	0.4632 (4)	0.0571 (10)
C9	0.7527 (4)	0.9218 (4)	0.4316 (4)	0.0531 (10)
C10	0.6675 (5)	0.9974 (5)	0.4371 (5)	0.0660 (12)
C11	0.6634 (5)	1.0514 (6)	0.3517 (6)	0.0813 (15)
C12	0.7383 (5)	1.0324 (5)	0.2624 (6)	0.0766 (14)
C13	0.8208 (5)	0.9568 (5)	0.2539 (5)	0.0678 (12)
C14	0.8274 (4)	0.9014 (4)	0.3399 (4)	0.0546 (10)
C15	0.8993 (4)	0.7841 (4)	0.7909 (4)	0.0528 (10)
C16	0.9893 (5)	0.7856 (4)	0.9107 (5)	0.0645 (12)
C17	0.8795 (4)	0.5500 (4)	0.8631 (4)	0.0523 (10)
C18	0.7565 (5)	0.5656 (4)	0.8766 (5)	0.0616 (11)
C19	0.6478 (5)	0.4537 (5)	0.8582 (5)	0.0671 (12)
C20	0.6589 (5)	0.3245 (5)	0.8251 (5)	0.0597 (11)
C21	0.7840 (4)	0.3102 (4)	0.8158 (4)	0.0497 (9)
C22	0.8927 (4)	0.4221 (4)	0.8339 (4)	0.0505 (9)
C23	0.8044 (5)	0.1736 (4)	0.7828 (4)	0.0509 (9)
H1	0.4901	0.6314	0.4276	0.077*
H3	0.6240	0.8883	0.9161	0.084*
H4	0.4732	0.8366	1.0253	0.117*
H5	0.2568	0.6588	0.9013	0.118*
H6	0.1834	0.5247	0.6656	0.105*
H8	0.9138	0.7590	0.4978	0.068*
H10	0.6157	1.0106	0.4959	0.079*
H11	0.6078	1.1032	0.3537	0.098*
H12	0.7322	1.0721	0.2071	0.092*
H13	0.8705	0.9430	0.1932	0.081*
H16A	1.0831	0.8531	0.9411	0.077*
H16B	0.9540	0.8179	0.9865	0.077*
H18	0.7471	0.6513	0.8982	0.074*
H19	0.5657	0.4651	0.8680	0.081*
H20	0.5839	0.2486	0.8094	0.072*
H22	0.9758	0.4118	0.8266	0.061*
H24	0.2833	0.5037	0.4425	0.088*
H25	0.9567	0.7971	0.3197	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0602 (3)	0.0454 (3)	0.0551 (3)	0.0173 (2)	0.0207 (2)	0.0301 (2)
O1	0.0742 (19)	0.0387 (14)	0.0608 (19)	0.0150 (14)	0.0068 (15)	0.0256 (13)
O2	0.077 (2)	0.0463 (15)	0.0521 (18)	0.0101 (15)	0.0121 (15)	0.0208 (15)
O3	0.0659 (18)	0.0432 (15)	0.082 (2)	0.0182 (14)	0.0167 (16)	0.0371 (15)
O4	0.0697 (18)	0.0461 (15)	0.078 (2)	0.0186 (14)	0.0332 (16)	0.0366 (15)
O5	0.0656 (19)	0.0557 (16)	0.075 (2)	0.0312 (15)	0.0324 (16)	0.0401 (15)
N1	0.059 (2)	0.0433 (17)	0.051 (2)	0.0153 (16)	0.0148 (17)	0.0232 (17)
N2	0.070 (2)	0.049 (2)	0.067 (3)	0.0058 (19)	0.010 (2)	0.0161 (19)
N3	0.063 (2)	0.0500 (18)	0.057 (2)	0.0218 (17)	0.0222 (18)	0.0335 (17)
N4	0.068 (2)	0.063 (2)	0.065 (2)	0.0335 (19)	0.0318 (19)	0.0383 (19)
C1	0.076 (3)	0.054 (2)	0.057 (3)	0.024 (2)	0.023 (2)	0.023 (2)
C2	0.060 (3)	0.046 (2)	0.054 (3)	0.015 (2)	0.019 (2)	0.029 (2)
C3	0.067 (3)	0.078 (3)	0.057 (3)	0.009 (2)	0.015 (2)	0.039 (3)
C4	0.097 (4)	0.116 (5)	0.063 (3)	0.011 (4)	0.025 (3)	0.049 (3)
C5	0.091 (4)	0.117 (5)	0.094 (5)	0.020 (4)	0.042 (4)	0.065 (4)
C6	0.072 (3)	0.072 (3)	0.100 (5)	−0.001 (3)	0.023 (3)	0.048 (3)
C7	0.067 (3)	0.048 (2)	0.061 (3)	0.013 (2)	0.019 (2)	0.028 (2)
C8	0.067 (3)	0.048 (2)	0.062 (3)	0.023 (2)	0.024 (2)	0.031 (2)
C9	0.050 (2)	0.052 (2)	0.052 (2)	0.0112 (19)	0.0133 (19)	0.029 (2)
C10	0.061 (3)	0.080 (3)	0.074 (3)	0.034 (3)	0.027 (2)	0.048 (3)
C11	0.079 (3)	0.093 (4)	0.092 (4)	0.047 (3)	0.026 (3)	0.057 (3)
C12	0.086 (4)	0.082 (3)	0.078 (3)	0.035 (3)	0.023 (3)	0.055 (3)
C13	0.079 (3)	0.069 (3)	0.056 (3)	0.017 (3)	0.024 (2)	0.039 (2)
C14	0.056 (2)	0.052 (2)	0.052 (2)	0.011 (2)	0.018 (2)	0.028 (2)
C15	0.052 (2)	0.039 (2)	0.055 (3)	0.0032 (18)	0.010 (2)	0.025 (2)
C16	0.081 (3)	0.038 (2)	0.062 (3)	0.016 (2)	0.004 (2)	0.027 (2)
C17	0.063 (3)	0.043 (2)	0.050 (2)	0.017 (2)	0.014 (2)	0.0272 (19)
C18	0.079 (3)	0.052 (2)	0.071 (3)	0.037 (2)	0.031 (2)	0.037 (2)
C19	0.072 (3)	0.074 (3)	0.086 (3)	0.041 (3)	0.041 (3)	0.053 (3)
C20	0.065 (3)	0.059 (2)	0.069 (3)	0.023 (2)	0.029 (2)	0.041 (2)
C21	0.063 (3)	0.045 (2)	0.047 (2)	0.021 (2)	0.0184 (19)	0.0273 (18)
C22	0.057 (2)	0.046 (2)	0.054 (2)	0.0228 (19)	0.0167 (19)	0.0286 (19)
C23	0.067 (3)	0.047 (2)	0.048 (2)	0.023 (2)	0.021 (2)	0.0319 (19)

Geometric parameters (Å, º)

Zn1—O1	1.942 (3)	C5—H5	0.9300
Zn1—O4^i	1.986 (3)	C6—C7	1.401 (7)
Zn1—N1	2.027 (3)	C6—H6	0.9300
Zn1—N3	2.011 (3)	C8—H8	0.9300
O1—C15	1.266 (4)	C9—C10	1.388 (6)
O2—C15	1.231 (5)	C9—C14	1.402 (6)
O4—C23	1.277 (5)	C10—C11	1.367 (7)
O5—C23	1.232 (5)	C10—H10	0.9300
O3—C16	1.424 (4)	C11—C12	1.383 (7)
O3—C17	1.360 (5)	C11—H11	0.9300
O4—Zn1^ii	1.986 (3)	C12—C13	1.361 (7)
N1—C1	1.311 (5)	C12—H12	0.9300
N1—C2	1.398 (5)	C13—C14	1.386 (6)
N2—C1	1.346 (6)	C13—H13	0.9300
N2—C7	1.399 (6)	C15—C16	1.518 (6)
N2—H24	0.8600	C16—H16A	0.9700
N3—C8	1.313 (5)	C16—H16B	0.9700
N3—C9	1.397 (5)	C17—C18	1.384 (6)
N4—C8	1.343 (5)	C17—C22	1.391 (5)
N4—C14	1.377 (5)	C18—C19	1.379 (6)
N4—H25	0.8600	C18—H18	0.9300
C1—H1	0.9300	C19—C20	1.389 (6)
C2—C7	1.381 (6)	C19—H19	0.9300
C2—C3	1.381 (6)	C20—C21	1.391 (6)
C3—C4	1.377 (7)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.382 (5)
C4—C5	1.388 (8)	C21—C23	1.511 (5)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.356 (8)
O1—Zn1—O4^i	110.49 (12)	C7—C2—C3	120.1 (4)
O1—Zn1—N1	105.98 (13)	C7—C2—N1	109.1 (4)
O1—Zn1—N3	119.11 (13)	C7—C6—H6	121.7
O4^i—Zn1—N1	100.62 (12)	C8—N3—Zn1	127.4 (3)
O4^i—Zn1—N3	111.56 (12)	C8—N3—C9	105.0 (3)
N3—Zn1—N1	107.20 (14)	C8—N4—C14	107.3 (3)
O1—C15—C16	113.4 (4)	C8—N4—H25	126.4
O2—C15—O1	125.0 (4)	C9—N3—Zn1	125.2 (3)
O2—C15—C16	121.5 (4)	C9—C10—H10	121.7
O3—C16—C15	113.4 (3)	C10—C9—N3	130.8 (4)
O3—C16—H16A	108.9	C10—C9—C14	120.3 (4)
O3—C16—H16B	108.9	C10—C11—C12	122.9 (5)
O3—C17—C18	126.0 (3)	C10—C11—H11	118.5
O3—C17—C22	114.8 (4)	C11—C10—C9	116.6 (4)
O4—C23—C21	117.5 (4)	C11—C10—H10	121.7
O5—C23—O4	122.8 (3)	C11—C12—H12	119.3
O5—C23—C21	119.8 (4)	C12—C11—H11	118.5
N1—C1—N2	112.4 (4)	C12—C13—C14	116.9 (4)
N1—C1—H1	123.8	C12—C13—H13	121.6
N2—C1—H1	123.8	C13—C12—C11	121.4 (5)
N2—C7—C6	132.5 (5)	C13—C12—H12	119.3
N3—C8—N4	113.4 (4)	C13—C14—C9	121.9 (4)
N3—C8—H8	123.3	C14—N4—H25	126.4
N3—C9—C14	108.8 (4)	C14—C13—H13	121.6
N4—C8—H8	123.3	C15—O1—Zn1	116.7 (3)
N4—C14—C9	105.5 (3)	C15—C16—H16A	108.9
N4—C14—C13	132.6 (4)	C15—C16—H16B	108.9
C1—N1—Zn1	128.4 (3)	C17—O3—C16	118.0 (3)
C1—N1—C2	105.9 (4)	C17—C18—H18	120.1
C1—N2—C7	107.3 (4)	C17—C22—H22	119.5
C1—N2—H24	126.3	C18—C17—C22	119.3 (4)
C2—N1—Zn1	125.4 (3)	C18—C19—C20	121.2 (4)
C2—C3—H3	121.0	C18—C19—H19	119.4
C2—C7—N2	105.2 (4)	C19—C18—C17	119.9 (4)
C2—C7—C6	122.1 (5)	C19—C18—H18	120.1
C3—C2—N1	130.7 (4)	C19—C20—C21	119.0 (4)
C3—C4—C5	121.1 (5)	C19—C20—H20	120.5
C3—C4—H4	119.4	C20—C19—H19	119.4
C4—C3—C2	118.0 (5)	C20—C21—C23	121.9 (4)
C4—C3—H3	121.0	C21—C20—H20	120.5
C4—C5—H5	119.0	C21—C22—C17	120.9 (4)
C5—C4—H4	119.4	C21—C22—H22	119.5
C5—C6—C7	116.6 (5)	C22—C21—C20	119.8 (3)
C5—C6—H6	121.7	C22—C21—C23	118.3 (4)
C6—C5—C4	122.0 (5)	C23—O4—Zn1^ii	107.7 (2)
C6—C5—H5	119.0	H16A—C16—H16B	107.7
C7—N2—H24	126.3
Zn1—O1—C15—O2	8.5 (5)	C2—N1—C1—N2	0.0 (5)
Zn1—O1—C15—C16	−174.1 (3)	C2—C3—C4—C5	−0.5 (9)
Zn1^ii—O4—C23—O5	−10.1 (5)	C3—C2—C7—N2	178.0 (4)
Zn1^ii—O4—C23—C21	167.9 (3)	C3—C2—C7—C6	1.2 (7)
Zn1—N1—C1—N2	−174.6 (3)	C3—C4—C5—C6	0.5 (10)
Zn1—N1—C2—C3	−2.8 (6)	C4—C5—C6—C7	0.4 (9)
Zn1—N1—C2—C7	174.7 (3)	C5—C6—C7—N2	−177.0 (5)
Zn1—N3—C8—N4	−164.1 (3)	C5—C6—C7—C2	−1.2 (8)
Zn1—N3—C9—C10	−14.3 (6)	C7—N2—C1—N1	0.1 (5)
Zn1—N3—C9—C14	164.0 (3)	C7—C2—C3—C4	−0.3 (7)
O1—Zn1—N1—C2	52.6 (3)	C8—N3—C9—C10	−178.0 (5)
O1—Zn1—N1—C1	−133.8 (4)	C8—N3—C9—C14	0.3 (4)
O1—Zn1—N3—C8	14.4 (4)	C8—N4—C14—C9	−0.9 (4)
O1—Zn1—N3—C9	−145.6 (3)	C8—N4—C14—C13	176.6 (5)
O1—C15—C16—O3	168.1 (4)	C9—N3—C8—N4	−1.0 (5)
O2—C15—C16—O3	−14.4 (6)	C9—C10—C11—C12	0.5 (8)
O3—C17—C18—C19	179.6 (4)	C10—C9—C14—N4	178.9 (4)
O3—C17—C22—C21	−179.7 (4)	C10—C9—C14—C13	1.0 (6)
O4^i—Zn1—N1—C1	111.1 (4)	C10—C11—C12—C13	0.5 (9)
O4^i—Zn1—N1—C2	−62.5 (3)	C11—C12—C13—C14	−0.7 (8)
O4^i—Zn1—O1—C15	172.5 (3)	C12—C13—C14—N4	−177.2 (5)
O4^i—Zn1—N3—C8	145.0 (3)	C12—C13—C14—C9	0.0 (7)
O4^i—Zn1—N3—C9	−15.0 (4)	C14—N4—C8—N3	1.2 (5)
N1—Zn1—N3—C8	−105.7 (3)	C14—C9—C10—C11	−1.2 (7)
N1—Zn1—N3—C9	94.3 (3)	C16—O3—C17—C18	0.3 (6)
N1—Zn1—O1—C15	64.4 (3)	C16—O3—C17—C22	−178.7 (3)
N1—C2—C3—C4	177.0 (5)	C17—O3—C16—C15	−73.2 (5)
N1—C2—C7—N2	0.2 (5)	C17—C18—C19—C20	−0.4 (7)
N1—C2—C7—C6	−176.6 (4)	C18—C17—C22—C21	1.3 (6)
N3—Zn1—N1—C1	−5.6 (4)	C18—C19—C20—C21	2.4 (7)
N3—Zn1—N1—C2	−179.2 (3)	C19—C20—C21—C22	−2.6 (6)
N3—Zn1—O1—C15	−56.4 (3)	C19—C20—C21—C23	178.9 (4)
N3—C9—C10—C11	176.9 (4)	C20—C21—C22—C17	0.7 (6)
N3—C9—C14—N4	0.4 (4)	C20—C21—C23—O4	0.2 (6)
N3—C9—C14—C13	−177.5 (4)	C20—C21—C23—O5	178.3 (4)
C1—N1—C2—C3	−177.6 (5)	C22—C17—C18—C19	−1.5 (6)
C1—N1—C2—C7	−0.1 (5)	C22—C21—C23—O4	−178.4 (4)
C1—N2—C7—C2	−0.2 (5)	C22—C21—C23—O5	−0.3 (6)
C1—N2—C7—C6	176.2 (5)	C23—C21—C22—C17	179.4 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H24···O2^iii	0.86	1.93	2.747 (5)	158
N4—H25···O5^iv	0.86	1.93	2.688 (4)	146

Symmetry codes: (iii) −x+1, −y+1, −z+1; (iv) −x+2, −y+1, −z+1.